Preface

Being the CTO of a small and mid-size enterprise has been a totally different ride compared to what I’ve seen in the big corporate world. One thing that’s clear to me now? The title might stay the same no matter where you go, but what you’re actually doing as a CTO can vary wildly depending on the industry and the company’s growth stage. Sometimes, the things I thought were my greatest strengths turned out to be my biggest stumbling blocks as the company evolved.

In this piece, I’ll dive into some of the mental frameworks that have helped me navigate these shifts. Whether you’re already a CTO or working your way up, I’ll break down what I’ve learned about the CTO mindset, the key areas to focus on, and the common traps to watch out for if you want to thrive as an executive.

Company Life Cycles

Every company goes through a natural cycle, starting with the exploration phase, where the goal is to find product-market fit. This phase often involves significant costs, as the focus is on discovering something innovative — it’s not the most resource-efficient time.

Once product-market fit is established, the next step is to build out key capabilities to serve the market effectively at scale. At this stage, implementing standards and structure is essential to manage resources efficiently and support growth.

Finally, as the company reaches its total addressable market, activities gradually shift in the late stage. Investment in exploration winds down, and cost efficiency becomes a priority, providing a path to maintain a competitive advantage.

Ideally, executives will reinvest in exploration cycles to initiate another period of growth. This graph illustrates the technology evolution S-curve, where each stage requires the CTO to align their focus and activities with the company’s current phase. The ability to shift between initiatives — balancing innovation and optimization — is key at every step.

Executive Partnerships

As an executive, your core team is really your fellow C-suite members. It’s essential to understand and support their priorities and goals, leveraging technology to serve their functions while also communicating the needs of the tech organization. At each stage, clear communication and articulating the ‘why’ are foundational.

Most critical is aligning with the CEO and understanding their motivations. Throughout a company’s lifecycle, the CEO’s focus will shift across different areas, and your role is to adapt accordingly.

Understanding the CEO’s current focus allows you to support them effectively, covering blind spots and helping them navigate different stages of the S-curve.

• For an Enabler CEO, it’s essential to signal when to shift from pursuing novelty to building operational leverage and meeting customer needs more robustly.
• For an Asset CEO, encourage a balance between harmonization and diversification, ensuring that valuation constraints don’t stifle innovation.
• For a Cost Center CEO, recommend clear budget distinctions between P&L and R&D spending to maintain investment in innovation, keeping the company competitive in the market.

Startup Phase

In the early stages, the driving motivation is often getting an idea off the ground. Securing capital and achieving the first few proof points are the top priorities — without runway, there’s nothing to scale or operate.

During this phase, you’ll likely take on a hands-on Tech Lead role, building the foundation, hiring a team, or both.

Strengths

• Tech Debt — Speed is an asset when the tradeoff is quality. Taking on tech debt upfront can be worthwhile if it helps you secure additional funding or bring in new customers quickly.
• Small Team Size — Fewer people means the communication channels are more efficient while the decision process is easier.

Pitfalls

• Mission, Vision, Culture — Don’t miss the chance to establish these foundational elements early on.
• Architecture Standards — Setting clear guidelines now will lay a strong foundation for the future; don’t skip defining key dos and don’ts.

Growth Phase

At this stage, the primary focus should be on discipline and structure. It’s essential to reduce variation and prioritize rigorously, saying no to non-essentials so you can scale the core elements effectively and efficiently.

Strengths

• Structure — Establish standards and policies to minimize variation from macro organization policies all the way down to the technology choices.
• Focus — Saying no reinforces what truly matters, sharpening your direction.

Pitfalls

• Spreading Too Thin — Too many priorities while being anable to fully staff teams can lead to a domino effect of under delivery.
• Not Investing in Glue — Not investing in management or supporting functions soon enough.
• Conflict Avoidance — Staying busy can mask unresolved misalignments; address these directly to maintain the cohesion of mission.

Mature Enterprise

At this stage, the focus shifts to winding down R&D and driving efficiencies, reallocating budgets toward new S-curve innovations. Alignment with the executive team on business strategy is crucial to maintaining competitive advantage, which ultimately comes down to sustaining strong margins through premium pricing and cost control.

Strengths

• Risk Management — Knowing when to solidify and stabilize.
• Cost Management — Identifying the right moments to reduce expenses.

Pitfalls

• Penny Wise, Pound Foolish — Failing to invest in the next wave of innovation.
• Poor Strategy — Lacking a clear direction or simply imitating competitors.

Closing Thoughts

I hope these mental models offer readers insight into the type of CTO they aspire to become, helping them thrive in their role. I often liken it to raising children — some people are drawn to specific stages, while others find meaning in every phase of guiding a child to their full potential. Knowing what lies behind and ahead allows a CTO to be an ideal partner for the company, contributing effectively at each stage and planning for succession when it’s time to transition the role to someone better suited to the company’s next chapter.