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On The Flip Side

On The Flip Side

By Wingman
On the flip side is a podcast for sales folks who want to lead their best sales life. On every episode, we interview sales and marketing folks and ask for their hot take on traditional selling norms, established sales best practices and much more. If you believe in challenging the status quo and taking a walk down the other side, this podcast is for you.
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Anxiety in sales is not optional: Jeff Riseley on how to manage it instead

On The Flip Side

Goal it up: Josh on getting inbound right
“It always starts with a goal.”   Before you even begin to set up an inbound motion, think about what that goal is. Ideally, it's one that’ll have an intrinsic value for both sales and marketing, says Josh.   According to him, the age-old rift between marketing and sales can be mended by establishing trustworthy inbound processes.   Josh Harcus, founder & Head of Growth at Huify, is an expert on all things inbound. He is also the best selling author of Closing Culture.   In this episode, Josh shared his insights on:  - Obvious mistakes people make while setting up their inbound motion. - The ideal way of setting up a lead follow-up process. - Building the right tech stack.
May 31, 2022
Own your power: Jennifer on encouraging diversity in technology
Waiting to meet every requirement in the job description? You might just be waiting longer than you need to, says Jennifer Ives.  She suggests saying yes to opportunities when they present themselves instead. “Women like to be overqualified for things, and we need to stop that. We need to say, yeah, I have six or seven of the ten items that they're looking for and I can do an amazing job. And I can learn the other three on the fly.”  Jennifer, a geospatial engineer by profession, is passionate about encouraging more women to shine in technical fields and leadership roles.   In this episode of On the Flip Side, she also talks about:  - Barriers that stop women from taking up leadership roles. - Initiatives company leadership should take to ensure diversity. - How to encourage young people to not be held by their gender.
May 24, 2022
How to social-sell on TikTok: Leslie Venetz on becoming a TikTocker for sales
Turns out, the only thing holding you back from getting started on TikTok, or any other platform for that matter, is your own brain.   So, Leslie’s advice is to stop putting up false barriers for yourself and stop overthinking.   “Just admit your first videos are probably going to be terrible, but that’s okay. You’ll iterate, you’ll learn what does and doesn’t work.”  Leslie Venetz (aka the SalesTipsToker) is among the first salespeople who started using TikTok for social selling. She has also been working to transform sales into a more inclusive and respected profession.   In this episode of On the Flip Side, Leslie also talked about:  - How one should go about research for creating content on TikTok. - The tools you need to get started on TikTok. - Why sales still gets a bad rep.
May 10, 2022
Managing people and partnerships: Autumn Carter on bettering technology partnerships
“In technology partnerships, you have to be everything all at once.”  Be it sales, customer success or marketing, people in partnership roles have their fingers dipped in all every other team in the company.    To get a better understanding of the partnership team’s role in a company, we hosted Autumn Carter on our latest episode of On the Flip Side.   Autumn, Manager, Technology Partnerships at Aircall, is all about creating partnerships between companies and people.    Other than taking us through what a technology partnerships team does, Autumn also talked about the following in this episode:   - Things people get wrong about technology partnerships.  - Tips to become a better people’s manager.   - Why a fun work culture works.
April 30, 2022
Winning sales traits: Troy Barter on how to scale sales teams
In Troy’s opinion, SDRs and AEs should ideally be resilient – be able to take the metaphorical punch and get right back up. These are the traits that you want to look for when you’re adding more members to your team.    Troy has over 15 years of experience in sales and over 8 years of experience as a sales leader in SaaS. He is currently the president of Barter Revenue Consulting.    In this episode of On the Flip Side, Troy takes us through the process of scaling up the sales team the right way:   - When to hire for outbound and inbound  - What makes good SDRs and AEs  - How to get the most out of your sales team
April 23, 2022
Align goals with technology: Asa Hochhauser on building the right tech stack
Sales teams everywhere are heavily dependent on technology today. And it totally makes sense–when you have to close more deals, it’s only fair to automate the grunt work.  But, are you sure you have built the right tech stack?   Are companies really making the best use of all the technologies they have at their disposal?    If not, where are they lacking? What's the most common thing that they overlook when they plan for a tech stack?   And, what would it take to build a great tech stack in 2022?  These are exactly the kind of questions that Asa answers in this episode of On the Flip Side.    Asa was the VP of sales at until recently and has led various other sales teams throughout his career. He is also the founding member of Sales Hacker, Inc.
