How solving hard problems drives career growth with ClassPass’ CRO Brian Fields

The hardest problems often lead to the biggest growth opportunities, but only if you’re willing to face them head-on.

In this episode of Reveal, host Dana Feldman chats with Brian Fields, Chief Revenue Officer at Mindbody and ClassPass, to discuss how his passion for taking on challenges has shaped his career and leadership approach. Known for his supportive yet firm leadership, Brian shares insights on navigating high-stakes circumstances, empowering teams, and fostering resilience in times of change.

Don’t miss this conversation to learn how to turn discomfort into growth.

Dana Feldman:
What do the world’s best CROs have in their playbooks? This is the place to find out. This is Reveal, the Revenue AI Podcast by Gong. I’m your host, Dana Feldman.

Hi, I’m Dana Feldman and this is Reveal, the Revenue AI Podcast by Gong. Each episode we’re focused on helping you build the ultimate CRO playbook. And we promise to give you access to the most influential revenue leaders at the world’s top companies that you too can achieve your revenue goals.

In this episode, I’m delivering on that promise once again with my guest, Brian Fields. Brian is a very experienced executive with an incredible background in revenue generation and corporate development.

He currently serves as the Chief Revenue Officer at Mindbody where he is driving strategic growth across their business units. And Brian has also held key leadership positions at well known companies like Grant rupaun where he led strategic partnerships and corporate development. And before that he held senior roles at Tribune Company and Booze & Company. And this together brings a very interesting discussion today from his vast experience and expertise in economics and finance and he’s brought those to those organizations as well. So we’re very excited to have him on the show today to share his journey and insights on leading high growth businesses.

So Brian, let’s dive in. Welcome to the show.

Brian Fields:
Thanks Dana. Thanks for having me here.

Dana Feldman:
It is. I think we’re going to have a lot of interested listeners around you making the transition to the dark side as I call it over in sales for, for the people that have the finance backgrounds. Um, you said something really interesting. You said that you were lobbying, I think the CEO Groupon to get into the sales role. Why? What piqued your interest there?

Brian Fields:
Part of me was like it’s time to get a real job and like, and have some real accountability which, which is really, you know, it’s the truth of wanting to try my hand at can I run a business successfully, Can I lead a larger team, Can I coach people? I had a real interest in doing it. I think again my experience working with complex deals in corporate development, whether it be an acquisition or an investment or a partnership, really got me interested in the aspects of sales that are driven by negotiation and ultimately every sale is a partnership. So I felt like I had learned a lot of the requisite skills of completing a sale and I wanted to try my hand there. And it’s one of those things, you never know, do you walk into that kind of role and just, you know, absolutely. It didn’t say, I want to go back to spreadsheets and working in my cubicle with my small team, or do you love it and thrive in it?

Dana Feldman:
Couldn’t be more excited I think. Mindbody, I am a raving fan, end user and when y’all came on the scene I was like thank you for making my life of gems and passes and all the various places I was going so easy. So raving fan on this end and really excited to have you on today. Let’s start really just at the beginning and I tend to like to do this with all my guests but I would love for you just to take us a little bit through your journey to CRO, a little bit more about that background, how you got there and then I’ll have of course some some more things I want to ask you just about what does it take to be a CRO?

Brian Fields:
I guess I have my own unique journey to the seat I’m in today. It really started with, I’d say a non traditional background into a sales leadership role in that I have actually not ever worked as an individual contributor in a sales team nor been a manager of a direct line of sales reps. So I started off my career in management consulting, worked for a couple different firms for six years, got my MBA in finance and then worked in corporate development and business development for over a decade at Tribune Co. And then pretty early on in the days of Groupon. And I think what I really learned from those roles was how to use data to influence and make decisions as well as negotiation, deal making and commercial skills from on the corp dev side. And eventually an opportunity opened up at Groupon to take on a sales team for our live events business. And it took about two months of lobbying of the president of Groupon to put me in that role. Having again never worked in sales and managing a team of two people at that point to move into a team with about 40 people and multiple lines of managers and a very new role.

