Subscribe to our Newsletter
Zetta Bytes AMA: Hiring a CTO
July 2019

Question for ZB-AMA: I’m the founder and CEO of an early stage AI startup. My technical team is growing, and I’ve decided I need to hire a CTO. I’ve got a few candidates — which one should I hire?

Answer: We have worked with a lot of founders who have asked for help hiring a CTO or VP of Engineering. We almost always start by questioning the underlying assumption that there’s a single “ideal” CTO for any and every startup.

Hiring your startup’s first CTO is a high stakes decision. Every leadership position is crucial, but this leader is responsible for delivering your product (across software, data, algorithms, and operations.) This is the core of what your company is and does. As an early stage startup, the majority of your employees will report to this person, giving them an outsized impact on company culture. If you’re a non-technical founder, it can be a struggle to feel confident hiring someone whose skill set falls outside your own competency. If you are a technical founder, it can be a struggle to replace yourself and let go!

You still have to do it. Maybe because your technical co-founder really wants to stay hands-on, and with the team growing past 5 (or 10, or 20…) they are finding too much time gets sucked away into management instead of the technology work they really want to be doing. Maybe you have the “champagne problem” of growth: you or your co-founder had no problem managing a few engineers and scientists, but now you’ve raised significant financing, you need someone focused almost full time on hiring, onboarding, and managing. Most commonly, CEOs wait until things are going wrong before they seek to hire an outsider. When we give them the space to be candid about what’s going wrong, we most often hear about failure to hire, failure to ship on time, or failures of product quality.

Whether you are hiring proactively, or to solve a problem, finding the right technical leader begins with identifying what your startup needs.

It helps to have a mental framework about the competencies of technical leaders. At Zetta, we’ve worked with hundreds of technical leaders across many startups and larger companies, and noticed some patterns around what makes leaders a good fit.

The ultimate responsibility of the technical team and thus the technical leader, is to ship a high quality product that we can build our business around. So the right leader is one who can put in place the right technology, the right data, the right people, the right process and the right vision to continuously deliver a high quality, innovative product with a highly productive team.

That calls upon our technical leaders to have four kinds of skills:

  1. Technical vision Your CTO may or may not be the technical visionary behind the company. It’s rare for a non-co-founder to be the inventor of core and novel technology and IP. But a hired leader must still have the know-how to reliably scale a complex architecture to deliver on the founding team’s key inventions and insights. Because the field of AI is moving so quickly (new capabilities, new infrastructure, new tooling) the leader must be ready to confidently course correct as the platforms change. And your leader must set overall technology direction, drive key decisions and reconcile disagreements, and attract premium talent.
  2. People leadership Your technology leader is also the manager of a team or an organization, and must excel at the tasks in that domain: establishing a great culture, hiring, coaching, and, yes, firing. As an organization grows in size, you will require next-level people leadership skills like organizational design, reinforcing culture, and the hiring and coaching of managers, not just engineers and scientists. An AI startup further requires sensitivity around the different and blended profiles across software engineer, data engineer, ML engineer, data scientist, and research scientist — assessing and enabling each to perform at their best.
  3. Operational leadership Startup technical leaders are responsible for delivering your product or service with very little room for error. They have to excel at planning. They need to implement a release process (and reinvent that playbook regularly as you grow), track the right metrics, supply the right tools, and create a culture of accountability. In an AI startup, they need to be ambidextrous — supporting research projects with high technical risk and unknowable outcomes on one hand, and driving reliable delivery of an intelligent product on the other.
  4. Product Vision In AI-first startups, the technical invention is often the core innovation in the company. In that case, the head of the technical organization is also a crucial company-wide keeper of the product vision. Even if that’s not the case for you, in every tech company, the technical leader must deeply understand and convey the product vision to successfully lead their team to build that product. If they are to accept accountability for delivering the right product, they must be able to engage with and whole-heartedly buy into the product vision, not merely accept requirements and engineer to spec.

