Opportunities for Managers

Startups move through numerous phases from their inception as an idea through to their growth as a full-fledged company. As these stages progress, various opportunities can arise where you can get involved as a manager. We’ll take a look at these with reference to the diagram.^[45]

Let’s begin by briefly walking through the diagram from left to right, taking in the stages.

• Co-founders: This is where the people with the initial idea create a business and get started. Unless you’re one of the founders yourself, you won’t be concerned with this stage. The co-founders will be looking for a problem-solution fit: is it possible to build a product that solves some business problem? Typically this results in building a minimum viable product (MVP) to see if customers purchase it and what they can learn from them. Most, if not all, input at this stage will be from the co-founders.

• Initial investment: If the initial MVP gains traction and looks like it may become a viable business, then startups seek initial investment so they can begin to grow faster than they could organically. This initial investment can come from angel investors (typically wealthy businesspeople), startup accelerators, specialized investment funds, and more. It’s enough money to see whether an increased investment in the product can increase its impact in the market. A big chance here is to get involved as manager number one. We’ll talk about that shortly.

• VC rounds: Assuming a startup’s product continues to do well, then the company may decide to take on even more investment to keep growing faster and faster. VCs are private equity investors that grow their funds by investing in fast-growing businesses. During these stages a number of opportunities can arise as that money allows many more engineers to be hired, teams to be created, and possibly even create positions that allow you to run multiple teams.

• Beyond: Once a company grows beyond the VC stages, it’s probably beginning to get as big as many other big companies!

We’ll look at the two previously mentioned startup stages that bring a lot of opportunity: the stage that brings initial seed investment and the VC rounds that will follow.

Becoming Manager Number One

One of the biggest career growth opportunities for managers is becoming the first manager. This usually happens after some initial investment. But what does that mean? Typically, within the co-founder group, there will be a CTO and a CEO.

The CTO, despite the big job title, will typically be the lead engineer that is building the technology. Their priority will be getting the product built so that the MVP that has gained traction can continue to scale, support new features, and serve existing customers. The CEO will be usually focusing on all manner of things: new sales, hiring, building a plan for the future, and so on.

What this means is that the engineering department doesn’t have anybody focused on management. By management we don’t just mean people management either: we mean the management of process, hiring, communication, and delivery—the person that keeps the wheels turning efficiently. This could be you.

You would be expected to do what you’re doing as a manager of a team, but the scope of that role covers the entire department, even if it’s small. The impact is therefore felt across the whole company. The seeds that you can begin to plant at this stage—assuming that the startup does well—can blossom into the engineering culture of a department of tens or maybe hundreds of people.

And what is this role called? It’s typically given the title of VP engineering. If the CTO is creating the product, then the VP engineering is responsible for creating the engineering organization. Here are some of the things that a startup VP engineering may be responsible for:

• Ownership of the delivery process, from technical aspects, such as how to deploy frequently with no downtime, through to the way in which releases are communicated to users and to the rest of the company.

• Performance of the engineers, encompassing line management, one-to-ones, performance reviews, and creation of all of the processes that surround those activities.

• Resourcing and prioritization of projects. What’s going to get done and in which order, with limited engineers available?

• Hiring new engineers, including the creation of the hiring process in the first place, and working out which roles and skill sets are required.

• Keeping the CTO focused on building. If there’s anything that doesn’t fall into the examples above that is getting in the way of the CTO, then it’s likely to fall on the VP engineering to solve it.

• Building stuff! Given that the company is so small, it’s unlikely that a startup VP engineering isn’t contributing code.

When you look at the VP engineering role from this perspective, you could imagine it as an engineering manager role with the accountability, risk, and autonomy turned up to 11. If you don’t know how to do something, or if there’s no process at all for some particular issue, then guess what? It’s up to you to solve it!

The relationship between the CTO and VP engineering at a startup can be summarized in the matrix diagram. A good VP engineering can turn a small band of pirates into an efficient naval vessel, with plenty of room for the fleet to continue expanding.^[46]

So, remember that this early stage of life for startups could offer an exciting career opportunity for you. Don’t be put off by the lofty job title. Instead, if you continue to enjoy and succeed in management, and if you’re feeling up for a challenge and the ability to have a large impact, then a startup that has received some initial investment may be looking for someone exactly like you. Just keep an eye on job advertisements that offer the role where the team size is small, often in the low tens of people, and lean in to your network to find out what’s not yet advertised. Don’t be put off from applying.

In addition to the challenge and excitement that this role can bring, if the startup continues to succeed, you may have the opportunity to define and hire a substantial department, giving you the opportunity to move into a manager-of-managers role much quicker than you’d be able to at a larger organization. It’s the perfect opportunity to tee up much bigger roles in the future.

So yes, you could be VP engineering. Maybe even sooner than you think.

