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Daniel Doubrovkine

aka dB., former CTO at artsy.net, fun at playplay.io, NYC

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Three years ago I wrote about the difference between a CTO and a VP of Engineering at a startup, but only hired a VP in 2018. In this post I will explain why I decided to do it, and discuss one possible separation of responsibilities between a CTO and a VP of Engineering.

The List of CTO Responsibilities

My CTO role over the years included pretty much everything related to building software, ranging from coding to architecture, company strategy and Engineering budget. I also once served a coffee to an investor. With years I felt like the list of things I was doing became infinite, yet a lot of new hires had no idea about what I did anymore. Did I?

To Divide a List One Must Have Such a List

To produce an organized set of responsibilities I needed structured data. In the spirit of openness, I created a public Slack channel called #log-db and posted my activity log into it, weekly, available for everyone at the company to see.

Mapping Quarterly Goals into Activity Types

While week-to-week work varied a lot, quarterly goals did not. My Q3 2018 goals were the following.

  • Increase engagement with the Engineering team
  • Improve leadership visibility into the Engineering team
  • Recruit a world class VP of Engineering
  • Recruit two Engineering managers
  • Catch up with Engineering headcount
  • Deliver on the “Buy Now”, “Make Offer” feature roadmap

Looking at each week of work I could see some buckets or patterns.

At the company level I gathered context, communicated both directions, represented technology and upheld company values. Practically this meant participating in two weekly executive meetings and several 1:1s with business and practice owners in the company to understand and communicate about their work.

I spent a lot of time and energy hiring, including explaining the company vision, mission, organization, history, team, product, technology and evaluating candidates. During the week of September 28th I did 2 calls with an external sourcing firm, 5 interviews, 2 onsite informationals, 2 reference calls, 5 follow-ups related to candidates, and had approved 3 offers.

Within the product organization I represented 30+ engineers as a single voice, collaborated on roadmaps and processes. During the week of September 28th I participated in a product roadmap review, a discussion about a difficult organizational transition plan, and sat in a weekly product organization leadership team sync.

To my staff I was responsible for the structure and team, peoples’ careers and their engagement with work. During the week of September 28th I attended two stand-ups, dealt with someone’s visa issues, worked on a Q4 headcount proposal, a budget, and did multiple skip-level 1:1s.

In public I spoke on behalf of the company. During the week of September 28th I did an interview for a podcast and gave a talk about building software at a big auction house. I also wrote two semi-technical blog posts.

Last, but not least, I tried to stay out of the way of the Engineering team actually writing software. I did release new versions of two open-source projects, and figured out how to implement geo-location as a custom GraphQL scalar type for a pet project.

Thinking About Work in Terms of Time to Impact

Thinking more strategically, I divided my work in terms of time to impact.

Looking at my weekly activities it became clear that I was spending almost all my time in the shorter term section of this list and that I was not able to make time to raise my head and to look at anything further on the horizon. I needed help.

I’ve always strongly believed in giving away my legos, aka the work I do the most of. Since the majority of my activities revolved around people and product I decided to hire a VP of Engineering to take over those.

We have built an incredible Engineering brand, so I was able to close an exceptional candidate in just under two months coming from Spotify and Instagram.

Let’s call him Samuel ;)

Dividing CTO and VP Responsibilities

Two months into Sam’s tenure we’ve made the following announcement.

Title: Dividing CTO/VP Responsibilities To: team@

Team,

I wanted to provide an update on Engineering leadership, specifically regarding the division of responsibilities between Sam, our new VP of Engineering and myself, the CTO.

tl;dr Sam is assuming all people and product delivery Engineering responsibilities

Effective today, Sam will be responsible for all people-related aspects in Engineering, including engagement, recruiting, retention, compensation, promotions, individual performance management and organizational structure. He has already begun managing the Engineering pipeline at all levels, reviewing resumes, approving/rejecting personally every applicant in our ATS, ensuring every candidate is followed up with the Engineering management team. Sam inherits an exceptional team of Engineering Managers and Directors and has already begun running and evolving the structure of the Engineering Manager weekly meeting. Sam will own the closing of each candidate and the recruiting pipeline. He will also own the Engineering budget, review actuals vs. budget monthly, build yearly, act and adjust accordingly across people expenses, T&E and COGS. Finally, Sam will own and run the software capitalization process with the Finance team, quarterly.

Sam will also begin representing the Engineering team as a single voice in all aspects of PDDE planning and execution. He will be the primary collaborator to the VP of Product, Design and Data around the product roadmap and processes, collaborating around product delivery and resource allocation. He will also work with the VP-level business owners and the rest of Artsy management to represent Engineering in the cross-company initiatives. Sam will be the “E” in “PDDE”, and will be communicating decisions made by PDDE leadership to Managers and Engineering Directors during weekly stand-ups and regular Engineering updates.

I am excited to see the improvements in each aspect of the above responsibilities and am confident that increased focus in people and product aspects will help prepare the team for growth in 2020 and beyond as we achieve our company goals.

While I am obviously going to continue closely collaborating with Sam in areas of high level Engineering strategy, resource allocation and team culture, I will primarily focus on representing Engineering at the company leadership level for strategic planning, such as the company’s yearly goals, and will continue communicating company-wide context to the Engineering leadership team. I will also be communicating technical aspects upstream to C-level, VP-level business owners and the rest of Artsy management, representing Artsy technology in public, with partners and customers, taking on speaking engagements, interviews or lending quotes for publications. Internally, I will now have more more time to think about technical aspects of our systems and software architecture and help us be successful from the technology point of view within the short term 2019 goals, and beyond 2019. Finally, I will continue being committed to our open-source work through hands-on involvement and leadership.

Famous Last Words

The two key tools I used in dividing my work with a new hire were a bucketed open activity log and a time to impact framework. These are likely universally applicable for such purposes at any level of a company.