Scaling a future of work culture
Interview with Jessie Scheepers, Head of people, at Pleo
A couple of weeks back, I met Jessie Scheepers from Pleo to talk about people operations and culture in their massively growing startup.
Listen in (or read the transcript below) to hear:
- what keeps Jessie up at night as the head of people
- how to avoid hierarchy and bureaucracy creeping in as you scale and grow
- what concrete things Jessie and her team is trying out
- what could larger organizations learn from startups and what is actually quite similar
Susan: Hi, Jessie. I just came in through your reception while you were having a big virtual announcement and everything was super quiet. And the first thing I noticed was this coffee machine that’s standing there. A self-service coffee machine, meaning that you have to take ownership of your own coffee, which is quite nice.
Jessie: Haha, yes, it’s kind of that whole feeling we want to establish — a bit homey, not super polished and formal.
Susan: So we we are here at the headquarters of Pleo. Jessie, you are obviously a big part of the team here. Could you tell us a little bit more about who you are and about your role here?
Jessie: Yeah, sure. So, my name is Jessie and I am the Head of people here. But I avoid my title at all costs. I am not a big title person. I’m originally South African, and have been living up here in the Nordics for about four years now, actually. Something that’s been the red thread through my career is that I’ve worked in a couple of different scale up environments. I started working in Cape Town, so got used to working in the emerging markets with completely different people and cultures. Before coming to the Nordics, I worked in the UK, Germany, theBaltics and France.
Susan: So I’m guessing there is no typical day in your work week. Even though you don’t like the title game, your job is to concern yourself with the people and the culture. What kind of activities are you working on? What what’s your main focus?
Jessie: When I joined Cleo a year ago was about the first time we had raised this series A. So I stepped into the situation, where we had great product market fit, raised capital and were doing well with around 50 people on staff. We decided it was time to expand into two new markets. A year later we’re 150 peole and my team, which was just me, has gone up to nine and actually 10 soon. Quite a scale up journey. So what a lot of my role has been is to build up that team and set the direction for people in Pleo that isn’t just reactive to keep the current people happy, but really trying to like look forward into the future. It’s pretty tricky when you’re growing like we do, having 20 new people starting at the beginning of this month.
Susan: Right. So being strategic about building up the business while executing. Before we dive into that, let’s go back to the beginning. If you think back at your first week at Pleo, how was that like? What did you occupy your time with? What did you talk about? How did you get started?
Jessie: One thing I noticed was how people reacted around me. Around HR! When I came in, this part of the business never existed before. So everybody at lunch would be like: “Oh, don’t say that — H.R. is here.”
The expectations were that “HR” were going to be this reactive support structure, that is there to enforce company policies. So, my job was to try to change that mindset, which took a lot of talking to people.
Susan: It’s so funny because, from the outside, you would think that in a startup environment people would bring a different mindset than you expect in corporate. But perhaps we’re shaped so much earlier in life about that expectation, like in high school, in university, or in internships, we’ve taken. Even though you think you want to be in a fast moving business, you still have this weird perception of what it actually is that we need to do about people development.
Jessie: Yeah, exactly. It’s very interesting because whenever you’re building something new and it’s a bit scary and unknown, I think a lot of people just look back to what’s been past successes. And it’s very scary to do something that might not exist today. So, yeah, whenever someone’s building teams or building up new, new things in a business, I think it’s the same problem wherever you go. Sometimes it’s probably a good idea just to stick with what’s worked. Sure. But I didn’t do that. I rocked the boat wherever possible.
Susan: What have you done concretely to change the mindset?
Jessie: The way I look at it is that we are the team that focuses on anyone from the first day they hear about Pleo until the day they leave. The whole experience. I started by asking: where’s the biggest pain? And surprise, surprise, it was on hiring. So I started there. I mean the whole company is build on the idea that Pleo is a future workplace product. If you trust someone enough to hire them, trust them enough to spend company money. Pretty simple. So that trust and that feeling of treating someone like a human is what I tried to start bringing out through hiring. How do you show that it’s a really great place to work externally and not just get lost in the crowd? How do you stand out? How do you create visibility? One thing we focused on is to be authentic, which I think was interesting because a lot of people didn’t expect that. It set up really good foundation because it changed the perception quite quickly.
Susan: Do you remember any reactions of people when you “rocked the boat”?
Jessie: Yes, a couple of different things. First off, engineers are notoriously tough to hire, especially software engineers. Everyone’s like, oh, you never going to get this right. In my first month, I made a promise to hire two front end engineers. So I I searched for hundreds of hundreds of people around the world. I hired two incredible guys that work remotely. That was the proof to gain the trust we needed internally. Secondly, when I hired for my own team. no one came with a typical recruiting or H.R. background. And people were very dubious.
Susan: So you’re saying that you’re very conscious of hiring people from different perspectives, different backgrounds. How does that shape the way you work with people internally?
Jessie: Well, if you hire the same profiles over and over, you’ll be answering problems in the same way. What we really focus on is diversity of thought, which is a bit different. An example: The people ops person who focuses on looking after people in product has a background in computer science or engineering. There’s such a natural connection and appreciation for the work, they speak the language, and you become much more embedded than “normal support functions”. They come to their stand ups. They know exactly what’s happening. That’s been really cool to see because I wasn’t sure if it would work.
And I mean, honestly, we got a whole bunch of things wrong. We do not have strict policies to settle or exact knowledge of how to do certain things. But we learn as we go. I think talking to your peers collectively in the company, there’s a lot of knowledge.
Susan: That’s a tricky bit for a lot of organizations- knowledge that is hidden in pockets everywhere. How do you actually make that visible, bring it out? Even though people weren’t necessarily hired for that specific skill, they bring a whole “backpack” full of knowledge and skill that you might not even be aware of it.
