Found In The Rockies

Jeff Gibson (MonetizeNow) \\ Scaling sales and billing with streamlined systems

February 15, 2023 Les Craig Season 3 Episode 12
Found In The Rockies
Jeff Gibson (MonetizeNow) \\ Scaling sales and billing with streamlined systems
Show Notes Transcript

In today’s episode, have one of Next Frontier Capital's portfolio company founders on the podcast - Jeff Gibson, who is the CTO of MonetizeNow. Jeff and his co-founder Sandeep are revolutionizing billing systems and streamlining the process.

Here’s a closer look at the episode:

  • Jeff’s early days in Missoula, MT.
  • Jeff’s start in tech with Advanced Technology Group.
  • The transition from Montana to San Francisco.
  • Learning data engineering on the fly at Atlassian.
  • The challenges of building a product-lead growth platform.
  • The problem with tech debt and tech debt.
  • Deciding to team up with Sandeep to solve this problem.
  • Definition of Quote to Cash.
  • Deciding to leave Atlassian and start MonetizeNow.
  • Raising capital
  • The hiring process for the first hires - finding engineers who will do well in a startup
  • Exploring use cases for larger companies.
  • Keeping ties to Montana.
  • How Jeff met the team at Next Frontier.
  • Jeff’s advice for a young software engineer from a small town.


MonetizeNow Website:

Jeff LinkedIn:

Jeff Twitter:

MonetizeNow Twitter:

Jeff  00:00

So I figured, you know, every company, every b2b SaaS company wants to be a product lead growth company, you know whether they can or not, that's another story. And so they're, they're all going to scale and experience these same problems. Like who is solving this and I actually was like, Oh, someone will solve this, like this company will solve it, this company to solve it. No one really make any progress. So no innovation in the space and then just seeing the problem grow were kind of the two themes.

Les  00:30

This is Found in the Rockies, a podcast about the startup ecosystem in the Rocky Mountain region, featuring the founders, funders and contributors, and most importantly, the stories of what they're building. I'm Les Craig from Next Frontier Capital. And we only do this maybe once or twice a season. So it's an extra special occasion on today's show. I'm thrilled to have one of Next Frontier Capital's portfolio company founders on the podcast. Today, we have Jeff Gibson, who is the CTO of MonetizeNow. Hi, Jeff. 

Jeff  00:36

Hey, great to be here. Thanks for having me on. 

Les  00:38

We are super excited to have you on I gotta tell you no pressure, but you're the first CTO and co-founder we've ever had on the podcast. What do you think of that? 

Jeff  01:20

Seems pretty excited. Yeah, I'll it'll be a good it'll be good perspective for for people who normally hear from you know, people on the non-technical side of the house. 

Les  01:29

Awesome. You're gonna talk nerdy talk nerdy to me is that you're gonna talk nerdy to me. A poison joke. 

Jeff  01:36

Yeah. Sounds like a hip hop song.

Les  01:40

Yeah, anyway, awesome. Well, look, I'm really excited to get started. I think, you know, one of the one of the things I think people will be really excited to hear about you know, this is founded the Rockies, we feature founders and funders in the Rocky Mountain region, I'd love you to, for you to start at the beginning of your story, kind of where you grew up and where you're from, I think people will be excited to hear. 

Jeff  02:01

Yeah, absolutely. So born and raised in Missoula, Montana. I think me and my brother were kind of the few people who got out of Montana for a little bit. Before that, I think our family's there for maybe like 100 years came over as like miners, kind of like, you know, literally, like lived in the mines in Butte. Some of us didn't make it out. And then we found a way over to Missoula,

Les  02:18

Goodness. 100 years of mining. Wow. Yeah. Awesome. Cool. So, Butte is the big copper mine. For our listeners who who aren't aware of that.

Jeff  02:28

“The Berkeley Pit” is a good, it's an interesting read. You can go down a rabbit hole on that one. Yeah. So I got my start in Missoula, born and raised went to school there high school, the University of Montana there, started my career there. study computer science. I did some interesting work in my early career, doing things with satellite imagery, worked for various companies in Missoula, and then kind of fell kind of fell into working for ATG Advanced Technology Group. And they were, you know, if people don't know, they were just this teeny little thing in Missoula that decided they wanted to be a big consultancy. And they started out with a couple of people in one office, and then they grew to hundreds and hundreds of people and got acquired by Cognizant, so that's sort of where I learned a little bit about, quote to cash and finance and like sales process.

Les  03:18

Yeah, by the way, ATG is one of those kind of incredible Montana stories, I think I would have to say, you know, somewhere, you know, unfortunately, fortunately, whatever, like, RightNow gets all the press, but like, just just as significant is the ATG story. It's, it's absolutely incredible. Right? 

Jeff  03:36

Yeah, absolutely. I mean, really, like I think, you know, when it got started, I don't know how 789 years ago, it was just two people, basically sitting in the equivalent of a basement in Missoula, deciding that they wanted to consult for you know, fortune 1000 large tech companies and be a big player in the game. And they did it, they were growing by like, 300% 400% a year, hiring people getting huge contracts. I, you know, when I was there, one of my big projects was, you know, helping Atlassian go public by cleaning up their IT, you know, their IT strategy in their back office to their integration strategy. So, here I am sitting in Montana, you know, telling, you know, Atlassian, what they need to do to get ready to go public, so they, you know, don't get slapped on the wrist for having bad internal process. Feels pretty cool. Felt very important at the time, kind of a big, kind of a big thing for Missoula, I think which back then other than RightNow Technologies didn't have a lot of, you know, big stories. I think now there's so far and others, but, you know, back then it was it was not a big story.

Les  04:34

Yeah. That's incredible. And tell it tell us a little bit to just about as a young man growing up in Montana. I mean, you were probably quite the anomaly be in the computer science guy in your class, right, like growing up. I mean, yeah, just tell us about tell us what that was like.

