Hitting 7-Figure Revenue in the First Year

MATT DURAZZANI: Hello, everyone. And a special welcome to Cliff Simon. We're excited to have you here today, Cliff. You're a great addition to our Revenue Maverick program. For this season, we're actually starting with a different agenda where we're really focusing on learning from experienced leaders, some of the scenarios and challenges that they had to face and how they were able to overcome some of those experiences.

Um, I would like to take just a brief moment to introduce Cliff to the audience. Um, Cliff is the Chief Revenue Officer of Carabiner Group. Cliff brings a wealth of experience, not only in sales, but also in revenue operations. And his full-time focus is really building revenue operations for clients that has A hyper focus interest in not only growing the revenue, but at the same time, ensuring their massive retention, something that he is really, really passionate about. He's a believer of when you identify your ideal customer and you learn to tailor your experiences, your expertise and services to them in the right way, that's when they will have such a great experience that will never want to leave you. And so we're very excited to learn from Cliff today and his experience, this organization and what he has accomplished. And so, Cliff, without further ado, I would love to turn the time to you and, and kind of maybe give you a moment to introduce your organization.
CLIFF SIMON: Thanks, Matt. Appreciate you having me on the, on the podcast. And thanks to BoostUp for sponsoring. This is pretty cool. Um, as far as Carabiner goes, yeah, um, we've been around for, uh, three years now. We just actually turned three, two weeks ago, uh, as of the recording of this podcast anyway. So August of, uh, of 20, um, I joined fairly early on the company was about three and a half months old and came on board as employee number three and we had a, a pretty cool start to it where the company was a Salesforce consultancy and pretty shortly after, uh, joining up, I saw the writing on the wall, had opportunity to take the revenue growth architecture course with Learning by Design. And after that first day in class with Jocko, I was like, Oh my gosh, this is everything that we need to be doing as a company.
Like, we're already touching so much of it. Revops as a service has to be what we focus on. So we went out and grabbed the trademark on it. Um, that, and like, we make Revops easy and change the entire messaging positioning of the firm to be Revops as a service, and that's led to some incredible growth, some really cool stories, um, some awesome tech and I don't know, just a really interesting brand that's grown up over the last few years. 
MATT DURAZZANI: That's awesome. Really excited. So, uh, maybe, maybe we can jump around into that great experience. Uh, one of the things you mentioned to me is that when you first came on board, um, you were asked to really achieve some pretty high, um, you know, goals.
And in your very first year, you guys were able to achieve over a seven-digit success. And, uh, and so, uh, before we kind of look into the, in the secret sauce of what you did, maybe, uh, can you get us started a little bit with your go to market plan, what was your strategy to get it, get you guys 
CLIFF SIMON: started? So, seven figures in the beginning was the initial goal, and we're a bootstrapped company.
It's not like we have funding, right? All this, we call it revenue backed, right? We're running off of the revenue that our clients give us. We had a very large Tam and Sam to go after. Salesforce and HubSpot Consulting is a huge marketplace, right? You know, 38 plus billion dollars. Our question about how to go to market was, how can we be different?
Right? Everyone is going to say they are technically capable. Everyone has expertise. What are the things that are going to separate us and specifically separate us in the part of the market that we wanted to play in, which was the upper echelons of the SMB and in the mid market, right? I have no desire to go play against Deloitte and Accenture and Cognizant, you know, PwC, whoever else, uh, that are playing in the true enterprise.
So we focus on a couple of things, customer experience. Most consultancies want to take a bunch of your money, run away, build something in the dark, come back and say, here, this is what the SOW said, this is what you're going to get. So instead of doing that, we went with no SOW. annual partnership where we were incentivized to do really good work, not just because we want to do good work, but because we're also the folks that are maintaining it for the long haul, right?
So there's a little bit of self serving there and building it out in the open, showing our customers everything, showing them the documentation, being really nimble to not have to deal with change orders, right? And holding up processes. And changes to priority from an organizational perspective for weeks at a time.
So all of those things sort of went into why we came to the market the way we did. Um, the other piece of that was pricing, right? People spend a lot of money on consulting and it doesn't necessarily have to be that way for us. We're. Looking to make money on year two and year three, not necessarily on year one, which is why we came in at a lower cost than most of our competitors in the market did as well.
Again, because we theorize that we would be able to take long term relationships based off of a really great white glove experience and have those people continually renew. Um, I came on board, my first customer here is still with us, um, you know, going, I think they just renewed again. So they'll be here at least four years, um, which is really exciting.
So it works. 
MATT DURAZZANI: Totally. Um, and so, so it sounds like, uh, a lot of your initial plan really was, um, you know, being nimble, being transparent with the customers and really focusing on giving them a very, very good experience. And not worry so much about what initial revenue you can get from them, but it's like, if we build that experience, money will follow.
