Interview with Rowan Bailey, Co-Founder of Workbounce and former Head of RevOps at Peakon
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Interview with Rowan Bailey, Co-Founder of Workbounce and former Head of RevOps at Peakon

Created
February 7, 2022
Tags
Revenue Ops
Author
Charlene Chen

We kicked off this year by interviewing Rowan Bailey, Co-Founder of Workbounce and former Head of Revenue Operations at Peakon (acquired by Workday).

"I ended up following a career path I didn’t imagine when I started, which came from the need to solve larger-scale problems for the sake of my own sanity!”
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Rowan, what has been your professional journey? Did you know that a career in operations was something you wanted to pursue or did you fall into it?

I knew pretty early on that the start-up scene was where I wanted to be. Aside from the smaller teams, higher autonomy and the general “get sh*t done” attitude, the background threat of extinction seemed like a great way to learn a lot, fast. I applied to join Perkbox back in 2015 and enrolled a month later as a post-sale account manager.

I ended up following a career path I didn’t imagine when I started, which came from the need to solve larger-scale problems for the sake of my own sanity! We were enjoying the early stages of rapid growth, which meant handling a sudden influx of customers with the classic “build the plane after you’ve jumped off the cliff” approach. I scaled the customer success team before moving over to a pure ops/business intelligence role. The team was serious fun, I loved the adrenaline, and learned a lot.

"If a system isn’t being used, a process adopted, a data point used to make better decisions, be a hero and get rid of it.”

In 2017 I joined the Peakon team just as they opened their new London office with the mandate of building out a Rev Ops function. The company grew fast, through several stages of complexity and maturity (e.g. multi-territory, multi-product) which were fun to tackle from an ops angle, especially alongside a talented team. Peakon was an incredible blend of values-driven decision-making and raw energy. The formula worked well, leading to a  $700M acquisition by Workday last year.

I’m now building Workbounce with my co-founder Adam to tackle some of the challenges we faced scaling the GTM function at Peakon, reducing friction for customer-facing reps finding and sharing information. We’re building remote-first, which I’m excited by and am approaching as one big operations challenge. It’s a chance to build efficiently and bake in some core beliefs we have, such as outcomes over hours. It’s a lot of work, but I’m loving it.

What are some of the biggest lessons you have learned in your ops career?

Without getting too philosophical, I think the biggest changes in my thinking have occurred in my approach to problem-solving. As with all impactful lessons, there’s nothing like learning the hard way.

  • Don’t confuse people problems with tech problems.

If your reps aren’t getting replies to their messages, buying a new engagement tool to scale their efforts won’t help. Tech can all too easily gloss over or distract from a fundamentally flawed approach. This buys time and a nice scapegoat when ultimately things don’t improve, but meaningful change comes about when first principles are constantly under the microscope. The opposite is also true. Throwing new hires at missing or poorly leveraged tech is expensive.

  • Take a breath, and listen.

The urge to start solving a problem straight away is strong and hard to ignore. This seems to be a familiar trait across other operations professionals I’ve had the pleasure of meeting and working with. Jumping into solution design on a solo hunt for an answer and a dopamine hit is tempting, but deliberately slowing down and listening helps you triangulate, prioritise, and sharpens your proverbial axe. Building slack in the system to allow for this is essential to give yourself the space to listen, manoeuvre and get creative.

  • Keep things simple.

This is probably the biggest one for me, and easier said than done. Debt compounds fast, and it becomes increasingly difficult to resurface. Not all problems require additive solutions, most of the large and most satisfying advances stem from subtraction. A quick Google yielded the quote I’d half-remembered - "Great design is eliminating all unnecessary details." - Minh D. Tran. If a system isn’t being used, a process adopted, a data point used to make better decisions, be a hero and get rid of it.

"Tech can all too easily gloss over or distract from a fundamentally flawed approach. Meaningful change comes about when first principles are constantly under the microscope.”

What resources have inspired you and helped you to develop professionally during your ops career?

Engaging with operations communities and user groups was a real eye-opener and something I wish I’d started earlier, especially when operating as a “team of one”. I’ve met so many people that have been incredibly generous with their time and insight. My favourite forms of engaging with communities are in-person events where possible, or 1:1 conversations.

Related to the above, being proactive in networking. I’ve found reaching out directly to people whose work I respect and am curious to learn more about generally leads to great conversations.

I’ve also been fortunate with great colleagues and managers who all taught me a lot.

What inspired you to focus on Revenue Operations/start a Revenue Enablement company?

Operations and Enablement are two sides of the same coin where output is highly leveraged. Reducing friction and providing insights for a whole team is rewarding in its own right, but it’s exciting that we’re now able to achieve that for many companies at once. That’s the inspiration behind Workbounce, removing drag in finding and sharing information and driving valuable customer interactions.

What do you think are some of the most useful skills to have as a Revenue Ops professional?

Aside from the ability to teach yourself, the most useful skills are probably soft skills. Being inquisitive, proactive and analytical will mean you ask questions, build, then ask more questions.

A strange blend of positivity and cynicism also seems to be beneficial—a balance between “anything is possible” and “but that doesn’t mean we should do it”.

Communication skills and patience come into play hugely, more than I appreciated when I started out. Gathering requirements, getting buy-in and buying yourself time to build thoughtfully all lean on your ability to communicate with others.

If someone wanted to learn how to be a great RevOps professional, what advice would you give them?

Take the time to deeply understand the roles (internal customers) you’re trying to serve. Even if you’ve been in a Marketing/Sales/CS role yourself, your understanding of the current day-to-day, objectives and frustrations of the teams you’re working with is essential to designing and building solutions that get adopted. This means being open to learning new ways of doing things and trying not to form your own unshakeable opinion too fast.

Talk to other ops pros and demo what people are building out there, even when you’re not actively looking for a solution. Your wider understanding of how others think about scaling challenges will give you a large arsenal to draw from when you encounter problems that feel similar.

What do you hope your career in operations/entrepreneurship will bring in the near/long-term future?

Short-term, I’m seriously excited about the prospect of building a remote-first company. It’s one big operations challenge I’ve not faced before. I’m hoping we can lead from the front in empowering individuals to work asynchronously with a high degree of autonomy, whilst still building an enjoyable and supportive team environment where people can do work they are proud of.

This feels slightly contradictory, so will require some creativity to pull off. Building a culture of written communication and documentation, budgeting for quarterly meet-ups, VR headsets, and removing Slack as a comms crutch are all on the table at the moment.

Rapid-Fire Questions Inspired by Brené Brown's Dare to Lead podcast:

ON: What is one thing you’re deeply grateful for right now?

Rowan: The freedom to work remotely - I’ve been travelling in Portugal for the last few months and have been absolutely loving it.

ON: If you could snap your fingers and improve one operational inefficiency in your company, what would it be?

Rowan: Anything HMRC related.

ON: Fill in the blank: Operations is...

Rowan: Exploration.