Jeff  04:52

Yeah, it was it was interesting. I was always like a bit of a computer nerd, like building computers, building websites. There wasn't a lot of I mean, there's just sort of like early to age days of like, you know, the internet so there wasn't exactly like a YouTube or like a Code Academy out there. So you know, a lot of it's just taking whatever I could find. So like, learn C++ in 21 days, like on the, you know, the DVD you get with the magazine. That was kind of basically it. Yeah, computer science program, University of Montana. You know, they're a liberal arts college. It's not as big as Bozeman’s computer science program. I think when it first showed up, they had maybe like, nine to 10 people graduating a year. So it was primarily focused on research science, not a lot of, you know, SaaS wasn't a thing. Not a big focus on business software,

Les  05:36

SzzS. So people are like SaaS, how do you spell that? What is it exactly? Incredible. I love I gotta say, I just love the origin, your origin story, because it's just, it's so it's so cool. It's so Montana. But at the same time, it's so there's, there's just this incredible diversity of experience that you had early on your career, and then you led into this a little bit like Atlassian was, was a was a huge customer that that ATG had, and you worked directly with them. Talk to us about kind of how your career then progressed in that direction, right? Because you ended up there.

Jeff  06:08

Yep, Yep, absolutely. Yeah, I was there for six years. So I mean, you know, Atlassian has such an interesting culture. And it was so much fun. And it seemed like there was kind of endless challenges. So, you know, after I think I worked with them right up until they went public, you know, I was there in Sydney for the launch, you know, for the when they rang the bell. And I kind of just had this moment where I'm like, hey, this, this company is pretty cool. Like, you know, they flew me all the way out here to Sydney to like, drink their free beer and like, be a part of this moment. Like, maybe I just like, stick around. And that was that was basically the conversation. One of the people I was working with, I'm like, Hey, like you asked for your team, like, maybe I could just hang out for a few years. And you could pay me.

Les  06:48

The best job interview ever. Yeah. Nice.

Jeff  06:52

That was basically the extent of the job interview. So then I, you know, I, I moved out to San Francisco for six years, I worked out of the SF office, and then ended up leading teams, San Francisco, Mountain View, Austin, you know, had a team and I helped, like, start the office in Bangalore help go out there and hire, had a team there kind of all over the place. Worked on platform for six years. So pretty much if you buy a product from Atlassian, I've built or worked on many of those services, platform strategy, if you've ever logged in, or edited or collaborated with anybody that Atlassian like, I had my fingerprints all over that. So it was it was quite an experience. I really enjoyed it. And I learned, I mean, I learned a lot about about software, but also just the way about, like how product led growth companies can succeed. I mean, Atlassian being the world's largest product led growth company and kind of a little bit of a, like an early mover in that space in b2b. You know, they kind of wrote the book on it. So they have some problems of scale that other companies, you know, really don't have, or sort of like they could read the book that was already written. And then they can implement that.

Les  07:56

I had no idea, Jeff, when my love affair with Confluence and JIRA began, you had your fingerprints all over it. That's amazing.

Jeff  08:03

Only on the only on the cloud product. Don't blame me the early ones.

Les  08:09

Awesome, man. That's great. So what and I remember, I think you shared this with me previously, you had Did you have an option of like choosing? Was it either Austin was at Austin vs. Tell us that story. Because that's a good one.

Jeff  08:21

Yeah, this is a funny story. I'm sure my wife appreciates having this story memorialized. So that kind of the joke. The joke is, and the reality is, is that my boss was very cool. And he's like, I just want you on the team. Like, you know, you can do whatever you want to do with your life. You tell me, you can work out of the Sydney office, you can work out of the San Francisco office, you could work out of the Austin office. And so

Les  08:44

Nothing like calling your own shots, man as a new hire, it's incredible.

Jeff  08:47

I was like, this is the sweetest deal. And so you know, I go back to my wife and I'm like, let's go to Austin because like, you know, big house, like low cost of living like low taxes. This sounds great. You know, like, maybe second choice, we go to Sydney, like, that'd be pretty fun to like, live abroad, like live on the beach. 

Les  09:06

Ride a kangaroo to work, or whatever.

Jeff  09:08

I don't, I don't want to spread any of those stereotypes. But they do really ride kangaroos to work. They smelled like horses.

Les  09:17

That’s what we do in Montana. We ride horses to work.

Jeff  09:19

Exactly. That was I got that joke a lot. In Australia. It's only fair. I give them a ride to kangaroos. No, but I my wife’s first choice was San Francisco. So we ended up in San Francisco.

Les  09:32

All right. Good husband. Make the wife happy. Happy wife, happy life. All right. So so what was it like what was that transition like, by the way, so you know, you know, growing up in Montana used to kind of the Montana way life and now you're in SF. Was it smooth or was it abrupt?

Jeff  09:53

It was abrupt. I didn't really do all that much traveling either before I ended up moving there. So I had pretty like, I mean, San Francisco is a city and I just didn't really have a lot of city experience. But it's also a very strange city. And the fact that like, most people, you know, they head, they like, go toward the city when they commute to work. And San Francisco, everybody lives in the opposite place where they work in the opposite place where they live. So it's a strange city and getting the hang of it took a while. And also just like, Big City Life, like, you know, there's things like crime and there's like homelessness, and there's all these other things. So it was quite a culture shock coming from like, small town, like walk everywhere. drive across town in 15 minutes. But yeah, yeah, I got the hang of it. I sold my Jeep. I lived the whole time there with no car. So I commuted the whole time. That was interesting. Like, it was fun. Commuting is not really a thing in Montana. Well, I mean, reading cars if you call that commuting, so taking trains, buses…

Les  10:53

The BART, right. Did you take Bart? 

Jeff  10:56

Yeah. Yep. So I got used to that. I mean, there's a lot of fun things to do. It's an expensive city too so you suddenly realize, like, you suddenly realize the real cost of living in San Francisco, and it's a shock, no matter how much you want to prepare for it.

Les  11:08

Yeah, it's like, it's like the sales tax on your night out would be the equivalent of like, your entire night out bill in Montana.

Jeff  11:15

Exactly. Yes. One one night buying everyone drinks is like the equivalent of like, two drinks.

Les  11:23

For sure, great. So but but your wife was happy you guys were happy. You're enjoying life in San Francisco and, and crushing it, crushing it for Atlassian? How long? How long was that journey, that chapter?

