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Your Execution Year

The odometer on your startup is turning over 1095 days - your third year building your passion into a business. You've raised your seed and Series A, recruited the first twenty employees, snagged the first thousand customers or the first million users, and landed your first press clippings. The product/market fit is snug, the vision is crystallized, and the steep slope of hockey stick growth looms before you.

And between you and that peak's summit is four straight quarters of pure, unglamorous agony. Welcome to your Execution Year.

Everyone talks about honing the fundraising pitch and the billion dollar exits, setting up your cap table and the timing of your IPO, but no one talks about when all the talk evaporates into the real numbers that will make your business sink or shine - the year your team's execution decides whether or not you make it. Veteran "30th employee" Rob Spectre from Twilio talks about a few lessons learned through his five execution years.

Additional Supporting Materials


  1. Why does startup culture and media focus so much on the beginnings and the ends of startups while focusing so little on the middle? (hint: because the middle is really *hard*)
  2. Why is sales so underappreciated as a linchpin of a tech company's growth? Who says, "You know - that Steve Jobs sure had a great conversion rate" or "You remember the scene in The Social Network when Justin Timberlake set up that awesome comp plan?"
  3. What aspect of successful distributed systems can be adopted to get a startup through the execution year? What does failing fast, early and small mean pragmatically for a startup?
  4. How much faster can I spend the Series B than the seed round? How do I keep the organization hungry after we get our first little bit of cushion?
  5. My VP of Engineering just came to me with this new programming language/datastore/asynchronous web framework and he thinks it is so super we should re-write our entire infrastructure to it? Why does he say it'll only take three months? How fucking stupid is this idea?



Rob Spectre, Director of Developer Evangelism, Twilio

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