5 Ways CTOs can engage effectively with their CEOs

Philip Reynolds
Anamcara Capital
Published in
5 min readFeb 6, 2024
Photo by Vardan Papikyan on Unsplash

Preamble

Ventures and CTOs come in many different flavours. This article is focused on providing some (hopefully) helpful insights for founder CTOs who have scaled up their business. In a SaaS, this might be a couple of million in ARR or 50–100 employees. It’s generally post product-market fit. There’s typically a real board with multiple investors and a senior management team is starting to form.

Hands-on CTOs who were such an asset as a builder can quickly lose their value if they don’t grow with the business. The CTO’s role must evolve from technical to more strategic responsibilities.

1. Be an Effective Peer

T-Shaping is a wonderful way to grow your engineering team. But T-Shaping isn’t limited to your engineers. As the business grows, you will need to speak Product, Sales, HR, Finance andMarketing.

One critical way to help your CEO and the business is to work with and communicate effectively with your peer leaders. If the CEO has to regularly step in to translate, moderate or mediate between you and your peers, that means you’re not doing your job.

If reducing operational costs is a critical goal for 2024, your job is to form a strong partnership with the CFO or COO. If it’s hiring, then you are partnering with HR or your Talent teams.

2. Learn how to communicate without jargon

Most of us have been in situations where we are completely lost once the conversation moves to insider jargon. I remember being at a party with a group of junior doctors all chatting away about whatever the procedure du-jour was. Lots of in-jokes discussing whatever lecture or procedure of the day was going on. I also feel like this whenever I collect my car from the mechanic and they try and justify whatever’s on the bill.

It’s not a particularly nice feeling. It’s also worse if the person who’s communicating with you is being condescending because you don’t know the jargon.

The reality is, I don’t know much about cars. I really just want it to get me from A to B, reliably.

While you may get some peers or board members who are technical, you must learn to communicate effectively without jargon.

  • Analogies and metaphors are your friend. Technology is full of jargon but it’s also full of abstract concepts. Make them concrete using real-world analogies that ordinary folks can relate to.
  • Focus on outcomes, not output. Rather than talking features, talk benefits. Even opaque things like technical debt can be talked about from a benefit and productivity perspective.
  • Tell stories. Storytelling is one of the most distinctive traits of strong leaders. Sharing real-world scenarios that illustrate how your organisation or the technology you’ve built has delivered growth or customer success.
  • Simplify. There are times where it’s simply unavoidable to talk about detail. You get to decide at what level you communicate. Sometimes you want to be at ground-level, sometimes at 30,000 feet and sometimes at 10,000 feet. Staying at 30,000 feet all the time doesn’t engender trust.
  • Visuals. Sometimes a picture or a graph can tell a story in 3 seconds that would take 3 minutes to tell. Visuals and graphs can be particularly useful for scale related problems.

3. Know what’s expected from you

This sounds obvious. It’s funny how often we all fall in to the trap of forgetting what part of the jigsaw puzzle we are.

The CTO in a product focused venture is, first and foremost, responsible for product delivery and execution. Outside of that, you are frequently running one of the largest cost centers in the business, one of the largest contributors to COGS. You’re (typically) also the steward of huge risk areas like cybersecurity. Outside of product delivery, availability and performance are massive areas of customer success.

That’s a lot of ground to cover. Make sure you know how you’re covering it.

4. Learn to speak boardroom

The language of the boardroom isn’t difficult. But it has its own set of concerns.

  • Growth and Revenue — Understand how the technology contributes to the company’s growth. Be prepared to discuss how the tech stack enables scalability, customer acquisition, and entry into new markets. Highlight past successes where technology directly influenced revenue growth.
  • Profitability and Unit economics — Understand your costs, particularly headcount.
  • Risk Management — Clearly articulate the measures in place to protect the company from cyber threats, data breaches, and other tech-related risks. The board want to feel confident you’re proactive on this and that you’re equipped to handle these areas.
  • Capital Allocation, Investment and ROI — Build your capability in explaining non-feature related investments such as technical debt, security or infrastructure
  • General trend awareness (market and industry trends) — A part of your role is to inform and educate the board on general market and industry trends. Public Cloud, Mobile and AI have all been major trend areas in the last 10 years.

You must understand the boards job, what it is trying to achieve and be able to articulate your role in achieving it.

It is critical to develop 1–1 relationships with multiple board members. Particularly those with technical and product backgrounds.

5. Build a strong management team

All of this sounds like a lot while you keep the delivery engine going. And it is. As you grow, you must put people in your management team that allow you to fully delegate areas of criticality.

If you are spending your time putting out fires that they should be, it becomes difficult to progress and do the jobs necessary above.

That means:

  • Hire complementary skillsets — If your organisation skills leave a lot to be desired, bring someone in to your team who is a master at that.
  • Hire domain expertise — you will need specialists for areas like CI/CD, Infrastructure, Security, AI, Mobile. As with all hires that specialize, the goal should be that they elevate your ability in these areas. Their job is not just to maintain the status quo.
  • Developing Talent — Along with hiring, you’ll need to develop talent internally. Inevitably, sharp, ambitious leaders will emerge from the ranks and put their hands up for more responsibility. Make sure to give them that.
  • Effective Communication — One of the most critical things about being aligned with the business is then cascading that alignment down to your own team. What are we optimising for? How do we make decisions?

The time to start is now

A lot of these may feel like scale-up and bigger company problems. The problem for CTO’s is that you can’t just show up in year 5 and click your fingers to figure this out.

Your growth in to this role at scale is inextricably tied to the business and requires investment and a mindset of personal growth from day 1.

Once you hire your first team member, your journey away from builder has started.

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Philip Reynolds
Anamcara Capital

Acquiring B2B SaaS. Venture Partner at Anamcara. ex-Engineering at Workday.