Brónagh Crowley is a scaleup master. She takes teams and companies from very small, to very large, very fast.
Brónagh gained her experience (and a few scars) as an early team member at three hyper growth startups - Hopin, Adyen and Web Summit. She is currently leading the sales organisation at Ultimate, AI powered customer support platform.
I spoke to Brónagh about the importance of good hiring, the growing appreciation of second or third time founders, and her slam-dunk interview question.
Cecily Motley: What start up story do you whip out at dinner parties to break the ice?
Brónagh Crowley: I’ve worked in startups for about 12 years. Some a lot smaller than others so we had to learn to be creative to be taken seriously by new customers. For about a year and a half, I had a fake assistant called Wendy who used to schedule all my meetings and had her own email, her own LinkedIn and her own life story. Anytime I was late or early for meetings Wendy would let them know. But it was always me. That worked quite well until we actually hired someone called Wendy, and she wanted the email address back.
CM: That’s one of the best ones I’ve heard. When it comes to managing teams, what is your greatest management success?
BC: If there’s something I’m proud of in my career it’s the teams I’ve hired. I’ve been fortunate to hire some incredible people and even rehired those early hires later, which is something I’m very grateful for. I’ve also had success with moving people into the right roles. At startups, you can hire someone in one role or team, realise they're in the wrong position but that they're incredibly talented in other areas, and you have that ability to move them to where they're going to be most successful. That’s something I really enjoy.
CM: What’s your ‘slam dunk’ interview question?
BC: I actually stole this from a former colleague (shout out to Peter). “Do you consider yourself a lucky person?” I’ve found that the people who do consider themselves lucky will always find a way and if they can’t, they’ll make one. Especially within a startup, that kind of mindset is crucial, so this question really distinguishes between who will thrive and who won’t. It’s been a really interesting barometer.
CM: You’ve managed a range of different sized teams. What are your teams’ biggest challenges?
BC: I think challenges definitely grow as the teams get larger. In terms of daily challenges, I would say - within a sales organisation - it's surprising the amount of refereeing you do. There have been some quite prickly conversations when implementing rules of engagement across a competitive sales team.
CM: How do you embed a positive culture in those really competitive environments?
BC: I think it comes back to hiring. I love competitive salespeople but I also prize kind people. And how would I know this? In an interview, I will ask them to describe times that they’ve had conflict within their teams, greatest mistakes they made or even stories of their work achievements can share a lot about their ability to work well with and credit other people. Its very important to go deep on every question.
At the end of the day, a lone shark might be very successful if you are opening up somewhere isolated such as Australia, for example, when you need someone who can work very independently. But what I've found is that if you do let someone quite toxic into a team, the ripple effect across your team’s productivity is immense. While I do want that competitive, ambitious person, I still want someone who's kind and will be a positive culture add. I think it's also important we say “culture add,” not “ culture fit,” because we need to welcome diversity of every kind.
CM: What has been your biggest people blunder?
BC: This was a long time ago, but I had a colleague who accidentally emailed the wrong team that they were all getting a pay rise. So that team then realised they were underpaid, and that the other team were getting a pay rise and they were not. The outcome of that was tricky to deal with to say the least! It hit home the importance of planning pay transparency and levelling across an organisation, which I believe in.
CM: What do you waste the most time on?
BC: Slack notifications. I do have them switched off but the amount of times I’m in “deep work” and I go into Slack to check something and I’ve been mentioned in 30 posts. It’s so distracting, even if I’ve only been CC’d for visibility. I love working with people from different time zones because I get those quiet windows, or I often find I do my best work at night. I’m also trying to put in as few meetings as possible on a Friday, because that is typically the day for wrapping up, so I try to get as much focussed, quiet work as possible.
The book Deep Work by Cal Newport talks about the fallacy of multitasking; it just doesn’t exist. I always try really hard to get a few hours of that deep work but Slack does make that challenging.
CM: What would you pay good money to know about your peers and competitors?
BC: To be honest I try not to focus on either. I think you can waste a lot of time focusing on the competition. We try to focus on our customers instead: what do they need? What do they care about? That’s the way to be the best product for them.
Focusing on your peers can also be harmful because you’re worrying about what someone else is or isn’t doing. What I say to my teams, and what I try to focus on myself, is: are you making progress on who you were yesterday? You need a lot of focus in a job like this. If your eyes are elsewhere, that's distracting.
CM: Do you think AI is going to take your job?
Personally, no. I think there is a lot of fear mongering around that right now but also I'm lucky that I’ve primarily always worked within a client and sales-facing role, so my work is very relationship driven, internally and externally.
But I think AI will remove a lot of the mundane aspects of my job. It also helps my teams become much more efficient: we've got auto note-taking and call summaries and so on now; all those parts of the job that you don't want to do but take up a lot of time.
CM: You started working in startups 12 years ago. What has been the biggest behavioural shift you’ve seen since the beginning of your career?
BC: I started working in startups in my 20s. I think at that time there was a culture of celebration around 30 under 30, the younger the better; it was very much about the wunderkind. 12 years later, we’ve seen that there are some startups that have really gone awry due to a lack of experience. What I’m seeing now is that people appreciate the companies who are coming at it with that second or third time founder. The average age of a successful company founder today is around 45. So there’s less of a ‘stars in their eyes’ for that 20-year-old genius who’s coming to take over the world. There’s a lot more understanding and appreciation of people who now have the experience and mileage to go the distance.
CM: What do you think will be the biggest behavioural shift in the next 12 years?
BC: Well I think AI and its potentially transformative effects goes without saying. I think the world of work we all experience today will be dramatically different over the next decade.
The other thing is this persistent shift towards remote work. I think it is a huge social equaliser, the fact that you suddenly have almost no limits on where or who you can hire: from the city or country they live in, all the way through to their personal situation - whether they are at home working as a carer, whether they have a disability. I think that's an incredibly positive thing for global society. Meta has paid £149 million to break their office lease; I don’t think this trend is going away. And we’re actually seeing new communities cropping up instead. For example, I know a lot of remote workers who have become much more engaged in their local community. What they used to have in an office - after an hour and a half commute - is actually within their own village or small town. I don’t think that’s going anywhere.
CM: What’s your life hack?
BC: Always ask for a discount. I used to tell my sales team to do this to practise negotiation. I kept prompting them: next time you’re booking a hotel? Call and ask for a discount. Next time you’re in a vintage shop? Ask for a discount. It is surprising how far you get. It’s also very satisfying!