Jessie: Such a tough question.It’s actually something I’m focusing on this morning because there’s so much potential. Something that’s been very interesting, was to witness other teams being really autonomous and putting their hands up. Instead of trying to control it, I said let’s try it out. For example, we have this most incredible woman in sales, Marie-Louise, who does sales enablement. When we hire a lot of high potential sales people, she does a sales bootcamp to train them from everything she’s learned. Nobody asked her, it’s not part of her job — but she just had energy for it.
Susan: You are going from the mindset of we are here to provide to the concept of we’re here to create the conditions for you and creating a platform to maybe multiply it.
Looking at your current growth and the way you are hiring and expanding. How do you maintain and scale that culture of trust that is so crucial to your business?
Jessie: Trust is a big one for us. It’s one of the biggest things we look for in a hiring process. We give loads and loads of feedback when we’re hiring. And we have about eight different people who meet you during your journey. You start to develop this relationship early on and develop a strong relationship with the persons you might work with. Even when we’ve rejected someone, they come back with reflections and appreciation for the feedback they receive along the way.
But if you see someone putting up these walls and not really trusting you in the process, we don’t make an offer — even if it is a super impressive resume with experience from top tech companies. That is quite an unpopular decision. It also sends a huge signal into the organization. This is top priority for us. This is the guiding principle number one.
What makes my role so much fun is that our product is inherently trust-based. So we have to build an internal future workplace to not be hypocrites. That’s also your best argument card if people are resisting something like working hundred percent remotely.
Susan: There’s the inherent element of building and maintaining trust. There’s a recruitment part of your business, which is huge. Are there any other headaches that you currently have that you’re dealing with?
Jessie: You get to this tipping point that I think every company or different teams gets to where you’re deciding on the operational structure of how you’re building the teams and how different parts of the company work together. How do you share knowledge to make sure two different teams aren’t trying to solve the same problem? How do you build teams without building up too much unnecessary structure around it?
Susan: Where do you get that inspiration? Or is it more experimental?
Jessie: A bit of everything. Speaking to other companies and then having the freedom to test it out. Even if we don’t know if something will work for the company, we try a lot of things out within people ops. If it doesn’t work, it’s totally OK to back to the drawing board. You learn something. But just trying to roll something out across a growing company would not work.
Susan: What are some of the most recent things you’ve tried out with a new team?
Jessie: Like I said earlier, I’m not a big fan of traditional hierarchies. The way we divide our team is how much complexity you can deal with. Your salary is based on that. When you feel comfortable, you can take up more. Part of that is also peer-to-peer feedback to become more self-managed. Once a quarter, we have now also started what we call “the uncomfortable session”.
What we do is give feedback on every single person before we meet. It’s very structured — five words about them, three things they do well and three things they could do or stop doing. Then we all stand in a room to read the input, unedited and raw. Person by person we do a round robin. Each person has a minute to tell their peer what they’ve seen working and what hasn’t been working, finishing with a self-review. We finish up with making an action plan on who can help whom with what.
How to give feedback in a compassionate way is an important skill to learn. The first time we tried it, you could cut the tension with a knife. Everyone’s sitting a bit freaked out. But now we’re all quite used to it.
Susan: Are there teams trying this out as well or is it still at the stage where you’re prototyping it?
Jessie: We do a lot of internal promotions to help, especially our new managers. We’ve been starting to nudge people also invited people to our sessions I’ve also shared openly what people have said about me. We need to make that shift as a leader. You don’t have to be perfect. You don’t have to know all the answers. Feedback is vital because that’s the only way you can do the job you’re supposed to do, which is to create the space for other people and transparency.
Susan: Speaking about transparency and vulnerability, that’s easier to do face to face. You sit down with the person. You have a coffee. You look them in the eye and say, I’m sorry. What about all of your remote workers? The people that are not sitting next to you. That might not feel that immediate sense of belonging. How do you bring those in and what do others in your organization do?
Jessie: You need to jump on a phone and do not write anything down. We have a new rule in our team with our stakeholders that if we write something that’s more than two sentences long, let’s rather get on the phone. But it’s hard for people to feel included, not just from a work related note. What we’re trying to do is to tune in for a chat about what you eat for lunch or how are you doing. One of our guys works in Canada, so I randomly call him when I am making dinner and he’s making lunch. We just catch up.
Our office manager focuses not just on our physical office here in Copenhagen, but all “offices”. So when it was Easter time, we all had Easter eggs on our desks on the day and he sent Easter eggs to every single remote offices. Even though maybe not everyone celebrates Easter, it’s a small thing. But if you didn’t do it, it’s a trigger for someone to not feel included, again.
Susan: Looking into the different challenges that you have, they don’t sound that far off to any other organization when it comes to the internal workplace, creating a future workplace. What are the things that you have tried out and worked that larger organizations could copy with pride?
Jessie: The really interesting thing is whenever I’m speaking to people from larger companies is that most people have a misconception about working in small teams. Just because you’re a big company, you are still made up of many smaller teams. Run an experiment in that team and find a manager that is supporting them. It’s actually very easy to try to be more vulnerable or offer flexibility. Maybe that’s just an experiment within your team. Ask yourself: Would I put my head on the chopping block for this? And if it’s okay, that also gives you the confidence to try more things. But at one point you need some top down freedom or trust. There is a reason there are only so few stories about large companies that have done that.
If you want to read more about the future of work experiments that Pleo is running, head to their blog
Reach Jessie Scheepers on Linkedin if you wanna hear more about her “uncomfortable sessions”
Last but not least, like we said at the end of the podcast, if you have found the formula for scaling culture, it’s about time you share it… :)
