The Engineering Leadership Podcast

Maia Brenner (AI Specialist & Head of Business Development @ Tryolabs) shares the fundamentals to begin your company’s AI/ML journey! We cover the most common challenges & pitfalls eng leaders face when investing in AI, how to understand feasibility/impact & ROI of different AI/ML initiatives, how to build your AI roadmap, how to break down massive AI/ML projects into small experiments, and how to accelerate different phases of your AI/ML strategy with partners like Tryolabs.

ABOUT MAIA BRENNER

Maia Brenner is a passionate data scientist and economist with strong programming skills, a mathematical and statistical background, and work experience in consulting and the public sector. As an AI Specialist at Tryolabs she helps clients maximize the full potential of data science and machine learning to solve their business problems.

Maia's experience in the consulting industry covers several projects related to demand forecasting, price optimization, customer segmentation, and natural language processing applications, among others. As a technical consultant, she has helped design and develop AI solutions for companies from several different industries such as Retail, Finance, Pharma, Logistics, Transportation, Hospitality, Education, and more.

She is also a professor in several universities and enjoys working on initiatives of AI4SocialGood. She has helped in the application of Machine Learning to improve the Public Education sector and is involved in Gender Inequality research groups.

SHOW NOTES

• The origin story behind Tryolabs (2:33)
• Common AI/ML challenges Tryolabs helps solve (5:48)
• Most painful problems with building AI capabilities (7:50)
• What are the fundamentals to build an AI organization? (10:11)
• How do you integrate AI/ML into your core business? (12:42)
• What problems can (or can’t) be solved with AI/ML? (15:18)
• How Tryolabs helps companies to identify specific AI/ML use cases (16:59)
• Common pitfalls when investing in & integrating AI/ML into your company (18:19)
• How to start small & experiment with AI/ML solutions (20:14)
• How Tryolabs scopes & iterates their AI/ML projects (24:42)
• Metrics, KPIs & other ways to determine feasibility, impact & ROI of your AI/ML project (26:53)
• How to build an AI/ML roadmap for your organization (30:34)
• How Tryolabs accelerates building your AI organization (34:28)

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Richard Wong (SVP of Engineering @ Coursera) shares how the dilemma of speed & quality evolves as a company scales. We cover how to balance building new features & fixing quality issues, internal & external signals to help you determine your priorities, & how to gain alignment. Plus how to avoid over-engineering!

ABOUT RICHARD WONG
Richard oversees Coursera's infrastructure and product development. Prior to joining Coursera, Richard held various engineering leadership roles at the early days of LinkedIn, with a key focus on scaling the Jobs marketplace and Talent Solutions to become its first billion-dollar product.

Richard also oversaw the product development for Linkedin international expansions. Prior to LinkedIn, Richard spent over a decade at Microsoft leading various product development teams including MSN Hotmail, Active Directory, Windows Server, and System Center. Richard received his Master’s degree from Stanford University.

SHOW NOTES

• The dilemma of speed v. quality (1:49)
• Richard’s personal example of speed v. quality dilemma (5:58)
• How Coursera improved product quality (7:47)
• Tactical steps to improve product quality (10:34)
• How to avoid over-engineering & leverage customer complaints to improve product quality (16:37)
• How to balance speed & quality as an engineering leader (20:06)
• How to get alignment on quality issues with executive & cross-functional teams (25:25)
• How to prevent spending too much time on quality-focused engineering work (29:46)
• What are the signals for when you need to shift between speed v. quality? (33:22)
• How the dilemma of speed v. quality change as you scale (38:52)
• How Richard allocates resources to focus on new features or quality (42:02)
• Rapid Fire Questions (48:28)
• Takeaways (54:17)

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Brad Henrickson (Leadership Coach, Former CTO @ Scoop Technologies) shares how to reclaim ownership of your time by using an energy/calendar audit! You’ll learn the mechanics of how to conduct an energy audit and how to transform energy-draining moments engineering leaders commonly encounter, into energy-giving moments. Plus how to apply this at scale to amplify energy AND increase ownership throughout your entire org!

BRAD HENRICKSON, LEADERSHIP COACH, FORMER CTO @ SCOOP TECHNOLOGIES

Brad is a seasoned technology leader with a broad range of experience from founding companies, to building product, to maturing organizations to driving culture and results in highly dynamic environments.

Brad has an extensive range of skills including but not limited to: building recruiting and hiring pipelines, organization design and SDLC design, people management, product management, board representation, budgeting, performance management, culture advocacy and delivery of critical technical projects.

Outside of the technical domain you will find Brad out rock climbing, surfing and mountaineering. He grounds himself through his connection to the outdoors and through his meditation practice which he has been doing for 20 years.

LINKS & RESOURCES

Welcome to our community’s FIRST DEBATE! Farhan Thawar (VPE @ Shopify) & Jerry Krikheli (Sr. Director of Engineering @ Facebook) hash out which org structure should rule them all… Should you go flat? Or should you become a hierarchy? You’ll hear how each structure impacts culture, innovation, and velocity!

FARHAN THAWAR, VP OF ENGINEERING @ SHOPIFY

Farhan Thawar is currently VP, Engineering at Shopify via the acquisition of Helpful.com where he was co-founder and CTO. Previously he was the CTO, Mobile at Pivotal and VP, Engineering at Pivotal Labs via the acquisition of Xtreme Labs. He is an avid writer and speaker and was named one of Toronto's 25 most powerful people. Prior to Xtreme, Farhan held senior technical positions at Achievers, Microsoft, Celestica, and Trilogy. Farhan completed his MBA in Financial Engineering at Rotman and Computer Science/EE at Waterloo. Farhan is also an advisor at yCombinator and holds a board seat at Optiva (formerly Redknee).

JERRY KRIKHELI, SENIOR DIRECTOR OF ENGINEERING @ FACEBOOK

Prior to Facebook, Jerry was VP of Engineering at Houzz where he oversaw all infrastructure, platform, and engineering across Consumer, Marketplace, and Industry Solutions initiatives. Jerry was also an engineering director at Google responsible for developing early versions of the display ad serving infrastructure and launching YouTube ads as well as video ads on mobile apps. He has a passion for building high-performing systems, products, and people.

SHOW NOTES

• The rules of the debate (2:45)
• Opening Statement: Why hierarchical organizations? (3:39)
• Opening Statement: Why flat organizations? (6:25)
• Culture in flat organizations (9:09)
• Culture in hierarchical organizations (10:55)
• Culture rebuttals (14:19)
• Innovation in flat organizations (19:49)
• Innovation in hierarchical organizations (22:01)
• Innovation rebuttals (24:57)
• Velocity in hierarchical organizations (26:05)
• Velocity in flat organizations (28:42)
• Closing Statements on Flat vs. Hierarchical (30:16)
  
  

BROUGHT TO YOU BY...

You've found the mythical product-market fit & are scaling fast... now what?! Bill Coughran (Partner @ Sequoia Capital; Former SVP Engineering @ Google) & David Singleton (CTO @ Stripe) cover common mistakes scaling engineering orgs make, signals to help you identify & develop good managers internally AND find great hires externally. Plus how to balance short & long term demands while scaling & more!

DAVID SINGLETON, CTO @ STRIPE

David joined Stripe from Google, where he was VPE, leading the Android Wear & Google Fit teams. At Google, David led teams that built some of the company’s most ambitious products, including its first apps with voice search; publisher products for Google Adsense; Google Offers; and Google Mobile Search Apps. He was also one of the first engineers at Google London and oversaw much of the growth of the London engineering office from inception to the large scale it has today.

Prior to Google, David spent 3 years as a senior engineer at Symbian, the pioneering mobile phone operating system, where he developed software for Nokia & Samsung smartphones & worked on both the Bluetooth stack & PC Connect software.

BILL COUGHRAN, FOUNDER'S COACH & PARTNER @ SEQUOIA; FORMER SVP ENGINEERING @ GOOGLE

Bill Coughran works as a founders' coach and partner at Sequoia Capital to help build spectacular technology-centric companies. Previously, Bill was Senior Vice President of Engineering at Google with oversight of Chrome, YouTube, maps, google.com, underlying infrastructure systems, and security.

SHOW NOTES

• What are the most common mistakes scaling organizations make? (2:24)
• What's the best way to add managers to a technology organization? (4:40)
• Signals to identify potential engineering managers to develop from inside the organization (7:32)
• Finding the right external hires while in hyper-growth (signals & warning signs) (8:41)
• What questions do you ask for hiring references? (11:23)
• Navigating doing things that don’t scale in the short term (16:17)
• “Second system syndrome” & avoiding the urge to rewrite your system (19:12)
• How to retain early employees at a hyper-growth startup (21:30)
• What Bill’s most excited about in the tech industry right now (24:18)
• Tips to help turn ICs into leaders (25:20)
• Deciding on org structure when you’re scaling fast (27:26)
• Navigating speed & long-term quality building your architecture at an early-stage company (29:43)
• Final advice from Bill & David (31:37)

BROUGHT TO YOU BY...

