Hiring Startup Engineers: a field manual

Hiring engineers is the most important part of building your startup. It requires significant attention and a systematic approach. A good process combined with clear evaluation criteria will set you up for success.

This field manual covers the essential aspects of hiring your first few crucial engineering roles.

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Before starting to hire

Decide whether to avoid hiring at all (yet)

Before hiring, do a quick sense check. Do you really need to hire?

Every hire increases your burn rate and pushes profitability further away. Does the work have to be done? Can you stop doing something else that is no longer necessary, so that you free up more time, and do not have to hire? Can you get the work done with a contractor that allows you to easily reduce spend if you need to?

Keep your team as small as possible. Similarly to code, more people exponentially add more communication pathways to the business. Smaller teams are easier to lead and manage effectively and require less management experience.

How much of the coding can you do yourself? This year, it is more than ever given the AI tools available. Resist the temptation to hire too early and see how close you can get to problem solution fit without hiring - the job is not to build, it is to build a product that solves a problem.

Get your values draft done

Assuming that you need to hire, begin by defining what matters most in your hiring process. Your values will guide who you look for and what skills matter most.

There is lots of information here about how to define your values. At a minimum, it is good to have an idea of your top core values before you start hiring. These will help give your job description a much better chance of attracting the right people.

Choose boring technology

Architecture impacts hiring. Your technical stack choice directly affects the quality and the quantity of candidates in your pool. Early employees will need to work across the entire stack. Choose as few languages as possible to maximize your hiring pool.

Select established technology that is easier to hire for. TypeScript currently dominates the London market. Rails remains an excellent choice for rapid development. A Haskell/Rust backend might be technically interesting, but you will struggle to staff it.

Planning your hire

Prioritise startup experience

This is the most imporatant differentiator for startup hires. Do not even consider people without startup experience.

Startup work differs fundamentally from enterprise roles. Large companies provide extensive tooling and support systems. At a startup, you have none of that. You will have to make do with rudimentary tooling.

Look for candidates who have worked in resource-constrained environments. They should be comfortable building systems from scratch. Avoid those who consider platform work beneath them.

Hire senior first

Your first hires should be experienced engineers. Avoid candidates in their first job - they require too much training and mentorship time that you cannot afford to provide. Second-job developers can work well but need additional mentorship support (this is something that I do). Focus on hiring senior engineers who can work independently and help establish strong technical foundations, but who have startup experience. Engineers with too much experience in larger companies can struggle with the chaos and uncertainty of a startup.

Consider more junior roles after 4-5 senior hires. The team will then have capacity for mentorship. Focus on high potential individuals over pure years of experience. There is some excellent advice in this blog post about hiring low experience, high potential people.

“A-players vs C-players” is nonsense.

I really do not like the context-free A-player vs C-player argument. Saying somebody is an A-player without considering the context is an oversimplification. It might be that they just don’t quite mesh as well with your culture, or know your language as well, or are in a tricky life stage.

Context matters more than abstract talent ratings. Success depends heavily on culture fit, technical background, and current life circumstances.

That said, some people are a much better fit than others in a startup, which is likely to be high pressure, high uncertainty, and high change. This does not suit everyone; hence the need to hire for startup experience.

Choose people who are a force of nature if you can, that are smart and get things done. Do not take someone that crosses a core value, even if they seem amazing otherwise. It will not work out.

Writing a job description

Make your job descriptions clear and conscise. Avoid putting in lots of requirements as you will be screening for applicant confidence and not for fit.

Talk about your values in the job description. Your mission and purpose are really important - Gen-Z and millenials are known for treating mission as extremely important when selecting a company to work for. Your mission and your values will both make you stand out, and will help attract exactly the right sort of people to hire.

Talk about salaries - put them clearly on the job description. It is ok to name a range. How much you want to pay will depend on local information: talk to your recruiter, or ask fellow CTOs, or your coach/mentor (or ask me!) to find the bell curve, then decide what mix of salary and options you will offer. We have tended to offer 50% percentile salaries with generious options. We made all our salary and options ranges public - one of our core cultural values at Cherrypick is “work in plain sight”.

In terms of designing your options scheme, I love the Index Guide to Options. It is a very helpful guide to getting started.

Choose important questions to ask at application stage

This is crucial. Choose some thoughtful open-ended questions that will help you understand how a candidate thinks. Vacuous answers from ChatGPT are a red flag and allow early screen outs.

More soon!

I will be adding to this post over time. Still to come:

• Getting people to the interview stage
• The interview stage
• Making a decision
• The offer stage
• Onboarding

Get ahead with AI.

AI has changed the world forever. New AI products come out every day. Everyone else seems to be moving fast and it's easy to feel left behind.

I've dedicated myself to learning the very latest AI tools and techniques and have used my experience as a founder and CTO of multiple businesses to separate out hype from what works now.

I've applied what I've learned so far to my own businesses, and it's transforming everything. It can for you too.

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