And after a couple months he relented. From there. Obviously learned a lot of lessons the hard way, but eventually took on larger and larger teams at Groupon, eventually becoming the chief commercial Officer with about 600 teammates in the org and then ultimately sitting in the seat I’m in now at Mindbody as CRO. So definitely a unique journey into that role.

Dana Feldman:
So as you made that transition, were there any beliefs that you had held prior about sales organization sales roles that either were disproven or proven that just kind of surprised you?

Brian Fields:
There’s like a saying of, show me the incentive, you know, the compensation plan, and I’ll show you the behavior. And so, you know, you learn that very vividly, quickly with sales teams. They really put themselves on the line in a way that no other part of the organization does. And I’ve really grown to admire that about the sales teams. I’ve also learned that the way you set up the compensation and incentives is one of the most important things a sales leader can do, because that will drive the types of actions and behaviors the team takes.

Dana Feldman:
I appreciate you saying that. I know my chief legal counsel here. He often says, you know, it’s so interesting, like, we get to show up every day and do our job, and our pay is guaranteed. You guys in sales are showing up every day, and, you know, typically half is not guaranteed. And so there’s a lot of respect for going out there and doing it that way.

Brian Fields:
It’s a unique mentality that sticks that out and really enjoys it.

Dana Feldman:
I’m curious. I didn’t go the management consulting route out of college. I would love to know, like, are there frameworks or approaches or things you learn through that experience that you kind of take with you no matter where you go in leadership? And you kind of find yourself reusing those each time?

Brian Fields:
Number one, really, starting with, like, the main principle of consulting tends to be that you take a difficult, complex problem and you approach it with hypotheses that you’re testing, right? And the hypotheses are then tested using data you collect. And a lot of it is based on ultimately a recommendation with imperfect information or data. And that applies so well to anyone who’s leading a sales team in that, you know, you have to be able to take a problem and take it apart, disassemble it a little bit, and understand what are the key drivers behind the answer to this problem. What are some hypotheses on what those drivers are going to be? How do I test them quickly and then make a decision with always imperfect data and information?

Dana Feldman:
I want to get in to learn a little bit more about how you drive results with your teams in there. Before I pivot over there, though, one. One last question. Just at the kind of beginning around your journey as you look back on your career journey, anything that you wish you would have done differently or even a mistake maybe you made that, that our listeners can hear from you and learn from.

Brian Fields:
When I look back and some of this just comes with experiences we all sense, I think that there’s stages you need to make in your organization from time to time. And it could be because you spot a specific individual on the team or the way a team is structured that isn’t optimal for where you are now. And maybe that worked for a different time, but it’s not what the organization needs now. And it’s very tempting for everybody to say, I will kick the can on that and deal with it next year. And that just never works out. I don’t think it’s in the best interest for the individual and I don’t think it’s in the best interest for the rest of the team or the company. So really tackling those hard conversations, hard decisions head on is something that, when I think back a decade ago, I may have acted much more slowly on that than I do today. Having just learned what the downside is from that.

Dana Feldman:
Well, probably a combo of getting comfortable with the hard conversations and just then like having the know how, the know how. Is there any particular mechanism you use with your teams to make sure that you’re really looking at where that talent is compared to where the company needs to go?

Brian Fields:
Absolutely. Big fan of the nine box framework. There’s different ways to think about it, but it’s very different from the annual like performance management performance review process to actually I like to sit down every year with my leadership teams, my direct reports and have a very open discussion about the talent in our organization more broadly. So that, number one, we put everybody into those, you know, the nine box to understand, okay, where are your far right high performer, high potential and making sure you’re supporting them and giving them opportunities and also understanding maybe the high performers and lower potentials and understanding like, okay, what is the right spot for them long term? Are they holding back some more rising stars within the organization, how to kind of get ahead of that and finally allowing the transfer of talent to happen and the identification across different teams in the large organization. A lot of people won’t even know necessarily, okay, like, you know, this person over in this different part of the organization is a real star, but we need to. They’re topping out in terms of what they can do. Having that open, transparent process makes it so that say, okay, like, you know, that person, I’M going to tap them the next time I have an opportunity. So really trying to create a system where people move around.

