Hiring for Growth: Lessons From Startup to Scaleup

In 2021, our team has grown by 50% (from 20 to 30 people), and we've onboarded new team members all over the world—from South Africa, Indonesia, Mexico, and the Netherlands. We've introduced new roles, new departments, and our first director-level titles.

It's been quite the year at Float.

Our team growth has correlated with revenue growth, and we now have customers in many more places. The shift from startup to scaleup has been one of the most exciting and rewarding phases in our 10-year journey of building a self-funded and sustainable company. For myself, it's been a challenging transition as CEO, overseeing the realignment from a predominately product-building focus to a team-building mindset.

Here are some lessons I've learned about growing our team and knowing when the time is right to hire.

Start a company with generalists, scale a company with specialists

Every role needs to be a generalist when your team is less than 15 people.

In the early days of Float, we all had a job title, but it might not have been obvious what it was on any given day. Michael would represent customer success for any inbound requests, write our knowledge base content, update release notes, and edit our blog posts. Nermin would complete quality assurance testing for our latest feature release, field technical questions from our customers, and ensure that our product ticket backlog was up to date.

During this first phase of growth, it's important to specifically seek out candidates that thrive in small team environments with a level of ambiguity in their roles. These folks are naturally curious and aren't sensitive to job titles (or the need for hierarchy). They find comfort in the ad hoc nature of work and understand the playbook hasn't been written yet, and that they can play a hand in authoring it.

Surviving and achieving product-market fit unlocks a new phase, where you can start to hire specialists with deeper expertise in narrower fields.

With each new hire above 15 people, our job descriptions became deeper in their requirements. We'd seek individual contributors that had honed their respective crafts, usually within a larger organization, and were looking to join a small company where they could have a wider influence and more visible impact. Too often, great individual contributors get promoted to managers, a role that ironically takes them away from their passions (which got them to where they were in the first place).

We wanted those people.

At 30 people, we added a management layer to support our team. However, the strategy remained the same: Set the vision, hire specialists, and empower them with the tools and space to be the best in their craft.

And with each specialist, each new role, our output became richer and fuller—a song both wide in frequency and deep in dynamics.

Hire when you know someone else could do it better

If there is one piece of advice I can give for when the time is right to hire it is this: Do the job first, and do it until you know someone else could be doing it better.

Scaling a team requires a strong sense of self-awareness. You've got to be humble. I've learned time and again, whether it was leading our paid marketing efforts or the customer success and sales initiatives in our early days, it was time to stop when I saw an opportunity beyond my capability. Otherwise, I risked being a blocker to future growth and success.

Siobhan, and later Alison, would join as directors of marketing and customer success. Each brought with them years of experience in their respective fields. In handing over the reigns, it was rewarding not only to see them replace me in the role but dramatically enhance and extend our success in those domains.

Don't outsource what you don't understand. Do it, understand it, and then find someone that can do it better than you.

A flat hierarchy is a pro up to 25 people, and then it’s a con

I realized along our journey, at a certain point, you can no longer keep adding team members left and right; you need to start thinking up and down. Utopian visions of a flat hierarchy, embracing self-management, just don't work in practice. And in recent years, we’ve seen many a roadkill along the path to Holocracy.

When we began, our team felt like one big family. Collaboration felt easy, we’d have just-enough process, and the team could be fed on two pizzas at a stretch. However, as the team scaled above 25, I noticed cracks forming, project plans getting lost in translation between product and customer success, and new starters increasingly not knowing who to ask when they had a question. I could no longer add the value I wanted to across a growing number of 1:1s. It felt mentally taxing just to get through them.

Up to that point, we had spent a lot of time thinking about how we could improve our product without enough focus on improving our team and culture.

And so before the cracks became chasms, my co-founder Lars and I set about changing that. We'd establish just-enough hierarchy to better support our team, improve communication, and increase our capacity to identify and hire new roles. We hired Georgie to lead our operations and later Colin, our first director of engineering, to manage our largest department. Later we'd promote and hire directors across both marketing and customer success.

And by building out that hierarchy, we also unlocked another benefit: a path for growth within our organization. Are you heading toward 25 team members? Start thinking about hierarchy.

Always plan 90 days ahead, but no more

Our average time to hire, from establishing that a role is required, to the candidate’s start date, is about 90 days. When you’re thinking about growing a team, you must be thinking about your needs 90 days out.

It's tempting to build an org chart top-down. Perhaps you've observed roles that your competitors are hiring for or job titles you've seen at companies you admire. You feel that to replicate their success, you need those roles too. I know this because we made the same mistake. We hired a "growth marketer" because some of our favorite SaaS companies had that job title, and surely we needed one too!

First, we ignored lesson one; we weren't doing enough of the role already ourselves. We learned very soon after hiring this person that no one role should own growth and that there needed to be a clearer growth strategy to allow the role to succeed. The result was a green specialist hire without the right support—a recipe for failure.

Your focus is constantly shifting when you're starting out, as your target audience, the competitive space, and external factors all influence market dynamics. You need to give yourself the flexibility to lean into the momentum and the room to follow opportunity. Plan for 90 days ahead, but no more.

Start the hiring process in reverse

Hiring for us at first looked like this:

1. I'd write a job description.
2. I'd share the job description with the hiring team for their thumbs up.
3. We'd hit publish.

All too often, a week into screening candidates for the role, we'd realize in our internal comments that we had a very different impression of the ideal candidate. The job description had done a good job of representing the what, but did very little to align the hiring team around the who and why.

To resolve this, we started the process in reverse by identifying the ideal candidate first. Working with our people operations manager, Linda, we developed a job requisition template, a document that required the hiring manager to define the why and the who and then link to 3-5 candidates that would be perfect for the role today.

This last point helped immeasurably. It ensured the role was real, there were talented folks capable of filling it, and it created alignment within the hiring team on who we were targeting, not just what. I encourage you to include this step in every new hiring process.

Here is a copy of the Float job requisition template we use.

Your company is not a snowflake

I distinctly remember our 25th hire and the feeling that I was entering unfamiliar territory as a leader, wading into deep water without my floaties on. So I did what I do in most moments of anxiety and lack of clarity: read.

I’ve spent the past year reading books on scale, chatting with smart folks in my professional network, and exploring some fantastic online resources. It’s amazing how often I felt like our problems were unique, with challenges only we could solve, only to find an exquisitely detailed chapter on the very issue at hand and how another founder solved it.

In doing this research and talking with others, the one surety I discovered is that almost all companies have encountered the same challenges at some stage in their growth. By sharing these lessons, I hope that each challenge you face in the future will feel less intimidating and more rewarding when you're ready to grow your team.

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