We assess technical leaders across these four dimensions: technical vision, people leadership, operational leadership, and product vision. We also assess the relevance of a leader’s past experience to your business model and your technology stack. How much weight to place on each dimension depends on you and your startup.

Most candidates for the job have the basics down in all four dimensions or they would not succeed in leadership roles to begin with. But it’s still rather common that they are strongest in one or two areas, and work well in a team with complementary strengths — for example a highly visionary CTO hire might know they need a great operational lieutenant as a chief of staff or running a program management function. Or an operationally savvy leader may work well when partnered with a visionary founder-CEO. You don’t have to hold out for a candidate who is flawless across all four dimensions (as well as deeply experienced in your domain.)

The best leader for your technical organization meets the baseline across all four dimensions, complements the strengths of your existing leadership team, and is strongest in the area that is galvanizing you to make this hire. To make the best hire, you have to really level with yourself on what problem you are solving.

When your startup has achieved product / market fit, sales are booming, and you are desperately trying to keep your head above water to hire the engineers and deliver the products that customers are demanding, what you need most is excellence in the people and operational dimensions. Generally the founding team has plenty of vision that is still unrealized, and you want someone who will support and drive the implementation of your vision, not wrestle you with competing ideas.

If a technical co-founder has topped out, chances are that has manifested as morale issues in the team, falling behind on hiring, or inability to ship the product. These also point to people and operational leadership as the key gaps to fill. If this means you’re losing your incumbent technical leader, consider whether that creates a vision gap to fill, too.

If it’s product quality that is suffering, or you are lagging against competition with richer feature sets, your top priority is technical and perhaps product vision — a leader who can not just ship what you’ve imagined, but broaden the scope of your imagination or chart a different technical direction.

One of the most common patterns is a technical co-founder with a background as an individual contributor, who struggles with the operational demands of a growing team. It’s not uncommon for that person to decide they would rather focus on vision and technical direction, and hand over the operational side of the job to a VP of Engineering. Think carefully about the reporting structure in this case.

If, with the right support, your co-founder can grow into a great people and operational leader, hire a director or VP as a lieutenant and lean in to coaching those skills.

If you don’t see that potential, or don’t have time to develop it, resist the temptation to leave them in charge of the department — they should report into the new leader as a chief architect. If you, the technical co-founder, and the incoming hire have very special chemistry and commitment to collaboration, you can contemplate a peer relationship of CTO and VP Engineering, both reporting to you.

Some AI startups contemplate dividing the role in two, with one leader for research (say, Chief Data Scientist) and one for software engineering (say, CTO or VP Engineering). That’s a good idea if your goal is to shelter the research team from pressure to ship, but most startups can’t afford to fund open-ended research. If this team is critical to delivering the product, they need to report into the person responsible for delivering the product. Otherwise, you may find that the only person *actually *on the hook to deliver the product is the CEO. Not recommended.

Once you’ve zeroed in on the key hiring criteria, and you and your interviewing team are in consensus about what you need and why, assessing candidates becomes pretty straightforward.

Universally, we seek motivation, passion, brains, and alignment with our company’s values. Someone will hit the ground running faster if they have experience with our technology stack and business domain, especially when the market is idiosyncratic (like health care or fintech) or the tech is novel (like machine learning!)

You can get a good sense of all those traits with questions that probe into the four dimensions of technical, people, operational, and product leadership. And both screening candidates and arriving at a decision is dramatically streamlined when you and your team are clear on which of those dimensions matter most.

This may be the most important hiring decision you’ve made since your co-founders. It’s natural to approach the hire with a lot of care. That hard work is worth it because a great hire in this seat will be your partner in building the company — before you know it, you’ll wonder how you ever got by without them!

168 South Park
San Francisco, CA 94107

135 W 26th St #10A
New York, NY 10001

© 2023 Zetta Venture Partners