Jeff  11:33

Um, so Atlassian for about six years, if you kind of count like some of the ATG time, until, you know, working, leaving Atlassian to you know, to start my own company? Yeah, I, I think I, I ended up moving offices, a couple of we had changed offices. So we had like this sketchy office at Atlassian, which was kind of cool, and then moved to the financial district. And then we opened the Mountain View campus. And so I was kind of back and forth. So I, you know, the company grew tremendously, where I pretty much knew everyone's name, too. You know, I can't even remember, you know, the people who are I saw last week near my desk.

Les  12:10

Crazy. And you and in your progression was actually like your pasted pretty, it seems like pretty hot as an engineer. I mean, you started out as a Quote to Cash Solutions Architect, he became an engineering manager on the data platform and then finished up as an engineering manager on the Cloud Platform. Is that, is that? Yeah. Is that right? Yep.

Jeff  12:27

Yeah, so I was, I was more or less like, they didn't even have a job title for what I did when I first started there. But it was Quote to Cash Architect, you know, they didn't really have that they really have that concept. That was like the first one of those, you

Les  12:39

You probably taught him what that meant, right? Is that where you'd like the guy that educate them on that

Jeff  12:45

I was the Quote to Cash guy, a lot of like, what I was doing was explaining Quote to Cash. The idea was like, the systems that got us to being a public company would not actually scale to like 1 billion to 3 billion in revenue, they needed a lot of work. Right? Like, like, it wasn't a sale, 70 company, it wasn't a partner, it was a partner heavy company, things were changing, they needed a lot of change in systems. And so it's not just something you dream up, if you've ever done it for the first time. So my role was really, you know, hey, what are like? How are we going to do this? How are we going to roll this out? What should this look like? What do we have to build? What do we have to buy? And that was great. And I think, you know, again, I alluded to this being the world's largest product led growth company, they have challenges where you can't just go buy something off the shelf, you can't just be like, hey, I need it, I need a product led growth engine, like I'll go buy this. So it was a lot of built, there's a lot of engineering involved a lot of custom stuff. You know, their billing team has designers stuff you wouldn't normally have expected back in the day. And then I did that for a while. And I went on to solve some problems in the data space, I lead a couple of data platform teams in the US. And we were basically trying to build a graph of data across all customer data at Atlassian. So if a customer uses a product, can you trace that to a support ticket if they've used the feature, you know, and then if you throw in the fact that Atlassian acquires, you know, a pretty decent sized company every year? A lot of different data, a lot of places, yeah, if you're a customer support person, or you're trying to connect all these things, it was it was a big challenge. So I think…

Les  14:10

Did you learn that on the fly? I mean, that's like it that's an entire body of like, research and like, how did you learn that on the fly like that, hold the network graph piece of that, or

Jeff  14:19

Just learn sort of learned everything on the fly. There's a bunch. There's a bunch of smart people at Atlassian used to ask a bunch of questions and listen, like most people will give you the answers. And then you kinda got to tie it together. But no, I mean, I didn't know what data engineering was. And here I am, like, leading, you know, a bunch of teams on the data engineering side of things leading data platform building, you know, custom data ingestion platforms. We were processing billions and billions of events a day in real time. I'd never done that before. So that was like kind of new to me. By I figured out I had a great team, actually, like many people from that team came and joined me at my current company. So I'm working with like five or six or seven Atlassians that kind of crossed my path where I'm at currently

Les  15:00

That's how all the good CTOs operate love it. Good stuff. So Wow. So what I mean, what a great kind of progression then for you at one of the one of the best, you know, tech tech companies out there that just spans across, you know, just as a platform. I mean, that's amazing experience. And then at what point so then you worked on the, the engineering cloud or as an engineer manager on the Cloud Platform after the data platform. How long did you How long did you do that for?

Jeff  15:30

So I was there for about a year, year and a half, that was another interesting role. Like, I tell people that it's mostly just a politician. Because when you're talking about when you're talking about a platform team with 1200 people that you're working on strategy for, then you're thinking about every product, that he's used the platform, and then you're acquiring products every year that they have to get on the platform, you're basically a politician. And so the acquired company, like would you like to go on the platform? Hey, we don't want to we can't, this won't work. It's too scary. You know, like, there's a lot of unknowns. And so the project that I worked on, there was, hey, we need to get all these acquired all these acquired products on the platform, you know, we need single login, we want to single collaboration experience. They all have different models like Trello, and JIRA, not the same, even though they seem seem similar. Also, hey, we're building we want to build a bunch of new products. So is the platform ready to do that? Can you prove out it's ready? What's missing? Who needs to be staffed? So existing? Aquired? And then new products? How do they all get on the platform? And then what does the platform even look like? As you know, connection of offerings?

Les  16:37

In a way I would even say, I mean, correct me if I'm totally off here, as you're much more of a technologist than I am, but like, when engineers make it to this cloud kind of role, like, that's really the pinnacle of you said it as like politician. But I would also say it as like, You got to be the expert. Right? You really like that's the pinnacle role for an engineering manager? I would I would make the argument for.

Jeff  17:03

Yeah, I think I agree. And I think it also layers up on like, what level of impact you in management, you can kind of like, oversee, like, there's definitely some managers that are just like managing a team of five people. And all they do is build one thing, right. And then eventually, they have two teams that are doing similar things, and three and 4... Eventually, I think my challenge is that I was working across like, hundreds of services. So like, I didn't really, it wasn't, my team didn't actually even own a codebase. We were literally contributing to other people's codebases, for my teams, when in that role, you know, we were convincing other people to do our projects, we were, you know, we were asking for, like 20, 30, 40 people to deliver on, you know, themes and changes that are across multiple teams and services. That was really hard. I sort of missed the days where I'm like, I had a codebase, I knew every line of code in it, like, we wanted to make a change, we just made it. It was sort of different. And I think that's the truth of cloud, right? Yeah, if you're building on Cloud, you're building a connection of services that you buy different teams build some combination, you know, some are growing, some are being on a shelf, right? There are in maintenance mode, and trying to like, interact the constellation of what's actually happening to build an experience. It requires a lot, like the days of server were simple, you know, it Atlassian the days of cloud got very complicated. And then you know, growth, acquisition, different strategies, cloud companies change every month, they change strategy every quarter. So lots to keep a drop, keep across.

Les  18:34

Yeah, what a what an what an experience. It's amazing. So at this point, you know, you've had this your careers have this incredible trajectory. You're at Atlassian when did you decide like, yeah, maybe I might want to do my own thing, or is it hang my own shingle. Like, what what happened?

