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- [00:01]
A
We had sponsored the lanyards and literally every single person there was wearing a name tag with the lanyard that said Green Fly.
- [00:14]
B
Welcome back to another episode of Builders. As always, this show is brought to you by Frontlines IO, Silicon Valley's leading B2B podcast production studio. If you're bringing technology to market and want to learn from your peers, we have a library of more than 1200 interviews with Venture backed founders and marketers. Where they talk, all things go to market. Of course, if you want to launch your own own podcast, we offer podcasts as a service to more than 80 tech startups. The idea there is very simple. You show up and host and we do everything else. Now with all that said, let's jump in today's episode. Our guest today is Mark Keeney, CRO of Green Fly. Mark, welcome to the show.
- [00:53]
A
It's great to be here.
- [00:54]
B
I saw a lot of posting about the olympics on your LinkedIn page, so let's go ahead and start there. A fun question though. What was your favorite sport that you watched so far in the Olympics?
- [01:03]
A
Ah, the obvious answer would be hockey, but that the figure skating. Alyssa Liu became literally my favorite person on the planet. Like I can't stop sharing her with my daughter as like a role model of awesomeness. But I grew up with the Miracle on Ice. So men's hockey back in 1980, I'm aging myself here, but that movie Miracle, I probably played for my kids a thousand times. So the combination of men's and women's ice hockey, that was everything.
- [01:29]
B
I mean winning gold, both teams, that was pretty epic. And I've watched hockey, I've loved hockey for the last, like, I don't know, since I was like five years old, something like that. So it's been part of my life for a very long time. It was cool to see. I have a young one and a half year old daughter and she loved watching the Olympics. We were watching almost everything that we could and it was just such a blast to see.
- [01:45]
A
So fun.
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B
Let's talk about the business side of that. So I know you weren't working with the Olympics, you were working with someone else. Who else were you working with?
- [01:51]
A
Yeah, so Greenfly as a company, we power the short form content for most major leagues worldwide. So throughout the course of the Olympics, a lot of those Olympians are actually using Green Fly in their day job. So NHL players, professional Women's Hockey League pwhl, those hockey players have access to the green fly platform. So in partnership with their respective leagues that content all those Amazing moments, the highlights, the fan ugc, all that stuff you see on social that was literally coming through the back end of Green Fly in real time. And we were able to distribute it with the league, the teams and the players and then they would post it out on their social channels. So a lot of that interactivity we saw over the weekend, we were just in the back end having fun, watching it kind of unfold.
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B
Wow, super cool, super, super cool. And what's your background? How'd you get into this?
- [02:44]
A
Yeah, the abbreviated version. I kind of grew up in the media business. I spent the first 20 years of my life mostly working CBS, Viacom, Comcast, big media companies and saw a transition over to digital media and social and had an opportunity to kind of pivot into technology. So I went to work for a company called sprinklr, one of the big players in the social media management space. Ran North American sales for a company called Khoros. And then I got a call from this company, Green Fly. Their founder, Sean Green, former major league baseball player that I knew growing up, I'm like, wow, that's kind of cool. And their pitch to me was everything that I've done in the course of my career essentially bottled in this one company. It's sports, it's entertainment and it's social Martech kind of all wrapped into one. And it was just literally like I said, how do I sign? Let's go. And that was three years ago. It's been an incredible run.
- [03:36]
B
How big was the org that you inherited then?
- [03:38]
A
We're still a fairly small company, mid stage startup. So at the time we had about 35 employees. We doubled in both revenue and headcount in that time. So we're sitting just under 70 in terms of headcount. And we're in a kind of a pivotal moment in our evolution as a company. So very exciting time.
- [03:56]
B
I've interviewed a lot of CROs and one thing that I found is that they all have slightly different responsibilities. It's not one of those titles that it's just crystal clear what exactly you're overseeing and responsible for. So what's on your plate?
- [04:07]
A
Yeah, selling stuff. You know, it's funny. Well, like I run sales, cs, dotted line into marketing in the sense that, you know, our CEO and myself basically kind of like work together on the marketing side. Him really on the brand and vision for Greenfly, me more on the demand gen piece. But I think when you look at the day to day, like I feel like I'm almost a selling CRO in the sense that a big part of my job is to not only drive the sales team and the CS team from just driving, building pipeline, growing the company, but also really thinking about, like, how do you take a small company that has a limited tam in the sense that sports and entertainment are our primary verticals, how do we build out future verticals, how do we expand beyond that and maximize the revenue opportunity that's coming in? So I'm probably doing more selling in this particular company than I have in a very long time. And I love that piece.
- [05:01]
B
I was going to ask that. You must love that piece. I would imagine.
- [05:03]
A
You know, it kind of goes back to you and I bantering about the Olympics. Like I sort of feel like when your customer is, whether it's Netflix or whether it's the NHL or I'm sitting in the NFL offices, like running around taking pictures of, you know, something from the Patriots in their headquarters, like there's just this sort of energy and passion that can come from that. And when you know that you've got a product offering that can help solve major problems that these leagues and customers are facing, it kind of just makes the selling piece easy.
- [05:34]
B
When you're looking at different markets to expand into, what are you evaluating and how do you test it to know this is a vertical to go after?
- [05:41]
A
You know, for us, I think we had to resist the temptation to go wide quickly because we've got a niche technology and the wider we go, we start to compete with companies we shouldn't be competing with. And I'll use sprinklr as an example. When we're talking to a brand that's got a big marketing organization, they think social media, they think sprinklr. But we don't compete with sprinklr. We're a distribution vehicle for short form content. We power the ecosystem, we do a lot more stuff. So we had to bring it in a teeny bit. And rather than go wide, we looked at it and said, okay, we're going to focus on brands. But for us sports adjacent brands that are activating that athlete network in and around, say the NHL. So we think about something like an Adidas or a Coca Cola, a Nike, you kind of pop to mind Verizon. These are companies that sponsor major league sports. So there's a natural sort of bridge. They can look at a green fly and kind of be familiar with what we do at the NFL and say, wow, they can move content. Can we use Greenfly in a way that's going to help us activate campaigns around the content we're already sponsoring. So that became an opportunity for us to get a higher not only win rate, like that's where we kind of win, but in terms of like having a value proposition that gets the phone to be answered. You know, we're calling the right people at the right brands with the right messaging instead of spraying and praying.
- [07:08]
B
This show is brought to you by Frontlines Media, a podcast production studio that helps B2B founders launch, manage and grow their own podcast. Now, if you're a founder, you may be thinking, I don't have time to host a podcast. I've got a company to build. Well, that's exactly what we built our service to do. You show up and host and we handle literally everything else. To set up a call to discuss launching your own podcast, visit Frontlines I.O. podcast. Now back to today's episode. You say calling there is that physically cold calling. Is cold calling still an effective method in your market?
- [07:37]
A
Yes, in the sense. And you know, it's funny you say that because like there's a debate internally about like how the best way to approach it. And in my mind it's like I'm always, I pick up the phone. Like we don't get on the phone enough, you know. But I think philosophically at Green Fly, we get on a plane whenever we can. If we've got an opportunity to sit down in Atlanta with Coca Cola, we're going to be there. So getting in person is very important to us as a company. I think the second thing that also comes with like, if you've got narrow verticals with the right targets, getting on a plane and going to see Coca Cola is not a waste of time.
- [08:09]
B
Right.
- [08:09]
A
But I think in terms of like our outbound, I think there's a combination of really industry events that put us in front of the right people and then using our, you know, ABM and or you know, SDR outreach to schedule meetings at those events with those key stakeholders. And typically it's one of those things. It's, you know, there's no shortage of entertainment and or sports related conferences. You can probably have 15 to 20 of the right meetings at those meetings that have 80% hit rate of a follow up meeting that creates actual pipeline with probably a 50% closing rate, which is pretty good.
- [08:48]
B
And do you do booths at those events? I talked to a lot of leaders who said we're done with booths at events, we're still going to events, we're just not spending the money on the booths anymore.
- [08:55]
A
I hate to give this secret it's an awesome one. We do not do booths at events. But one thing that we found that was the best and most cost effective sponsorship we've ever done is the lanyard sponsor. So we were at an event in our biggest competitor, had a big booth in a huge activation, but we had sponsored the lanyards and literally every single person there was wearing a name tag with the lanyard that said green fly. And it was the sort of thing I just literally remember one of our biggest shared customers laughing because they were at the, you know, fill in the blank competitor's booth and the competitor couldn't stop looking at the greenfly logo on this guy's shirt. So.
- [09:41]
B
And was the cost similar for the booth versus the lanyards?
- [09:44]
A
Super cheap?
- [09:45]
B
That's crazy.
- [09:46]
A
It was one of those things that we, you know, because there are a lot of industry events and we were a small, nimble company. Look, we more so have like a boots on the ground approach where we try to figure out regionally who's in la, who's in New York, who's in London, how do we get people there? You know, we've got people in all those markets. So if we can have one to three people on site at an event, if we can have a focus list of customers and prospects, we can turn each one of those events into a, you know, a 30 meeting, two day wraparound, talk to 12 to 15 customers, up to 12 to 15 prospects. It's pretty good.
- [10:22]
B
So lanyards over booths, that's one of your secrets. What other secrets can you share? Don't tell anyone that. Not for the competitors. Not for the competitors. But for the other scarrows, I won't tell us all.
- [10:34]
A
Yeah, it literally made my day because literally it's one of our biggest partners that happened to call it out. And they said to us jokingly like, oh, we thought you guys, we thought you were the presenting sponsor of the actual event itself. So it was a good value.
- [10:48]
B
Any other secrets you can share with non competitors?
- [10:50]
A
You know what, I think there's a lot of debate around the cost of events. Like when you think about like AI and technology and kind of supercharging your outreach, we are a niche company with really three verticals we're keyed in on. So when you think about that, if there's a sports event in New York, Sports Pro in New York is coming up in a couple of weeks. And literally when you look at the NFL, NHL, NBA, Major League Baseball, National Women's soccer leagues, mls, they're all based In New York, they'll all be at that event. So we can go to that event with all six of those customers in and around that event. So I guess the secret for us in terms of optimization is being at an event or sponsoring event is one thing, it's important for visibility and brand and legion, but it's making sure that you've got an incredible plan to optimize the entire opportunity. And that is like one of those things. If it's a two day event, you got this three day window that wraps around, you should be able to fill it with, you know, as I jokingly said before, 12 to 15 customer meetings, 12 to 15 prospect meetings. I think that's a realistic two day vendor in New York City that's worth the stake that you're going to have. And you know, you're going to wind up generating a ton of pipeline and some good qualified leads and customer, you know, touch points.
- [12:09]
B
So going back to something you had said earlier was, you know, get on the plane. I remember like 15, 20 years ago I was given that advice and that had a meaningful impact on my career. And to this day I still do it, even when it doesn't make any sense. And it's, you know, almost always worked out for me. So that sounds like a, you know, kind of sales principle that we're aligned around. What other sales principles would you say really define how you think about sales?
- [12:30]
A
Yeah, it's an awesome question. And we've been really working on a lot of, I mean every company we've been exploring how AI can really 10x our effectiveness. And I gotta be honest with you, there's some things we've been dabbling in the past couple of days, even that are just like, wow, game changing. But one of the things that happened to me earlier this week I saw a notification on LinkedIn, a woman that it was my first hire as a sales manager. I promoted her three times. I hired at four different companies. She just got promoted to an SVP role and a board seat at a company. And I just sent her a note on LinkedIn and she sent me a note immediately back. And we were reminiscing about my boss and me and her. And the reason I bring that long winded story into this is that like one thing I don't want to see get lost in great sales leadership and great go to market strategy is just how important the people are and how important the relationships we have with those people are. And I think that like one of the missions that we're on right now with using AI strategies, we want a bottoms up strategy to make our people better and a top down strategy to create more efficiency on how we manage deal cycles, how we manage pipeline, how we look at different triggers within the sales process. And the goal would be to free up our leadership's time to be more involved in infield coaching and to free up our sellers time to be more effective at closing deals. But at the end of the day, as we're mapping, you know, kind of the artificial support of that, never losing sight of how important that manager to seller relationship, that second line leader relationship to the whole like it's one of those things where I think if we're not smart we're going to lose that and we're going to have companies that can scale on paper but are not sustainable. And I sort of feel the ones that will truly get to that 10x in the future will be scalable and turbocharged because they've got passionate people that are part of a team that are driving a team that are driving results for that team. This show is brought to you by the global talent company, a marketing leader's best friend. In these times of budget cuts and efficient growth, we help marketing leaders find, hire, vet and manage amazing marketing talent for 50 to 70% less than their US and European counterparts. To book a free consultation, visit globaltalent.co
- [14:56]
B
the audience would hate me if I didn't ask you about those experiments on AI. What are some of those ones? You said something this week or last few weeks has kind of blown your mind. Can you tease us?
- [15:04]
A
Top secret. I think it's one of those again. And this is just probably aging myself as a leader but like I've always been very systems oriented as a leader. So great Salesforce hygiene, using that salesforce hygiene in an old school workbook and kind of bringing those two things together where I've got my go to market on a spreadsheet and we're moving the rock right every day, every week, every month, every quarter. And I sort of feel like what we've been experimenting with just a couple of simple things where we're bringing together slack and email and calendars and activity in salesforce and pipeline and sales stages all into kind of the vortex of Claude and in that process getting an analysis by account executive of their quarter's worth of activity ranked by sentiment, ranked by intent, like literally at our fingertip. And one of those things were like you think about prepping for a one on one or setting a plan for a week in a nanosecond we essentially mapped our entire sales organization. And I just sort of kind of see this like, this sea change of like one on ones being richer, admin time being cut by 90% and that 90% being converted in field coaching. More time with customers, more time with, you know, with sellers, on sales calls, like doing the actual work. Like, I think what you're going to see is that you're going to be able to really kind of turbocharge the evolution of a salesperson. In the flip side, when I say we're trying to map it bottoms up and top down, the top down can get lost in an inspection. Inspection is super important, but it's not just micromanagement and like the helicopter coming in like the drone is watching. The bottoms up piece is important because what we're trying to map with that is the learning, the coaching, the teaching. So we take. Obviously you're familiar with Medic or Bamanter is something I've used for my vista days. But taking kind of like that Medic mindset, mapping it into intent and now helping, like almost like creating coaching with AES that isn't their manager saying, do we know what the budget is? But like identifying gaps in their deal cycles in real time. I think it's. You're going to see something pretty special.
- [17:22]
B
Have you played around with any AI tools that were promising but just didn't live up to the hype?
- [17:27]
A
I think it's funny. It's like you were in our meeting earlier today. We had a meeting today with our sales lead, our CS lead and our head of analytics. And I think that, like, where I think a lot of these tools fall short is there's a vortex created. You know, where you kind of get in this rabbit hole of like trying to tune it and fine tune it and come up with this and manage that. So we basically. So the straight answer is yes. Like, I think that we've found a variety of time sucks in this process and I think for us, we kind of had to lens out and we call them the metrics that matter. So sort of looking at like, what are the metrics that really matter to our org and how do we map them in a way that we can go top down and bottoms up constructively? So we started there and I think that gave us the opportunity to build something fairly simple but powerful.
- [18:15]
B
I'm going to end with two different questions for you. We'd like to ask for advice and this is for two different audiences. So the first one is for the founders that are listening in. If a founder wants to hire just an amazing CRO like yourself, what should be top of mind, who should they be looking for and just assume that it's for, you know, early stage startups.
- [18:32]
A
I was going to joking response like I would say get out the checkbook, right, we're very expensive. But honestly the real answer and radically I have my sleeves rolled up. I think you really want to particularly early stage, you've got to make sure that you're hiring someone that can check the ego at the door and do the hard work. Because as you're trying to build the future of a company, the future of a sales organization going say from a CEO led sales organization to now a sales team building out best practices, scaling and growing. There's a lot of growing pains and there's a lot of lack of resources. So you can find someone that's got the pedigree and the experience and they work for big companies. Much like my time at Sprinkler. I was very well resourced and all of a sudden you come into a smaller company that's expecting you to bring a lot of those resources that are up here and apply them. It requires a lot of heavy lifting and a lot of hard work. You need someone that's willing to do that.
- [19:27]
B
And final one for you. Let's speak to the CROs that are listening in 2026, obviously here. What advice would you have for them in 2026?
- [19:35]
A
Wow, that's a great question. It comes back to the AI conversation we were having. Like I sort of feel like if you don't embrace what AI has to offer you in the near term, avoid the vortex, but really look for ways that AI can 10x your team. I think it is going to be a game changing opportunity for you to take a small, fledgling, growing sales team and make them mature and 10x their potential very quickly.
- [20:05]
B
Amazing, Mark, that's. We're going to leave things before we do wrap. For those who are listening and that want to follow along with you, where should we send them? Where should they go?
- [20:12]
A
My LinkedIn is probably the easiest way to find me and communicate with me. I'm there all the time.
- [20:18]
B
Sounds good. I'll see you at the golf course.
- [20:20]
A
Look forward to it. Take care, bro.
- [20:22]
B
Thanks. Bye bye. Well, that's all for today's episode of Builders, brought to you by the Frontlines. If you want more amazing content like this, visit Frontlines IE where you'll find the library of more than 1500 interviews with founders, marketers and other GTM leaders where we unpack the tactical lessons from their journey. And of course, as always, if you do want to launch your own podcast, we'd love to have a conversation with you. Visit Frontlines IO Podcast as a service. Mention that you listen, mention you love the show, and we'll give you a 10% discount. Thanks for listening. We'll catch you on the next episode.