Nailing Your Scale-up CTO Interview
How to interview the company you're interviewing for
👋🏻 Welcome to this first (real) issue of Lead & Scale, the newsletters for all the leaders navigating the complexity of scale-ups. With so many topics to address, I've chosen to go from the start: how to successfully interview for a scale-up CTO position?
Read time: 7 minutes
Interviewing for a CTO position is no ordinary process. Checking all the company and board's boxes is the easiest part. The difficult part is assessing whether or not you'll be able to deploy your tech strategy, deliver the company's broader business goals, and scale the engineering team.
In other words, if you apply to the company, you are also interviewing them.
Before you make your mind, here’s a 3 steps process to help you understand where you’re putting your feet.
Meet the main stakeholders
Interview the engineering leads
Audit the codebase
⚠️ Most hiring process I’ve been through involved only 4 or 5 interviews. Adding these steps creates lots of meetings for your future colleagues. Be sure you only do it before you make your finale decision.
Meet the Stakeholders you'll have to Interact with
The good part with the scale-up is that it's getting a little more organized than a startup. As a consequence, most important roles are filled or about to, and you should be able to get the information you're looking for.
Spoiler: most stakeholder you want to meet are not technical at all.
1. The head of HR
The first person you’ll meet is the head of HR. From day 1, HR will be one of your most important partner. Hiring, onboarding, retaining... HR is everywhere when you build a team and culture.
Here’s a few topics I like to discuss with a scale-up company’s HR, whether they're in the hyper growth or post-growth structuring phase:
Are they all by themselves or do they have a team already? The best HR I’ve met started building a strong team before anything else.
What are this year open positions? What's the hiring budget?
What has been the past 3 years turnover rate?
What’s the engineering hiring process?
Is there an onboarding process, or are the new recrues left alone with their manager?
Do they know about building a career plan, especially for engineers?
How comfortable are they with building a distributed team? What about an hybrid team?
Do they work with external recruiters already? Is there a budget for that or is it an absolute no go?
What’s the management processes inside the engineering team, if they happen to know it?
These questions help you assess the company’s HR maturity level, the kind of engineers you’ll find there, and the existing link between the engineers and HR.
2. The Head of Product
The second person you want to meet is the head of product. As a scale-up CTO, you have to find the right balance between shipping new feature, scaling the tech stack, and spending time on R&D. Here’s a few things I like to know:
Who do they report to? In some companies, the product reports to the CEO when some others report to the CTO.
Where does the roadmap come from? How often does it change?
What’s the balance between this year new feature and tech consolidation?
Do the company sales teams or customers weight into roadmap changes a lot?
What product management methodology do they use, if any? Spotify? Safe? Something else tailored to the company’s requirements?
Is there a QA team already? If yes, who is the QA team reporting to?
3. The Head of Sales
Meeting with the head of sales will teach you a lot about your upcoming strategy, whether you're joining a B2B or a B2C company. After all, you’ll build, deliver and operate the product they're selling.
What's the company's revenue target?
Who are the biggest names? Why did they sign in the first place?
What are the average sales time, customer acquisition cost, and LTV?
What's the churn rate? The churn rate is usually an indicator of the good or bad relationships the product and sales have.
What’s the sales process? What's a typical acquisition cycle? What upsell levers does the company have?
What does the sales team pipeline look like?
In the past, I have faced situations where the sales team would come to the CTO, telling them “I’ve sold this feature, I know it doesn’t exist, but you must deliver it by next month”. That's not something you can hear when a major part of your job is building a strong, predictable structure.
4. The CFO
As a tech person, it took me a while to understand how much I needed to build a trust relationship with my CFO. I wanted to focus on building great tech stacks, and forget about money.
I was wrong. When you're a tech lead, money is everywhere: in the revenue plan, in your infrastructure, in your hiring capabilities... and there's no way you can ignore it.
Once again, there's a few things I like to understand before I join a company:
What's the company's burn rate, and how long can they keep doing so?
What's the global tech budget? What's the split between salaries, infrastructure and external tools? Is the budget respected? If not, by what margin?
What's the CFO understanding of the tech needs? "Nothing" is an acceptable answer, educating them is part of the job.
When is the company supposed to reach profitability?
Indeed, you don't need to meet the CFO to get most of these answers, but experience has taught me you should meet them sooner than later and see if you can work together.
Meet the Engineering Leads
Meeting the engineering leads is a no brainer, and I assume you're surprised I did not prioritize them. I did it on purpose because meeting them is a no brainer. If you reach the point where you meet the company's main stakeholders, you must have met some of them.
When I used to interview for startup, all I wanted to know was how technically good the engineers were. Interviewing for a scale-up is different. The company has grown well, and your priority is not to move fast and pivot even faster.
Here’s a few things you might want to know:
What proportion of engineers (and eve more important, of tech leads) started their careers in the company?
How long have the tech leads been there for? And what’s their leftover motivation level?
When did they take their last 2 weeks break? I live in a country where you have at least 5 weeks of vacation per year, but I have also met several engineers who didn’t take a single day for 2 years.
Why did they chose this stack over another one? How did they chose?
Beyond their technical level, meeting the tech leads tells you a lot about their engineering maturity. After you join, you’ll have a few weeks to chose between training them or bringing in a few people you trust. Both options have their good and bad points and must be weighted.
Ask to audit the codebase
If they refuse, consider it a major red flag and run away.
Auditing the codebase allows to assess both the company's technical debt and software engineering maturity. It is the foundation on top of which you'll have to build your strategy and deliver the company's business vision.
The question you need to answer is not "do they have a top notch codebase?" but more "what's the required effort to deliver and scale in due time?"
A few things you need to check:
How many languages and technologies do they use? Is there a (good) reason to use so many technologies?
Is the code tested? If so, are there large, critical untested parts?
On a scale of 1 to fly, you fool!, what does their technical debt look like?
After meeting the main stakeholders, the tech leads and understanding the company codebase, you should know whether or not you’ll be able to conduct your mission as a CTO.
Last but not least, ask why they need to hire a new CTO, and if you can have a call with the previous one. If they refuse, you’ll know something is rotten in the land of Denmark.
Is there anything you do when interviewing for a CTO position I didn’t think about? I’d love to hear about it in the comments.
Thank you for reading me, and let’s meet next Tuesday 8:00AM CEST.
Photo by: Mina Rad.