Your 60 First Days as a CTO

A Roadmap for Success

👋🏻 Welcome to Lead and Scale, the newsletter for CTOs and leaders navigating the complexities of scale-ups. Today, we’ll see how to nail your onboarding as a new CTO by building your voice, understanding your impact, and establishing trust.

Your 60 first days as a CTO look like nothing you’ve ever experimented.

Every time I joined a new company as an engineer, the first month looked exactly the same. My manager arrived a few minutes before I did to welcome me. I spent a few days learning my new colleagues' names, guessing the company's jargon, and trying to figure out the best program on the coffee machine. Not every company got me a laptop on day 1, but when they did, I spent the first week installing and configuring my favorite software. Then, I was able to start diving into the technical stack and close my first tickets.

Things changed drastically the first time I moved to a leadership position. A new leader joining the company always brings both fear and high expectations. People suffering from poor past decisions hope you'll change their lives overnight, and people who've been in their comfort zone fear you'll change their lives overnight as well.

Spoiler: you won't.

Days 1-30: Listen, Learn and Align

As a new CTO, it's tempting to make an impact on things from day one, to tell everybody who's the boss.

It's a trap. I fell for it.

As a CTO, your first priority is not to change things, but to understand why you got hired.

1. Meet Key Stakeholders

When I got my first leadership role, I thought I was just a tech lead on steroids. It only took me a few days before I knew it was much more than that.

A CTO is not just a tech leader; they must align technology with business goals.

Establish a discovery funnel that allows you to learn the company's vision and what problems block it from executing properly.

Start meeting with the CEO and the executive teams. Not only will they give you the company's vision and strategy, but you'll also learn a lot about the company's balance of power. You might not like politics, but a political game exists in every company, and you can't lead if you don't understand it.

Then, meet product, marketing, and operations to understand pain points and opportunities. Shadow some SDRs, BDRs, and account executives to learn the acquisition process. And join some customer calls to get direct feedback.

Finally, have your first 1:1s with the engineering leads and key developers to assess team dynamics. Focus on people at risk and cross-team frictions, especially with the product team.

💡 Tip: Spend one or two days with customer support to get a real-life view of the clients' pain points.

2. Assess the Technology Stack and Infrastructure

This stage is the trickiest, for you'll be tempted to change things immediately. Focus on data gathering and linking your previous meetings with what you see.

• Review the codebase: What bottlenecks add unnecessary complexity and slow product development?

• Audit the infrastructure: Is it scalable, up-to-date, and cost-efficient?

• Understand DevOps and CI/CD: Are deployments seamless and efficient?

• Evaluate security and compliance: Is the company at risk, and are practices aligned with what's communicated to customers?

3. Learn the Team Culture and Dynamics

The biggest difference I’ve seen between a good and a bad CTO is about micromanagement. Good CTOs don't micromanage; they empower teams.

As a CTO, your biggest impact comes from unlocking your teams so they can deliver seamlessly.

Empowering teams goes through building frictionless team dynamics. To assess the existing team dynamics, pay attention to:

• How engineers collaborate: do they communicate publicly or privately on Slack? Are they active in meetings? Do the PRs get lots of useful and actionable feedback?

• How product and engineering interact: Are they aligned or siloed? Are engineers included in the product design? Are feedbacks about feature feasibility and impact talent into account?

• Team morale: Are people engaged or frustrated?

💡 Tip: If employees hesitate to speak openly, there may be trust issues. Address these early.

4. Quick Wins, Big Impact

While large-scale improvements take time, quick wins with big impact build trust.

• If DevOps is slow, could a small automation fix it?

• If deployments break often, could a post-mortem process help?

• If documentation is weak, could a small initiative improve it?

These low-hanging fruit show you're proactive without rushing major changes.

💡 Tip: Ask employees what quick wins they would pursue if they had the resources. Let those with the most impactful ideas lead the changes.

Days 30-60 – Build, Prioritize, and Execute

At day 30, you should be done with your audit, and your team should be used to seeing your head popping around. With this strong foundation, it's time to take action.

5. Define a Tech Strategy

Now that you've audited the codebase and infrastructure and identified pain points, build a technology roadmap.

People like to anticipate the course of events in the short, medium, and long term. This is why I tend to build roadmaps over 1, 3, 6, 12 months, and beyond. I find it convenient to reforecast my budget over the year as well.

• Identify must-fix issues (e.g., security risks, downtime problems)

• Highlight scalability risks (e.g., can the infrastructure handle growth?)

• Expose cost problems (e.g., oversized Kubernetes clusters)

• Align with business goals

💡 Tip: Present a 9-12 month roadmap during an all-hands meeting and focus on expected outcomes. It will establish your voice in the landscape.

6. Strengthen the Engineering Culture

As a CTO, you need to lead the engineering culture:

• Promote a culture of ownership: Developers should own their work from the first line of code to the 24/7 on-calls

• Reinforce development best practices: Code reviews, automated testing, post-mortems

• Encourage innovation: Engineers should have time for R&D

If you inherited a low-trust culture, work on psychological safety. Engineers should feel safe speaking up.

7. Optimize the Hiring & Talent Strategy

Many new CTOs inherit hiring challenges:

• The company is hiring too fast, too slow, has low or high hiring standards

• Most startups have too many juniors and not enough seniors

• Salaries and benefits are often not aligned with impact and seniority

💡 Tip: If retention is an issue, exit interviews will uncover hidden problems.

8. Improve Processes Without Over-Engineering

Process improvements should enhance, not slow down engineering:

• Are sprints too long? Too short?

• Are daily standups adding value?

• Is tech debt addressed regularly?

Find small but impactful tweaks that increase efficiency without adding bureaucracy.

Your first 60 days as a CTO are about building trust, understanding challenges, and laying a strategic foundation. The best CTOs don't just manage technology—they align it with business, people, and culture.

Thank you for reading. See you next Tuesday, when we'll talk about fixing engineering hiring issues.