CLIFF SIMON: Long term partnership, right? If you're able to continually provide recurring impact for your customers, you will get the recurring revenue. But you have to keep bringing them impact. And how do you do that? Well, you have to understand their business and understand where their business is trying to go.
You have to understand how they serve their customers. So, and. That, that value changes continues on. That's right. 
MATT DURAZZANI: That's right. Okay. One of the, one of the things that, uh, um, I've been meaning to ask you is that how did you identify it early on since you have such a large TAM, a large market to go after?
What is your ideal customer profile? How did you identify that in the first place? 
CLIFF SIMON: So we went with the things that we knew well as a team. Um, Seamus, our CEO comes from a financial services background and he comes from a higher ed background. Early on, that's all we did as a business. My background, SaaS.
I've been doing SaaS for the last, you know, I guess seven and a half years before joining Caribbean, or so I guess it's been about a decade now. Um, all, all together, those were the three main markets that we focus on. So highly regulated financial services, um, Really big digital transformation in the higher education nonprofit space, and then driving really, um, fast moving implementation and digital transformation from a Rev Ops perspective, you know, that Rev Ops as a service product in the high growth, high tech SAS ecosystem.
And for us, we wanted to be able to come in early and offer that help early on. When we first started up, most of our customers were series A, series B, where they had gotten funding, they were looking to build that next set of capability, but it was becoming really onerous for them to go out and hire an entire team to do this.
So instead of hiring a team and spending. Half a million dollars to a million dollars on salary. You could bring us in and get all of the little pieces of that team that you needed at a fraction of the cost. And then allow you to have that, that really good structure to build off of and to project your company forward.
Yeah, 
MATT DURAZZANI: that's a, that's a great way. We were going to, so I think, uh, a great takeaway I'm taking from this one is leverage the internal experiences that you have in your current employees, right, in your current leadership. Um, so that probably brings. I would assume networking as well, right, as to build the ability to go after some of those markets, but it also really understanding how those vectors, verticals, wherever you want to use as a term, really operate so that you understand that business and how to position yourself internally.
So that's, that's 1 takeaway. And the other one that I really like that you mentioned is, um, really tried to identify maybe from an analytical perspective. Also, those organization that maybe we're at a certain point in their financial growth where they actually had the ability to invest, but not only that, but also had the, that's the time that normally you have to build out these type of teams.
So we're right in position to say, hey, what about this other alternative 
CLIFF SIMON: option? Yeah, yeah, and then it just so happened that the other place that we consistently saw need was when people were leaving, right? There was a gap to be filled for a lot of our customers. We ended up becoming the keepers of the tribal knowledge because.
The way RebOps has grown over the last three years, that operator would be in seat 20, 24 months. That's dropped dramatically. You're seeing like 10 to 12 months on average because people can get so much more money jumping around from job to job. Sales people did it all the time, right? But we never saw that with operational folks.
Now we're seeing it constantly because the job market for RebOps has grown exponentially. Last year, it 3x'ed in three quarters. It was crazy. Wow, that's amazing. 
MATT DURAZZANI: That's amazing. Yeah, um, so, give me a sense here. So, you started out, you had that plan, you guys had figured out who you were going to go after and kind of the way you wanted to position your pitch there.
Um, what type of, uh, team Uh, roles did you have in place to start with? Uh, so it was you, it was the CEO. 
CLIFF SIMON: Yeah, it was the two of us and two other consultants very, very early on doing the actual work, but I was doing everything go to market. Um, my entire theory on go to market, especially in today's day and age, is that people in the B2B space want to buy like they buy in B2C, right?
We have fantastic consumer experiences. Things feel like I'm checking out or, you know, Amazon's made everything so frictionless. I can say I want something I can look at reviews, whether they're robot generated or not, that's a whole other topic. But I can do a bunch of my own research, just like many of our buyers do today, right?
Um, we go out, we do research, but then what do we all do? We all ask our friends. What do they think about this? What have they tried? What have they used in the past? Have they had any good experiences? Have they had any bad ones? Right? And we weigh that so much more than we weigh anything else in our decision making process.
That's why in the consumer world, word of mouth and referral is the leading way. Well, we wanted to build a go to market engine that was built off of that. Pre COVID, when I worked in other roles, I would go to conferences. And if my company wouldn't pay for me to go to the conference, I'd go to the hotel.
Or the bar or the restaurant near the conference and find people with the right badge on and strike up conversations, right? It's about developing thought leadership and relationships in the places that your customers go to get help. In this modern day and age, post COVID, everyone retreated into online Slack communities, forums.
