Trying To Replace Yourself, with Eric Tobias

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On this week’s episode of Scaling Software Teams, we talked with Eric Tobias, former CTO at iGoDigital and current Partner at High Alpha, a Venture studio that conceives, launches, and scales next-generation enterprise cloud companies.

(It just so happens that one of the companies that High Alpha has invested in is our company, Woven, so this is a really fun conversation with someone who has gotten to know our business very well.)

Over the course of our interview, Eric told us all about parlaying an early love of basketball and bootlegged music into a passion for the internet, how he grew his first team during the dot-com era, and the lessons he learned starting and scaling iGoDigital.

Additionally, Eric explains why so many tech leaders find themselves becoming “the bottleneck” for their organization - holding onto QA and day-to-day projects so tightly that it actually stifles growth.

This observation gave birth to his obsession with “engineering himself out of the process.”

Here are a few of the key lessons we picked up from Eric Tobias:

Continuous Delivery works for communication, too

Every Friday, Eric would send a note to update all stakeholders about the progress he had made that week. This allowed him to take stock of what he accomplished, created intimacy with the people involved in making him successful, and helped him gain momentum in tough times.  

When You Hit A Roadblock, Take (Any) Action

There is no shortage of roadblocks in startup mode, and Eric recalled a moment at iGoDigital in which one of their largest clients was having issues - but no matter what the team did they simply couldn’t solve it.

With their backs against the wall, their Head of Engineering hopped on a plane to San Francisco to talk through their problem with experts who he trusted.

But rather than finding the solution through these meetings - this Head of Engineering got the solution because they overheard two random Twitter employees talking about Mongodb at a coffee shop.

He tried it, it fixed their scale problems, and it was in production within days. The lesson? When all else fails, the only failure is not taking a shot to try something else.

Great Leaders Are Constantly Replacing Themselves

Working in a software startup, it’s easy to forget that we’re not building software - we’re building a company.

To scale that company, we can’t be the bottleneck. We must continue to grow beyond our jobs and replace ourselves. That’s the only way we’ll be successful.

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This show is brought to you by Woven. At Woven, we help software teams screen engineering candidates so they can spend less time on bad interviews, uncover hidden gems, and back their hiring decisions with evidence. If you want to learn more about how Woven could help you scale your software team, you can check us out here.


Our team is always looking for your feedback about how to make the show better. If you have anyone you think we should interview, tweet us at @woven_teams and our team will reach out.

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Tim Hickle