From 80 to 200: a year in Pleo's people operations

In February 2019 I was standing on a stage at Aarhus University speaking on “How to tell your dad that you’re working for a startup” - with a photo of my dad on a slide and everything.

The takeaway from my talk was that “hyper-growth” is the new buzz word when people are hiring - and if you want to stand out as a candidate today it’s smart to have some experience from this type of working environment.

And hyper-growth is all good to speak about: but what about the reality of it? This is what I’ve faced here in Pleo for the past year through building and scaling - not just a People Team itself - but also the company from 80 to 200 people just in 2019. 

It’s been...wild.

15 stages (link to the one from TechBBQ), 5 podcasts (link to our latest one with Susan from Implement), 1 eBook (on the Future of Work) and a couple of blog posts later here I am: learning by doing and growing a startup People Team of 3 to the 11 that we are today. Looking back this doesn’t really sound possible but it was easier than it sounds if you take it chunk by chunk. I’ve outlined those chunks below.

Early on: Jan 2019

At the beginning of last year, I had a message from my boss, our CEO Jeppe. Being on holiday (and being used to getting DMs from Jeppe) I was worried: what could be so important that he’s messaging me when we’re both on leave?

He sent me - as well as all 78 of us in the company - a happy new year message that was specific to my role and what I’d achieved, as well as what we were looking to achieve in 2019. “We have a big task ahead of us - we’ll grow from 80 to between 120-150 people this year”.

Little did we know that instead of planning for 150 people as an upper limit - we'd be hitting the 200 person mark by the end of the year.

Our early year plans started to materialise: hiring forecasts were set, people were promoted, new teams formed, we moved to our first office that was just ours (no sharing!), seating plan discussions began and remote setups were set up. Top of my mind was to build our brand new, 3-month-old People Team of 3 into a bigger, strong backbone of proactive support for this expected growth.

Building a Future of Work People Team

Now, Pleo is a future workplace product with the idea that if you trust people enough to hire them, you should also trust them enough to spend company money. This means that to stay true to our brand, we need to build a future workplace internally.

We do this through things like being human, having remote work options and trusting one another.

But for me, there’s a whole bigger discussion about building future workspaces by structuring teams differently. Our product teams had reshuffled to be all these small entrepreneurial teams themselves: it was time to build our People Ops team to follow suit. 

There’s a guy called Frederic Laloux who wrote Reinventing Organisations and shows how it’s smart to build organisational structures differently.

I decided to take bits and pieces from his - and others - work on this to build our team. This was risky. Here we are, a young team that hasn't proved itself that now wants to do something atypical to help us scale. Luckily, Pleo’s a trusting place and was given that trust to try it out. It's worked surprisingly well for us.

We worked around these core principles: 

1. Being human: we are a team that brings our whole selves to work - and are very matter-of-fact about who we are, how we work and when we need one another's support.
2. Sharing a common purpose: we all agreed on how our part of the business contributes to our company - and our greater community. Then, whatever work we do, we’d angle it towards that shared purpose.
3. Striving towards self-management: even though I’m in charge of the People Team, we chose not to follow a traditional hierarchy. We decided that everyone's voice should be weighted equally. This brings about distributed decision-making. On top of this, each team member has the freedom to set out how they can best contribute to our purpose.

So the way our team was going to work was set. But next up came: who would this team be? Would we be 3 forever?

Taking risks: hiring the unusual

Next up came our second high-risk decision. Instead of hiring typical recruiters or HR managers I wanted to hire people who deeply know about the domains of the teams with which they’ll work. I don’t know of many other companies who do this, so I was a bit unsure. My gut said that there are people who have a lot of domain knowledge of their area but might not be working in it. If these people have a high EQ, deeply care about people and are entrepreneurial and smart - they could be a perfect fit. Maybe I could convince them to join the team.

To give you an example, meet Ioannis - number 4 of Pleo's People Team.

Ioannis studied Computer and Electrical Engineering. He has a deep interest in how products work - and also on how organisations are built. He can have deep discussions on new languages or frameworks that we could use in Pleo’s tech stack and at the same time he’s an advocate on how to be more human in how we work.

Out of the 11 of us today we’re a mixture of engineers, computer scientists, product owners, business analysts, entrepreneurs, salespeople and psychologists - and Ioannis. We’re a scattered bunch from South Africa, Greece, US, Kenya, Germany, Argentina, and Brasil. We’re building something for people that we deeply care about.

