Sit down with Peppy’s SVP Growth – Rob Massa

Introduce yourself to us. Tell us about you, your life and your career before Peppy.

My name is Rob Massa, I’m the SVP Growth here at Peppy. I’ve spent the last 17 years in high growth VC backed startups and I’m really passionate about building commercial organisations.

Originally I’m from the US and I moved to London about six years ago when I was working for a startup called BounceX, which is now called Wunderkind. We grew the business from $8 million in ARR (annual recurring revenue) to $100m ARR. During my time at Wunderkind, I was asked to move to London to build out the European expansion, which is how I ended up in the UK. That was supposed to be a two year stint before returning to the US, but here I am six years later sitting at a WeWork in Covent Garden working for Peppy!

Outside of work I love spending time with my family and friends, my children and my wife. I’m also really into fitness, if I don’t incorporate some sort of fitness or meditation into my daily routine I get super stressed. I make sure to do that to get all the endorphins so I am able to do my job in the best way possible.

What attracted you to join Peppy?

When I was first approached by Peppy – Healthtech wasn’t something that ever really crossed my mind. However, as my conversations evolved with the team at Peppy, I was really bought into the Peppy mission and what it stood for!

One thing people don’t know about me is that I have a big personal connection to men’s health issues. I watched my father wait way too long to call the doctor. He had a few issues for quite a while and he finally called the doctor and got diagnosed with bladder cancer, he unfortunately passed away six months later. I often think if he had called the doctor a little bit earlier, or had something like Peppy where he had access to advice and support at his fingertips, things may have been different. So the more I was learning about Peppy and the mission it struck a chord with me and led me to joining the team.

How has that evolved over the last year?

When I first joined, I was motivated by our mission to democratise access to personalised healthcare services, to make it as inclusive, engaging, and universally available.

Over the course of this past year, this motivation has gotten even stronger. It’s one thing to appreciate a mission from the outside and another to be directly involved in its success. I’ve had the chance to witness how our services empower people, improve their health, and elevate their quality of life. The stories I hear from our users have been incredibly moving. It’s not just about offering a service; it’s about being there for individuals during their vulnerable moments, providing guidance, support, and care when they need it most.

What does the SVP growth do at Peppy?

As the SVP Growth at Peppy, I essentially oversee anything that drives revenue into the business. I oversee all of Sales, Sales Development, Marketing, Partnerships, and Client Success. Ultimately I’m responsible for driving the top line number and helping my team overachieve and succeed at every opportunity.

What impact do you feel that you and your team have had on Peppy’s success over the last year?

It’s been quite a journey over the last year. We saw a lot of growth towards the end of last year which was awesome! Obviously, market conditions are a little slower this year, but we’re still doing fantastic in relation to the current market.

One of the things that I’ve really enjoyed has been working with our Growth leadership team (Sales, Sales Development, Partnerships, Marketing and Client Success). We’ve formed a very close group and work cross functionally with one another. That’s made a major positive impact particularly on the experience that each Growth employee has.

The Growth team as a whole has a massive impact on Peppy’s success, because our roles touch many different layers of the customer journey. Everything from generating new leads via marketing campaigns to bringing a customer onboard to leading renewal and expansion conversations; almost every interaction the customer goes through is with the growth team.

Most importantly, we’re responsible for getting Peppy into the hands of the people that really need it. It’s really nice to take the skills I’ve learned over the last 15 years to do something that’s actually positively impacting thousands of people on a daily basis.

What is your single greatest achievement so far at Peppy?

Peppy successfully raised $45m in Series B funding in the beginning of this year, which was an incredible feat. Going into the fundraise conversations, we as a business needed to make sure we were in the best position possible to be able to secure the capital that we need. It was critical that we weren’t just hitting our revenue targets, but overachieving on them.

For the first 6 months in my role I focused on enabling the Growth team to accelerate our growth really quickly, which led us to successfully overachieve on our revenue targets last year. This set us up for landing the funding that we needed to continue thriving and scaling. For me, that has been my biggest accomplishment since being at Peppy.

Which personality trait of yours has served you best for your success for Peppy?

At Peppy, like at any startup, there’s sometimes lots of balls in the air and things move and shift quite quickly. I believe one of the things that I do quite well is multitask – it has definitely served me well because there’s always so many things going on which I’m able to stay on top of.

If you could click your fingers and move departments within Peppy; which department would you move to and why?

I would move into the Men’s Health Practitioners team. I’d like to be able to give men who are seeking help, the support and advice they need daily and help them with their health issues. Particularly because of my personal connection to Men’s Health issues, I think it would be quite rewarding work.

Who within the Peppy team inspires you? And why?

I can’t pick just one person so I would say the entire clinical team inspires me, because of the huge impact they’re having on people’s lives. We have seen in many cases that they’ve gone as far as potentially saving people’s lives, which is incredible. This is really inspiring to me and it keeps me going on a daily basis just thinking about it!

If you would like to work with people like Rob Massa, make sure to check out our careers page here!