Brian Fields:
Right. And go into new challenges versus getting stuck in, in one area, in one role.

Dana Feldman:
Yeah. How can you, how can you tap into them for multiple areas and keep them interested and retained as well?

Dana Feldman:
Yeah. How can you tap into them for multiple areas and keep them interested and retained as well?

Let’s talk a little bit. I mean, you are CRO of Mindbody and hey, you’ve got to drive some results. There’s no doubt. Right. So talk to me like what’s been the most effective thing that you’ve implemented to drive results with your team that our listeners could learn from?

Brian Fields:
The way I approach many things is with each of our areas of the business is like working with the leader of that business to ask them how are you running your business? And that isn’t always obvious. It is for probably like a specific sales team that they say, okay, I have sales goals and I have to hit them. But especially when you move into CX and areas like customer success or support or implementation, to ask them like how are you running this like a business is maybe a new question for them.

So really working with each leader on what are the key metrics that they’re tracking or working towards, how do each of those tie back to the income statement to the P and L? Right. Like if it’s a metric that doesn’t tie back to the income statement, we’re a lot harder on why we’re tracking it. What does good, great and bad look like for each of those metrics? Right. You need some point of reference for those and then developing goals of where we’re going to move those towards and making sure there’s a work back plan from that.

So it’s having the right metrics that you’re tracking, what are the goals you’re working towards and then do you have a plan to get there? And it’s pretty simple but when it’s done well, you can have a very tight way of managing like the, the broader business at scale.

Dana Feldman:
Do you have a rhythm to that? Like OKRs and we review them monthly. What, what does that look like for you?

Brian Fields:
Yes. So we have multiple layers of, of OKRs within, within Mindbody and ClassPass, we have company wide OKRs then our ELT or executive leadership team have our own OKRs and then each function within the company has quarterly OKRs as well. And so those OKRs are set but before the beginning of the quarter we make sure that they tie back to some company key result. Again ultimately tied back to our annual plan and have a broad review of those really driven by our finance organization, but it’s very transparent.

Those get set before the quarter, we do a mid quarter review. Again, everybody’s, all the leaders are there at the various departments to review their OKRs with a focus on their top three or four most critical ones and drilling down on the ones that are lagging versus the ones that are performing. And then we do a review at the end of the quarter as well.

So it’s in part to drive accountability. It’s also, we have general targets of like, we don’t want to achieve a hundred percent of our OKRs. That just means you’re sandbagging, probably shouldn’t be achieving 20% of them either. There’s some happy medium where you’re stretching yourself there.

Dana Feldman:
I probably should have asked you at the beginning, maybe just clarify. So as CRO of Mindbody, what are all the functions that roll up to you?

Brian Fields:
There’s two main businesses within Mindbody. There’s the Mindbody software business and then there’s ClassPass, which is the consumer subscription business. And both of those roll up into me, specifically the sales organization which is SMB sales, Mid market sales and enterprise sales Revenue operations, the international business. And then CX and CX would be for both Mindbody and ClassPass implementation success and support.

Dana Feldman:
Gotcha. Okay. All right, thank you, thank you. I just, when you mentioned the CX, I was like, the listeners will want to know like, what does this function cover?

I imagine that, you know, I, I smile a lot about your run at Groupon when it went through one of the craziest times. I mean, when that hit the scene, that was like, that was crazy. I loved it.

But even at Mindbody now. Right. I imagine that there has been a tremendous amount of change and change management that you’ve really had to lead the teams through. And I think all of us that are in this software business, it’s been a wild ride over the last three years and I think things are starting to come back.