Jeff  18:51

You know, actually, I tried very hard to not do my own thing. Atlassian is great gig and I had a great job. I had a great team, I was doing really cool, important stuff. Like I was like a little bit of like, I've been there for a long time at this point longer than like 80 or 85% of people if you can imagine how fast the company has grown. So I didn't really I wasn't like I want to leave Atlassian to go do something else. It was sort of like you know, I had met my my co-founder years ago and he's like, we got this problem. You understand this problem? I understand this problem. Let's go solve it and I'm like, I don't know life's pretty good like they feed me well. They've got like 20 different types of free wine like they got kombucha on tap like I don't know if I want to

Les  19:31

Sandeep - you got to check out this lunch buffet man. I can't give this up.

Jeff  19:36

I mean, you know, there's there's a reason why they have all that free food right? You just you forget how to cook and then you become like a pet you have to go to the food dish you can't ever leave. I was sort of like domesticated by like, all you know, the perks of the good job and like the interesting work. But like the thing that always bothered me is that like, the very first thing that I joined Atlassian to solve, which is, you know, build a billing and monetization platform that can serve the world's largest product lead growth company. It just was, it became clear to me that it was almost impossible to do this, no matter how much you invested or what you looked at, you could just really like, everything had to be so custom. And when I joined Atlassian, there was 17 engineers on the billing team. And when I left Atlassian and there was like, I don't know, like 177 engineers on the billing team, just on the billing team, just on the billing team. And it's like, oh, it's grown by like 20 or 30%. Since then, based off like, what I can extrapolate, and the word on the street is that is just not normal, like, they’re a product, lead growth company. They don't do anything that crazy. Like, why is monetization just as difficult problem? And every time I just thought, like, became more and more challenging, it's like, oh, like acquisitions like that presents a challenge, like experimentation that presents a challenge. Like, we're shifting pricing models like usage metering, just like I just like no, like, in my head, I know what could solve this problem. But like, when you have to build it yourself, it's not so easy when you can buy something and be like, Hey, we're just going to use this. That's one thing, but they just never had an option to buy anything. So I figured, you know, every company, every b2b SaaS company wants to be a product lead growth company, you know whether they can or not, that's another story. And so they're, they're all going to scale and experience these same problems. Like who is solving this and I actually was like, Oh, someone will solve this, like this company will solve it, this company to solve it. No one really make any progress. So no innovation in the space and then just seeing the problem grow were kind of the two themes.

Les  21:41

Interesting. Yeah, it's definitely like a extreme multi-dimensional problem. Right? And maybe that's it, maybe the complexity of engineering a solution has been the moat to keep people from trying, do you think or is there? Are there other things? Are there other other reasons why no one has attempted this until now?

Jeff  22:01

Well, it's, it's it's a lot of things. And I think like the fact that they can, like I mean, they have a lot of engineers. In fact, they put that many engineers on solving the problem is great. There's not a lot of companies that can do that. Like, there's some product teams that have like, there's product teams and 1000 person companies that have 177 engineers, like that's their whole engineering.

Les  22:20

That's right.

Jeff  22:21

The challenge is, is that like, the way the wave requirements come in, or one at a time, with high urgency, hey, we need this one thing, just build me this one thing. And an engineer, a product manager and engineering manager is really like, hey, in order to build this the right way, like, can we get more requirements? Could it be more generic, we want to build into a platform, we don't want you to come back, like every day with like a new order, we want you to like, tell us what the platform looks like. And then we'll take the right time to build this. In a fast moving company, you never get the time to build it. Right? Right. I'm the business. You work for me, you build me this thing, like, my team is the one that makes the money, your team is the builds the thing that makes the money, right, like do this right now. And this was always the challenge is that like, you know, if you talk to anybody on the billing team, they're like, I want to build it right, I want to build the right platform, you can build it from scratch, we can redo these things. And that's just not interesting to anyone, right? Like spend a year building the right thing is never going to win over deliver me this thing next month. And when you, and basically what you're describing is tech debt, right? Oh, yeah. Like that tech debt into product. Eventually, you pay that tech debt off, like it becomes bad the product needs an overhaul like tech debt on a financial platform is a whole other thing, right? You cannot like, this is not an easy thing to change, people get very sensitive about billing and about selling. So when you load up on this much tech debt, and you really just keep mandating and thinking about, you know, how I can make this thing, you know, do what I want, and not how I can think that there's this thing as a platform, you can end up with a mess. And historically, the teams that work on this are filled with a bunch of smart people that are under-resourced, and never get the time to clean up the mess that they're asked to make. You do that for a decade, and you end up in a rough place. And for most large companies about the size of Atlassian, or b2b SaaS, complex offerings, selling product like growth, they're in the same messes. If you ask like, you know, us a company that sells similarly to Atlassian, or just really any cloud company, Hey, how's your billing and selling systems? They'll tell you, it's a mess. And so they sort of all arrived at the same conclusion. And my thought was, maybe it doesn't have to be this way. You know, this would be an interesting problem to solve. But also, it's like, a massive drain. Like, if you think about the purpose of a software company is to provide some value, right? And they're not providing value because they're cleaning up difficult business problems. And some, maybe those companies

Les  24:36

That they've created for themselves. Yeah. Yeah.

Jeff  24:40

Yes, right. Some companies are not doing that interesting of things. But other companies are putting people on the moon, right? Like, what productivity gain, you know, like, what productivity game of like self driving cars and putting people on the moon and like AI is really existing because people are like, I can't figure out the link. Right. So it's like, you know, on one hand, it's like, obviously, there's there's a tremendous opportunity, multiple billion dollars easily if a company can solve this problem. On the other hand, there's like, is this actually holding back what software can do? And like, what would the world look like? You know, what would software look like if we could move past this and actually work on solving problems? So a couple different levels of motivation. Very, very interesting to me.