We started building a significant brand in those areas, right? Uh, we're the exclusive RevOps partner of Pavilion, formerly Revenue Collective. Uh, same thing with RevOps Co op. We have a really good relationship with the team over at RevGenius and Wizards of Ops and Sales Assembly and Sales Hacker and on and on and on.
And because of that, we've been able to build a brand far greater than. What a typical marketing engine would have done on its own, right? You amplify that then through the good work that we're doing with our clients, the relationships they have with their private equity and VC, uh, operating go to market partners, and the rest of the board, and now that's...
We get deals, like, I don't even know where they come from sometimes, and you have to ask and go through the process. Like, oh yeah, well, we heard about you from this board member who heard about you from their friend over here. So, word of mouth is super, super powerful. Doesn't happen overnight, and it takes a lot of time, right?
It took us, probably on average, four months within a single community to be able to generate business out of it. But all that came from a give first mentality. Show up consistently in those communities. Be empathetic. Trigger on people's desire to have that instant gratification. So if someone asks a question that you can answer, answer the question, give them value, help them with their problem, and ask nothing in return.
Only that, perhaps, if they have a friend that needs help with RevOps down the road, that they would remember my name, right? And that was the first 18, 20 months of us being a company, right? I was doing on average 40 to 60 Zoom calls a week, booking on average 83 meetings a month. doing that. Never picked up a phone once, never cold emailed once.
Super powerful, but it takes a lot of intentionality, it takes a lot of empathy, and it takes a willingness to show up consistently in those places. Yeah, 
MATT DURAZZANI: that's amazing. Um, I think, uh, I think that's a great story for a lot of people that are really trying to, um, you know, crack the code on how to start.
And, um, and I think in 2023, technology has empowered us with some additional tools that maybe in the past we didn't have. These community forums that you're talking about, right, and a better way to potentially than just doing a lot of email marketing. Um, I love what you said about, you know, just, um, learn to start giving first.
Don't expect anything in return. Perhaps, maybe, you know, just remember me if some of your friends experience something similar where you can refer them to me. But, um, it really, the giving away first, it's, it's key. Now, a question that follows up 
CLIFF SIMON: on very easily. I was going to say, it's, it's also, it's also the relationships, right?
You're, you're developing relationships. Go out and learn and learn with other people. The relationships that you build in that shared experience is incredible, right? Um, I went through CRO school with Pavilion. I still meet with that group of people. There's now somewhere between eight and twelve of us that show up every two weeks and have for the last two years, right?
Um, the amount of referrals or just life help that's come out of that's been incredible. Um, the other place is just learn, go out and learn, right? Half the time I was meeting with folks, this is my first time running marketing. I would meet with a VP of marketing, at least two or three of them a week, just to continually learning about what's going on there.
Not only did that help me internally, but it helped me educate my customers on all the cool things that were happening within the ecosystem and that were happening within that specific part of the, uh, the industry. So having conversations, networking. Finding mentorship and mentoring others is just, there's so many knock on effects, right?
And go to market success happens to be one of them for us. 
MATT DURAZZANI: When you talk about the first 18 months of your business where a lot of these communities and really showing up and be part of that, uh, did you actually have a lot of sales during that period 
CLIFF SIMON: of time? So we were doing. Okay. In the beginning. Um, and then we made that shift to RevOps as a service and what we were seeing as our normal revenue intake on a quarterly basis changed to our normally revenue, uh, normal revenue intake for us on a monthly basis.
Um, by shifting the messaging and the service offering. Um, and it wasn't a huge shift, right? We were already doing 80 percent of it, but we weren't touching all these other things that people were asking us to, and we'd have to go find somebody else to outsource it to, and it was a whole mess. Now we, because we can internalize it, we're able to guarantee the work product going out the door.
And again, all that because we're focused on the customer experience. So, um, ravenously, or however, maniacally, whatever you want to call it, right? Um, the, the team had grown at that point. Um, We had an AE that started, I want to say, about six months into me being here. Um, took him a little bit time to get ramped up, but I think he got his first deal on a typical ramp cycle, right, like four months.
Um, now we do an enterprise sale. But, um, the team had grown and we were bringing on folks and continuing to build out that structure. After the first year, we went from being three people to being eight at Christmas to being 20. That following January to being 30 in February, like we, we were hiring like crazy as a bootstrap company.
It was really fun to see. And, um, yeah, the revenue kept pouring into, and we went from doing, um, significant dollars in a single quarter to, uh, you know, hitting that million dollars in the first year. And then all of a sudden like, wow, we just did a million dollar quarter. Like it happened so fast. Everyone says that first million is the hardest, but that second million, it took us five months to do the second million.