April 16, 2022
Building the dream team: Kyle Coleman on hiring and onboarding SDRs
“What do you do when you don’t know what to do?”   The only wrong answer to this question is that you didn’t try anything at all. Right answers can be anything like “I asked a senior for help” or “I googled my way out of the problem”.   Kyle asks this question every time he interviews an SDR. The answers let him know if the candidate has a penchant for curiosity, which for Kyle is one of the key traits that an SDR should possess.   This is but one of the great ideas that Kyle shared on this episode of On the Flip Side. Kyle is the VP of revenue growth & enablement at Clari. He has over 10 years of experience in the field of sales and a great digital presence on LinkedIn.   Apart from what to look for in an SDR, Kyle also talked about the following in this episode:   When should you hire your first SDR?  The ideal hiring and onboarding process (acc. to Kyle).  How to keep your sales team motivated?
April 10, 2022
Set yourself up for success: Pradeep Sridar on working through the holidays
What started as a LinkedIn poll morphed into a lively discussion about whether sales folks should shut shop during the holiday season. Pradeep says there are ways to make the most of this time.    “During the rest of the year, you are net fishing. Now you have the time, bandwidth and mental capacity to go rod fishing and land the exact customer whom you’d like to talk to in the next financial year.”   Pradeep is the VP of Sales at Wingman. He is also the founder of    In this episode, Pradeep talks about how the holiday season can be fruitful for sales teams:   - How to use the holiday season to your advantage  - Top ways to build your pipeline during the holiday season  - The right way to do video prospecting
February 06, 2022
The art of cold emailing: Stan Rymkiewicz on how to make cold emails warm
The trick to nailing a cold email is knowing how to go about writing one. If you think cold emails are just spam, you need to listen to Stan. Because folks, cold emailing is not dead.    Stan is the cofounder at, a Chrome extension that shows you sales lead research on prospects on your Google Calendar. He also founded Opara, a lead generation and account-based marketing agency, in 2018. Stan is also an ex-pro Olympic athlete!    In this episode, you’ll get to know about Stan’s compelling take on cold emails:    - The benchmark for a good cold email  - The function of CTA in a cold email  - Tips to make cold emailing work
February 04, 2022
Lead with value, not your product: Brent Keltner on how to hook in your buyers
Still using old formulas in a new market where your buyer is already armed with all the knowledge they need? Maybe it's time to move to a new way of selling with value, says Brent Keltner.   Brent is the founder and President of Winalytics, a go-to-market- and revenue acceleration consultancy that helps companies build their go-to-market strategy across sales, marketing and customer success teams. Before starting Winalytics, Brent spent more than decade as a revenue leader in enterprise to early stage companies. He’s also a Phd in social sciences from Stanford University.   In this episode, Brent talks about the top 3 trends to look out for in 2022 and more:  - Programmatic prospecting  - A mindset shift in selling  - The basics of any good go-to-market strategy
December 14, 2021
Sales and women: Kasturi Das on the need to remove the taboo
Sales is not seen as a profession for women even today.   Listen to Kasturi Das Talukdar talk about her experience of being a woman in sales and what needs to change.   Kasturi is the Director of Business Development at Whatfix, a digital adoption platform that helps enterprises enable their users to quickly adopt any software application thereby eliminating the time spent in referring multiple resources for help and support.   In this episode, Kasturi gets candid about what it takes to succeed as a woman in sales.   Learn about things like:   - The societal taboos for women in sales and what needs to change.  - How to make the most of mentorship opportunities.  - Her experience as a young graduate working in the Middle East.