Les  25:17

I love I love what you said about the specifically using the moon analogy and putting people on the moon because it actually reminds me of the JFK quote, you know, and who knows if it's made up or not, but it's like, you know, when you when you ask the person that's sweeping the floor, you know, what do you do here? I'm putting a man on the moon. It's like, it's, it's that was a terrible paraphrase the quote, but I think everybody knows that one. But But my point is, it's like, there's, there's, it's like picking up nickels or sweeping the floor is like, is actually allowing the the enterprise that has the big, audacious goal to, to go go out and do it, right. Like you're, you're removing that friction. So yeah, that value prop is really, really exciting and compelling. So what what was the spark? So you, your founder, Sandeep Jain, right, that you guys knew each other for a while you said, what was the spark where you guys said, Let's do this? Or how did that come about?

Jeff  26:15

Yeah, so he, he had looked me up, he was looking for a big problem to solve. And he had talked to some people at some large companies that said, like, forget about what you were thinking about, let me tell you about like a worst problem in the world to solve. Or maybe not maybe not worse, but a bigger problem in the world, so and so he got turned on to all the SaaS companies, especially product like growth companies, where things were a disaster in the billing space, or in the selling space. And so he sort of looked me up, he saw my ATG background, he saw that I was at Atlassian. And he looked me up. And this would have been like, I don't know, four or five years ago. And he started just like, cold, called me on LinkedIn. And he's like, Hey, like, you know, I hear you understand this problem, like, can we talk about it? And like, you know, a lot of random people look at you on LinkedIn, you know, reach out to you on LinkedIn. And so I kind of like, tried to like size him up, he's like, he's not trying to sell me anything. Like, I'm looking at his background, and I'm like, I don't see what the play here is like, maybe he just really does want to learn more about the corporate passion. So sure, like all like, here's my number, like, let's chat.

Les  27:14

You didn’t know he was shopping for a CTO? 

Jeff  27:17

No, I had no idea. That's amazing.

Les  27:19

And you responded, what great serendipity, then that, that that worked.

Jeff  27:24

Yeah. So I mean, we chatted, we talked about the problem. You know, I think being at a company like Atlassian. And working across so many different departments, like I kind of, not everybody sees the big picture about why quote to cash is broken, or about why monetization is broken. Atlassian like, I was kind of right in the middle of it. And then also, you know, for my time, at ATG, I had a pretty unique insight about how all the pieces connect, not just like little bits of bits and pieces of it. So we got to talking and we just kept talking, you know, and then you know, well, what's this? He's like, Well, what's the solution? I'm like, this is the solution like this, and this and this, and this, you do this and do that, like, here's why these products don't work. Here's why they won't change, here's why they can't change. And he's like, oh, you know, you sound like you, you know this, like you want to do a startup with me? Like, would you be interested in solving this problem? I'm like, Nah, I'm pretty happy at Atlassian, we kind of did this dance for a while of like, talking about like, eventually, like, it kind of made a little bit more sense than were like, maybe, like, maybe we should do this thing. And then we just started talking, you know, more frequently started thinking about things, what would it look like? And the story kind of just progresses from there.

Les  28:29

Amazing. And you've said it a couple of times now. And I want to make sure I always try on the cast to make sure you know, we don't gloss over like words, assuming our listeners know, acronyms and things, but quote to cash. Can you talk about that a little bit and explain what that actually is? So people can really could get a get a better understanding of, of what's broken, what's broken about it and what it is.

Jeff  28:52

Yeah, Quote to Cash is sometimes more of like an academic term, right? Where it's like, the average person on the street, like going to market may not know this term. But Quote to Cash is really just about like, thinking about like a systematic and holistic approach to like how all money flows in the company. Right? If you sell servers, you build the thing. You tell somebody the price, you sell it to them, that's the end of it, right? Quote to Cash used to be like, produce something, say what the prices are, sign a contract, give them it, right. But in SaaS Quote to Cash is a lot more, right. It's about omni channel. So I have people buying off the web through partners through sales, people buying upselling themselves, right? I'm going to upgrade I want to downgrade. It's all subscription. So every year things are changing. I'm adding new products I'm expanding, I'm contracting. And then you think about things like you know, how do I accurately pour revenue to Wall Street? Right? How do I handle refunds? How do I handle chargebacks? So it's like includes payments include selling and includes billing includes finance, and most people, their job titles are siloed. So I work in Finance, and I do this, right. And so they don't think about Quote to Cash, they think about finance, or I work on the sales team, and I think about sales, or I work in it, and I'm responsible for these systems, or I'm a business person, and I give these requirements and Quote to Cash, where it actually all comes together. And you figure out, you know, when the rubber hits the road, like, how does business actually get done at this company?

Les  30:23

Yeah, exactly. That's a beautiful explanation. And, you know, I have my kind of, like, my pea brain would say, This is why, like, when I tried to add a new Microsoft license to my work, like, why can't I just add it, I have to, like, go into a different portal and add it license before I can actually like assign the license. And like, that's a simple example of the complexity that thinks all of us have experienced the frustration there. But right, I mean, when you multiply that times 100 times 1000 times 10, that this is a seriously complex space to manage. And fate, by the way, based on what you said about all the siloing, that happens as well. So…

Jeff  31:04

Yeah, and I think, you know, something like, I remember the first time I ever heard this was from Atlassian, I'm sure if it existed before that, maybe it was like a Martin Fowler thing. But like, there was like an interesting kind of saying like that, like the systems that you build, like basically reflect your team structures. Right. And I think that makes a lot of sense. Like budget goes to teams, priorities, go to teams missions, go to teams, and then people build things to complete those missions, or help them with those missions, or they buy things. And, you know, when every team is siloed, then they build or use siloed systems. And then this, this basically leads to an entire industry of integrations, right? For the past 20 years, there's all these different tools and methodologies for tying these things together. And it doesn't work very well. Or as well as you might think. So you talked about, you know, I go to add a license, and they go to this different portal, you know, that's a silo, that's an integration, that's a change of experience, that's a gap. And your ability to make changes in one system is limited by what the other system can do. So to some extent, like you're getting the least common denominator of like, what all of your systems can do, that's basically your go to market if you buy systems, right? If you build systems, the least common denominator and of what all the people build for you, is your go to market. Right? So but you know, the sales team needs this finance team can't support that, okay, then the sales team doesn't do that, right? Or, realistically, the sales team always gets their way. It's like good luck, finance, figure it out. And then the sales team is like really mad, right? So like, you have people like, you know, loading up four terabytes of spreadsheets to figure out how to close because you got all these manual processes. And that's, you know, that also has its, you know, its inherent thing, because then Finance says no to everything, because they know they're gonna get burned. So people start to build like, walls, right? Yeah. All the like, no, sales or finance, like, it's an endless battle, you know, sales, like we make the money, finance is like, but we allow us to maintain being a public company by like, actually reporting what we make, you know, and like, they, you know, accuracy over speed, like big deals over, you know, consistency. There's a lot of trade offs there. These people build and buy different systems that help them support their missions that are not always compatible.