Catching and Surfing a Wave

The management track presents two difficulties with entry and progression:

• Landing an initial management position. Since very few people have formal training in management (else why would this book exist?), getting the chance to be a manager in the first place can be challenging. When applying to open roles at companies, those with previous management experience often have the upper hand over those with none.

• Always having a route for growth upward. A manager’s progression can be bounded more tightly by the size and structure of an organization. After all, managing more people and teams involves traveling upward in the org chart. What if there’s nowhere to go?

Startups can offer an environment that can make these situations a little easier. As we mentioned previously, startups that do well have some favorable properties:

• They grow and change rapidly. Investment or fast organic growth can double or triple the size of the engineering team in a short space of time. This means that a handful of people working in a flat hierarchy may now require more structure in their org chart, including the introduction of more line management. This creates roles you can step into, especially if you’re already working there. Additionally, continued success can expand the department further, and you’re well placed to continue the journey upward.

• They have less money to spend. Given that startups are unlikely to be poaching highly paid managers at larger technology companies, you can use this to your advantage: you’ll have more of a chance to make the jump into management even if you haven’t had prior experience.

• Each individual can have a big input in decisions. If you join a startup as an individual contributor with a desire to move into management, then you’ll have a lot of say in creating the conditions in which that can happen. Your influence at a small company will be much greater than that of a large corporation. You can make it happen for yourself.

Sampling Different Roles

Another benefit of joining a startup is being able to sample all manner of different roles. Given that there are limited people, it may be the case that you get to lean into—or even try your hand at—various skills that you may not have at a larger company. Perhaps you get to be a full-stack engineer rather than just a back-end one. Perhaps you may get to contribute toward product design or the roadmap itself. There are many opportunities for self-starting individuals to have fun and round out their resumes.

So here’s some advice for how you could approach and join smaller companies in a way that allows you to have your career as a manager in mind:

• Co-founder stage: If you know of any startups you’re interested in that are just getting going—perhaps you know them through colleagues or friends or have met them at a conference or meetup—then register your interest. Tell them that what they’re working on seems exciting and that if they begin to grow that you’d love to get involved, potentially as an engineer with scope to grow into a manager. Have these people as part of your network.

• Initial investment stage: When startups raise money, they often put out press releases. Make sure you stay on top of what’s happening in the industry by reading websites such as TechCrunch, Hacker News, AngelList, and Product Hunt. Companies getting initial raises are still small. Find out who works there and reach out on LinkedIn or Twitter. Be direct: say you’re looking to either land a first management role or grow as a manager, and you’re interested in what they’re building. See if you can make connections. If you’re already experienced, are they looking for manager number one? You never know what’ll happen.

• Subsequent VC rounds: As startups grow to a size where they begin to raise VC capital (often called Series A, B, C, or beyond depending on how many prior raises there have been), then you’re likely to be dealing with a more standard recruitment process. However, a short cover letter stating your intention to go down the management track in the future, even if there are only individual contributor roles advertised, can open other doors for you. Just state your intention.

A world of exciting small companies is out there. However, there are risks. Joining a startup may be intense, difficult work, without the structure, compensation, and benefits that you’ve been used to in the past. The environment may not be for everyone. You’ll have to work out whether it’s right for you.

Not only that, most startups fail. Many have great ideas that never find their product-market fit. Some are unable to raise enough money to continue. Perhaps the startup may pivot its offering so many times that what you build is nothing like what you were originally expecting to be working on. Are you comfortable with change? Are you a cathedral builder or a bazaar browser?

Startup Compensation and Equity

It is unlikely that startups will be able to pay as much in base salary as established technology companies. They simply don’t have as much money available at early stages. You may find, however, that they offer equity in the company as part of the compensation package, typically in the form of stock options that vest over some period of time. Before you get sucked into dreams of becoming a millionaire as the NASDAQ bell rings, you need to remember a few things: Most startups fail, and even those that are successful may take over ten years for the equity to be exchanged for real money. Don’t count on it ever happening. Be there for the experience instead. Everything else is a bonus. If you’re unsure about the terms and conditions of any offered equity, including how much there is, whether it’s a preferred stock class, or anything to do with the vesting schedule, then seek legal advice. Betting your happiness on an uncertain and unpredictable future will likely lead to disaster, even if that disaster is confined to the boundaries of your own brain.

It’s not all gloom and doom though. Due to their size, startups expose you to all aspects of a business—from engineering, to sales, to marketing, to angry clients—often because the lack of people means that everyone needs to support each other closely, regardless of their role.

If you’re interested in expanding your knowledge of how a whole business works, they’re a fantastic way of being able to get up close and personal in a short space of time. One year at a startup can feel like five years at a larger company because of the intensity and variety of the work. You can move on to your next role as a more fully rounded professional.

Remember that startup experience is highly sought after because being impactful in that environment involves being enterprising, self-motivated, collaborative, and quick to learn. Even if the startup itself doesn’t work out, your next gig will be all the better for it.