How my role as CTO has changed as we've grown from 1 to 100 engineers

I was an engineer #1 hired by a &quot;CTO&quot; and we grew to 50 engineers. His story&#x2F;growth didn&#x27;t really change much, however. He was a coding machine, a true &quot;10x engineer&quot;, and programmed day and night. He even started up a second company while working on the first. He built both codebases from scratch, and even re-wrote the first company&#x27;s core codebase at one point.<p>He did attend exec meetings and make all major technical decisions, but I never really felt he had to grow into anything.<p>When we got big enough to start worrying about compliance, security, and HR tools, we did it together and moved on to the next thing.

&quot;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.&quot;<p>For me this is the key quote.<p>I have a friend who went the other way from the author of this article. He started as one of two company founders working out of an apartment doing all the technical work while the other founder focused on business stuff.<p>When the company grew to a point where he had to decide between staying technical and people management, he hired a VP of Engineering, stuck to coding, and still codes 6-8 hours a day.<p>The company is now at about 200 people, is <i>profitable</i>, raised a series A after figuring out the business model, and blowing past the goals set by the investors. His stake in the company is worth many tens of millions today.<p>Just an existence proof that &#x27;sticking to coding&#x27;, <i>can</i> be a viable strategy, if an unusual one.<p>He is not interested in blogging&#x2F;social media etc, or else I&#x27;d have persuaded him to write up his experience.<p>I have to agree with dang. <i>Most</i> people running successful startups don&#x27;t have (or take) the time to write about it.<p>Which is too bad (imo). We could use more writeups from the successful subset.

Hi all!<p>I&#x27;m the author of this post. Happy to answer any questions here about how my role as CTO of Gusto has changed over time!

Did 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?<p>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?<p>Third question: how are you doing? I remember in S08 when you were working on PicWing. We’re still working on Poll Ev!

I have a few questions!<p>1) Did others in the org recognize you couldn&#x27;t spend as much time on code, and they appreciated your time elsewhere? I can imagine there being some growing pains as you slowly gave your responsibilities to someone else, and in the meantime things not getting finished as quickly&#x2F;productively. (Not to mention the fact that an average engineer wouldn&#x27;t like spending 12-14 hours per day coding)<p>2) What is your favorite advice from the books you&#x27;ve read? What made the biggest impact on your actions?

I use Gusto and like it for it&#x27;s simplicity. It makes a complicated part of running a company much smoother.<p>That said, I&#x27;m very curious what exactly all those engineers are doing every day. What&#x27;s the most meaty part? Payroll? Dealing with govt? Keeping the servers up?<p>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.

When you were larger, you state:<p>&quot;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.&quot;<p>Since you chose the management track, what did you do&#x2F;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?

We went from 1 engineer (me) to 4 last year. So I&#x27;m in the 2-10 stage. I coded prototype and first X customers, which has become literally 20X in the past year. I still code most of the time, and the primary problem I am encountering is being willing to transition technically difficult aspects of the product. This <i>has</i> to happen, as I am finding myself becoming a huge bottleneck.

&gt; To accomplish this, I decided to fly to New York to hole up in a hotel room for three days to read a few highly-recommended management books.<p>&gt; I decided to focus on growing Gusto’s engineering team, and not our code. The technical books on my desk starting getting replaced with books like Mindset, High Output Management, and The Score Takes Care of Itself — still three of my favorites today.<p>If the three books listed in the latter excerpt were not those three books you read in the hotel, can you please tell us what books they were?

How did you maintain compliance and security before you could have someone full time on it? How did you deal with audits? Did you hire an engineer full-time dedicated to this, outsource it, or do it yourself? (I ask because I do this now but at 8 people it&#x27;s starting to take up too much of my time as CTO)<p>How does it work at your size now?

What do people think about the career trajectory as an individual contributor in an early stage startup? I&#x27;m the kind of person who not only enjoys coding, but hates dealing with management, hiring, meetings, etc. I always fear that I will be pushed to take on a management role. At the same time though, I really enjoy working with a group to build something from scratch. In your opinion, do you think it&#x27;s better that I don&#x27;t join an early stage startup?

This surprised me at first:<p>&gt; having difficult conversations with individuals is never fun<p>But apparently &quot;difficult conversations&quot; is a Valley euphemism for &quot;firing people&quot; and doesn&#x27;t mean &quot;discussing difficult engineering problems&quot;.

- How much do you miss coding? Do you ever do it?<p>- How would you and the company be different if you stayed on the technical track? Was it a legitmate option?<p>- You mentioned you had to give up one or the other, what made you decide go management over technical?

Yikes, that open office picture looks like my nightmares.