November 21, 2021
Prospecting is like a sport: Tito Bohrt on how to become an all-star
"Sales development is like a sport. You can't be good at only one or two things to succeed. You need to be good at all of it."   Tito Bohrt is the CEO of AltiSales, which offers world-class training for SDRs. AltiSales helps companies build and revamp their prospecting muscle in a data-driven way, from creating outbound strategy, conducting data research, developing cold calling scripts, and finally outreach via LinkedIn, SMS, or direct.   In this episode, Tito gets candid about what it takes to succeed in an SDR role.    Tito talks about:   - SDR salaries and the great resignation  - Hiring top talent across the world  - How you can get started with prospecting and sales  - Latest trends in prospecting
November 21, 2021
Take a leap of faith: Alex Boyd on how marketing can win
"Marketing just needs to take a leap of faith."    Alex Boyd is the Founder and CEO of RevenueZen, a marketing agency that help startups understand how to craft their Go To Market strategy.    In this episode, Alex shares his top learnings from his experience of running his own marketing company:   - Keep your prices appropriate! Don't undersell yourself!  - Find the right partners and employees.  - If you're tooo married to attribution, you'll miss out on the best marketing opportunities.
November 13, 2021
Raise your hand: Dr. Cindy on how to create opportunities for yourself
"As women in leadership positions, we have an obligation to help the next generation of women leaders to find their seat at the table."   Dr. Cindy McGovern is the CEO and Founder of Orange Leaf Consulting, which specialises in helping companies grow their business through assessment, planning, training, execution and measurement.  She’s also a passionate public speaker and loves to present new ideas in sales strategy, personal development and leadership.   Join Dr. Cindy as she dives into how women in sales can raise their hand and find their seat at the table.   Learn about things like:  - What's really holding you back from reaching up - How to push forth in the face of resistance - How you can empower the next generation of women leaders
October 29, 2021
Own your power: Joyce on how women can win in sales
"As a woman who sells, a lot of times I walked into those rooms as the first and only woman. So you find a way to still be yourself but find a way to connect with everyone in the room. And no one in that room is trying to figure out a way to connect with you. They're trying to figure out a way to get you out of that room, right? So it was my job to find a way to connect with everyone in the room so that I could build those relationships that I needed to be successful."    Listen to Joyce Johnson tell it like it is - on the flip side.    Here's what you will learn:  - How to use what you have and raise your hand. - How you can become a better ally for women in sales. - How setting up employee resource groups might help.   Joyce is a 7-time author, speaker, coach & founder of the Why Sales Network, which includes training, podcasts, webinars and other sales programs to empower the next generation of sales leaders in the B2B space.
October 29, 2021
Get your seat at the table: Jennifer Fisher on how women can do this
"When I started out in sales 30 years ago, I was the only woman on my team!"    So much has changed since then, and so much needs to change.   Listen to Jennifer talk about finding your humble confidence as a woman in sales.    - How can you find and become a good mentor.  - How can you become a better ally for women in sales.  - How a lack of confidence might be holding you back from leadership roles.     Jennifer Fisher is a senior sales leader and currently VP of sales at Worldstrides, which provides educational travel and experiences to students. Jennifer has spent almost 30 years in recruiting, hiring, training and managing high-performing sales teams.
October 14, 2021
Sales prospecting is tough: Matthew Roberts on how to cultivate the winning traits
Sales prospecting today is a tough job. You need to connect more, convince more, and ultimately, sell more.   Join Matthew Roberts, who leads on sales development at Mosaic Tech, as he reveales his holy grail for winning as an SDR.   Hint hint: It has a lot to do with grit, coachability and creativity.
