Michelle Cheng, Notion's Talent Director, sits down with Harrison Rose, co-founder of Paddle, to talk about the leadership lessons that shaped how he and co-founder, Christian Owens, went from the pair of them, to leading over 300 Paddlers.

Building a team from 1 to 100 people with Michelle Cheng: Growing Paddle’s team over a decade with Harrison Rose

Michelle Cheng, Notion's Talent Director, sits down with Harrison Rose, co-founder of Paddle, to talk about the leadership lessons that shaped how he and co-founder, Christian Owens, went from the pair of them, to leading over 300 Paddlers.

Amid uncertain fundraising conditions, widespread hiring freezes and a global cost of living crisis, founders are facing insurmountable pressure as leaders. Everyone is watching from the wings to see whether founders rise to the challenge of navigating their organisation through difficult times.

I spoke with Harrison Rose, CEO of GoodFit and co-founder of Paddle about the leadership lessons that shaped how he and co-founder, Christian Owens, went from the pair of them, to leading over 300 Paddlers to its $1.4B valuation. 

This personal transformation involved with building a company is often overlooked, but we would be remiss not to credit it as one of the single most important factors in a startup’s success. Great leaders are made from a culmination of key moments, and these are just a few that Harrison had to share on the subject of building a team. 

1 - 30 People

Recognising we were creating a movement, not just a business 

The average age of founders in the UK is 36, and then 43 when they take their company to IPO. While this isn’t as young as mainstream media might have us believe, most founders are building the plane for the first time while flying it. 

Christian and Harrison were 18 when they started Paddle. Pre-product and pre-revenue, team members weren’t choosing to join based on Paddle’s performance, but rather based on a belief that they had a problem worth solving and confidence in Christian and Harrison as the right people to solve it. A saying Chris Tottman has for this is “you’re persuading the most highly intelligent, highly rational people in the world to do something completely irrational and join you on the journey”. People are deciding to take a leap of faith and join based on the personal credibility of the founders. 

“From 20 to 30 people,  you're creating a movement. You’re looking for a group of people that believe in the change in the world you're trying to drive.”

Harrison’s advice to founders for winning over great people was simple: make it clear you're working in the best interests of the company and everyone in it. Of course, it’s easier said than done, but one thing Harrison and Christian did right was that they had the self-awareness to recognise and, more importantly, admit that they were doing it all for the first time. Rather than pretend to have everything nailed, they established a culture where they asked for permission to learn and as a result, granted others to do the same. 

“It's one of the things I'm the most proud of. We didn't realise that, as founders, we had the absolute luxury that we could be our whole authentic selves. We created an environment where people could be themselves and tell us if they disagreed.”

Walking through the office, Paddle felt like a place where brilliant people were learning from one another and were empowered to challenge each other across all levels. There was a high degree of trust and guests would be routinely greeted by one of the cofounders sitting on the couch in reception. It worked and it was beautiful. But it didn’t scale. 

30-120 People

Getting used to not just being ‘me’, but rather a cultural figurehead

After their Series A, Paddle grew by 400% from 30 to 120 people in eight months. New team members joined in droves. Eventually, they needed to knock down a wall and spill into the neighbouring office space. Once that space was also exhausted, they bought scooters for quickly getting to a second office. Characterising the happy chaos of this period, someone promptly broke their wrist in the first two weeks after catapulting themselves off a curb on one of the scooters.

Amid this hypergrowth, something changed. Hiring almost a hundred new people meant that the cofounders no longer had a hand in selecting each hire or even knew individuals by name. 

“It was no longer twenty mad people that had jumped on board to change the world together.  I started to see the way I brought myself to work needed to change.” 

At this point, team members began expressing a desire to be led and inspired. It wasn’t a demand on Harrison and Christian to change who they were fundamentally, or start acting inauthentically, but rather a switch in awareness. Harrison recognised that eyes were on him. People were clocking his mood, which meetings he was attending and which he chose to sit out. Communication and ‘optics’ became an extra consideration. Whether he liked it or not, people were looking to him for cues on what they could say and do. 

Taking responsibility for how my messaging is understood

Harrison didn’t profess to be perfect throughout this stage. Initially, his preferred mode of communication was long form, stream-of-consciousness memos popped into the company slack. It was the most efficient way for him to communicate and he figured anyone that didn’t understand probably didn’t belong at Paddle anyway. On reflection, Harrison admitted this was a mistake: 

“You must assume responsibility for how you want people to perceive and understand what you’re communicating. Focus less on how you prefer delivering it.”

Harrison became more intentional about how he communicated. Entangled within all of this was the pressure associated with being a ‘cultural figurehead’. 

“You’re not just you anymore. People look to you for inspiration to define what’s possible for themselves. Your actions don’t belong to you, and contribute to the canon and mythology of how a founder should look and behave.”

It’s impossible and unrealistic to expect any leader to perfectly fulfil the expectations of hundreds of people. Founders quickly realise they don’t need to do everything themselves and that they don’t need to learn everything firsthand, for the first time. It’s here the value of hiring game-changing executives can pay off in spades. 

120 to 300+

Accepting the cycles and seasons of people 

On average, leadership hiring processes take over six months and generally only 40% of external executive searches transplant effectively after a year. Internal promotions tend to be better accepted by peers, contribute positively to company culture and have better long-term tenure. Unsurprisingly, founders prefer hiring from their own ranks. This was precisely what happened at Paddle: 

“You read about it everywhere, yet we did it wrong and everyone still does this wrong. You really do need to resist the temptation to exclusively promote from within.”

When it comes to building a leadership team, growing at such a breakneck speed forces a sort of reckoning in personal development. If people don't upskill at the same rate as the company, stagnation occurs at the cost of growth and the relationship can become strained. Throughout Paddle’s journey, Harrison oversaw the complete turnover of a few management teams. Reflecting on these cohorts of leaders, a signal of success in a hire was finding someone others were excited to work for. Counterintuitively, adding an extra ‘layer’ on the team wasn’t always a bad thing and promoting a top performer wouldn’t always be doing them a favour. 

Leading through uncertainty wasn’t easy, especially during periods where unpopular operating decisions had to be announced. During one such incident, Harrison and Christian found themselves the target of vitriol on company channels. Situations like this might deter one from ever embarking on the founder journey, but Harrison took a different perspective. He saw the value in these moments as formative to his own abilities as a leader, and to shaping Paddle’s culture. 

“Christian and I are unrecognisable from the day that we started Paddle over 10 years ago. On so many levels, not just because of the grey hair.”
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