And then the third million happened over the course of another, like, 45 days. It was crazy. Wow. 
MATT DURAZZANI: That's amazing. That's amazing. Um, well, it sounds like, you know, this definitely was, you know, consistency, seeing the momentum, bringing in a lot of people at the time, right? Um, One time that it comes to my mind is okay.
These are a lot of the people that you mentioned are frontline and a lot of the people that are listening to this are probably also operators. So, behind the scenes, the people that kind of build the vehicle for the rest of the frontline to join in and drive to those destinations. Right? And so what operational roles were critical to for you guys to execute this, this vision in the 1st year or 2 of your business?
CLIFF SIMON: So we brought in a director of delivery. Um, towards the end of that first year, we also brought in a director of operations. At the end of that first year, um, really helped take care of a lot of things from a financial perspective as far as financial reporting. Um, I still was doing a good chunk of fp and a around forecasting planning, um, but being able to offload that.
And on the other side, because we were so focused on the client experience, that director of delivery role was really focused on. Um, client experience, making sure we were skilling up the people that we have. What does it look like to go from a career progression in consulting? Um, we brought on a COO who was doing fantastic work for us, bringing in, you know, big four experience, right?
Former Deloitte, uh, guy. And um, Yeah, Lewis did a great job there. So we were bringing in all the pieces to build out the back end to make sure that we could continue to support what was becoming a very large go to market motion, and we hired another handful of AEs at the beginning of that year, um, but the momentum and we're A lot of the deal flow continued to come from was that referral word of mouth mindset, right?
So that first year, I think it was like 53, 54 percent of our business came from that word of mouth referral community led motion. We never stopped the things that we were doing there. We actually amplified it. And we went to that second year then doing 91 and a half percent of our revenue being either word of mouth community led or a referral from existing business.
Okay. Wow. That's 
MATT DURAZZANI: amazing. Um, so at least the three key roles that I stood out the delivery from the customers, the sex side, an operational guy, and of course, an operation executive to kind of help kind of keep all of those things together. I would assume you mentioned that, um, you were doing a lot of the, some of the reporting, some of the forecasting.
Um, I'm curious to understand, you know, when it came to be able to do the proper forecasting, um, Did you have to go and pull all these reports manually yourself? Or what was kind of the tech stack that you guys had to deal with in that first period of your, of your success? 
CLIFF SIMON: Yeah. Um, there was several different tools that were using a lot of it.
Just grunt work and putting the miles in through Excel, right? Um, we built everything in Salesforce from the beginning. As a Salesforce partner, we got a couple free licenses, but, um, for us, that was the key. Knowing that we had some business goals in mind for five, ten years down the road, we wanted to make sure we were capturing all the right analytics up front so that we would have enough significant historical data to be able to do forecasting.
Uh, and it was difficult in the beginning, right? Because the data sets were small and they were growing so rapidly. So you'll say, all right, what is the true curve here? Like, what is this S curve going to look like? Um, going back to, uh, winning by design, Jocko had put out a growth forecasting white paper, used that in conjunction with a tech that we use internally called Qflow.
ai, um, to do scenario planning and to be able to look at data trends over time, things like opportunity creation, um, win rate across the portfolio, as well as across the pipeline and by cohort. Um, that one's been a good one for us. Um, And then a lot of it in Excel, right? It's just crunching numbers together smashing stuff together and saying what makes the most sense.
Um, Last year or last year, I think that's yeah, it's about a year and a half ago at this time I was probably doing a ton of stuff in Excel where I was running together anywhere from five to eight or nine different models Along different regression curves to figure out where we would end up and help us to plan accordingly, right?
Because as we're growing that quickly, onboarding
New hawkers, right? So one of the key hires for us was actually bringing on an internal recruiter to be able to facilitate that and make sure we had a steady pipeline to meet the demand of the business. 
MATT DURAZZANI: So you didn't outsource recruiting at that point. It was enough for you guys to really have it in the house.
CLIFF SIMON: We outsourced it a little in the beginning just because we had a few roles that we needed to fill and they needed to be the right people. But yeah, we went internal with a recruiter pretty quickly thereafter. Uh, the cost made sense, right? That's right. 
MATT DURAZZANI: Okay, that's awesome. Um, one of the things that, um, you were talking about is, uh, um, when you work with these communities, you probably had an opportunity to share some of the success stories that you were having, right?
Uh, give us a sense on. How did you share those success stories where those, because probably a lot of those people are in those communities, right? And so did you share them individually? Did you do some type of broadcasting in these forums? Did you post on LinkedIn? What was your way to promote these stories so that other people would learn about them?
CLIFF SIMON: Yeah, so we wouldn't not go out and blast that in a community. I think it's a little tacky. