The Bermuda Triangle of Sales Ops - Featuring Meghan Gill, SVP Sales Operations and Sales Development at MongoDB

Live from Schenectady, New York, it's SaaS Talk with the Metrics Brothers, Growth and CAC.

And I'm Growth, better known as Ray Reich, the founder and CEO of Benchmarkit.

And I'm CAC, better known as Dave Kellogg, independent consultant, EIR at Balderton Capital, and the author of Kellogg.

And together we are the Metrix Brothers.

And we go together like foie gras and the Hudson Valley, Ray.

There you go, Dave, making me hungry again.

Yeah, but the operative word here is not foie gras, Ray. It's Hudson Valley.

Hudson Valley? Isn't that where Schenectady— isn't it in Hudson Valley?

Our fictional production location, indeed.

Um, I believe it's near the confluence of the Mohawk and Hudson Rivers, but But the real point today is that we've decided to vary our SAS Talk format and do a rare guest interview. And our guest hails from the Hudson Valley.

Yes, she does.

Wait a minute. Who's that talking, Ray? We don't do guest interviews on SAS Talk.

You know, we do if they agree to laugh at my humor. But I think we need to calm down there a little bit and make an exception here so our audience could meet Megan Gill, who's the Senior Vice President of Sales Ops and Sales Development at MongoDB.

Yeah, she has an incredibly illustrious career in sales ops. I'm super happy to welcome you to the show and make the exception. You are our second-ever interview guest. But like, look, name someone else, anyone else on earth who joined a company with an employee number below 10 and has run ops the entire time from literally zero to $2 billion in ARR. Wow.

That is amazing, and I can't wait to hear from Megan and learn about the Bermuda Triangle. But before we dive in, let's hear a word from our sponsor. The Metrics Brothers is proudly sponsored by Benchmarkit, the B2B AI and software industry's largest, broadest, and most contextualized benchmarking index. Dave Kellogg and Ray Grothright have put the Metrics Brothers podcast on on hiatus for the remainder of 2026. All episodes we have ever recorded are still available on your favorite podcasting app. You can reach Dave at Kellogg and Ray on LinkedIn at Ray Reich. Thank you so much for listening to the Metrics Brothers podcast.

Thank you, sponsor. So Megan, please, uh, tell us about yourself.

Thanks for having me. So, I'm Megan Gill. I run sales operations at MongoDB. I was employee number 8, so I joined pre-revenue as the first, basically, non-engineering hire. And I'm coming up on 15 years now at the company. So, obviously, I joined when I was 9 years old. Thanks for laughing at my bad joke.

Oh, trust me, if you've ever heard our show, we have a lot of them, Megan. Welcome to the team.

Yeah, you feel at home here with bad jokes.

So, the first stretch at MongoDB, I was very focused on marketing and building out our developer community. And I was in marketing for about 7 years. And then, I had an opportunity to make a lateral move and take over sales operations about 6 to 12 months before we went IPO. And I've been running sales ops since then. And I also had the opportunity to bring the sales dev team under my umbrella as well.

Oh, so I messed that up. I thought you were in ops the whole time. I didn't realize you're a marketing person. Yay! Marketing stuff. Go marketers! And then took over sales ops 6 months before IPO. Wow. What a time to take over.

Yeah. I mean, when I took over ops, you know, the sales ops was pretty straightforward. We went public, we were around $100 million in revenue, and the approach was we just need to add capacity. We need to add sales reps to grow bookings and grow revenue. And actually, the ops job became increasingly interesting and a bit of a differentiator as we grew. We shifted our model from, you know, a commit model to usage-based pricing. We had to reorient the whole go-to-market. We segmented into acquisition and growth. There became a much more important role of customer success and the sales engineer. So, that has definitely been a lot of fun to be part of.

Hey, Dave, I gotta ask a question here because now that we know Megan was in marketing and then she transitioned over into sales op right before the IPO—

Ray was in sales, just so you know, Megan. We have— even though Ray comes off as a quantitative GE guy, he was actually in sales. So we have the sales marketing battle. Go ahead, Ray.

So what was the synergies in your mind from being in marketing going into a sales op role? There had to be some catalyst.

There was a catalyst. So, our CEO, Dave, had a conversation with me about— I was talking to him about my career. And I was like, you know, I'm kind of on a track right now to be a VP of marketing. And he said, well, if you want a career to be a COO or CEO and you know marketing, you really got to understand sales. And he said that there was an opportunity to come run sales ops. And I was like, well, at the time, I had literally— I'd never even seen a comp plan in my life. So, I had no idea what I was getting myself into. The area I did understand was the top of the funnel from having run demand generation and demand gen programs and seeing the lead flow. And so, I was— I am fairly analytical from having that experience. And that's what I was able to bring to sales operations. But it is a bit of an unusual move. I think most people either grow up in ops or they come over from finance. You don't see many marketers moving over to sales operations.

So, during your time running Sales ops. How did the job change? Were there distinct phases? Right. So, it sounds like you took over at around $100 million in ARR. Today, you're $2 billion. So, what— how did the job change along the way? Or is it really the same stuff? Or— yeah.

It's definitely not been the same stuff over the 7 or 8 years. You know, I think about, and maybe you can link to it for your listeners, there's an HBR article called The Evolution and Revolution as Organizations Grow. So, when I think about the early stage, it was all about living to fight another battle. Just getting stuff done. And like I said, the early-stage approach to sales was very much just, we need to add capacity higher as quickly as we possibly can. We have a massive market to attack and we have a very small percentage of it. Then, you think about the phase when Dave joined as our CEO, the direction stage, which is all about creating a repeatable go-to-market. where you have a standardized sales process and standardized sales systems. And now that we're, you know, at this, the most recent stage we've been at is more around decentralization. So, for example, where planning every year used to be basically a job that I did with our CRO, we've now pushed that down to the next layer in management. So, the North America leader is essentially acting as a CRO for for that business unit with an ops person doing the job I used to do globally a few years ago. So, that's how the job has changed over time.

Yeah, I'd like to just click on that a little bit because you do have sales ops and then you have marketing ops. And I don't know if this is the right time to talk about it, but has the integration of the different ops functions, has that changed? It's $100 million to $2 billion. Don't you have Sales Ops and Customer Success Ops integrated?

We did. When we decided to shift the company towards a consumption-based model, the CSM team was organized under sales. And at that point, CSM Ops came under my purview. So, CS and Sales Ops are together. Marketing Ops reports into the CMO. And I know we were chit-chatting before this. I actually like that model at this scale because I like the idea of the ops team being very closely embedded with the business unit that they're supporting.

So, back to the prior question. When you were talking about hiring and onboarding, right? You said there's a stage where, and I totally agree with this, in enterprise software, it's just all about hire, hire, hire, build capacity. We're going to get whatever it is, $1 or $1.2 million in new bookings per rep. And so, get more reps, right? It sounds like during that phase, because normally to me, that should go together with standardization. Like, if we're going to hire all these people, we have a good onboarding program, standard process, standard methodology. And it sounds like in your experience, you went through first a hire, hire, hire phase, and then a phase where, wait a minute, we got to be repeatable. Am I correct? And if you're advising a young, high-growth company, would you say do it Mongo's way first, just get people on board? And then have a standardization phase, or would you try and do them closer together?

It's an interesting question. And I'm now advising some early-stage startups that are at the founder-led sales stage. And it's interesting seeing them transition. So, one of them, the coffee mug that I'm drinking from, Oso, authorization as a service.

Vendor plug.

Vendor plug. So, they have one sales rep. And so, they've moved from the founder doing all the sales to having one sales rep. And they don't have a perfectly repeatable sales process. But they have enough demand where they probably need a few sales reps to manage the demand that they're getting. And I'm encouraging them to hire those people because I don't want them to leave opportunities on the floor. And those opportunities are a chance to learn about what the customer needs and what your sales cycle could be. So, it is a little bit of, I think, an iterative phase. You can't figure out that process unless you've actually done, you know, gone through some cycles.

Yeah, I agree. For what it's worth, I didn't mean all the way down to that kind of founder-led to sales-led sales, but I'll answer my own question. I think somewhere as you start to go from 10 reps to 30, that's the time to think about, wait a minute, these people are going to cost us a lot of money, but figuring out what to standardize. For me, it would be hiring profiles and it would be some sort of onboarding. So, I want to say if I hire a person who looks like this and I put them through this training and give them this tooling, Because that's my definition of repeatability. What are the odds that they're going to be on quota, you know, a year from now or 9 months from now or whatever?

And I think the profile, the early-stage profile of reps, you know, again, talking about those early-stage reps, like they have to be the ones that are very creative and in many ways don't want a playbook. And they may not, they may not want to go to the next phase because they don't want to be told exactly what to do. So, that's a very different profile for sure.

Hey, Meaghan, I've got a question here that kind of double-clicks on this conversation. Sales enablement, sales training, has that always been part of sales ops at MongoDB, or is that a separate function?

At MongoDB, it's a separate function. I've seen it from talking to my peers at different companies. Sometimes it's in sales or rev ops, and sometimes it's a separate function. I think the skill sets, especially for MongoDB, where we're enabling on a highly technical product, a lot of the people who are in our enablement function are former sellers and former sales engineers versus analytics and systems folks that I tend to hire. So, it can work either way and I've seen it done both ways.

So, from $100 million to $2 billion, sales enablement's always been a separate function.

It has been.

Got it. Thank you.

Ray's a big active listener. So, I want to go back to your prior point because I think it's really good about The first reps, I call these people in the jungle with a machete, right? That's it. I'm going to give you a telephone and a machete and go sell $1 million of software. And you're right, when you start to scale, you're not hiring those people anymore. You're hiring people who want a road built, right? They want to give it a territory methodology, patch some tools, and go make money. And I just, I have a theory about what you do with the machete people, but do you, did they all leave or were you able to redeploy them to other roles and keep them with the company?

It depends on the person, right? Some of those folks that were, you know, I would say earlier in their career, up and coming and very adaptable, ended up adapting and either growing into leadership roles and building out the playbook. Some of them, you know, some of them don't make it and they just decide they want to go do something different because they don't like to have the playbook. And then others maybe make a lateral move and they're like, okay, well, we've built out this particular sales function. Now I'm going to build the partner org or some other function, right, that needs that kind of creative and innovative person.

So, exactly my point of view, which is too many startups develop this almost disposable people thing. We're like, oh, you were great from $1 to $10 million, but we can dispose of you and get more people. And you hit what my point of view is. There's always something new to start. We're going to open Europe. We're going to open France, right? We're going to open partners. We're going to do— like, to me, you got to just don't try and force those people into being a kind of regular growth stage sales rep. Go put them on the new problems where you basically— I said, there's figured out people and scaled up people, and go put the figured out people on figured out problems and conversely. Super, super interesting.

I mean, I think I'm going to— to some extent, I'm an example of that, right? I'd done 7 years in marketing and I was like, hey, what's next? You know, Not that our marketing machine was perfect, but I was kind of excited about the thinking about what the next challenge was. And so one of the pieces of career advice I give to a lot of people earlier in their careers is not to be afraid to make that, that lateral move because it definitely broadens your horizons. Okay.

Awesome.

So I have to ask you a question because when you made that transition, did you expect to be involved in the Bermuda Triangle and what the hell is it?

Yeah. Yeah. So, the genesis of this episode is I was talking to Megan and she said something about the Bermuda Triangle of sales ops. And I'm like, okay, we have to interview on this.

So, I often joke that sales ops is in the Bermuda Triangle navigating between the CRO, the CFO, and the CEO. And a big part of the job is getting the executive alignment on what the go-to-market approach will be. So, that's the Bermuda Triangle. Did I expect to be there? I had an inkling that's where it would be. But I didn't really understand fully until I was in the thick of being a sales ops leader.

So, ships are often lost in the Bermuda Triangle. So, I got to like, how did you avoid catastrophe? And were there times where it was like, uh-oh, if I play my cards wrong, my boat's going to sink? I'd love to hear some not detailed stories, but just the idea of How do you navigate successfully in the breeder's triangle, basically?

I was thinking about this last night and I was reminded of something my dad, who passed away a couple of years ago, used to always say to me. He says, life belongs to the decision makers. And his approach was always, it's better to have a decision, a suboptimal decision than no decision. And so, that's kind of the approach I've always taken when it comes to sales ops. We're always on a very tight timeline when it comes to planning the forecast, pretty much everything. And so, if there's something that's blocked and we're fundamentally misaligned, let's say between sales and finance, my goal, my approach is just to escalate as quickly as possible in a very straightforward, dispassionate way and say, look, it's more important we get to alignment and decision and we can move forward than getting to the perfect outcome. It's better to basically be directionally accurate than perfectly incorrect, right? So, that's been my approach is to to be very fast to escalate and bring these issues to the execs and really force them to make a decision.

So, how do you— so, I've always felt that the perfect sales ops person was a trusted advisor to all 3 of them. Like, you worked for sales, the CRO was your boss. And I don't know if that was true, Margot, I'd love to know, but normally the CRO is the boss.

Yes.

But you're not a partisan, if you will, right? Like, you're somehow trusted by everyone. That's really, I think it's a really hard role, but a super, like I was CEO and I had trusted relationship with my ops person, maybe even more so with the CRO that I could say, what do you think we can really do? Or what is the model saying? And I'm just curious how you deal with that. You become a trusted advisor to all 3.

Well, I think for one, I never want to just be a, you know, what's the word? A talking head for the CRO, right? I've got my own point of view and I do challenge my boss and I I think that's what makes it a good and healthy relationship. And I try to approach everything in a very data-driven way. And a lot of times, it's just a matter of presenting the data in a dispassionate or objective way and letting people reach their own conclusions. Sometimes I feel like it's better— yes, I might have an opinion, but sometimes it's better just to be objectively presenting the data and gain that sort of trust that, like, There's no spin on this, right? It's just, this is just what the data is saying. And let the executives form their own opinion.

So, I have a line I have used in the past, Ray. I promise I'll let you go next. But I often say when things get a little heated, it's like, hey, I don't make the news. I'm just telling you about it.

I got to use that one for sure.

Go for it, Ray.

Okay.

Well, I got this 3-ring circus, right? The CFO, the CEO, and the CRO. But beyond gaining that alignment and highlighting the decisions that need to be made to them, how do you define the role of sales ops?

I think of sales ops as the brain of a go-to-market organization. The job of sales ops is to provide proactive insights into the business. And then, in terms of the actual functional pillars, there's a few key areas. So, one is systems and processes. Another is compensation design. So, how do we target the reps? What are we focusing them on? What are the behaviors we're driving? Another is driving your annual planning process, which is really critical in being aligned with the CFO and the CRO. And then, the final is a field ops organization. So, somebody who's acting as, as I said, as you decentralize the decision-making, it goes to the next layer down. Those leaders need their own operations people to do the job that I once did as the business partner to the CRO. So those are the main pillars within the sales ops organization.

I have one question I got. I can't let it go. And that is, if you have an integrated GTM organization, what about the data? Because data hygiene and data management becomes such an issue between marketing, sales, and CS ops. Is that part of sales ops responsibility?

It is. I mean, ultimately, like, I mean, that's one of the, you know, you were segueing into the next topic, which is integrated ops versus ops embedded in the business. There's pros and cons, I think, to each. The pro, I think, of having an integrated ops function is that you're not fighting over definitions of different metrics where, you know, your finance team says your renewal rate is X and sales says your renewal rate is Y, and they were using a different methodology to calculate it. Like, that's a, you know, a very frustrating thing that happens in the real world. I think the trade-off when you have a centralized org where everybody's reporting into a centralized head of operations is that you do lose some of that intimacy with the business. So, I think it's trying to find the right balance. So, I mentioned before MongoDB, we're aligned to the sales and CS org because that's how our company is organized. And so, marketing has their own operations function. And it's our job to be aligned in terms of the metrics that we're presenting.

I've often likened it to— so, I'm a huge fan of integrated ops. And look, you're large scale. I work mostly with $0 to $100 million companies. So, at your scale, All bets are off in my opinions, but at smaller scale, I like it because I always feel like it's like a tag team cage fight. Like the CRO comes out and tags their ops person and they go in and they fight, they tag out, FP&A comes in. And I don't want to have a tag team cage fight. And it seems like, look, I did an interim gig at one company where I united with the CRO, sales and marketing ops, and they had it work for sales and I was running marketing and I didn't care. It's like, as long as I get my reports, as long as you come to my staff meeting and get my analytics, I'm good. And the whole thing will work better. And then when they hired a full-time replacement after I did the gig, the first thing they did was break it off. And it just broke my heart because you end up with these warring ops people. And I just, I hate seeing that. Sounds like you don't have the war, but you're at big scale. You probably have standards for everything.

I mean, look, it's definitely a challenge. I do think At a certain size, you need to have that. If you have that just field operations team, right? So, people who are embedded in the different— so, for example, we have a team supporting our North America sales leader, a team supporting our EMEA sales leader. And they're a little bit more of the jack of all trades that is the glue between all of the different ops functions. I feel like that kind of gets a nice blend where you have centralized teams that are setting like, these are the right reports. These are the right queries to be pulling. These are the centralized dashboards. And then a field ops team that is basically the interface, the UI for the sales leaders to work with on all of those kinds of analyses. So, I feel like that's the Goldilocks scenario when you get to scale.

So, Ray, I think we're running out of time. So, you want to do one last question?

Please do.

So, this one's not in the script. So, sorry, it's a curveball. And we can go back and do the script if you want after, but I have to ask. What advice would you give? Just say I'm running ops at a $20 million company, right? And what advice do you give that person on how to grow with their company, make it to $100 million? Make it precise. I'm running ops at $20 million. I still want to be running ops over $100 million. How do I do it?

It's a good question. I think that one of the challenges that people have, especially at the smaller stage in ops, is that you're always firefighting and not necessarily able to get ahead of get ahead of things and drive the more proactive analyses. So, you still need to firefight. So, find a way to balance the firefighting and the day-to-day operations with the longer-term strategy. And that might mean having the right team in place, right? Do you delegate some of the day-to-day operations to people who are very good, like you mentioned earlier, I forget how you termed it, but the people who like to execute on the existing frameworks, and then have some folks that are dedicated to thinking longer-term on where things are going and really analyzing and understanding the data. And then, I guess, the second piece of advice I would have is to get the data foundations in place because whatever you can do to get the foundations in place is going to make your life so much easier as you grow. And it's harder and harder to untangle that tech debt as you get bigger.

Meaghan, this is an incredible opportunity to learn from someone who scaled We're not gonna be able to do it in this episode, but I'm gonna have to get you on another episode to talk about how your metrics changed when you went from to a consumption usage-based environment, 'cause I'm sure that was a huge part of what you did when you first took the role. But thank you so much for telling the story. I just cannot tell you enough. Dave, I think we should wrap up for this one.

I think we should too. Megan, do you have any final words? I'll do the final wrap, but anything else you'd like to share with the audience?

Really appreciate you having me here.

Awesome. Well, we're so happy you came. Uh, that was a lot of fun, Ray. We may have to have Megan back one day if she'll come.

Definitely.

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