Bootstrapped startups and the shit I learn in therapy

Setting titles in an early-stage startup is difficult.

Everyone does a little bit of everything. Take Andrew on our team. He’s “Partner/CEO” on our About page. But he’s also head of sales, chief client strategist, CMO, and something like the head of employee satisfaction. ✨

How do you boil that down into a title?

Other roles face this dilemma too. Holloway says:

“Titles can be confusing. Systems Engineer could mean very different things to different teams or companies depending on the degree of specialization. Someone who works on applications could be an Application Engineer or a Fullstack Engineer or a Frontend Developer. And yes, you’ll even see Programmer thrown around as an actual title.”

Prefixes make this even more mind-muddling. You can append all sorts of qualifying words (Junior, Senior, Lead, Chief, and Director) to any given title. 😬

Which begs the much do titles matter anyhow?

Are they a form of jargon, with one part meaning and two parts obfuscation? Or are they something more?

Startup world doesn’t agree on this topic (shocking)

If you analyzed how successful startup founders and businesses handle titles, you’d see a wide variety of approaches:

  • The “we don’t have those here” approach: On their culture pageStripe proudly announces a no-title policy: “We have a flat structure without titles—it’s about what you do, not what you’re called.” Their COO (yes, that’s a title 🤷🏼‍♀️) Claire Hughes Johnson explains, “Growth is a large part of employee culture at Stripe, and if you're growing quickly, you're going to have the wrong job titles with the wrong people quickly.”
  • The “nonsense till you grow” approach: Joel Gascoigne, Buffer’s CEO, didn’t adopt the CEO title for himself or distribute c-level titles until they had 11 employees. He says, “If I had used it earlier, it would have been a title with little value.”
  • The “set in stone” approach: Ever an advocate for clarity, Basecamp defines 5 simple programmer roles: Junior Programmer, Programmer, Senior Programmer, Lead Programmer, Principle Programmer. They provide a similar structure for designers, ops, data analysts, and support roles, too.
  • The “give them whatever” approach: Over at a16z, Marc Andreessen argues, “people ask for many things from a company: salary, bonus, stock options, span of control, and titles. Of those, title is by far the cheapest, so it makes sense to give the highest titles possible.” They’re like icing on the deal; spread them on generously and thick. 🎂
  • The “IDK...I made it up” approach: On ep. 222 of the Startup Chat, Steli Efti humorously digs at startups run by a CFO...where there’s no revenue, no customers, and seemingly no finances to manage. Clearly, some organizations invent or adopt whichever titles strike their fancy. 🤔

So, who’s right?

Our stance: titles are positioning for people 🎯

Titles may not cost you money to hand out, but they certainly aren’t cheap.

They’re important for how the world views your employee and what they can earn in the future. While you might like to think your team will stay #togetherforever, most of your employees will move on. 💔 When they do, the title you gave them will impact their job options.

For example, we’re in the midst of interviewing candidates right now, and if someone told us they worked for 5 years as a Happiness Wizard, we’d have no effing clue what that means. But if someone told us they were an HR Director, well cool, we understand that. 😎

In this way, titles are just positioning...but for people. 📍

That positioning applies to the work employees do inside your company as well. Imagine you’ve appointed go-getter Casey to a top sales role for your B2B enterprise SaaS product. When Casey sends cold emails, “Casey, employee at SuperSnare” or “Casey, Biz Wiz at SuperSnare” will send weaker signals than “Casey, Director of Sales at SuperSnare.” Which one will a corporate employee best receive and understand?

On the flip side, other customer types may be more likely to buy from a company with whimsical long as they’re not total nonsense. 💁

In either scenario, titles are part of our shared work vocabulary. We don’t set them flippantly because we know they communicate valuable information and impressions to customers, other employees, and future employers.

6 practical tips on setting titles

Look, we’re still figuring the whole title thing out ourselves. But after several hiring cycles, here’s what we’ve learned:

  • Define the role. ✍️ What do you need the hire to do? What will and won’t they be responsible for? Who, if anyone, will they report to? What might fall on their plate? What does success look like in this role?
  • Accurately name the role. 🎩 Steve Blank tells the unfortunate storyof a founder who hired a VP of Sales when he needed a VP of Customer development. It didn’t go well. Know what you need (define the role) and then accurately name it.
  • Use plain-English. 💬 Yesterday, I saw a job post for a People Team Coordinator (wth?) and several listings for Marketing, Sales, and Social Media ninjas. If you want a healthy pool of applicants, avoid these tactics. Remember that candidates search for jobs. Make sure potential employees can find and understand your listing.
  • Use a variety of titles. 📊 Some founders simply designate every hire as an employee or founder. But we agree with Steli Efti on this: “...if you have 30 people and they’re all might be your way of being edgy, and cool, and different, but it’s also going to confuse the fuck out of every new person you hire and everyone externally.”
  • Provide context in the job post. 📣 Whatever title you land on, there’s room for interpretation. A candidate from the corporate world will interpret the title differently than a candidate fresh out of startup land. To ensure potential employees understand what the title means in the context of your startup, provide a detailed and thoughtful job post. (Psst! Steal ours for inspiration.)
  • Be empathetic. 💙 Keep in mind the way you as a founder think about titles is different from the way your employee as a hire thinks about titles. Yes, they’re passionate about your startup. But they should also be passionate about their own career growth; titles factor into that.

What’s been your experience with titles?

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