Startup to IPO: Founder Lessons
Leadership lessons on scaling yourself as the company grows, advice to executives interviewing with founders, and the top trait Brain looks for in executives
Hello, it’s Ethan & Jason. Welcome to Level Up: Your guide to grow fast, avoid mistakes, and make optimal career moves.
FYI, we have 4 upcoming events:
(June 25) The Magic Loop: A 5-Step Framework for Rapid Career Growth. Jason presents the core pieces with advanced forms at The Graphy Summit. RSVP here.
(July 2) Be Visible, Get Executive Sponsorship, & Build Key EQ Skills. Jason & Rohan (Product at Airbnb; ex-Stripe) breakdown each piece. RSVP here.
(July 9) How to build Executive Presence. We will answer questions first using EthanGPT and then Ethan will add more insight. RSVP here.
(July 10) How to ask for what you need & what to do if you get a 'no'. Ethan & Chaitali (CTO; x-Google Director) share what you need to know. RSVP here.
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Leadership Lessons from Startup to IPO with Brian Distelburger (Cofounder of Windmill & Yext) & Jason Yoong
Watch on YouTube.
Brian cofounded Yext in 2006 and took it public on the NYSE in 2017 (a true startup to IPO roller coaster ride that few experience — rarified air).
After 18 years at Yext, Brian is unto his next big thing: Windmill (AI superpowers for managers). Join the waitlist here.
In this talk, you’ll learn how Brian scaled himself as Yext grew into a 2,000+ person company, the hardest leadership trait he had to develop, the biggest company challenge as the startup speed boat evolved into a large ship, his advice to executives interviewing with founders, and what traits he looks for in executives today.
Thank you to Andrew Yeung "The Gatsby of Silicon Alley" for connecting us.
Key Lessons
Work your ass off. That’s how you build initial trust with senior executives and founders. Brian advises (especially for junior employees) to always be there, be around, volunteer for things, and jump in even if you do not know how to do it (try to figure it out). That builds the initial trust. The next piece is to be extremely smart when asking for help (and how you do it) — show judgment (don’t cry wolf all the time).
Building TRUST with high performing talent across the company (not just direct reports) was the top way Brian scaled himself as Yext rocketed from founders to 2,000+ people. Leaders who struggle to scale have a hard time trusting others to represent them and do good work with different responsibilities. Brian would purposefully bring new employees (including fresh college grads) into executive meetings and then do a debrief to understand what they saw and their takeaways, It served two purposes: steepen the learning curve and build trust.
Communication, specifically giving people context, was (and still is) the hardest leadership trait Brian had to develop as Yext scaled. What seems obvious to the founder is usually not obvious to others if they do not understand the WHY and HOW you got to the decision. It’s critical to ensure clear understanding because that is how teams buy into the vision, execute against it, and now have a POV to make better decisions themselves for future similar challenges (this is how leaders scale).
How did Brain learn he needed to give more context? He kept messing up over and over again. He was frustrated and finally “maturity set it” (no one told him, he realized it himself via mistakes).
Ignore the classic “MBA Playbook” advice, instead, find a handful of trusted advisors who deeply understand what you are building and are going through what you are experiencing right now (not 10 years ago). The best advice Brain got was from other founders. Classic business school advice does not translate well because the way you build companies evolves too quickly — do not copy a playbook.
At the early startup stage, Brian looked for people who were more “Generalists” then once Yext hit a few hundred people, he looked for “Specialists”. For example, at the time of recording, Windmill was a team of 7 and Brian looked for people who can do many different things (“wear many different hats”). Joining an early stage startup is a good way for early career professionals to gain broad experience and quickly figure out what they are good at and get energy from.
Maintaining a high pace was the biggest company challenge as Yext scaled, to set the tone for the team, Brain led from the front. Brian spent a lot of time with customers and constantly flew across the globe (Yext had offices in Europe and Asia) to attend important meetings in-person. The way to make this sustainable is to build a strong executive team bench.
When it came to executive conflict, Brian found it was rarely personality driven but more people did not have respect for the other’s ability to do their jobs. The main reason is executive compensation where they are tied to the overall company’s performance (last thing you want is a peer dragging you down).
Executives who performed the best were excellent culture fits (and most came via warm referrals). To define culture, Brian quotes MIT Professor, Edgar Schein: “How we do things around here” — specifically how you make decisions, hire, fire, promote.
Brian’s advice to executives when interviewing with founders — be straightforward and ask questions around how the company operates. When interviewing potential executives, Brian goes deep on domain expertise and cultural fit. On the flip side, for the executive interviewing, ask a lot of questions around the company’s operations to understand if the culture is a fit for you (otherwise you may find yourself in a quick “in and out” situation — don’t get caught up in the title and compensation).
For Brian, if an executive comes into an interview with a plan or playbook, it will rub him the wrong way. He prefers the executive come in with a few specific thoughts and asking why the company does certain things and what they learned from that (e.g. “I notice you setup things this way with partners in these markets or communicate using these messages, can you help me understand why you are approaching this way?”).
Traits Brian looks for now when interviewing executives — AI first comfort with tools. Previously, Brian made the mistake of hiring people who were not comfortable with technology (for a technology company).
Brian believes the industry is heading towards a company structure where functional (domain) experts will run orgs instead of “professional managers” (all of his founder friends agree with that).
Follow Brian on LinkedIn and checkout how Windmill can help you better manage and run your teams.
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Level Up Community: What’s Happening
E2 Growth Salon (Executive Empowerment). Hosted by Lisa St John (Mentor at Harvard Health Lab Accelerator & Former Managing Director at Alibaba Group) and Santhi Boppana (Biotech & Healthcare Leader), E2 is a special and exclusive invitation to our newsletter paid subscribers, featuring an intimate dialogue with Professor Robert Siegel of Stanford GSB (a renowned strategist, investor, and advisor to Fortune 500 CEOs) alongside a select group of visionary executives.
The event on July 29 (in Palo Alto, CA) is capped at 30 dinner seats and is currently full. All new RSVPs will go to a waitlist and confirmed only if spots open.
If you are a newsletter paid subscriber and want to get on the waitlist, access the link here.
If you are not a newsletter paid subscriber and want to connect with other members virtually and in-person, read more here (we’ve had community-led meetups in Seattle, DC, Toronto, Atlanta, SF, NY, PA, and more).
Thank you Lisa & Santhi (members are very excited for this event)!
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More advice from rocketship founders, watch (or read) Jason’s talk with Dee Murthy (Co-Founder, Ghost) on what he looks for in his executive team.
Too often, execs rely on hierarchy to scale, but long-term effectiveness comes from peer-level influence and being seen as someone who elevates others, regardless of title.
Also agree on the shift away from generic MBA playbooks. Every fast-growth company is an edge case in some way. The right moves usually come from live context, not a case study from ten years ago. That’s why advice from other operators in the same storm always beats theory.
On hiring, the “AI-first” mindset as a baseline is spot-on. Domain experts who know how to wield new tools will outpace traditional generalists fast. I’ve seen that play out in brand and product teams already.