12 Things I’ve Learned as a Startup CTO

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As Sailthru went from the germ of an idea to an actual working prototype to a full-on real business, to performing at scale, I’ve learned a lot about growing not just an Engineering department, but a business from nothing to something. Here are a few things that I’ve learned along the way since co-founding and running Engineering at Sailthru, NYC’s fastest growing SaaS company.

1. Don’t put too much on your plate

When you have great people, delegate to those great people. In the beginning, I tried to do everything — code, design, recruit, take customer feedback, wake up in the middle of the night to every single alert, stay up all night hacking and wake up for board meetings the next morning. I loved the thrill of it. We didn’t hire our first full-time developers until the beginning of 2011, but it took me until the middle of 2012 for me to give up reviewing every commit. By then, the entirety of the system had gotten too much for me to shoulder on my own, but luckily we had built the beginnings of an amazing team.

When you hire great people they know how to get things done. Don’t worry: no matter how much you delegate, there’s always plenty more to do.

2. Use Support and Client Services as a feedback loop

These people are on the front lines. If something’s not right, they’re the first to hear about it from customers. The Support team can have a better understanding of the ins and outs of the product than anyone else at the company. I recognized this the first time Support started reminding me of my own edge cases. Client Services should always be appreciated. They’re always working to drive client successes and to help you to understand where the clients need the product to go, not just where the company wants the product to go.

3. Theme, but don’t push it too hard

We play the Lonely Island’s “I’m On A Boat” whenever features release (get it?). We’ve been doing that for years, ever since Neil and I did it at a karaoke night (I can neither confirm nor deny whether footage exists). Our internal success metrics are called the USS Sailthru. We’ve had numerous boat parties. This is all fun and feels right. But for some reason, we don’t call ourselves “Sailors”. Not sure why — it just doesn’t work.

4. Be careful about people whose egos come first

A healthy ego can be the driver behind successful people, but the team always has to come first. Most people have some kind of ego, but when one person’s is too much, it impacts everyone else. Nobody, no matter how talented, is worth bringing stress and drama to the team. When you lose people who are emotionally draining the team, it’s a relief.

5. Acknowledge high performers

When people on your team go above and beyond pulling their weight, you need to let them know. Giving positive reinforcement may not always be obvious or easy, but it’s imperative to make sure your high performers feel appreciated…or you run the risk of losing them.

6. Celebrate your successes

There are always going to be highs and lows — that’s the nature of a fast-growing business. Acknowledging and celebrating the great things you accomplish as a team is really important. We started celebrating big features with exploding confetti and team dinners. It’s help us create a culture that strives for continued success.

7. Always stand for experimentation, innovation, and learning

The most important thing that a technology company sells is innovation: the creative work of the engineers who make everything possible. Creativity doesn’t take place in a vacuum. It’s always important to support and encourage trying the crazy ideas that nobody thought would work, or experimenting with a new technology. It’s not always going to result in a product or feature that gets to market, but the journey everyone takes in the process is worth it.

8. Be available and accessible

If you walk into Sailthru and want to find a member of the executive team, just walk to the middle of the office, fourth row from the windows. Our seats are right in the middle of the open space. Letting people know that they can always talk to you – that no matter what, you’ll make time to hear them out – is really important.

9. Send engineers to career fairs

We have some awesome recruiters, but if you’re talking to engineering students at career fairs, one engineer is worth their weight in resumes.

10. Take a personal interest in your clients

In any business, there’s nothing more important than your customers… and 3x that for a B2B business because your customers are most likely fewer and farther between.. Start with building a personal connection with them and finding out what their business is all about. Find out “what keeps them up at night?” Answer that question. Help them win and they’ll not only want to work with you, they’ll trust you.

11. Have a Minister of Common Sense

It’s good to have someone on the team with an even keel and a good grasp of reality, maybe even a well-tuned bullshit detector. Whenever I have an idea and I’m not totally sure whether it’s a good one, I’ll run it by my Minister of Common Sense. That’s not his real title — but maybe it should be. The bottom line is that we all need an editor, someone who helps us see our ideas in context and can help us prioritize.

12. Have fun

Your company becomes your family and the challenges you face, you face them together. But, while building a company is hard, it should also be a lot of fun. Find the time to relax and enjoy the ride (for reference, go back to #1).