Les  33:17

Yeah, by the way, why is sales always at the crux of all like, all of a company's problems? Like, because if it isn't sales and finance, its sales and engineering, right. Oh, that salespeople are promising features that are on the roadmap. Oh, the engineering team can't build it fast enough. Like it's always sales, that's always sales. That's the crux of this. Yeah.

Jeff  33:36

It is. But they I mean, to be fair, like, they are the ones that close the deals, right. So like, they're trying whatever they can do to close a deal. And I think, you know, unfortunately, there's like, there's some, like, you know, different levels of ethical selling of like, yeah, we do that we do that build that feature for me. But you know, like, we already built the feature, it exists. It's coming next week, and then it's like, the feature never shows up, you know, I think so there's like, I think inherently like, they're like, looking to get a signature on the line. And then they're like, good luck. You know, I think, to some extent, like product is kind of off the hook for everything that happens after that, or, or finance is on the hook for everything that happens after that. And, you know, I mean, one of the things I spend a lot of my time thinking about is like, how could you actually bring, like, why is it like sales versus finance? Why isn't it like sales and finance, sales and marketing, marketing and finance, you know? And, you know, I mean, that's, that's sort of like what I'm building, right? It's like, I'm building a unified way for all actors in the Quote to Cash to come together and work across a single system and solve problems together and spend a lot less time doing manual things and building integrations. You know, and so I think, just some of that experience of like all these breakdowns, it's really interesting. So I feel like I maybe I'm over exaggerating, because I focus on these a lot, because they're sort of what I'm trying is trying to solve, but when you're in a SaaS company, there's definitely a lot of friction. So I've seen some, some interesting scuffles.

Les  34:56

It's it's a brilliant vision, Jeff, and I gotta say the maturity, I don't think I've ever heard a CTO say sales and that's incredible, incredible maturity. Amazing. So quickly take us through the just kind of the founding story, the your initial funding and kind of initial launch and kind of maybe what you've learned over the kind of the initial initial rollout of MonetizeNow. By the way, we haven't even said it yet. That's the name of the company. MonetizeNow, not monetize yesterday, not monetize tomorrow, MonetizeNow.

Jeff  35:29

That’s right. Yeah, that didn't kind of stuck. I think we had some other iterations. But I think that was the one that we kind of, we ended on. naming things is hard. I think that's the old joke. And like, software, it's like, the two hard problems are like, cache invalidation, naming things and cache invalidation. That’s the joke. No, I mean, the story. So listen, so I'm, you know, me and my co-founder, we have jobs where like, we have families, things are relatively good. Should we do this crazy thing? You know, I think there's a lot lower being a founder. But we're also like, you know, we're not freshmen to college, we also realize that there's a reality of being a founder that this is actually very hard. Right? Many startups don't succeed, many don't get funding like it is long hours. So as we're sort of noodling over, like what this would look like, and like when we jumped ship and go start a company, we're kind of starting to think about, you know, is this a problem? Can we validate the problem? Before we build the problem? Can we get interested investors before we build it? Like, if we can't get funding, no one's interested and we can't validate the market size and like, let's not move forward, you know, and then it's like, okay, everybody says they want this thing. You know, like, can we get funding for it? Like, what would it take to get funding? And so we took a pretty slow approach, we talked to quite a few people, just trying to figure out if this was a fundable idea, what it would take to get funding. We met a lot of people along the way, we loaded up on a ton of angels. We had, we have like, maybe like 800 or 900k, in like angel funding spoken for, you know, before we have raised our Seed, and we didn't end up actually taking all that angel money, we ended up rolling into a seed, but everyone we ran into is like, this is such a problem. And it pisses me off, like here's a check was basically a great conversation.

Les  37:09

That’s great validation, though, right? I mean, when when you got check writers that are willing to acknowledge that are acknowledging that that's, that's great, early, early validation. I mean, granted, they're not customers, but you know, the industry experienced you know, professionals. 

Jeff  37:22

Yeah. Absolutely. So we kind of, we're kind of getting to a point where, like, you know, I'm, I started like Moonlighting, and like, I had an old laptop. And so I'm writing a ton of code, you know, just staying up all night weekends, reading a lot of code, building out sort of what the MVP would look like, in case we ever have to demo it. We're talking with investors, we're figuring out, you know, what we might do? And, you know, one thing led to another, you know, at first, it was a 10k, check. Then it was a 50k. Check. That was 100k. Check. You know, it's interested people interested investors, things started to warm up and we got some warm intros to people. We were pretty cautious about like, we were building something that really never been built before. So we were kind of cautious about making sure we got investors that would support us. And so yeah, we ran across a couple of great investors from Two Sigma Ventures and Uncork. And they were, both of the partners there were friends. So they kind of brought each other in on this deal. And they were very friendly. Like they very much believed in the mission, they had a lot of experience, they had a lot of companies in their portfolio, that understood this problem. That was something important to us. We wanted people who like felt the pain, so they understood what we were trying to solve. And, yeah, basically, you know, we quit our jobs. We had like three or four term sheets, we ended up going with Two Sigma and Uncorked. And we, you know, we put our good jobs. Two weeks, three weeks later, we founded the company, had some, you know, checks in the bank. And, you know, we went off we started from there, sort of like, we didn't really even have much to show or even like a single person other than me and Sandeep. But so we kind of started like, from literally like square one. And yeah, it's grown grown incredibly since then. But it was very, very, you know, this is an unusual way to start something right. You quit your jobs, enjoy Christmas. start a company, get millions of dollars in the bank to build something. Hopefully you can deliver up.

Les  39:11

Well, at least you enjoyed Christmas. I gotta say, yeah. Yeah. And then, so what? So it was just the two of you, and then you how did you like, what was the was the process for the first few hires?