Marianna Tessel (CTO @ Intuit) & Aileen Lee (Founder/Managing Partner @ Cowboy Ventures) cover how to navigate the build vs. buy decision! They share the frameworks they use to make a “buy” decision, how they assess engineering talent during acquisitions, how they decide between vendor software vs. open-source vs. building yourself. Plus the leadership skills that help Marianna lead a 5,000+ person team!

MARIANNA TESSEL, CTO @ INTUIT

Marianna oversees Intuit’s technology strategy and leads all of Intuit’s product engineering, data science, information technology and information security teams worldwide. Marianna's been at the forefront of significant tech transformations, including virtualization, cloud, and dev ops.

Marianna previously served as Executive VP of Strategic Development at Docker, held leadership roles at VMware, Ariba, and General Magic working on the forefront of significant tech transformations, including virtualization, cloud, and dev ops. the forefront of significant tech transformations, including virtualization, cloud, and dev ops.

AILEEN LEE, FOUNDER & MANAGING PARTNER @ COWBOY VENTURES

Aileen is founding Partner at Cowboy Ventures, a team that backs seed-stage technology companies re-imagining work and life through technology, what they call “life 2.0”. Cowboy Ventures works with startups like Guild Education, Lightstep, Dollar Shave Club, and Tally.

Aileen periodically writes about technology insights and is known for coining the business term “unicorn” for public and private companies valued over $1bn.  She has been named to the Forbes Midas List of best investors and Forbes Most Powerful Women, as well as to Time Magazine’s 100 most influential people.

Prior to Cowboy, Aileen was a partner at Kleiner Perkins Caufield & Byers, was founding CEO of RMG Networks, and worked at Gap Inc in operating roles. She has degrees from MIT and HBS, is mom of 3, wife to a startup founder, an Aspen Institute Henry Crown Fellow and co-founder of the non-profit All Raise - aiming to accelerate success for women in the technology ecosystem.

SHOW NOTES

• About Marianna’s role at Intuit (2:33)
• How many acquisitions / build vs. buy decisions have you had to make? (4:35)
• Marianna’s evaluation framework for buying companies (6:26)
• Assessing engineering talent in acqui-hires (9:37)
• How do you decide to buy vendor software or build yourself? (15:41)
• How do you define what’s core to the business vs. context? (19:11)
• Where are you looking to buy instead of build right now? (21:40)
• Hard & soft skills that helped Marianna advance her career and run a 5000+ person team (23:48)
• Were you always good at the "developing talent" and "managing" part of being a CTO? (26:50)

BROUGHT TO YOU BY...

Guillermo Fisher (Director of Engineering, Infrastructure @ Handshake) shares the impact of mission & values alignment, supporting your team’s internal mobility & professional growth, plus interesting infrastructure challenges & actualizing values on the infra team. This episode serves as a great reminder of WHY we become engineering leaders - to empower our teams to become great leaders in tech.

"The engineering team pivoted! Trashed OKRs! Trashed the roadmap... and said, 'We're going to build out virtual career fairs.' And so we did the work over the course of the year. Delivered career fairs in that same year... which is amazing! And have since served thousands and thousands of career fairs."  

GUILLERMO FISHER, DIRECTOR OF ENGINEERING, INFRASTRUCTURE @ HANDSHAKE

This episode covers productivity practices to scale both your time & mind with Ashton Kutcher (Actor & Investor) & Ryan Petersen (CEO @ Flexport). They share their most essential productivity tools & systems, how to filter decisions & say NO to optimize your time, leverage your company’s culture to scale your time/mind. Plus energy audits, networking hacks, powerful questions, and more!

ASHTON KUTCHER, ACTOR & INVESTOR

Ashton’s career has spanned over many years with well-known projects on screen and film, but it's his passion in technology, entrepreneurship and investing that has brought him notable recognition. He’s been named TIME magazine’s “100 Most Influential People in the World,” as well as being honored by Vanity Fair's New Establishment List, which identifies the top 50 of an innovative new breed of buccaneering visionaries, engineering prodigies and entrepreneurs. Twice, Kutcher was named one of Forbes magazine’s “World’s Most Powerful Celebrities,” and one of Fast Company magazine’s “Most Creative People.”

RYAN PETERSEN, FOUNDER & CEO @ FLEXPORT

Ryan Petersen is the founder and Chief Executive Officer of Flexport, a full-service freight forwarder and customs broker. Since founding Flexport in 2013, Ryan and his team have worked to make global trade easy for everyone. Ryan led Flexport from inception to the company it is today: supporting over 10,000 customers and suppliers across 109 countries and doubling revenue to nearly $450m last year. His areas of focus include setting company strategy, ensuring the company tracks to goals, and most importantly, building and maintaining Flexport’s unique culture.

Prior to founding Flexport, Ryan helped run an e-commerce company and co-founded ImportGenius, one of the largest providers of business intelligence to the import-export industry. His experience and frustration with global logistics served as the inspiration to start Flexport. Ryan holds a Bachelor’s Degree in Economics from the University of California, Berkeley and an MBA from Columbia University.

SHOW NOTES

• How Ashton & Ryan first met & their early entrepreneurship hustles (2:15)
• Productivity tools & systems (4:06)
• How to say “NO” to optimize your time (7:08)
• Leverage culture in your organization to scale your time and mind (10:32)
• The power of predictability on company culture and productivity (15:26)
• Networking Hack: Connect through social impact (17:40)
• Creating a personal mission statement & the “energy audit” (19:02)
• How to avoid being reactive to your to-do list (21:26)
• Productivity as your company scales & cultivating sub-cultures within your org (23:17)
• What question should you be asking yourself right now? (25:01)

SPONSORS

This episode covers effective strategies to help you “close” engineering candidates with Darian Shimy (VP of Engineering, Weebly @ Square). We share how to strategically approach closing throughout the interview process, how storytelling & vulnerability help you connect with candidates, how to communicate the value of your company/compensation & strategically navigate offer negotiations!

DARIAN SHIMY, VP OF ENGINEERING, WEEBLY @ SQUARE

As an engineering leader who scales teams and products, Darian Shimy is an industry veteran with over 25 years of experience. He is currently at Square with prior leadership positions at Weebly, Attensity, and eHarmony.com. He received an MS in Computer Science from The University of Southern California and continues to code as a hobby. Outside the professional setting, Darian is a softball coach for various age levels from the recreation to the competitive level.

SHOWNOTES

• How Darian approaches closing engineering candidates (2:33)
• Who’s involved in closing conversations (4:55)
• How to address candidates’ needs throughout the interview process (6:09)
• “Boomerang candidates” & maintaining relationships to rehire previous co-workers (11:23)
• How to make candidates feel they can immediately contribute and be successful (13:12)
• How to make remote offers an opportunity to close candidates (18:50)
• High leverage ways to show appreciation & gratitude for hiring candidates (20:44)
• Money’s role in the closing conversation (23:47)
• Navigating offer negotiation (25:16)
• How to help candidates navigate multiple offers (27:42)
• Is "no" the end of the closing process? (30:59)

SPONSORS

This special feature covers strategies to lead an effective technical interview! Through live examples, we share your 3 main responsibilities, how to give clarity & guidance, set candidates at ease, create consistency & get the best from candidates in your technical interview with Lusen Mendel (Director of Developer Relations @ Karat) & Rohit Grover (Senior Interview Engineer & Mentor @ Karat).

Lusen Mendel (they / them) is Director of Developer Relations at Karat, where they share interviewer best practices with interviewers around the world. Previously, Lusen helped build Karat's Interview Engineer organization. Before that, they managed engineering teams at Indiegogo and Rackspace, worked as a software engineer at a number of startups and research groups, and graduated with a couple of Computer Science degrees from MIT.

This ELC Hiring Summit special feature explores tactics & strategies to help you build powerful relationships & professional network! We cover the impact of vulnerability, why you should focus on “giving” first, how to break down power dynamics, prepare for important introductions & more with Dan Portillo (Managing Partner & Founder @ Sweat Equity Ventures) & Jim Cook (CFO @ Orbital Insight).

DAN PORTILLO

Dan is a former Talent Partner @ Greylock. Previously, he was VP of Success & Engagement at Rypple, and VP of Organizational Development at Mozilla, creators of Firefox. Earlier in his career Dan spent a decade building out successful early-stage, venture-backed consumer and enterprise companies. Dan also served as a Council member for Code2040.org, a non-profit creating opportunities for underrepresented minorities in tech.