But a lot of change has come as, as an effect of that. So would love for you to kind of share when you’re trying to drive a new initiative or you’re trying to drive change. How do you approach that? What are some of the steps you take and maybe even some lessons learned that you can share with the listeners too.

Brian Fields:
We have some frameworks to deal with. That one is what we call the DACI framework. People may be familiar with RACI. So the DACI is D-A-C-I.

And so every time we have a cross functional project, which almost everything is in, you know, in a modern software company we have this DACI structure we implement where the D stands for the driver of the project which is a named person who’s going to, even if they don’t do all the work, they are the one who’s driving the day to day project and change. The A is the person who’s accountable. And it doesn’t again have to tie into just reporting lines, it’s just who’s going to be accountable for these results.

And then the Cs are the contributors to the project and the Is are the informed. And every time we kick something off instead of just saying well let’s have a project and you know, loosely run it. We have a very strict way of managing this with we start a DACI and the DACI, you know, has a document that the driver creates that identifies the purpose of the DACI, how it’ll be measured, the milestones and who each of the letters are in that DACI.

And that’s what allowed us to really, you know, we basically do all of our work over Slack. So we’ll have a Slack channel for it and people can watch the progress and the check-ins. And it makes it very structured and transparent in terms of how you drive that.

That’s the main thing. And the other stuff I call out on that would be it’s very important I think when you’re pursuing a big change that you have people focused on that.

So where I’ve definitely seen patterns of when that goes awry is, you know, it’s a very important project and a very big change. But the main people driving are spending like 5% of their time on it. That’s where it’s like a side job.

So we will peel people out for a project of their day to day job and say hey, just for the next three months or six months or longer, just focus on this, just get this right. It’s important, it’s a big change, just be focused. And that’s where you know, I’ve really seen the best results as well.

Dana Feldman:
How do you go about, and maybe there’s not one way you do, but how do you go about prioritizing which of those projects you’re really going to? I mean, asking to kind of step out and be like, go focus on this thing. I imagine there’s a lot of pre-thought behind why we’re going to go do that.

Brian Fields:
There is, I’ll give an example. Over the last year, like I think a lot of companies, we’ve pursued a lot of AI-driven projects. We were moving a little slow in the beginning around customer support and launching some basically agent-assist chatbots in that area.

And I think part of it was because it was everybody’s third job, right, to do that. And we peeled a very strong up-and-comer out of our support organization and tasked her with driving this project, selecting the vendor, putting together the project plan, driving the operations, and owning the results.

And we just started to see, you know, up and to the right in terms of how fast the project was moving, how the change was being embraced by the teams, and very rewarding for this person’s career as well.

And it actually turned into more projects along the same lines, even outside of, again, the reporting line. So it really was where our management team chose that this was an important area for us to nail and focus on.

And in a company of 2000 people, shame on us if we can’t find the resources to have one person really drive it and focus on it.

Dana Feldman:
I think there’s one aspect of this that’s like giving that opportunity to drive these projects, these really important things. And then I think there’s also this idea of how to get the ideas in the first place, right?

Tapping your team to get innovation from them. Right. How do you actually pull that from your team, get ideas, let that surface up for you as a leader?

Brian Fields:
We have a long-range plan. As a company, it’s a rolling five-year plan, and every year we publish a strategy memo to the entire company, which is really focused on like the next year, but it’s detailed. It’s 15 to 20 pages long.

The real author of that is the CEO, but others contribute to it, and we distribute that to the whole company. And it really helps with full transparency about where we are going long-term.

Also, where are we going to be focused over the next year, more of a short-term basis. And by sharing that with the entire company in December of every year, it allows them to start to percolate, you know, like, “Okay, I understand these are going to be our most important areas. There’s the context why.”

They can come with suggestions. So I think having a well-thought-out plan for the company vision, short and long term, sharing that very transparently, and then letting people do their work is key to getting those ideas.

