How my role as CTO has changed as we've grown from 1 to 100 engineers
engineering.gusto.com
How my role as CTO has changed as we've grown from 1 to 100 engineers
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Re: How my role as CTO has changed as we've grown from 1 to 100 engineers
#2Hi all!
I'm the author of this post. Happy to answer any questions here about how my role as CTO of Gusto has changed over time!
Re: How my role as CTO has changed as we've grown from 1 to 100 engineers
#3Really interesting post, thanks! You mentioned a few recommended readings (High Output Management, The Score Takes Care of Itself), which are all great general management books. Have you noticed much divergence from their advice when specifically applied to engineering management at high-growth startups?
Re: How my role as CTO has changed as we've grown from 1 to 100 engineers
#4I use Gusto and like it for it's simplicity. It makes a complicated part of running a company much smoother.
That said, I'm very curious what exactly all those engineers are doing every day. What's the most meaty part? Payroll? Dealing with govt? Keeping the servers up?
I think unexpected scaling pains are one of the most interesting and unsolved issues with being a CTO and would love to hear more about that at Gusto.
Re: How my role as CTO has changed as we've grown from 1 to 100 engineers
#5I use Gusto and like it for it's simplicity. It makes a complicated part of running a company much smoother. That said, I'm very curious what exactly all those engineers are doing every day. What's the most meaty part? Payroll? Dealing with govt? Keeping the servers up? I think unexpected scaling pains are one of the most interesting and unsolved issues with being a CTO and would love to hear more about that at Gusto…
I can certainly share some of the meatier areas that engineers at Gusto work on.
- Calculating payroll and filing quarterly and annual forms are very complicated tasks that (a) is different in every state and (b) changes frequently as federal, state, and local tax laws change. Doing payroll in 50 states is similar to doing payroll in 50 different countries
- Benefits is similar to Payroll in the sense that it's also very different in each state. The business logic is complex and a significant amount of engineering work goes into simplifying it for us customers
- Because we move billions of dollars per month through the banking system, we have a lot of the same technical challenges as a Stripe, Square, Paypal, Venmo, etc. We have a dedicated FinTech, Payments, and Risk teams for this.
- Security is super important to us, since we have a lot of PII/PHI and financial informaiton
- Gusto is about 600 employees today and we invest in lots of internal tools for non-engineering functions, an enterprise data warehouse, and security.
- We are also looking into what the future of payroll looks like. A personal goal of mine is to rid the world of the concept of a "payday". Why shouldn't employees get paid whenever they want for the work that they did? https://techcrunch.com/2018/06/21/gusto-flexible-pay/
- Technical debt: When you grow as fast as Gusto does, you inevitably accrue technical debt and it's important that we carve our engineering resources to keep that low.
There's a lot more in there, but hopefully it gives you a sense of how 100 engineers can add up pretty quickly!
Re: How my role as CTO has changed as we've grown from 1 to 100 engineers
#6Did you have to get up to speed on al the details of fraud, risk, and FinTech? If so how, what resources did you use to figure it out? If not, did you hire expertise, bring it in-house, and only have to implement bits of it into Gusto?
Second question: how did you determine to shift development from SF to Denver? What criteria went into selecting Denver over other areas? How did you figure out what to move their and keep in SF?
Third question: how are you doing? I remember in S08 when you were working on PicWing. We’re still working on Poll Ev!
Re: How my role as CTO has changed as we've grown from 1 to 100 engineers
#7When you were larger, you state:
"At this point, I believe technical co-founders have a binary choice: Stay on the technical track and hire a professional manager (usually given the VP of Engineering title), or give up coding and focus on the management aspects yourself. It really isn’t possible to do both."
Since you chose the management track, what did you do/who did you hire (in what levels) to take care of engineering at the level you were previously doing? Or were you effectively functioning as a standard IC so any developer could take your role?
Re: How my role as CTO has changed as we've grown from 1 to 100 engineers
#8- How much do you miss coding? Do you ever do it?
- How would you and the company be different if you stayed on the technical track? Was it a legitmate option?
- You mentioned you had to give up one or the other, what made you decide go management over technical?
Re: How my role as CTO has changed as we've grown from 1 to 100 engineers
#9When you were larger, you state: "At this point, I believe technical co-founders have a binary choice: Stay on the technical track and hire a professional manager (usually given the VP of Engineering title), or give up coding and focus on the management aspects yourself. It really isn’t possible to do both." Since you chose the management track, what did you do/who did you hire (in what levels) to take care of engine…
It was important to us to be deliberate about hiring senior ICs since I was more on the management track. We already had some in the company so that helped as well.
Re: How my role as CTO has changed as we've grown from 1 to 100 engineers
#10- How much do you miss coding? Do you ever do it? - How would you and the company be different if you stayed on the technical track? Was it a legitmate option? - You mentioned you had to give up one or the other, what made you decide go management over technical?
Definitely miss coding! I still do a little during our hackathons but otherwise don't have that much time to commit to any projects. I would just slow down the team.