Engineering Founders

Prioritizing & ignoring fires, mastering pivots, unexpected barriers to scale and scaling human-centric elements of your product w/ On Freund


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On Freund, Co-founder & CEO @ Wilco, shares how the value of practice influenced the idea behind Wilco. We also cover what it’s like finding product-market fit within a new category, how to scale seemingly “unscalable” elements in your product, challenges faced while building out human-centric elements, and surprises you may encounter while scaling. On also shares his strategies for pivoting your go-to-market strategy based on evolving market factors or customers and why being able to adapt is one of the most important skills you can hone as a founder.

ABOUT ON FREUND

On Freund (@onfreund) is the co-founder and CEO of Wilco, a startup dedicated to empowering developers to unlock their full potential. Throughout his career, On has managed development teams, most notably as VP Engineering at Handy and WeWork. He is also a proud angel investor and a humble former VC. On is married to an immunologist and is a father of 3. Outside of work, you'll most likely see him playing drums or tinkering with home automation.

"The other lesson that I've learned is that in many cases the barrier to scale is going to come out of left field. So you think you'll know what's the next thing to break, but it's actually going to surprise you.”

- On Freund   

Join us at ELC Annual 2023!

ELC Annual is our flagship conference for engineering leaders. You’ll learn from experts in engineering and leadership, gain mentorship and support from like-minded professionals, expand your perspectives, build relationships across the tech industry, and leave with practical prove strategies.

Join us this August 30-31 at the Fort Mason Center in San Francisco

For tickets, head to https://sfelc.com/annual2023SHOW NOTES:
  • The origin stories behind Wilco & its three founders (2:02)
  • How On’s value of practice influenced the idea of Wilco (4:56)
  • Challenges of scaling “unscalable” elements in an ed tech start-up (7:03)
  • Using AI to create and scale community experiences (9:32)
  • Lessons learned from scaling out human-centric product elements (10:47)
  • Barriers to scaling will come from where you least expect it (13:20)
  • Sometimes the time/mental/emotional overhead savings is worth the $10k cost to your cloud provider (15:06)
  • Questions to filter which fires to prioritize and which to ignore and accept the trade-offs (17:29)
  • Finding product-market fit when you’re inventing a new category (18:37)
  • Unique elements of marketing to university / boot camp personas (21:23)
  • Questions that On uses during the discovery phase of sales (25:05)
  • How Wilco’s go-to-market strategy has evolved & what caused the pivot (27:21)
  • Master the ability to pivot your market strategy as a founder (31:38)
  • Tips for marketing to your customers on an individual level (33:20)
  • Rapid fire questions (35:22)
LINKS AND RESOURCES
  • Rick Beato - an American YouTube personality, multi-instrumentalist, music producer and educator. Since the early 1980s, he has worked variously as a musician, songwriter, audio engineer, and record producer, and has lectured on music at several universities.
  • Stratechery - Recommended by The New York Times as “one of the most interesting sources of analysis on any subject”, Stratechery provides analysis of the strategy and business side of technology and media, and the impact of technology on society.
This episode wouldn’t have been possible without the help of our incredible production team:

Patrick Gallagher - Producer & Co-Host

Jerry Li - Co-Host

Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/

Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/

Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/

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Engineering FoundersBy The Engineering Leadership Community (ELC)