Dana Feldman:
You mentioned it just a minute ago, right around having this project around how you guys can bring AI into the CX side.

I’d love to ask you, what do you think is going to be the most disruptive innovations that we’re seeing for revenue teams?

Brian Fields:
I read something recently. Sam Altman, who obviously runs OpenAI, said he predicted there will be in the future a unicorn company founded by one person who remains a company of one, supported by millions of AI agents.

Now maybe that’s far-fetched, maybe it’s not. It’s provocative to think about, though.

What you’re seeing now is that AI tools certainly have proven that they can help with like pretty simple, like automating rote tasks, like very one-dimensionally, and helping you save time.

Whether it’s uploading a very long document and asking for a summary or what we’re seeing with agent support, customer support, and chatbots, some of the very low-hanging fruit that these AI tools can handle is out there.

But over the next decade, you’re going to see, and certainly over the next probably year, much more complex use cases for these agents than we’re seeing today.

Dana Feldman:
That is actually a really interesting proposition to think about. A company of one supported by all AI agents. I do not doubt that this is upon us.

So, okay, coming back a little bit more, I’d love to tap into your mind about just leadership philosophy. How would others describe your leadership philosophy? And, you know, are there any that have really influenced what that is, good or bad?

Brian Fields:
I’ve definitely been heavily influenced, particularly by CEOs I’ve worked for, mostly for the good.

I would describe my approach as demanding but supportive.

And so by demanding, I mean setting aggressive goals, working on hard problems. And by supportive, meaning don’t just have—don’t throw things over the wall and say, “Here’s a hard thing to do, good luck,” but, “Okay, I’m in it with you.”

Right. Like, let’s figure it out together, let’s work on this as a team. So holding everybody to a very high standard, including myself, and supporting them in that journey, that’s been a big part.

I also think it’s just very important to give teams problems to solve versus being overly prescriptive. Right. Because especially at scale, that just becomes—that’s what micromanaging is.

And I just don’t think that, you know, the best people want to work that way. And it also just doesn’t work well if you’re trying to micromanage 800 people.

So instead of saying, “Go do this,” you should say, “Here’s the problem I’m trying to solve.” Like, you go solve it, or I can help if I have something to contribute.

And I think you get the best out of teams when you do that.

Dana Feldman:
Before we wrap our conversation, I’d love to ask you one last question.

So, as a revenue sales leader, as a CRO, what’s the best piece of advice that you’ve received in your journey?

Brian Fields:
Love that question.

A former CEO one time gave me the book by Ben Horowitz, The Hard Thing About Hard Things. So I recommend everybody go read that at some point.

The advice was always: Try to work on the hardest problems. Right.

And you’re not going to bat a thousand on that. You’re going to have failures, which is totally fine.

And it’s the point in development and learning and growth—working on hard things and taking on those challenges.

And that’s how a lot of people will end up taking like a 2x or 3x jump in their career, is by taking a risk, working on something hard, not being afraid to fail, understanding that when you do something hard, you have to understand the difference between peacetime and wartime, and how to make those hard decisions and embrace it.

But to look for challenge and hard problems, and that’s been incredibly fulfilling for me in my career.

Dana Feldman:
I love that. Well, Brian, thank you. With that, we will close out the episode.

For all the listeners out there, thank you for joining us for this episode.

Please follow Gong on LinkedIn for our tactical takeaways for this conversation, including some of the best plays that they get to add to your playbook.

And be sure to follow the show so that you never miss an episode.

Thank you, Brian, for your time and the conversation and lots of good nuggets to take away for all of our listeners.

Brian Fields:
Thanks for having me, Dana.

Dana Feldman:
Thanks so much for joining us for this episode. Follow Gong on LinkedIn for our tactical takeaways from this conversation, including the best plays to add to your playbook. And be sure to follow the show to never miss an episode.