Want to join a startup? It’s all about timing

When your desired role and skills might match a startup’s needs

(Image courtesy Justin De La Ornellas. Used under Creative Commons.)

I was reading Tom Blomfield’s “When to join a startup” and it provided concise, thoughtful responses to a ton of questions I always get from work-a-day folks or recent grads who are looking to jump into the fray. In fact, if you haven’t read that, you should probably do so before continuing here.

Go ahead. I’ll wait.

Back? Cool. Good right? Tom’s post reminded me of another piece of advice I always try to give these folks. It’s implicit in Tom’s post, but I wanted to make it a little more explicit. It’s a little technique for projecting when the role you want will be available at a startup. Think of it as a way of predicting which startups might be hiring when.

Now, I’m no expert, but I believe this guide can to be a decent way of assessing startup stages from a different maturity level than just investment round (Friends & Family, Seed, A, B, C…). Because it’s based on the types of folks startups are hiring and when they’re hiring them. And by the time most early stage startups get around to posting a position, they usually already have someone in mind for that position. So it’s helpful to have a barometer that helps you predict where they might be going.

It’s fairly simplistic and follows a logical progression. But it might not be immediately obvious. And, as a caveat, please understand that this is a hypothesis. It’s not a theorem. So it doesn’t work for every single startup or situation. But it’s a start.

Founding team

Every founding team is different, so I wanted to provide some context on the founding team in this hypothetical hiring procession. I’m using the “hacker, hipster, hustler” model. Again, not perfect or applicable all of the time. But a good place to start.

With this in mind, we’ll find that most startups—at the founding stage, at least—have a CEO and CTO, and then they complement that with a third founder who plays the role of CMO or other “Chief” of community, sales, growth, and the like.

Now, I say “plays the role,” not to be flippant, but as another cautionary note for folks who are just dipping their proverbial toes in the churning startup waters. Because nine times out of ten, these folks are not actually qualified to hold C-level titles, nor do they have the wealth of skills an established C-level exec bears. But these are the titles that startup founders give themselves. And after anointing themselves with these magical C-level titles, they do one of two things:

  1. They attempt to grow into the role with the mentorship of more experienced execs and investors.
  2. They decide the role isn’t exactly for them, so they hire someone to serve that role.

If you’ve never dealt with startups before, this is important to keep in mind. The individuals with C-level titles at a startup may not have the background to be hired as a C-level at another company. But they’re the only C-level exec this startup has. And as far as the startup is concerned? They’re the best C-whatever the company has ever had.

In this example, the founding team will consist of the following roles:

  1. CEO: This person is in charge of handling all aspects of the business side of the startup. Things like managing the operations and finances, fundraising, hiring and firing, equity splits, and all that. As an added bonus, this person is usually the lead salesperson during this phase of the startup’s existence. Usually, this person also has the added stress of being the final decider on contentious decision on which the team cannot find agreement. Fun!
  2. CTO: This person is in charge of handling all of the aspects on the product side of the business. Things like the technology stack, the product roadmap, user experience, uptime, and the like. As an added bonus, this person usually has to shoulder all of customer support. More often than not, this role has eminent domain over product decisions, much in the same way the CEO has that purview over business decisions.
  3. CMO: This person gets to do everything else that the other two aren’t doing or cannot do whether it is marketing related or not. Generally, the person is the decision maker around brand, identity, social media, and promotions. In many companies, this person is a strong influencer on user interface and user experience, as well.

A little parable on the progression of titles

So our team is cranking along. Working crazy hours. Getting traction. Gathering momentum. And plugging away. Maybe they have funding; maybe not.

Suddenly, they’re starting to feel some pain. Not because of their abilities, but simply because there is too much to do. And they’re constrained by resources. They need more people. And so the hiring cycle begins…

  1. The CEO feels encumbered by all of the things on his/her plate. What’s more s/he’s in charge of sales, which is critical to the company at this point in time. And fundraising becomes a full time job, off and on, for more than half the year. S/he is beginning to hate operations because it seems like such a time suck. And the other team members are having a hard time balancing responsibilities and workload as the pace becomes more frenetic. To alleviate this, the company makes their first hire, the COO.
  2. With four C-level folks, the team is humming along. The CEO has more time to sell and fundraise. The other team members are feeling like they’ve got more smart hands to help. And there is someone to make sure everyone is on the same page. The COO is happy and feels like a contributing member of the team. The only problem is that along with all of the other stuff the CEO handed off, the COO inherited finance. And while the COO can deal with the financial aspects of the business, it’s beginning to take more and more time. Worse yet, the financial elements are starting to become more complex and pushing the envelope of the COO’s comfort level. Solution? The company makes the next hire, the CFO.
  3. Now, the team is focused on a variety of efforts. Product is being built. They’re closing sales. Still plenty of money in the bank. People are talking about them. Customers are happy. But there isn’t really that steady flow of customers like there was in the early days. And every new customer win isn’t met with the resounding joy it once was. Revenue is increasing, but not enough to keep the CFO happy—or busy. “We need more traction and customers” becomes the common cry. So the company hires a VP of Sales.
  4. The VP of Sales has hit the ground running, so there is an initial pop in both customers and revenue. But that run—no matter how deep the VP’s rolodex—is short lived. It’s back to the slog of educating the market on the solution, spending more time talking and researching than wooing and selling, reinventing the wheel every time because no one has had time to architect a sales process or strategically manage the pipeline. And the VP isn’t liking the looks of the numbers s/he has to hit. They need more promotional activity to feed the top of that funnel. And they need more tools to empower sales and deliver a consistent message to the market. To pour more fuel on the fire, the company hires a new CMO.
  5. From here on out, it’s a bevy of roles being hired, depending on the prevailing pain point. Maybe it’s customer service. Maybe there are so many customers it’s time for customer success and community management. Perhaps, it’s time for an evangelist or two. Whatever the case, it gets really hard to predict who might be the next hire. And you just have to try and guess based on market dynamics.

And there you have it. That’s a very broad brush stroke on how hiring cascades in early stage companies. Not always in that order—they may hire a CMO who hates sales and hires the VP of Sales—but pretty close.

So, if you’re looking to get into startups, you want to watch for the positioned hired immediately before the role you’re seeking. For example, COOs are almost always early. VPs of Sales and CMOs are almost always later. And if they don’t have a COO and CFO in place, it might not be the right stage for a true CMO to join the fray.

Hope this helps as you make your decision about joining the startup world.


Rick Turoczy (@turoczy) has been working in high-tech startups in the Portland area for more than 20 years. As founder and editor of Silicon Florist, he has blogged about the Portland startup scene for nearly a decade — even though numerous people have begged him to stop. That side project led Rick to cofound PIE (the Portland Incubator Experiment), a startup accelerator formed in partnership with global creative firm Wieden+Kennedy. Those efforts led to the founding of Oregon Story Board, a project that is using learnings from the PIE experiment to accelerate companies in the creative services industry.

All because of a blog. Weird.