JIM COOK, CFO @ ORBITAL INSIGHT

Jim Cook is the CFO at Orbital Insight and he has scaled some of Silicon Valley's most iconic brands. Companies like Intuit, Netflix, Mozilla...

He was one of the first finance hires at Intuit. He was one of the original six founding members at Netflix. He also launched the Bench Board Executive Network, which is a leadership network and knowledge sharing network for operational executives.

SHOW NOTES

• Early career lessons on people, relationships, & “giving” (2:24)
• Vulnerability & the impact of lowering your guard (8:37)
• Building authentic relationships & trust long-term (12:55)
• Breaking down power dynamics & building up “relationship credits” (14:49)
• Learning from mistakes, burning bridges & removing your ego (19:38)
• Tactics for effective relationship building & networking (24:27)
• How to prepare for an important introduction (28:24)
• How to balance your priorities & invest time to help others (29:21)

SPONSORS

This ELC Hiring Summit special feature dives into compensation! We cover where you should start with your comp strategy, how to create consistency/transparency in your program, competing on comp/equity at the early stages, how to consider geography, and when you should bring in external support with Thanh Nguyen (Founder & CEO @ OpenComp) and Cyrus F. (GM/SVP @ Hatched Labs).

THANH NGUYEN, FOUNDER & CEO @ OPENCOMP

Thanh has spent the greater part of his decades-long career partnering with founders and investors on compensation and HR strategies. He is a leading expert in his field and has helped thousands of tech companies, including Airbnb, Figma, LiveNation, Lyft, Uber and many others.

As founder and CEO of OpenComp, Thanh brings to market a solution that combines his experience with powerful data and technology to help companies get compensation right and pay employees fairly.

Before joining Connery Consulting, Thanh led Rewards at Salesforce.com where he remained for 9 years, spanning domestic and international HR and Talent leadership roles.

CYRUS F, GM/SVP @ HATCHED LABS

Cyrus claims to have dabbled in the software development space since the first bubble. He's the GM/SVP at Hatched Labs - a globally distributed group of crafters. He recently achieved the distinction of Assistant Cofounder to the Adventure Council®.

He doesn't have any venture capital, he owns no equity and he's not on social media. He looks up to his three and three quarters year old daughter who's already acquired four unicorns."

SHOWNOTES

• Where to start with your compensation strategy (1:30)
• Consistency in compensation (5:00)
• Transparency in compensation (7:13)
• How to think about DE&I proactively in your compensation strategy (8:57)
• How to compete on comp & equity in an early stage company (11:34)
• How to consider geography with your hiring/compensation strategy (16:53)
• When to bring in external support for compensation & hiring (20:13)
• Once you’ve established a compensation strategy, now what? (22:15)
• How to minimize differences in expectations on compensation for a role (24:07)
• How should you decide to globalize or localize compensation? (26:28)

SPONSORS

What IS engineering branding? What are the most effective things you can do to immediately improve your engineering brand & attract top talent? This special feature from the ELC Hiring Summit covers all things engineering branding & attracting top talent with Cosmin Nicolaescu (CTO @ Brex) Kris Rasmussen (VPE @ Figma) Brad Henrickson (Leadership Coach / former CTO @ Scoop Technologies) & Sam Wholley (Partner @ Lightspeed Venture Partners).

SHOWNOTES

• What are the most important things you can do to attract top talent? (1:52)
• How have you changed how you attract top talent post-pandemic? (4:44)
• Tactical tips to overcome the gap between virtual and onsite employee experiences (8:00)
• What IS engineering branding? (9:10)
• Easy, immediate actions to improve your engineering brand (15:18)
• How do you retain & engage engineers in the company long term? (20:09)
• Controversial, but effective approaches to branding & attracting talent (23:33)

SPONSORS

This ELC Hiring Summit special feature covers building a diverse hiring pipeline! You’ll hear how to approach DE&I holistically & what success looks like beyond the metrics. Plus how to balance headcount demand with DE&I goals, hold execs/managers accountable & ideas for effective DEI programs & partnerships with Ragini Holloway (SVP People @ Affirm) and Gabe Westmaas (VPE @ Checkr).

RAGINI HOLLOWAY, SVP PEOPLE @ AFFIRM

Ragini is currently Senior Vice President of People at Affirm and is an advisor for PeopleTech Partners and tech startups, including Shift.org and Pinkaloo Technologies.

Ragini helps high-growth startups scale recruitment and People processes, often from scratch. She took Credit Karma from 40 to just over 500, and has similar ambitious hiring goals now, already taking Affirm from 100 to nearly 1,000.

Ragini advocates for collaborative hiring practices and facilitates organic and authentic work cultures where people come together and discover common goals. Ragini is heavily focused in building diverse teams and designing employee engagement programs that drive ongoing workplace satisfaction and high retention rates.

GABE WESTMAAS, VPE @ CHECKR

Gabe is VP of Engineering at Checkr, building a fairer future through a better understanding of the past. The team is bringing automation, consistency, and fairness to the manual processes behind background checks. Gabe has led several teams through high growth periods, most recently at Airbnb, and prior to that in the crowdfunding space at Tilt, and the Cloud Servers team at Rackspace.

SHOWNOTES

• How to think about diversity, equity & inclusion holistically (1:37)
• Why authenticity matters & how it impacts your hiring process and funnel (4:48)
• Balancing headcount demands & hiring diverse teams (8:53)
• How to hold executives & hiring managers accountable for DEI goals (14:53)
• What a successful DE&I program looks like (beyond the metrics) (20:12)
• Aligning hiring managers & hiring processes with DE&I goals (22:57)
• Effective programs & partnerships to create hiring opportunities for URGs (25:51)

SPONSORS

This special feature from the ELC Hiring Summit covers optimizing and scaling your hiring process! You’ll learn signs that indicate it’s time to optimize/scale, tactics to create a consistent hiring bar, key metrics to measure efficiency, feedback loops & more with Catherine Miller (VPE @ Flatiron Health) Vinithra Varadharajan (Head of Platform Eng @ Airtable) & Keng He (Sr. Director of Eng @ LiveRamp).

SHOWNOTES

• The current size and scale of Cat/Vinithra’s engineering teams + their current hiring process (1:55)
• Early signs indicating it’s time to optimize or scale your current hiring process (3:34)
• Tactics to ensure you have a consistent hiring bar (5:28)
• Why engineering rubrics are essential to your hiring process (7:48)
• How to encourage engineers to become interviewers (when resistant to interviewing candidates) (9:41)
• Interview panel structures (17:13)
• Key metrics to measure efficiency in your hiring process (21:24)
• How many recruiters, sourcers or coordinators do you need? (22:33)
• How has remote work changed your hiring process? (24:11)
• Who owns the top of the funnel in your hiring process? (25:48)
• What are the feedback loops you have in your hiring process? (27:17)
• How do you mitigate concerns candidates have about their potential managers in your hiring process? (28:30)

SPONSORS

This special feature from the ELC Hiring Summit covers everything sourcing engineering candidates! You’ll hear the latest sourcing trends, most effective sourcing tactics, how to get candidates attention, increase response rates to your outreach, & source senior engineers with Kah Seng Tay (GM & Eng @ Airtable) Shauna Geraghty (SVP, Head People & Ops @ Talkdesk) & Mike Pinkowsky (Head of Eng @ Gem)

KAH SENG TAY - GM & Engineering @ Airtable

SHAUNA GERAGHTY - SVP, Head People & Operations @ Talkdesk

MIKE PINKOWISH - Head of Engineering @ Gem

SHOWNOTES

• Sourcing Trends (2:26)
• Shauna, Kah Seng & Mike’s most effective sourcing tactics (5:37)
• How to change your outreach to get attention and increase response rates (10:11)
• Where are you sourcing candidates from? (17:59)
• Strategies to source senior engineers (22:29)
  

SPONSORS

This special feature from the ELC Hiring Summit explores the current state of hiring and how the rise of remote work will affect sourcing engineering candidates, the interview process, and compensation with Bret Reckard (Talent Partner @ Sequoia), Maia Josebachvili (former Head of People @ Stripe), and Erica Lockheimer (VPE @ LinkedIn)

BRET RECKARD - Talent Partner @ Sequoia Capital

MAIA JOSEBACHVILI - Head of M&A and Investing (interim), former Head of People @ Stripe

ERICA LOCKHEIMER - VP of Engineering, LinkedIn Talent Solutions, LinkedIn Learning & Glint @ LinkedIn

SHOWNOTES

• Introduction to Maia, Bret & Erica’s & their experience with the hiring ecosystem (1:08)
• The current state of hiring for engineering leaders in 2021 (2:58)
• Sourcing Trends (8:10)
• How platforms like LinkedIn are evolving with sourcing trends (17:05)
• Interviewing tactics (21:26)
• How the priorities of job seekers are changing (27:42)
• How to uncover values & priorities during the interview process (29:57)
• Compensation predictions (34:30)
• Final Advice on hiring in 2021 (39:55)

SPONSORS

Melissa Binde, VP Engineering, Cloud @ Splunk, shares lessons from her time building Amazon Apollo. You’ll hear the origin story of Amazon Apollo, how to define the right problem, identify the right solution, and what makes technology endure 20+ years. Plus how to improve your engineering storytelling and pitch the right product features to the right stakeholders!

