The Engineering Leadership Podcast · Episode 171

Driving innovation at large-scale orgs, translating leadership skills to successfully scale early-stage startups

with Jeremy Burton

Mar 19, 2024
We dissect leadership lessons from across vastly different scales of eng orgs – ranging from 13,000-people companies to 10-person start-ups – with Jeremy Burton, CEO @ Observe. He shares how he effectively translated leadership skills from working at large-scale orgs to small, early-stage start-ups & addresses challenges faced when scaling at any point. Jeremy covers start-up strategies for bringing your eng teams closer to your customers & driving innovation at large-scale orgs; characteristics of eng leaders that promote successful scaling; gaining & communicating conviction; driving community engagement & building trust within developer communities; and more.
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Jeremy Burton is the chief executive officer of Observe, Inc. Prior to Observe, Jeremy was Executive Vice President, Marketing & Corporate Development of Dell Technologies, and served in various leadership roles at EMC prior to Dell. A 20-year veteran of the IT industry, Jeremy joined EMC from Serena Software, where he was President and CEO. Previous to Serena, he led Symantec’s $2 billion Enterprise Security product line as Group President of Security and Data Management. Jeremy also served as Veritas’ Executive Vice President of Data Management Group and Chief Marketing Officer. Earlier in his career, he spent nearly a decade at Oracle as Senior Vice President of Product and Services Marketing. Jeremy is currently a member of the board of directors at Snowflake, a seat he's held since 2015, and maintains a part-time role on the advisory board at McLaren Group.

"I hear so many times both in startups and bigger companies, 'Oh, we have a sales execution issue.' If your early sales team is not successful, it's never the sales team. It's always the product. Where bigger companies have built new products, they've probably taken it to market too soon and the salespeople will take it to a mature account. It won't be as mature as the other products. The customer will complain and the salespeople will hate it. It'll get a bad name and then it'll get killed. That's the typical mode of operation that I've seen in a large company, which is why you got to keep it a secret until you've got the MVP, then work with a small set of customers and set the right expectation. When you get it right, you've immediately got a distribution channel that you can scale. If you get it wrong, you'll never scale it and you'll just create a whole bunch of problems in your customer base.”

- Jeremy Burton   

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  • Operating at a scale of 13,000 people vs. early stage with 10 (3:13)
  • How Jeremy adapted to operating at vastly different scales (6:30)
  • Transitioning from a back seat role to the front seat (8:32)
  • Approaches to helping folks better operate in ambiguity & face the unknown (11:20)
  • Cycles that gave Jeremy more confidence to operate in instability (14:26)
  • The romanticization of start-ups & challenges with scaling (18:22)
  • Why eng teams should work directly with customers at start-ups (21:14)
  • Leveraging leadership at large orgs to bring eng teams closer to customers (24:36)
  • Strategies for innovation at large-scale orgs (27:38)
  • Dynamics at big companies that incentivize killing new projects (30:38)
  • Characters of eng leaders that lead to successful scaling / innovation (32:56)
  • Recommendations for gaining conviction & communicating that effectively (34:33)
  • Conversation frameworks for creating alignment (37:43)
  • How to create influence & community engagement for developers (38:55)
  • Gaining trust within your community & exuding authenticity (42:10)
  • Rapid fire questions (44:42)

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

Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer -

Ellie Coggins Angus - Copywriter, Check out her other work at

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