October 01, 2021
Focus on your customers' needs, not just your own: Sam Dunning on marketing today
Sam Dunning is the Sales Director and Co-Owner of Web Choice, as well as the podcast host of the Business Growth Show, one of the top 100 marketing podcasts today.   Join Sam as he dives into how to sell and market yourself in a time when traditional offline methods have left the chat.    Learn about things like:   - Building trust and credibility online  - How LinkedIn is more than just an online CV  - How understanding your customers > feeding your ego  - Why marketing and sales should communicate more
September 14, 2021
Sales is a noble profession: George Leith on trust and integrity in sales
“I believe that sales is solving people's problems for profit, and you got to make money at the end of the day. Cause you got bills to pay. Profit is an important component because without it, you don't have a business. But what I learned a long time ago is if your mission is to truly help your customer, the profits will take care of themselves.”   George Leith is the Chief Customer Officer at Vendasta and the Host and Executive Producer of the Conquer Local Podcast. Join him as he takes a deep dive into what drives a salesperson today.   Learn about things like:  - Building trust with your customers  - Why integrity matters in sales  - How commissions drive sales reps  - Why sales is about helping people
August 24, 2021
Your network is your net worth in sales: Collin Mitchell on how to build it with a podcast
Collin Mitchell is the CRO of Salescast and Host of the Sales Transformation podcast.   Salescast is a fully managed podcast service offering an end-to-end thought leadership platform. Working with salescast allows you to skip the line and put your thought leadership on autopilot.   In this episode, Collin talks about why every single person should have their own podcast, what it takes to get started, and what not to do.   Learn about things like:   - How to use podcast seasons to change the show format   - Why your podcast's cover art doesn't matter that much  - How to get the best out of your guest  - Collin's #1 benefit from podcasting  - And so much more!
August 17, 2021
How inclusivity is a team sport: Katherine McConnell on women in sales
Katherine McConnell is a revenue strategist known for scaling sales and strategic growth for businesses. She’s a member of RevGenius, Women in Revenue, HUMANS Community, and the list just goes on.    Join Katherine as she dissects what it means to be a woman in sales, how to tackle workplace sexism and how she set up the member onboarding programme at RevGenius.    Learn about things like:   - How community is at the core of inclusivity   - Why you should be an up-stander for change  - How individual contributions matter, even by male allies   - Creating a sense of belonging during the employee engagement journey  - And a lot more…
August 09, 2021
How to go from good to great in sales: Drew Coryer on the power of consistency
“I think if you boil down a sale, it comes down to two things - trust and value. Anything that results in a sale is going to fall under one of those two categories.”   Join Drew Coryer as he dives into what makes a good sale, what makes a good salesperson, and how to stay motivated in the face of fluctuating numbers.   Drew is an Enterprise SDR Manager at Formstack. He is an experienced sales leader, skilled in sales training, data evaluation, sales management, lead generation, team building, SaaS sales, cold calling and customer retention.   In this episode, we cover:  - What it takes to stay motivated over the long term in sales - How to decide between the SDR manager vs AE career track - The difference between good and great in sales - And much more...
August 03, 2021
Take care of the people in salespeople: KD on how to win in sales
"We didn't just spend the last year selling remotely."    We were selling through a pandemic. That's why the big resignation is real. Salespeople are now looking for something better and different. The best sales leaders will know what to ask, offer and how to lead in the sales industry.   Join Kevin "KD" Dorsey as he dives into what makes a great brand, sales rep, sales manager and sales leader.    This episode covers all the gold you'll need to win in sales:   How to build a great personal brand How to upskill and invest in yourself How to become a better sales leader How to win in a competitive market And so much more!   KD is the VP of Sales at Patient Pop, founder of Inside Sales Excellence, and well respected leader in the sales industry.
July 27, 2021
Invest in salestech or lose: Justin Michael on the competitive edge for sales teams
The sales revolution is here. Companies that invest in salestech will have a massive advantage over those that don't. Technology enables massive efficiencies and insights. Venture capitalists are investing in sales tech but sales leaders are yet to catch up.   Catch Justin Michael talk about all things tech-powered sales, including his latest book, why sales leaders shy away from salestech, and what needs to change.
July 20, 2021
Anxiety in sales is not optional: Jeff Riseley on how to manage it instead
At least 43% of salespeople struggle with their mental health, and the opportunity to reach peak levels of performance and well-being through better mental health is massive.   If you're passionate about creating better mental health in sales, you need to meet Jeff Riseley and listen to this episode. Jeff is the founder of Sales Health Alliance, a community of salespeople, sales leaders, health experts and technology providers who are building awareness around mental health within sales.    In this episode, Jeff talks about why and how to manage your mental health and develop resilience. It's gold y'all.
July 13, 2021
Be data-driven, but personal: Mark Shalinsky on where sales meets data
If you think an ecletic adventure is saved for Marvel heroes, you haven't heard Mark Shalinsky speak. After leaving his job as a biophysicist in a Harvard lab, he later found his superpower - cold calling. Now, as the COO of Data Sales Science, he does everything from shadow ops to creating data-driven tech stacks.   In this episode, learn about why it's important for sales reps to use data to their advantage, and why you should know how to use marketing automation tools.
June 15, 2021
Stop educating out of the blue: Jeff Molander on how to fast track conversations with your buyers
Jeff Molander is the authority on making social media sell and a sought-after corporate trainer to small businesses and global corporations. He's an internationally-recognized social selling expert, sales trainer, co-founder of the first Social Selling Summit and adjunct digital marketing professor at Loyola University's school of business.    Dive in to this episode to know more about sales outreach, with insights into transactional analysis and social selling with empathy. Listen in as Jeff talks about investing in yourself and the templatization of cold emailing.
June 08, 2021
You need to set up your sales team for success: Anupreet Singh
Anupreet Singh is the Sales Director at Slintel, a SaaS salesintelligence platform. He has set up sales teams and functions from scratch for various companies and firmly believes that the initial revenue target is achieved only when the entire organization works with the grit to support them.   If this episode could be summed up in one word - that word is honesty. Anupreet talks about selling with honestly, while being smart enough to make the sale. He also talks about creating a transparent environment where your sales team is empowered to deliver their best. Listen in for life lessons on buiilding high-performing sales teams.
May 18, 2021
Amazon Prime for B2B Sales: Jen Ferguson on how to connect with your audience
Jen is an award-winning, result-driven sales leader. She is recognized as one of the LinkedIn's Top 100 Sales Stars, with over two decades of experience in sales, marketing and leadership. As the Director of Sales for Inside Out, she leads a team to provide sales development resources and operational excellence; creating pipeline confidence for revenue leaders. Jen believes in leading and selling with heart. That all voices should be celebrated. In this episode, Jen Ferguson talks about how to short circuit rapport-building, having deeper discoveries and closing more deals quicker - the answer to all three is the same - and we wouldn't want to spoil it for you.
May 11, 2021
Visionaries are curious: Paula White on the secret aspects of creating a legacy
Leaders are lonely. They need to be careful of what they're saying and reinvent themselves constantly. But they can make this process easier by thinking about their legacy, says Paula White, a veteran sales leader.    Paula is the Founder of Side B Consulting and brings over 30 years of expertise in sales, leading teams, and developing/coaching others. She advises business leaders, owners and C-Suite executives on how to prepare strategically to define and develop a high-performing virtual Inside Sales channel.
April 19, 2021
Traditional sales training is a waste of time: Pauline O'Malley on what to do instead
Pauline O'Malley is a B2B business development strategist and creator of the RevTurbo® Selling System. Now in its 10th edition, RevTurbo® is applied by 400,000 selling professionals in Canada, the US, England, Australia, India and China.   In this episode, catch Pauline reveal why she stopped becoming a sales trainer, what's broken with most sales training as we know it traditionally, and what's a better investment to make for your team.
April 12, 2021
If a founder can't get customers, they shouldn't outsource their sales: David Zeff on scaling sales right
David Zeff is the CEO of Whistle, an agency that helps companies acquire customers by setting effective sales and marketing strategies and processes.  David is a passionate advocate of the 4-Hour Work Week philosophy and speaks of the power of money to set oneself free.  In this episode, David talks about bringing your whole self to work (or LinkedIn), the right time to outsource your customer acquisition, and what to focus on when in the early stages of your company.
April 06, 2021
Sales & marketing are the parents of revenue: Siddharth Sharma on building your first marketing team
Siddharth Sharma is Head of Marketing at Verloop, a leading customer support automation platform. He's passionate about all things technology and SaaS marketing.   In this episode, Siddharth talks about what it takes to build up a marketing team from scratch and how to make sales and marketing work better together. Founders, get ready to takes notes.
March 23, 2021
Don’t hire a VP of spreadsheets: Scott Leese on the right sales leader for early-stage companies
Scott Leese is a sales consultant and advisor to startups around the world. Scott wears multiple hats, from CEO/Founder at Scott Leese Consulting, Co-founder of the Surf and Sales Summit, podcast host and author, to founder of one of the most popular sales communities, Thursday Night Sales.  In this episode, Scott talks about the top mistakes that startups make when it comes to setting up a sales process and team and what to do instead
March 15, 2021
Can salespeople be authentic: Ike Krieger on what it means to sell without selling
Can salespeople close deals without selling? We didn't believe it either until Ike Krieger opened our eyes to this whole new way of thinking about sales.    PS: Have you wondered about how sales has changed in the last 40 years? Hear the stories from a communications teacher, an actor, a magazine salesperson and a charming sales coach, all rolled into one.
March 08, 2021
Why sales quotas don't work: Ed Porter on the philosophy behind sales quotas
Ed Porter is the founder of Blue Chip CRO. As a consultant and fractional leader, Ed helps companies create efficient and effective sales and support teams.   In this episode, he answers a number of tricky questions: How do you jump from managing a call center to being a CRO in tech? Why don't sales quotas work? Does a fractional CRO make sense? Why shouldn't you switch to tech sales? What hiring from within the industry is really a sign of?
March 02, 2021
Hustling vs hunting for sales: Illia Prokopenko on the difference and why it makes all the difference
Illia Prokopenko is the AE Team Lead at Growbots. From learning the ropes at his father's business as a child to door-knocking sales and now managing a sales team that works across time zones, Illia has seen it all.   In this episode, he gets into the weeds about the hunter-rockstar-killer mindet in sales. You'll learn why it's important to not treat your prospects as resources to be exploited but rather think of them as people to create meaningful relationships with. More problem solving, less selling. More honest conversations, less convincing.   And here's Illia's LinkedIn post about the hunter mindset.
February 23, 2021
Everyone can learn sales: Calvin Patterson on the importance of mentorship
Calvin Patterson is a Founding AE at Concert and Founding Member and Head of Mentorship at Revgenius.   In this episode, he talks about how it's important to take charge of your own development, asking the right questions, the importance of finding a mentor, and the metrics to track when you're starting out in sales. Hint: They go waaay beyond just numbers.    Bonus: Calvin talks about changing sales compensation plans and how to set yourself up for success.
February 15, 2021
Landing a sales job in 2021: Larry Long Jr on the EPICCCC way
Larry Long Jr is Director of Collegiate Sales at Teamworks.   In this episode, he talks about the EPICCCC things that sales reps need to do to find jobs in 2021. You'll also hear about how to choose the right community for yourself, the importance of social selling, and going beyond the echo chamber on social media.    Bonus: Practicing empathy is key for sales managers and leaders to help their teams win.
February 08, 2021
Micro-management is gross: Molly O'Sullivan on managing sales teams
Molly O'Sullivan is an independent consultant for technology integration, business process analysis, sales, marketing, social media, and branding services. In this episode, she shares her experience on managing today's sales teams. You'll hear about the best way to give feedback, the KPIs that matter, and how to break through the noise to reach your KPIs.
February 01, 2021