"We were heavily influenced by an early project manager I worked with who called it, the 'JEDI principle' - You make just enough decisions to implement! And so anytime we hit something. We would actually stop, if we were arguing, we'd stop and go, 'Well, wait, hang on. Do we actually have to decide this now? Or can we kick this down the road?' And so that helped us avoid getting too tied up in philosophical arguments."  

ABOUT MELISSA BINDE

Melissa Binde previously served as Splunk’s VP of Platform and Observability. Prior to joining the company, Melissa led Google’s GCP Site Reliability organization for almost five years, supporting GCP’s growth from 250M revenue in 2015 to almost 9B in 2019. Before that she led engineering teams at Nordstrom, helping them transition to online and cloud, a cloud startup providing business continuity as a service to SMBs, and several other startups. Ms. Binde began her career as one of Amazon’s first 1000 employees, spending almost ten years there developing tools and technologies that are still part of the company’s core AWS stack. Ms. Binde holds a B.A. from Swarthmore College.

LINKS

Sarah Clatterbuck, Sr. Director of Engineering, YouTube & Google Zurich Site Lead @ Google, shares the story of her transition as a site lead during the covid-19 pandemic. We cover her past experiences that helped prepare her for the role, what it was like bootstrapping a new team during a pandemic, re-introducing teams to in-person work, AND the story behind her 18-day staycation & its impact on team burnout.

"You can't worry about pleasing everyone because there are many thousands of people that I'm trying to represent. But you can try to think about what kind of decisions optimize for the most good." 

ABOUT SARAH CLATTERBUCK

Sarah joined Google in 2018. She is leading engineering teams working on the Creator Economy at YouTube. Prior to joining Google, she was a Sr. Director of Engineering at Linkedin focused on Application Infrastructure. Prior to joining Google, she was a Sr. Director of Engineering at Linkedin focused on Application Infrastructure.

She previously held roles at Yahoo! and Apple while progressing in leadership ranks. Her undergraduate degree is from the University of San Francisco and her graduate degree from San Jose State University. She is passionate about getting girls interested in technology and from 2013 until 2018, she served on the board of Girl Scouts of Northern California, leading the board STEM task group.

SHOWNOTES

• What is a site lead and the reporting structure? (2:28)
• Why Sarah became a site lead for Google Zurich and what the transition was like (6:57)
• How is the tech industry, community & culture in Zurich different from Silicon Valley? (10:52)
• Sarah’s past experiences that helped prepare her to be a site lead (13:16)
• Possible career paths & surprise lessons after becoming a site lead (19:00)
• Bootstrapping a new team during the COVID-19 pandemic (22:15)
• Integrating remote hires to in-person office culture (25:19)
• How to help your team feel included (27:07)
• About Sarah’s YouTube Channel (29:41)
• Sarah's 18-day staycation & combating burnout in your team (31:34)
• Rapid Fire Questions (35:20)
• Takeaways (41:32)

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Asif Makhani, CTO @ Handshake shares about making non-incremental career transitions, unique opportunities at startups, and exercising influence at mid-stage companies. Plus Asif shares questions to help you gain clarity before your next transitions AND how to attract & retain senior engineers at smaller companies.

"When you have the ability to take a step back, you begin to think a little bit more philosophically about your journey. And it's not just incremental thinking. When it's incremental thinking it's about, 'what's next in my career.' 

But when you are able to take a step back, it's about... 'What impact do you want to leave behind? When I look back 10 years from now, will I be happy? Will I feel a sense of fulfillment?' 

I think that line of questioning really gives you the courage to be able to break away from an incremental way of looking at next steps."

ABOUT ASIF MAKHANI

We’re taking a quick break for the next two weeks and will return on Tues 6/29/21! When we return, Asif Makhani, CTO @ Handshake, joins us to share his experience making company transitions! Sarah Clatterbuck, Senior Director of Engineering YouTube & Google Zurich Site Lead @ Google, shares her journey about becoming a site lead outside of Silicon Valley, & Melissa Binde VP of Engineering, Cloud @ Splunk shares stories about the long term implications of technical decisions.

We cover practical tools to eliminate workplace injustice and help your team “get sh*t done fast and fair” with Kim Scott, author of Radical Candor & Just Work + Trier Bryant, CEO @ Just Work! We discuss the root causes of injustice and introduce several strategies to help you interrupt bias, address prejudice & confront bullying in your organization.

"You can't possibly do your best work if you are being harmed by the way you're being treated by your colleagues..." - Kim Scott

"Whatever problem you're solving, whatever OKR you have... your people are the ones that get it done. So we have to optimize for that experience!" - Trier Bryant

ABOUT KIM SCOTT & TRIER BRYANT

KIM SCOTT is the author of Just Work: Get Sh*t Done Fast and Fair as well as Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity - (one of our community’s ALL TIME favorite books!) Kim was a CEO coach at Dropbox, Qualtrics, Twitter, and other tech companies. She was a member of the faculty at Apple University and before that led AdSense, YouTube, and DoubleClick teams at Google.

TRIER BRYANT is Co-Founder and CEO of Just Work LLC, the implementation counterpart to Just Work, the book. Trier previously held leadership roles at Astra, Twitter, & Goldman Sachs. She proudly served as a combat veteran in the United States Air Force, as a Captain leading engineering teams while spearheading diversity, equity, and inclusion initiatives for the Air Force Academy, Air Force, and DoD. Trier also advises leading companies like Equinox, Airbnb, SoundCloud, Alto, Rockefeller Foundation, and others on their talent and DEI strategies.

RESOURCES

• Read Just Work (The Book): https://www.justworktogether.com/the-book
• Contact Just Work (The Company): https://www.justworktogether.com/our-capabilities

SHOW NOTES

• Why Kim wrote Just Work after Radical Candor (4:58)
• How Trier got involved & became CEO of Just Work (7:23)
• The impact of workplace injustice and why it matters (10:33)
• The root causes of workplace injustice and the roles we play (13:51)
• How to interrupt and stop bias (17:01)
• How to use “bias interrupters” and make them a part of your culture (29:55)
• Why language matters & how to respond to someone concerned about the “word police” (34:22)
• How to address bias using “I Statements” (39:46)
• What to do when someone is “mansplaining” during your meeting (44:39)
• How to confront prejudice using “It Statements” (47:58)
• How to address bullying with “You Statements” (51:05)
• Takeaways (54:08)

---

Jan Chong, VP of Engineering @ Tally shares strategies to manage and navigate relationships with your leadership team, direct reports and peers. We cover the fundamentals of managing up, why you need to align with your peers first when you join a new team, plus ways to communicate your ideas and the priorities of engineering more effectively with your non-technical colleagues.

"Organizations are made up of humans that are making decisions based on the data they have. If you don't think about how that data is being seen and understood, then you're going to have a really hard time getting the outcomes or driving the goals that you want to achieve..."

ABOUT JAN CHONG

Jan Chong is Vice President of Engineering at Tally, a financial automation company helping people navigate the complex world of consumer finance to save money, pay down their debt and reach their goals sooner. She leads and oversees the company’s client engineering, infrastructure security and technical operations teams. Before joining Tally, Jan was a long-time executive at Twitter where she played a critical role in launching and scaling its core mobile and web products, overseeing a team of more than 300 people in Twitter’s consumer engineering organization. Prior to that, Jan ran client and server development at OnLive, a cloud gaming platform. She received multiple degrees from Stanford University, including her Ph.D in management science and engineering, and M.S. and B.S in computer science.

SHOW NOTES

• What is Managing Up (3:52)
• What to do when your manager has different expectations and perception of your performance (6:19)
• The fundamentals of managing up (8:42)
• Making the world of management visible (10:39)
• The three categories of “managing up” and why you should align with your peers first (15:07)
• Who you need to “mind-meld” with & how to replicate it remotely (22:29)
• How to align & “mind-meld” with your peer leaders (27:22)
• Managing up at different levels of seniority (33:28)
• What you need to do to “manage up” effectively (39:30)
• Unexpected differences of working with non-technical colleagues & Jan’s metaphors to explain engineering (43:23)
• Takeaways (51:05)

Nick Rockwell, SVP of Engineering & Infrastructure @ Fastly shares his recent reflections on incidents, resiliency, blamelessness, and accountability. You’ll hear why the heroic model of incident response is unsustainable, how to improve reliability by closing the long-feedback loop, plus opportunities to maximize post-mortems for process improvement AND emotional processing.