Given that you were essentially learning management while in the role, did you ever end up hiring people with prior management experience to report to you? What was the mentoring like for these folks - were there cases where your reports actually had more experience than you?

it&#x27;s refreshing to see someone who actually successfully scaled a company write an article about &quot;here&#x27;s how we did it&quot;, instead of bunch of failed entrepreneurs who write medium posts about why they think their startups failed to either feel better about themselves or to capitalize on their failure with the attention they get from the blog post (answer: they don&#x27;t know why they feailed, and that&#x27;s why they failed. The only way they know what they think they have learned through failure was actually something meaningful is to apply the &quot;lesson&quot; in their future endeavors and see if it works out. Until then, all your interpretations are nothing more than your opinion)<p>I would love to see more of these posts on Hacker News instead of failed startup post-mortems. Thanks for sharing!

Thanks for sharing this. I don&#x27;t have any specific questions but being at the tail end of 2-10 myself, it&#x27;s good to have reference points for when other people do certain things, like draw down to ~50% code or 0% code, how much time to spend on recruiting, etc.<p>I will say that I&#x27;ve been feeling a different type of code guilt. I feel guilty <i>when</i> I code, because I view supporting, coaching, and mentoring my team to be my 10x activity. If I&#x27;m coding, there could be 8 other people getting blocked or needing help, and I&#x27;m off trying to build 4 hours of context to solve problems.

Do you ever feel &quot;bad&quot; about cutting corners early on to push a product but now others are working on the the same codebase? I have this feeling constantly.

If you’re now focusing on the people and management, whose responsibility is technical strategy and execution?

Alt title could be: how I went from CTO&#x2F;Co-Founder to the CTO and VP of Engineering.

Which mistakes did you make when you were transitioning from an engineer to a manager? Were there any incidents with your employees that you wish now you had handled differently?<p>Thank you for taking questions.

Interesting read, thanks for that. Besides human management, how have your tech skills evolved? What directions have you taken&#x2F;discovered&#x2F;fell into, what have you learned?

Did you pick up any management education along the way? I spent time getting a masters in public administration and management when I made the move myself, and found it invaluable.

Sup Eddie. Besides books, did you go and ask people about how to be a great CTO? Who did you pick to ask, and how did you find those people?

Great post! What were some of the toughest decisions that you had to make in your capacity as CTO, as the company became larger?

to offer a counterpoint to the lovefest going on here, TFA is almost completely uninteresting. the role changed exactly as one would expect and predict.<p>the only interesting part is reading about the humble beginnings, the dedication and belief.<p>what would actually be useful to read about is failings, where OP failed in transition to manager and how he overcame those failings. I mean there&#x27;s a paragraph in there but it&#x27;s so boring -- &quot;I read these 3 books&quot;. ok there&#x27;s a little more meat than that but it&#x27;s too nonspecific to be interesting.<p>come on people, let&#x27;s not just throw love out there for no reason. it has to be earned. this article doesn&#x27;t earn it.<p>OP should read _the hard thing about hard things_. there are many anti-lessons there, don&#x27;t treat it as gospel. but read it as a guide as how to write something that actually delivers a lesson.<p>i await your downvotes ... :P

At what point do you start calling people direct reports? I find this turn of phrase really jarring

great article, loved it

I am a CTO, going from 2 engineers to a total engineering org of approximately 20.<p>Much of my time is non-coding, but I don&#x27;t believe you have to totally give it up. I try to leave a day per week free of meetings to code &#x2F; review code. I keep some projects that, while useful for the company, can be worked on irregularly and slowly, and are not super essential to be accomplished quickly (which is why they aren&#x27;t prioritized for the engineering teams).

This guy flew from San Francisco to New York to read books in a hotel? Like... what?

Fantastic article! I’m in a similar position as you, and will have to face the same decision you did, so this was refreshing and edifying to read. Thank you for taking the time to write it.<p>One thing that stuck out to me was your mention of focusing on “diversity and inclusion”. Why did that become a necessary thing for you to focus on? It seems political, and entirely unrelated to the actual work of building a good engineering team. Isn’t it enough to ensure that anyone and everyone has the same opportunity to get hired? At my company, my goal has been to ensure that all candidates get judged without focusing on attributes like gender or ethnicity; to make sure that the doors are open to everyone, no matter who they are. I then try to trust that the people who want to work in this field, and this company, are capable on their own to come to us.<p>Has that been your experience, or has there been good reason to put extra effort into finding&#x2F;favoring candidates with certain characteristics?

This comment is hard to word without sounding like I&#x27;m grinding an axe with the author or the blog post or something. I&#x27;m not. It&#x27;s a good post.<p>Anyway, I was disappointed but unsurprised to find that Ctrl-F &quot;leadership&quot; yielded 0 results. Anyone can read management books, and I am sure they&#x27;re super valuable for learning techniques to maximize the value the company gets out of its employees.<p>However based on my experience over the last many years, it&#x27;s not enough to be a skilled manager. &quot;Necessary but insufficient.&quot;<p>Leadership is a different skillset. I am sure Mr. Kim has learned a lot about leadership, he just didn&#x27;t split out the two in the blog post. Undoing the semantic smushing of management + leadership so they can be focused on independently is important, IMO.