From 3 to 20 designers : One year in a scale-up

Hello! I’m Paul, design manager at Pennylane. When I joined the company a year and a half after its creation, the design team was relatively small, and our presence wasn’t as prominent as it is now. However, I consider myself fortunate to be one of the early designers who witnessed and played a part in the entire story that I’m about to share.

Start from (nearly) scratch

This story starts in December 2021. For context, at that time I had been a Pennylaner for 3 months. We had recently reached the milestone of a 1000 client-companies when Pennylane was about to celebrate its 2 years of existence, with more or less a hundred employees onboard, including an internal accounting firm — the Lab.

On the design side, we were a team of 3 designers, split between 7 squads. One designer was focused on the Accounting side of the business. I worked on the SME (Small Medium Enterprises) side, basically the business owners interface of Pennylane, and our Product Design Manager worked on the transversal topics (Growth and Accounting Firm experience). Having to digest business and accounting knowledge while designing for two teams was a challenge in itself. Even more so when you have to build features from the ground up.

But our scaling ambitions were set by company leadership: we were anticipating the design team to grow up to 20 people by the end of the next calendar year. At the start of December I onboarded our 4th designer as she took over the scope I was responsible for. Knowing the growth to come, our design manager offered me to embrace the management path, that I would be testing with our new recruit. This is how, after 4 months at the company, I became a manager and this is when serious business definitely started for our team.

Hiring the team we dreamed about

Moving from 4 to 16ish designers was the target. With recent hires, I had the chance to move onto the accounting side, learning a whole new vertical. Working in a scale-up can also mean having to adapt and be able to embrace new teams and scopes on a frequent basis. The co-founders had complete trust in us to create the perfect team. Each arrival empowered everyone and added substance and identity to the team.

Regarding the hiring process, we wanted to keep it compact while making sure we had enough contact points and assessments to be confident on the profiles. After a technical exercise, the key step was the “fit interview” where other people from the company — not only designers, would discuss with the candidates. We recruited people at every seniority level, yet all juniors were actually coming from career changes via bootcamps and had previous experiences to vouch for them. This usually ensures a quicker ramp-up.

A typical month for the team at the time was :

• 3 to 5 recruitment interviews a week per person
• 1 to 3 design newcomers per month to staff, onboard and train
• Continuous delivery in a fast pace environment in a team

On top of that, I started to learn management and added weekly individual meetings with each newcomer to monitor all probation periods and assuring their ramp-up.

Six months later, in June 2022, the team was composed of 15 designers. Amongst them were 2 Design Managers and 2 IC Leads, all working in their own squad, and 1 Design System specialist.

Stabilise, structure, build to last

With almost all squads staffed, we were seeing the end of the line. Three or four more designers to find, a new Head of Design and we were good to go. At that time, the company decided to adjust the growth to the worldwide business context which was riskier ; a slow-down policy that was more than welcome. We finally had time to focus a bit more on the existing team and less on recruitment.

First of all, we could leverage on this new work force to progress on design centric initiatives, such as developing the design system ; namely write the documentation of all components. It was a way to both structure our tools and introduce the various components to the whole team. We also developed a better inter-departmental relationship with brand and started to use more and more brand assets in our product.

A second initiative was to create two “tracks” (or 2 groups of squads), mainly based on the SME and Accounting segmentation of our product. This allowed us to create focused design teams and accelerate knowledge-sharing and ramp-up on those 2 verticals.

We also took the time to reflect on the culture of the team, making sure everyone felt represented and serene in this growing environment. That was also a good time to question established rituals, keeping the good ones (a bi-weekly to share the knowledge, a morning coffee to kick-off the week) and cancelling the time-consuming formalities. We were also able to define our key project milestones, allowing a good collaboration between every profession.

Finally, we redefined our objectives as designers. We built a career-path for everyone to have guidelines to progress. The main takeaway was a shift in the ownership. As the team grew, we developed a better understanding of the business, unlocking the capacity to be more assertive in strategic discussions, bringing design topics into the roadmaps. Among those, we can quote a rebranding, a global UX overhaul to simplify half of the product, brand-new tables and a rework of the navigation.

Mistakes, Successes and Learnings

By going this fast and learning by doing, we made mistakes. The main ones I will remember were:

• Recruiting fast can make you recruit the wrong profiles. No matter how hard everyone tries to make it fit, sometimes the best options is to move on, admit the mistake early and end the collaboration. Never an easy moment, but ultimately, it is for the best of everyone involved.
• Staffing fast can put people in a position where they’re not set up for success. Seniority, personality fit, team dynamics, profile polarity are numerous variables you can’t anticipate in an ever-changing environment. Try to be flexible and open to staff change if someone seems to underperform in their current setup.
• Lack of anticipation can also be your worst enemy. When you’re busy extinguishing fires, you always light up the sparks of the next one. Take some time for a step back to discuss with your peers the potential challenges ahead.

That being said, after a year, a lot of things are also successful. The team’s motivation and dynamic are very good, the product is growing well, the design debt is getting smaller by the day. None of this would have been possible without a strong trust between each other, and the support from both the leadership and the recruitment team.

The least I can say is I grew and experienced a lot within a year. Way more than in my previous jobs. Pennylane is definitely a place I would recommend if you’re ready to learn fast and get challenged on a regular basis.

A story by Paul Le Texier, Designer Manager at Pennylane