"We started doing a biweekly meeting. We talk about resilience. We revisit everything that has not been closed, whether it's a year old, or it's a day old, , we're forced to keep coming back to it. So how to move away from that incident based post-mortem to something that's more like a continual revisiting of every thread or pathway that's been opened until they're not even open anymore. So that's the lines I'm thinking along."  

ABOUT NICK ROCKWELL

Nick Rockwell is SVP of Engineering & Infrastructure @ Fastly helping build the next-generation edge infrastructure for a faster, safer, more resilient Internet. Nick was formerly Chief Technology Officer at The New York Times, overseeing product engineering, infrastructure and R&D. Previously he was Chief Technology Officer of Conde Nast, and Digital CTO at MTV Networks. Throughout his career, Nick has worked at the intersection of media and the Internet, building digital products at scale. Nick graduated from Yale in 1990 with a B.A in Literary Theory.

SHOWNOTES

• Nick’s story of why incidents, resiliency, accountability & blamelessness are top of mind (2:20)
• The “heroic model” of incident mitigation and it’s emotional impact (6:41)
• Building a resilient system & transitioning away from heroics to a more mechanistic incident management model (12:12)
• “The long feedback loop” of incidents (15:57)
• Grappling with the risks of a more process-driven, mechanistic model of incident management (21:27)
• Dedicated vs. distributed incident response teams & how incident management evolves over time (24:43)
• Balancing individual accountability and a culture of blamelessness (28:37)
• Why you need to talk about incidents and process their residual emotions (33:12)
• On maximizing post-mortems for process improvement & emotional processing (37:01)
• Takeaways (40:15)

We have a conversation with Christina Wick, CTO @ Flowcode, on the current state of the gender gap in tech and what we can do as engineering leaders to actively bridge that gap. We cover stories of the historical impact of women in tech as well as what you can do to remove bias in interviews, performance reviews and feedback. Plus what you can do to intervene when you observe bias happening.

"The first time I heard someone talking about how "women should seek executive sponsorship" I got really annoyed... The term executive sponsor in project management usually means the C-level executive that sponsors or is responsible for the project. So like, why do women need an executive sponsor? I'm not some project! But then I thought about it... And men sponsor men all the time! We just don't label it that."  

ABOUT CHRISTINA WICK

Christina was previously VP of Engineering at Harry’s, a successful next-generation CPG company. Before Harry’s, Christina’s roles have ranged from running Product, Design and Engineering at Venmo, to defining strategies and building services in the mobile and devices space at Amazon, to AOL where she started as a Software Engineer and rose to the level of Sr. Technical Director responsible for over 50 consumer-facing mobile apps and websites and where she received an Apple Design Award for the Best iPhone Entertainment Application, AOL Radio, in June 2008.

Christina has a Bachelors in Computer Science, with minors in Mathematics and Psychology, and a Masters in Computer Science and Applications from VA Tech, with her area of concentration being Human-Computer Interaction."

SHOWNOTES

• The historical impact of women in programming & tech (2:03)
• The current state of the gender gap in tech (7:04)
• Three things you can do to start actively bridging the gender gap in tech (12:12)
• Stop gender stereotypes & vague feedback (14:04)
• Remove bias in performance reviews and interviews (17:01)
• Intervene when observing bias (23:44)
• Executive sponsorship (29:40)
• Establish norms and make it okay to talk about bias (34:29)
• The Impact of “throwing starfish in the ocean” (37:36)
• Takeaways (38:39)

Allan Leinwand, SVP of Engineering @ Slack shares his core philosophy & approach to creating developer productivity AND happiness! You’ll learn how Allan combines what developers want most + metrics, & analysis of the dev pipeline to optimize productivity. Allan covers how to translate those principles to remote/hybrid work and how to tell (and what to do...) if your dev teams are unhappy.

"I generally say developers want to do three things... They want to solve hard problems at scale. They want to see that hard problem when they solve it... get put to use! The third thing that I think, honestly, is they just don't want to work with jerks. I think if you master those three things then you end up with a very happy and productive development team." 

ALLAN LEINWAND SVP ENGINEERING @ SLACK

Prior to leading engineering & operations at Slack, Allan was Chief Technology Officer at ServiceNow, where he was responsible for overseeing all technical aspects and strategy. He has co-founded and held senior leadership positions at multiple companies and was a venture capital investor for seven years. He founded Vyatta (acquired by Brocade), the open-source networking company, and co-authored “Cisco Router Configuration” and “Network Management: A Practical Perspective” and has been granted a patent in the field of data routing.

Leinwand previously served as an adjunct professor at the University of California, Berkeley where he taught on the subjects of computer networks, network management, and network design. He holds a BS in Computer Science from the University of Colorado at Boulder.

SHOWNOTES

• Your team is more than the metrics! (2:19)
• The cyclical pattern & lifecycle of developer productivity (4:05)
• Allan’s essential components to developer productivity (7:48)
• How to account for people behind the metrics (12:12)
• The goal is not the metrics! The goal is to understand developer workflow! (17:40)
• How to know if your dev teams are happy (26:49)
• What to do if developer productivity goes up, but dev happiness goes down… (30:55)
• Staying present & how to context switch effectively (34:32)
• How to identify metrics serving the wrong purpose or incentivizing the wrong behavior (38:12)
• How Allan’s principles on dev happiness & productivity translate to remote & hybrid work (39:29)
• Takeaways (42:46)

Quentin Clark, Managing Director @ General Catalyst shares how to get your career unstuck at different scales & stages! You’ll learn different frameworks you can use to benchmark your growth and identify where you might be stuck. Plus different approaches you can take to get your company and the people you lead, unstuck at scale!

"The specifics of the framework are not as important as having one at all. Create some ruler... Like if you're a snail and you're trying to inch your way towards the head of lettuce, and you're trying to measure whether or not you're making progress every day... It doesn't actually matter whether or not you're using an imperial tape measure with inches or the metric system and a yardstick... 

You can make up your own ruler! As long as that ruler is consistently being used over and over again. This is why I say it's important for people to have A framework... not necessarily any one framework. And that they come back to it.”

QUENTIN CLARK, MANAGING DIRECTOR @ GENERAL CATALYST

Quentin is a product and systems technical leader with broad experience in the enterprise space. Incepted, built, and delivered successful products over many years - from servers to SaaS platforms and applications. He will be joining General Catalyst in January as a managing director.

Prior to embarking on a career in investing, Quentin was the CTO at Dropbox, where he led all of engineering, product, design, and growth. He worked with them through its IPO, its pivot to Dropbox Spaces, and drove the portfolio expansion starting with the acquisition of HelloSign.

He was at Microsoft for 20 years, most of that time focused on innovation - creating new products and value. The last decade of his time at Microsoft, Quentin was responsible for the high-growth data platform business, including SQL Server. There he worked for Satya Nadella leading the whole data platform business into the cloud.

After Microsoft, Quentin was at SAP for two years, first as CTO then as Chief Business Officer where he led strategy and product direction for the platform and ultimately for the whole company. Before joining Dropbox he spent a year angel investing and exploring the VC world.

He currently serves on the boards of Coda, Highfive, and Minio, and has been investing and advising very early-stage companies.

SHOWNOTES

• What does it mean to get “unstuck?” (2:55)
• How do you get unstuck? (5:32)
• How to divide your time between growth, grunt work, & what you’re good at (7:06)
• Where engineering leaders get stuck + how to benchmark your growth using the 6 areas of competency (10:42)
• How to get people unstuck at scale (15:55)
• Why it’s important to have a framework to benchmark your growth (21:22)
• Quentin’s story of getting unstuck in his career (25:20)
• “Give up” what got you stuck by changing your goals & intention (31:20)
• How to get your company and culture unstuck (37:15)
• Quentin’s podcast “Equivalent to Magic” (44:20)
• Takeaways (45:58)

Jeremy Henrickson VP Engineering & Product @ Rippling shares how to align, lead and scale a combined engineering and product organization! You’ll learn about the common tension points while scaling, different ways to structure your org, when to combine your orgs vs. split, and how to realign your teams when expectations get out of sync. Plus how to build credibility with new teams and acquire product skills as an engineering leader!

“When I have like a number of teams and each of them has like a product leader AND an engineering leader... the expectation that I set with them is like, "Look, you guys are gonna have different points of view. And that's okay. But when you come to me, you either need to one, have a really clear, shared point of view on something, because you've gone into this together and have thought it out. Or a clear point of disagreement, so that you know, we can tie break on, okay, which one of these is actually more important right now?"