Scaling and building

The tricky thing with a hyper-growth company is that speed is pretty unpredictable. For our team, we try to think 6 months ahead. How we’ve tried to cope with change in a calm way is in our working style and in the way we aspire to build our careers.

Working style

Most of us in People Operations are product geeks. We find product teams to be a source of inspiration for us in terms of working style. We try to work agile with standups, retros and we’re heading into a sprint-planning phase soon.

We’re learning about planning poker and working in stories. We’re still in early stages here but so far it’s helped us to be more nimble and to jump in and support one another when we need it most.

T-shapes

No one in our team has been hired as a recruiter - and not one of us has a full time recruiting role. We tend to shy away from titles and build ourselves up with T-shaped profiles. Each person’s T-shape is about their skills and their own career development. We then collect these T-shapes and slot them into our shared purpose; we use this to figure out how to weigh our work accordingly. 

The joy of being a team of T-shapes means that we can jump in for one another where we need to - and we also have more flexibility to take on a full project when an opportunity arises that speaks to our specific skills and interests. This is motivating because very few of us want to work on hiring full time. Having this openness keeps us motivated and gives us a chance to grow in the direction that we want to take.

Growing out of our shoes

If we go back to how flat team structures work (good old Frederic Laloux again) they say that this type of structure works best with <10 people. So now, we’re too big. For this, we’ve needed to change our team structure.

This brought up another key question for us: how do you scale a flat hierarchy?

Venn, not ladder

The easy way for us and our stakeholders to have drawn this out would be through an org chart with set hierarchies. But as I’m sure you’ve guessed - that’s not how we’ve done it. Salaries in our team are based on the complexity that each person can handle. We feel that direct reports can bring complexity - but this isn’t our guiding star.

We’ve spent a long time trying to figure out how to scale this team without building silos or unnecessary structures, while still holding ourselves to clear goals and responsibilities. The drawing below is the simplest visual way I can explain how we’ll be working in 2020.

Hopefully, this brings the clarity and distinction of responsibilities that we need right now. We hope that smaller teams help us to focus on being more human, tie our shared purpose closer towards our own personal goals and that it encourages even more distributed decision-making.

...but will it scale?

A big question I often get asked is whether this will scale and to be honest I have no idea. For now, it’s worked. We’ve grown our headcount between 8-20% month on month. We hired 120 people in 2019. We’ve more than doubled. And we’ve stayed ahead of the curve in a lot of ways. 

The next big challenge for us is bringing proactive, useful support for all current employees - and move beyond the idea of People Operations having hiring as the majority focus. We have fantastic people in Pleo with which I am so lucky to work. Now it’s up to all of us to make sure that we develop, stay happy and get even better at what we love to do at work.

We have a couple of talks already lined up, a podcast or two and I have the most exciting chance to be a guest lecturer at CBS this year to share thoughts on Diversity and Inclusion.

What 2020 will bring

This year, I got another DM from our CEO, Jeppe. It was on New Years Day. This time, I was prepared. This time, he’d sent out 170+ personalised videos to each and every one of us. And again, he shared his thanks for the past year - as well as the challenge for this one. The plan: let’s go from 200 - 350 in headcount by year-end, increase our internal promotions and transfers - while keeping a happy and motivated company as we go.

PS.

If you’re interested in what we’re doing and are looking for people to jump on a stage, a podcast, or a blog and share some stories - please reach out. If you’re looking for a job we always have an “Open Application” job post. Applying there’s the quickest way to get our attention - better than a reach out on LinkedIn.

And lastly - to the lovely salespeople out there. I used to be one of you, I know just what it’s like so I thought it would be good to shed some transparency on how we work and what my budget looks like this year.

We only have people hiring internally, so please don’t reach out to try to sell us recruiting services. It’s just not something that’s ever worked for us - and we have a pretty firm stance here. In terms of new tooling (to all my SaaS guys), we’ve finalised our budgets for the year so we don’t have space for anything else. A lot of you send great, personalised reach outs and it breaks my heart when I can't get back to you. The trouble is that we get 100s of cold reach outs a month so unfortunately we just don’t have the time to reply. We’re not ignoring you - we’re just a lean team and need to use our time in the best way that we can.

To the rest of you out there, have a terrific 2020 and we’ll see you around!

?? Jessie & the People Team