Top of the Lyne

Figma did it for design. Slack did it for team comms. Zoom did the same for meetings. Salesforce - CRM.

Every once in a while, a tool comes along that pushes the envelope of our imaginations and brings our presumptions crashing to the ground. And reinvents how sh*t gets done.

In 2023, user research and testing aren’t quite the same anymore. And for that, we have Maze and Jo Widawski to thank.

And if you’re reading this and thinking “What do I need usability testing for?” - you’re not alone. But you probably will be.

Jo started up in 2018 with a mission to democratize testing. Within 3 years, Maze had built the foundations of a new category, washed away the demons of complexity it was mired in, and put a new weapon in the hands of - not just researchers, but designers, product managers, marketers, and many others.

Today, over 60,000 brands ranging from Uber and HP to McKinsey and GE use Maze for user research and usability testing.

Building a new category is no easy feat. Jo will be the first to tell you:

“Building a company is a lot about shooting arrows and then during targets around them afterward, and saying it was your vision all along. When we started, we really believed that we just needed to build better research.”

With the targets now drawn, we thought it’d be worth getting to the bottom of how the hell Jo and Maze did it.

This is the story of how.

00:00 Price against value

00:31 Tweet Reactions

06:33 Verbalizing a category

08:50 Introduction

11:52 Maze's GTM evolution

17:44 Product taking the center stage

19:41 Switching to Enterprise

22:38 Layering sales in PLG

26:42 Early branding investments

29:08 Design pet peeves

31:32 Rapid Fire

34:02 Up next for Maze

D’Arcy spent 11 years at Oracle, selling database management systems on either side of the dot-com bubble bursting. He is the man you’d get if you wanted to carve out an early advantage in the enterprise sector while going head-to-head with only one of the most viral tools of all time. Box became Dropbox’s worst nightmare in the enterprise sector during D’Arcy’s seven years there. He’s who you’d get when you’ve cracked SMB and mid-market and are now beginning to go from $10M in ARR to $100M. You want a man like him at the helm if you’ve found PMF, just raised a Series B round, and are beginning to set your sights on the Fortune 500. And so late last year, we sat down with the current SVP of Sales at Productboard in an attempt to uncover the building blocks of the enterprise sales gene. We cover a lot of ground here with D'Arcy, including:

00:00 The Dropbox Problem

1:50 Meet D'Arcy

3:23 Early lessons on identifying ICP

5:11 Choosing sales

7:09 Priorities today as SVP Sales, Productboard

8:02 Dealing with a recession as an early-stage company

10:12 Economic headwinds 2008 vs 2023

10:59 Selling during the dotcom bubble

13:44 Selling in times of budget cuts

15:15 Value engineering

17:26 Speaking to the C-suite

18:23 Box vs. Dropbox

23:04 Role of marketing in enterprise sales

24:38 Trade shows

27:25 Where PLG fails

30:15 Setting up a post-sales process

32:31 Does persuasion play a role in enterprise selling?

34:58 Traits he looks for while hiring

36:20 What separates the best from the rest in sales?

39:09 Closing an 8-figure deal

40:39 Differences in selling software in the '90s vs '23

44:22 Differences in software buyers in the'90s vs '23

46:16 How to deal with buyers' preconceived notions

47:21 Next steps for Productboard's GTM

53:14 Building customer-centric products

54:15 Rapid Fire