Jeff  39:23

Yeah. So I mean, we, we were always like a remote company from like, day one. We knew this was something was very important. So for the most part, it was like, you know, where can we find people who will want to you know what to do this crazy startup people we can believe in people who believe in us. And so we were able to leverage hiring in a lot of different places. So actually, like, you know, one of the first people that we ever hired was actually in Bangladesh. And I don't know anyone in Bangladesh, and I didn't know anything about Bangladesh.

Les  39:54

But how did you source that employee?

Jeff  39:57

Like, I'm looking for like a back end engineer. Oh, Here's what I need. And it's like, you know, there was like a little like checkbox, it's like, you know, do you care? You know, which country this person is in, and I'm like, I don't care. You know, I just need, like, somebody who's gonna, like, follow me into battle. And so one of the first people we ever hired was from Bangladesh. And then, you know, that that worked out, that was great, you know, cleaning up some of my founder code, and then somebody that I worked with at Atlassian on a few different teams, you know, he kind of knew he kind of knew what you're working on. And we had talked about it and kept in touch. And I'm, like, you know, come join me, like, you know, like, do something crazy. Let's give this a shot. And he did. And so that was like, first two engineering hires. We ended up hiring, you know, some DevOps design really early. But yeah, it was mostly just finding, you know, we interviewed a lot of people, we talked to a lot of people. But it was mostly just following, you know, finding people would follow you, and also finding people who would enjoy a startup, we talked to a lot of people who we felt like they would not do well on a startup. You know, and I think like, that was a very challenging thing. There was plenty of great engineers, but engineers that want to like live in a startup environment, that was harder to find.

Les  41:04

I'm really glad you said that, Jeff, because I think that's such an important piece of the kind of early stage tech journey that a lot of founders kind of realized the hard way. I don't think it I don't think it happens so often on the engineering front, because generally CTOs are aware of the culture. That's why they signed up for it. They were probably in it before. And so they're tuned into this. But I'm glad you said that's the first time that's that topic is surfaced on the podcast. And I think it's important for all early hires, not not just engineers, but but for sure engineers.

Jeff  41:39

Yeah, yeah, I think one of the one of the early thing, one of the things we learned very early on is sort of like, the sort of like cultural fit. And like of the match of like, what people really wanted out of their career was way more important than like, the technical fit, I talked to some very smart engineers, who all they wanted to talk about was like, you know, I worked at a huge company, and to help scaled like a huge thing. And like, I really want to help scale huge things. That's like, to me, like a very big red flag, right? It's like, well, there's not a lot of scale. And we're not going to be building a lot of perfect systems, we're going to be doing a lot of really hacky stuff, right? We're going to dream things up, we're going to change our mind, we're going to break things. And so I think, you know, that was something early on, that we learned. But then actually to find really good engineers who can think on their toes and like, don't mind the ambiguity, but can still write good code can like make trade offs? That was hard. And I think I sort of like underestimate how hard it was to hire. Because I'd always worked at companies that had credibility, right? Like, when I would say, Hey, I'm hiring an Atlassian. I get like, 100 people that will apply, right? It's a very safe company, when I'm like, hey, I want to hire somebody at MonetizeNow, they're like, I don't know what that is, like, you know?

Les  42:49

Yeah, exactly.

Jeff  42:51

I discounted that quite a bit. That like, unless you have a bunch of customers, like, the early hires that you really don't have anything to show other than, like a crazy idea. Like, you know, most engineers apply a lot of scrutiny to so there's people who are like, you're a little too small. You're a little too early. And then it's it's interesting, like it's a magical state. You're also too late. Oh, I wouldn't want to be one of the first five people. Yeah, and I don't want to be I don't want to be five for 20. I want to be one through five. I'm like, well, where? Where are these people when I needed the one through five? Right? Exactly.

Les  43:24

Sorry, we’re at six. Yeah. Yeah. Interesting. And, and what? What about how has how, as a company has evolved, what are you thinking about now? Like, what's what's exciting to you? What's keeping you up at night? What's this next phase phase of growth look like for you?

Jeff  43:40

Yeah, so I mean, we, it's basically we're, what we're describing when we got started was about, you know, two years ago, like January of 2020. So we're two years, you know, in the future, we've got, you know, 21 people on the team, pretty large engineering team, two designers, DevOps, sales, you know, product operations, we have a pretty big team. And now we're starting to acquire customers pretty quickly. The product is very rock solid, it's great. People love it, we've gotten a lot of feedback, we've made a lot of iterations. I think now it's, it's, the interesting thing is just loading up a ton of customers, and trying to think about, you know, what do we build next? How do we stay ahead of things, we sort of I mean we built something that we built something that really didn't exist, there was no system that would let you bill and sell across all of your channels in one place. And so, you know, I think when you're building something that's never been built before your assumptions about the window a lot. So we learned we collected a lot of feedback, we perfected We made mistakes, now where you've sort of figured this out, and we sort of refine this. So now it's just like, how fast can we onboard customers? And you know, what use cases can we support you know, we recently just closed a deal with you know, a company that was actually you know, a public company. Right, and when you when you do billing and selling for Public Company, and you look at what their system requirements are. That's quite different. Yeah, so it was, I don't know if people on the podcast would ever hear of this thing, this system called Zora, and it's considered to be a very enterprise the billing system, but it's also no one really likes Zora, it's not a very friendly system. Right?

Les  45:19

It doesn't sound friendly, not friendly at all. I picture like somebody in like a bandana with a sword. I guess that's Zorro. But anyways, you

Jeff  45:31

Zora, you can Google for it, and you have a 50/50 chance that it's like spell checks you and like, says that it's a PokeMon, and not the name of a billing company. So yeah, I mean, that we're starting to support Bigger, bigger customers, you know, we had, we had one customer that had like, 100 salespeople, you know, so like, a building a CPQ for 10 salespeople, building something that you can do quoting for for 10 people, and then looking at sort of these larger companies that are starting to come come across. So that's something we're also considering now. It's like how to scale for to meet larger use cases, we definitely like do quite well, you know, we have lots of companies that have sales teams from sort of this, like, you know, five to 25 to 30 range. So now we're also looking to scale that up and go bigger there. 

Les  46:14

Very cool. What about you know, I just realized something, Jeff, this is Found in the Rockies. This is a Bay Area company. Wait a minute, what's going on here? I saved this. I saved this gem for you. Because I think this is one of my favorite parts of the MonetizeNow story. What's the deal? What gives? Are you guys in the Rockies or what?

Jeff  46:34

So we partially are? 

Les  46:38

I hope so. I know, I know, you said you, you know, went down this strategy of remote hiring, but tell us where some of your employees are?

Jeff  46:46

Yeah. So we have. We have two people in Montana. We have some we have some Montana people with two. Yeah, two people in Montana. I know there's others there may, that list will probably grow. So I always wanted, I always wanted some sort of a presence in Montana in my hometown. I mean, a lot of the people I've worked with, at ATG, we have two ex-ATG people in the company. So this is always something that I wanted to kind of stay close to it. And like my heart's kind of like, still a little bit stuck in Montana. And so I always dream that I'll still have like a large team in Missoula, I can leverage people I used to work with in Missoula. So I just made that this will still happen. So I think we still will be in sort of like, have a little bit of a tethering to to Montana, I think our fourth hire, maybe our fourth or fifth hire was actually in Montana. So our product operations managers in Missoula, Montana.

Les  47:35

Very cool. Well, I love that part of the story. And you know, this, but I'm just gonna say it out loud, and a public format that whatever NFC can do to help you continue, that Montana presence where we're all in, and that's actually how, believe it or not another fun thread of the story. That's how we got connected, right? Was was through Missoula, and you want to tell that story? That's a fun one. 

Jeff  47:56

Yeah. So I mean, like, you know, when I was thinking of, I mean, no offense, when I think about like, raising capital, I think about like New York and like SF, right? Like, these are the places I think about not to say that I have a lot of expertise in this stuff. And, you know, so it's kind of interesting. My product Operations Manager works out of Missoula. He's like, you know, Hey, Jeff, you know, there's this company, and like, they're like a VC firm. And they're based out of Montana. And like, I met this guy. And like, he asked me for, like an intro. And I'm like, sure, I don't know, like, what do I know about? What do I know about this company? I said, sure. Yeah. Like all you know, that sounds fun. Like, let's do an intro. You never know, you know, what will happen if you talk to them. And yeah, it turned out like that sort of set in motion, the steps that we were raising, you know, we're raising our Seed round, we ended up connecting, and then it sort of hit it off. And I think, you know, maybe that maybe it's the Montana connection that tipped this like scale, right? Because it's like, it's kind of the straw that breaks the camel's back. When you're deciding, like, you know, do we go forward? Do we not like, do we have enough conviction? Do we like, feel comfortable? I don't know. Maybe it was the Montana aspect that like, set this over. That's what I think. I think that was the like, it's about he’s a Montana guy like, you know, let's write him a check. 

Les  49:13

Let’s spit on our hands shake, cut a deal and do this. That Montana guy was Garrett Leach, who's also a native of Missoula, who's a senior associate at our firm and, you know, happened to be I think it was like, in a bar in Missoula.

Jeff  49:28

It was, which I think is how all businesses done in Missoula.

Les  49:32

Yeah. Yeah, either there, or on a horse. Yeah, exactly. Very cool. Well, Jeff, this has been such a pleasure having you on the show. I just I always like to kind of finish with one last kind of personal question and kind of fun question and that is for you, you know, for you know, maybe a young man or young woman who's you know, in the Rockies, you know, has dreams of being a software engineer starting their own company someday. I mean, you are an incredible example of somebody who's, who's who's done it and on their way to just doing continuing to do amazing things through throughout your career. What advice would you give to that young person? That's it, maybe in school, and some, you know, and maybe not even Missoula? Maybe they're in, like, Glenn dive or whatever, like, what what advice would you give?

Jeff  50:19

Yeah, I mean, a couple of pieces of advice, I think number one would be to, like, Montana feels very siloed. And I guess I maybe used this word siloed a lot. But it's kind of the way I think. You don't have to just you don't have to just get involved in tech or do something. And think about yourself in Montana anymore. Like, there's a big world, right? Like you can learn from other companies, you can get involved, you can work remotely, I would say just go after it. Right? Like, don't let the boundaries of your state define where you can gain or learn experience, the things that you can do. Just go for it. Like if you want to learn, go work for a company, go learn a bunch of information become valuable, figure out what a problem is, and solve it. The secret second is like, just be like, just be hungrier than other people. There's a lot of people out there that have very little motivation, very little hunger, they don't want to, you know, go outside the lines, they don't feel, you know, they don't feel comfortable being uncomfortable. You're not going to grow like that. And there's a lot of people that won't grow, you can quickly pass them if you're just willing to like, you know, whatever you might call it, fake it till you make it, try new things like live outside your comfort zone, whatever you might call it, just do it. That's sort of what I what I did. I just forced myself to just try things, learn new things. I embarrass myself a bunch, but I figured it out. I learned to just move forward.

Les  51:36

Well, I'm super grateful to have you on the show, as well as super grateful to have you as well as an amazing founder that's in our portfolio at NFC. And just want to thank you for being on the on the podcast today. To conclude, why don't you just tell our audience a little bit about where they can find more about you and about MonetizeNow online?

Jeff  51:58

Yeah, so if you know anyone who's struggling with selling your billing systems, and they're a SaaS company, come check us out Yeah, I mean, our typical customer tends to be scaling sales, scaling billing product, lead growth, b2b SaaS, but generally if you're just struggling to sell or bill, we can help out with that. Yeah, if you have any more questions, check out our website. Always feel free to add me on LinkedIn or hit me up if you want to maybe ask me about what it's like to be a founder or crazy ideas or you want to learn Quote to Cash you never know maybe you want to start a company together.

Les  52:33

Oh, I love it. Always hustling. Going after the next shiny object. Jeff, I gotta I gotta tell you. We gotta have more CTOs on Found in the Rockies. Incredible episode, so thanks again.

Jeff  52:45

Absolutely. Thanks for having me. Appreciate it.

Les  52:54

Thank you for listening to this week's episode of Found in the Rockies. You can find links in the show notes or go to to get transcripts, links, and contact information for today's guests. If you like what you heard and want more, please don't forget to rate review and subscribe to get notified as our new episodes drop every two weeks. We'll see you next time.