And either one of those is totally fine. But a shared understanding of the facts, a shared understanding of the trade-offs is sort of the floor that I draw on those conversations.”

JEREMY HENRICKSON, VP PRODUCT & ENGINEERING @ RIPPLING

Jeremy Henrickson is responsible for scaling a world-class engineering team across two continents. Previously as Chief Product Officer at Coinbase, he oversaw 5x growth of the product and engineering organization and transformed a scrappy startup into a global cryptocurrency platform with millions of users. He began his career at Apple in the 1990s and holds a BS and MS in Computer Science from Stanford. Jeremy enjoys playing board games and piano with his kids.

SHOWNOTES

• Jeremy’s experience scaling engineering and product at Coinbase (3:00)
• How to bridge the gap between engineering and product (5:26)
• How to think about hiring the right people for early and growth stages of a company (7:56)
• Finding both true believers AND skills for scaling + navigating hiring doubt through the “crypto-winter” (9:37)
• Common tension points while scaling engineering and product organizations (14:27)
• How much technical detail and context should be shared between product and engineering? (19:00)
• How to build trust and credibility when you’re leading a new team (21:11)
• Dunbar’s number and the different phases of scaling a product and engineering organization (25:43)
• Different ways to structure engineering and product organizations (29:20)
• When You Should Combine Engineering and Product Orgs & Jeremys different approaches with Rippling, Coinbase & Guidewire (35:16)
• What to do if you want to pursue a career in product AND eng leadership (40:13)
• How to get engineering & product aligned when they have misaligned expectations (43:02)
• Where to begin if you’re an engineering leader who just took over product manager responsibilities (45:21)
• Takeaways (46:29)

John Kim has had an unconventional career, pivoting from professional gamer to software developer, to serial entrepreneur. We discuss how to assess your career, make pivots, and balance your growth long term. John shares principles from complexity science to help you navigate unknowns, risks, & opportunities in your career. Plus other powerful frameworks to make better career decisions.

"So if you're working at a bigger company, what you're really trying to optimize for is how quickly can you move up in turn terms of 'Abstraction Layer.' It's not about titles. It's about, can you actually understand the next layer of abstraction within the business.

So if you're like an IC, what is the engineering manager's priority right now for your team? What is the, let's say a director of engineering's priority right now for the team?

And if you actually start caring about those things, you'll be able to make a lot more faster progress."

JOHN KIM, CO-FOUNDER & CEO @ SENDBIRD

John S. Kim is the Co-founder and CEO of SendBird, the world's no.1 chat API. The platform currently serves over 100M monthly chat users across the world's leading companies such as Reddit, Delivery Hero, Yahoo!, Rakuten, Paytm, Accolade, Livongo, and DHL. John is a serial entrepreneur, engineer at heart, and an expert in the API economy and communications tech space. Little known fact about John is that he was Korea's no.1 pro-gamer for Unreal Tournament.

SHOWNOTES

• How John went from professional gamer to #1 chat API company @ Sendbird (2:47)
• Creating vs. consuming & why John walked away from professional gaming (6:58)
• John’s early career pivots: from software engineer to social gaming & Y Combinator (9:08)
• How to apply the complexity science principles of “Convergence” & “Divergence” to your career decisions (11:17)
• Navigating “Abstraction Layers” & why you need to invest time to build “social capital” in your career (15:31)
• The “Human Capital” Framework & balancing the skills you accumulate throughout your career (19:04)
• Building emotional capital, training for cognitive empathy, & the tradeoffs of agreeableness (20:41)
• How to manage expectations & communicate with stakeholders when you need to pivot (27:34)
• How John applied these principles to make career decisions and pivot his company (30:23)
• How to pick careers aligned with your happiness and motivation (37:10)
• How to pivot your career using the “2PM” framework (people, product, market, money) (39:59)
• Future founders: Why you’ll be happier making 10 year career decisions & quick pivots (44:04)
• Takeaways (46:23)

Tia Caldwell, former Director of Engineering @ Slack, shares different frameworks she’s used to motivate teams and unlock their superpowers! We cover methods to identify, maximize, & balance strengths on your team, how to shift your team’s mindset from drama to EMPOWERED so they can better confront adversity & challenges. Plus we share the explicit conversations you should be having in your first 1:1s to create greater psychological safety!

“You don't need to have this manager game face. I think there's this perception that when you're a manager, you're supposed to be the person who knows the answers to everything… And while a part of the execution piece is really necessary with being an effective manager, I think the other part is relationship building. You need to invest the time in understanding how people work. Because people will be more open and honest with you, it'll help out with retention for your team and overall happiness. But if you don't… it's not going to go well because you'll be treating people as resources and not humans.”

TIA CALDWELL, FORMER DIRECTOR OF ENGINEERING @ SLACK

Tia led the Monetization Team at Slack, a leading global collaboration hub that makes people’s working lives simpler, more pleasant and more productive. Over the past 15 years, she has led and managed engineering teams at Netflix and Microsoft, covering a breadth of projects such as Xbox, Office 365 and Streaming Content Delivery.

We deconstruct two distinct career paths in engineering & leadership, and a co-founder relationship 15 years in the making. In part 2, Tom & Viraj share why they decided to start a company together, how they assess start-up opportunities, early company building & values-defining conversations, and other strong opinions on how they’re creating the engineering culture and execution at Common Room.

VIRAJ MODY, CO-FOUNDER & CTO @ COMMON ROOM (https://www.linkedin.com/in/virajm/)

Viraj led engineering organizations at Convoy and Dropbox, helping both companies scale their teams and products. Viraj was also a founding engineer at Audiogalaxy, where he worked alongside Tom, which was acquired by Dropbox.

TOM KLEINPETER, CO-FOUNDER & CHIEF ARCHITECT @ COMMON ROOM (https://www.linkedin.com/in/tomkleinpeter/)

We deconstruct two distinct career paths in engineering & leadership and a co-founder relationship 15 years in the making! Tom & Viraj share formative startup experiences that shaped their careers as a Principal Engineer & Eng Leader. Plus insights shaping their new company on assessing risk, dealing with open-ended problems, being decisive, & removing non-coding time for engineers

VIRAJ MODY, CO-FOUNDER & CTO @ COMMON ROOM (https://www.linkedin.com/in/virajm/)

Viraj led engineering organizations at Convoy and Dropbox, helping both companies scale their teams and products. Viraj was also a founding engineer at Audiogalaxy, where he worked alongside Tom, which was acquired by Dropbox.

TOM KLEINPETER, CO-FOUNDER & CHIEF ARCHITECT @ COMMON ROOM (https://www.linkedin.com/in/tomkleinpeter/)

Harpaul Sambhi, Founder & CEO @ Magical reveals the tools he uses to accelerate his personal and professional growth. You’ll learn how to engineer successful outcomes with your goals through accountability mechanisms, how to build a personal board of directors or leverage friendly competitions like the “master of the universe award” to learn, pivot, & grow faster.

"When we do our goal setting, especially if you're trying to compete with someone... is to do the personal side just as much as the professional side. And you get that layer of intimacy that is often not necessarily shown in these types of meetings. And as a result, they become an exceptionally vital part of your life.”

HARPAUL SAMBHI, FOUNDER & CEO @ MAGICAL

Alexis Rask, Executive Coach & Partner @ Sweat Equity Ventures shares how to ask powerful questions. You’ll hear simple tactical ways to increase the power of your questions, what the most powerful question is, common failure modes of open-ended questions, how to get over your fear of silence, plus stories of the most powerful questions we’ve ever been asked.

"When I say a powerful question, I'm saying 'What's the really right question, for this right moment, that is going to TRULY unlock someone's thinking, in a way that gets at new information.'"

ALEXIS RASK, EXECUTIVE COACH & PARTNER @ SWEAT EQUITY VENTURES

Named 40 under 40 by Silicon Valley Business Journal, Alexis is an experienced business operator turned Executive Coach to Silicon Valley's top founders and VCs. Prior to founding her coaching firm, Future Consulting, Alexis founded the Marketing Solutions team at LinkedIn in 2006. She opened offices, hired out the sales and customer success teams, and developed the go-to-market plans. She has also served as COO/CRO at Shopkick which sold for $250million in 2014. She is also a faculty member of UC Berkeley's Executive Coaching Institute.

SHOWNOTES

• What’s the most powerful question you’ve ever been asked? (4:40)
• Failure-modes of open-ended questions & how to use powerful questions to get to “the heart of the matter” (11:54)
• The impact of a more powerful question (18:55)
• Emotional intelligence & how to get the best from people (25:40)
• Why “WHY” is the perfect follow up question (31:24)
• How to use powerful questions in your 1 on 1’s (38:49)
• How to get over the fear of silence… (41:40)
• Identify opportunities to ask more powerful questions with the “mental review” (48:18)
• Takeaways (54:19)

Edward Kim, co-founder & CTO @ Gusto shares the different forms that “fear of failure” can take in your engineering org. Eddie shares incredible stories to help you spot the different signs of “fear of failure”. And you’ll hear different ways you can change your team culture, process and operations to reduce fear of failure.

“But as you continue to scale and you grow... that thing that you optimized for starts to become a disservice to you and the company. Because what happens is this fear of failure, if you take it too far, it starts to change a lot of things about the business.”

EDWARD KIM CO-FOUNDER & CTO @ GUSTO

Prior to Gusto, Edward was the CEO and co-founder of Picwing, a Y Combinator startup and photo-printing platform. Before Picwing, Edward worked as a senior project engineer at Volkswagen Group of America Electronics Research Lab, where he led research and development for cloud-based navigation and speech recognition systems for Volkswagen and Audi. 

Edward is also the developer of several award-winning Android apps that have generated more than $1 million in revenue. Edward holds bachelor’s and master’s degrees in electrical engineering from Stanford University.

SHOWNOTES

• What it means to “remove fear of failure” as you scale (2:25)
• Signs that indicate your company is optimized around a fear of failure (6:19)
• How to know when “healthy management” actually means your company has a fear of failure and is holding you back (10:54)
• Other forms “fear of failure” can take in your organization (14:20)
• MTTR over MTBF - Why you should prioritize recovering from failure over avoiding failure (17:40)
• “Rage-fixing” & Eddie’s breakthrough moment confronting fear of failure at Gusto (23:43)
• “Kicking the flipchart” & Eddie’s breakthrough moment #2 (27:52)
• How to maximize unplanned or unintended crucial conversations (33:54)
• How to decide when you need to abandon the agenda and “kick the flipchart” (37:37)
• How psychological safety can make your team more resilient to fear of failure (40:17)
• Takeaways (44:07)

We’re launching our new season next week! Check out this trailer for a preview of our first few guests... Eddie Kim (Co-Founder/CTO @ Gusto), Wendy Shepperd (GVP Engineering @ New Relic), and Will Larson (CTO @ Calm). Our first episode with Eddie Kim will be released on Tues 2/23, discussing how to remove fear from failure in your organization!

Erica Lockheimer shares with us her imperfect path to engineering leadership, why the unconventional path matters, and what you can do as an individual leader & organization to empower engineering leaders with unconventional backgrounds. Plus you’ll also hear how to overcome self-doubt and launch an apprenticeship program!

“Whether you're a manager or whether you're an individual contributor, you are a leader in your role. Use the voice that you've earned in the seat that you own.  What can you personally do to create a different outcome. And all of us have that power  in a role that we have.” - Erica Lockheimer

ERICA LOCKHEIMER, VP OF ENGINEERING, LINKEDIN LEARNING @ LINKEDIN

Prior to LinkedIn Learning, Erica served as the VP of Engineering heading the Growth Engineering team, where her focus was on increasing growth in new members and deepening engagement with members across LinkedIn's products.  She started the Growth Team from the ground up to now a high performing 120-person team.

She is also responsible for LinkedIn's Women In Tech (WIT) initiative that is focused on empowering women in technical roles within the company.  Prior to LinkedIn, she worked at Good Technology as Director of Server Engineering, In 2014 and 2015, Erica was also voted amongst the top 22 women engineers in the world by Business Insider.  Erica is a San Francisco Bay Area native, has 2 kids, loves to run and is a graduate from San Jose State University with a B.S. in Computer Engineering.

RESOURCES

Craig Martell shares the biggest mistakes leaders of ML teams make, what to do if you have no experience leading an ML team, key skills your ML team needs, plus different models/approaches to building an ML team. You’ll hear the most expensive and time-consuming parts of ML, how to estimate timelines, unique tech debt, and how to manage expectations.

“If I had to give one piece of advice about starting AI in your company, one of the first people I would hire is a really great data scientist, even if they can't code. Just so they're the one who's going to start training you and helping you think about, how to gather data, how the modeling is going to work, what you're going to need, whether that feature that you want to build is even modelable in the first place..." - Craig Martell

Craig is Head of Lyft Machine Learning. He’s also an adjunct professor of Machine Learning for Northeastern University’s Align program.

Prior to joining Lyft, he was Head of Machine Intelligence @ Dropbox, and led a number of AI teams and initiatives at LinkedIn, including the development of the LinkedIn AI Academy. Before LinkedIn, Craig was a tenured computer science professor at the Naval Postgraduate School specializing in natural language processing (NLP). He has a Ph.D. in Computer Science from the University of Pennsylvania and is the co-author of the MIT Press book Great Principles of Computing.

RESOURCES

• (ML training) Galvanize: https://bit.ly/3ckF6Gz
• (website) Andrew Ng: https://bit.ly/3cgerdU
• (courses) ML: https://bit.ly/3iNB9gf | AI for Everyone: https://bit.ly/2HeZKwl
• (course) Fast.AI: https://bit.ly/35SPwMD
• (book) "Hands-On ML with Scikit" : https://amzn.to/35SbGyh

SHOW NOTES

• An overview of the machine learning lifecycle (2:49)
• The most expensive and time-consuming aspect of the machine learning lifecycle (6:07)
• The key skills of a machine learning team (7:21)
• How do you build an AI/ML Team and what are the different models? (8:41)
• What to do If you’re an engineering manager with no AI/ML skills or experience (15:19)
• How deep does your understanding of AI/ML have to be in order to lead effectively? (18:48)
• How do you estimate project timelines for AI/ML teams? (19:15)
• What are the biggest mistakes engineering leaders make managing AI/ML teams? (20:52)
• How do you manage expectations in an organization that’s in the early days of AI/ML development? (21:33)
• What are sources of technical debt unique to AI/ML systems? (22:13)
• How do machine learning teams interface with product teams? (23:55)
• AI/ML resources for executive engineering leaders (25:44)
• When’s the right time to invest in AI/ML? (26:10)
• Can you apply the Pareto Principle (80/20 rule) to AI/ML development? (26:40)
• Takeaways (28:12)

ELC SUMMIT 2020

“Giving up control” is about empowering other people to scale yourself, and scale your effectiveness. Maria Latushkin shares with us why you need to give up control as an engineering leader and what holds people back. Plus you’ll learn tons of different ways to influence and manage your performance when it’s dependent on other people’s effectiveness.

“You are responsible for the delivery of the team. At the end of the day, nobody really cares like how much YOU work. You can be working around the clock. And it's not how great you are or what you produce. It stops being about you and it starts being about the function that you lead.” - Maria Latushkin

Maria is responsible for leading Omada Health’s technology vision and team. Prior to joining Omada Health and moving to the healthcare space, Maria has spent over 15 years in eCommerce, retail, and enterprise SaaS companies ranging from series B startups to large companies, such as Walmart.

SHOWNOTES

• Why you need to give up control as a senior engineering leader (2:07)
• What holds people back from giving up control? (9:27)
• The impact and trade-offs you make when you avoid or resist giving up control (15:31)
• How to influence and manage your performance now that it’s dependent on your team’s effectiveness (23:49)
• How to make sure people heard you, so that you know you’re on the same page (29:04)
• Does the discomfort of “giving up control” happen at every transition to a new leadership level, or is it a one-time thing? (32:44)
• How to regain “control” and empower your team (39:40)
• The Impact -  how you feel when you give up control (41:25)
• Takeaways (43:36)

A dynamic conversation between 4 current and past VPs of Engineering who cover tons of patterns and anti-patterns about being a VPE! You'll hear how leadership is different in large vs. small companies, mental models to determine your greatest leverage, why you DON’T need to act like an owner, how to put trust into practice when you’re transitioning into a new role, and about the imperfect path to become a VPE. 

SPEAKERS:

CATHY POLINKSY CTO @ Stitch Fix

JERRY KRIKHELI VP of Engineering @ Houzz

RICHARD WONG SVP of Engineering @ Coursera

ERICA LOCKHEIMER  VP of Engineering @ Linkedin Learning

And CLAIRE LEW CEO @ Know Your Team

SHOWNOTES

• What Cathy means by “the best leaders spot patterns, understand problems, then build systems to solve them” (3:55)
• Jerry’s view on how the practice of leadership is different at large companies vs. small companies (7:30)
• Erica’s perspective on how the transition to VPE is different than other eng leadership roles and how to put trust into practice (12:27)
• Why Richard resonates with “act like an owner” and what it actually looks like in practice as VPE (16:40)
• Cathy’s top 3 priorities as VPE that determine how she spends her time and how to refocus your team (23:50)
• Richard's mental model to determine where he has the most leverage for impact and why being technical isn't always about writing code (26:16)
• Jerry's 3 key hiring traits and how to create an environment where you're the first to know when something's wrong (30:10)
• The imperfect path to become a VPE and Erica’s advice for engineering leaders with an “unconventional” background (34:01)
• The common struggle to balance being a problem solver and being the bottleneck as a VPE (39:11)
• How they cope with and manage stress (42:55)
• Takeaways (45:00)

ELC SUMMIT 2020

We were overwhelmed by questions from our event with Doug and Emma! This is a bonus follow up conversation that further digs into measuring productivity through “Waterlining” and Kaplan Meier estimating, hashtags in communication, remote 1:1 best practices, and Doug shows us some of the creative ways he applies Zapier integrations for his personal productivity!

"What it does is it forces a debate as to A what's most important and B do we really want that thing below the line waterline? Because what happens sometimes is people are super excited about this thing. And then when you see this rank list of stuff, you're like, Oh, but wait a second. There's like running the business stuff below the water line. We actually have to get that up and staff that..." - Doug Gaff

DOUG GAFF - VP of Engineering @ Zapier

Doug is the VP of Engineering at Zapier, the software solution that helps your other software work together more effectively. As the leader of an organization with over 100 engineers, he has learned a lot about effective management and leadership. Doug currently resides in the Greater Boston Area.

EMMA TANG - Engineering Manager @ Stripe

Emma is an Engineering Manager in Data Infrastructure at Stripe based in San Francisco. Her team focuses on building distributed computation infrastructure to support Stripe's business. At Stripe, we believe in investing in our remote culture, and have built out the remote engineering hub, and tripled the number of remote engineers in the last year.

SHOWNOTES

• How to Measure Productivity - Waterlining and Kaplan Meier (2:44)
• Waterlining as a tool to discuss priorities (9:10)
• Using hashtags to understand intent and to increase the bandwidth of communication (11:02)
• Best practices for remote 1:1’s when you don’t see the productivity levels you want (17:37)
• Tips for onboarding new grads (23:03)
• Doug’s remote work routine and lifestyle (24:47)
• Doug’s favorite Zapier integrations to increase productivity (29:21)
• Takeaways (33:45)

ELC SUMMIT 2020

Doug Gaff and Emma Tang discuss high-bandwidth communication, innovation accounting, preventing developer burnout, influencing teams, and communicating priorities. They’ll help you move from frustration and survival in remote work, back to optimized productivity!

“Personal stuff is totally in bounds and people just listen. And they don't try to solve a problem for you. And I might be like, I'm red today. I didn't get any sleep. I'm stressed about this thing. I'm not sure I'm going to get it done or this thing's happening personally. I'm worried about a friend who's not well...  and it requires a certain level of vulnerability and you've got to have a trust, comfort level, but, that's another thing like as leaders, the best thing you can do is demonstrate this kind of behavior so that other people know it's okay to do it.” - Doug Gaff

DOUG GAFF - VP of Engineering @ Zapier

Doug is the VP of Engineering at Zapier, the software solution that helps your other software work together more effectively. As the leader of an organization with over 100 engineers, he has learned a lot about effective management and leadership. Doug currently resides in the Greater Boston Area.

EMMA TANG - Engineering Manager @ Stripe

Emma is an Engineering Manager in Data Infrastructure at Stripe based in San Francisco. Her team focuses on building distributed computation infrastructure to support Stripe's business. At Stripe, we believe in investing in our remote culture, and have built out the remote engineering hub, and tripled the number of remote engineers in the last year.

SHOWNOTES

• Ideas for Remote “Offsites” (3:27)
• How to ensure clear, high-bandwidth communication (5:44)
• How to make engineers feel connected to the mission and company (9:44)
• Measuring productivity with “Innovation Accounting” and “Waterlining” (15:03)
• It's time to trust your people and fix your cultural anti-patterns (21:19)
• How to prevent developer burnout (25:03)
• How to influence leadership teams remotely (28:26)
• How to communicate priorities to multiple groups and teams (33:00)
• Health metrics to track your team - Happiness surveys, pull requests, and “innovation accounting” (35:11)
• Takeaways (38:34)
  

ELC SUMMIT 2020

Martin Casado and Sonal Chokshi explore what makes a great VP of Engineering at startups! You’ll hear how successful VPEs are evaluated, the ideal experience and success criteria. You’ll hear rapid-fire responses covering how to scale yourself, KPIs, the ideal VPE hiring time for startups, and what VPEs should definitely NOT do.

MARTIN CASADO, GENERAL PARTNER @ ANDREESSEN HOROWITZ

He was previously cofounder and CTOr at Nicira (acquired by VMware for $1.26 billion). At VMware, Martin was SVP & GM of the Networking and Security Business Unit (which he scaled to a $600 million run-rate). Martin’s early career was at Lawrence Livermore National Laboratory working on large-scale simulations for the Department of Defense, networking, and cybersecurity.

He holds both a PhD and Masters degree in Computer Science from Stanford University, where he created the software-defined networking (SDN) movement and cofounded Illuminics Systems (acquired by Quova). He’s been awarded both the ACM Grace Murray Hopper award and the NEC C&C award, and he’s an inductee of the Lawrence Livermore Lab’s Entrepreneur’s Hall of Fame. Martin serves on the board of: ActionIQ, Astranis, DeepMap, Imply, Kong, Pindrop Security, RapidAPI, SigOpt, and Yubico.

“In my experience over a number of engineering leaders is whether or not they're a good engineer is totally orthogonal to the actual role. And in fact, someone that's deeply passionate about a particular architecture technology or approach can be very damaging because you have a power asymmetry in the team.” - Martin Casado

SONAL CHOKSHI, EDITOR IN CHIEF @ ANDREESSEN HOROWITZ AKA "a16z" 

Sonal built and oversees all of Andreessen Horowitz’s editorial operations, including showrunning and hosting the a16z Podcast, leading production of the a16z Crypto Canon; and more. Prior to a16z Sonal was a Senior Editor at Wired. Prior to that, Sonal was responsible for content and community at Xerox PARC. Before moving back to California from NYC, Sonal was doing graduate work in developmental and cognitive psychology at Columbia University's school of education and worked as a researcher "ethnographer" on NSF grants around teacher professional development and early numeracy. She studied English and Psychology at UCLA.

SHOWNOTES

• Hiring misconceptions & Why VPs of Engineering are so valuable (4:21)
• Ideal experience and success criteria for a Startup VPE (8:45)
• Does a VPE need to be a good engineer? (10:56)
• Two key areas VPEs are evaluated (13:01)
• How to balance product and engineering as a VPE (17:34)
• The hard issue of managing people (19:54)
• Why engineering analytics and conscious decisions are important to building great engineering orgs (22:24)
• Good KPIs and how to scale yourself as a VPE (24:19)
• When is the right time to become a VPE at a startup? (26:25)
• What a VPE should NOT do (27:44)
• What is a CTO’s role and how do you work with them as a VPE? (31:00)
• Takeaways (32:0)

LINKS

Your job as an engineering leader is to win and increase your capacity to win. In Part 2, Wade Chambers discusses how to measure success for engineering leaders, what great looks like, AND how to increase your team’s performance and improve their potential! You’ll also hear how to get unstuck and move your career forward.

"And the more that you can come up with, well, what does it mean to be a great manager? Or what does it mean to be a great leader? Answering those questions for yourself and actually getting to the point where you have confidence and are willing to stand behind it because it's well-reasoned and like it's a principled point of view... will help you improve" - Wade Chambers

Wade oversees all aspects of engineering and technology innovation as the CTO & SVP of Engineering at Grand Rounds. With more than 25 years of engineering leadership experience, he has deep technical domain expertise and a successful track record of scaling teams and leaders, market-defining technology innovations, and business growth for companies of all sizes including Twitter, TellApart, Yahoo, and Opsware. Before Silicon Valley, Wade served in the military and the White House Situation Room.

SHOWNOTES

• How to measure success, “win, and increase your capacity to win” (2:32)
• How to increase the potential of people on your team (8:24)
• How to get unstuck in your career (12:31)
• The 3 “buckets” to help identify where your career growth is stuck (16:53)
• How to maximize learning and growth from the books you read (21:23)
• How to get to the core principles that drive your behavior (25:52)
• Wade’s final thoughts on closing the gap between where you are and where you want to be (29:38)
• Takeaways (31:41)

ANNOUNCEMENT

Nominations for the 2020 Inspiring Leadership Award are now open!

We created this award to recognize role models of engineering leadership, for the work they do every day to make a difference in their teams and organizations.

Share their story with us and submit a nomination at: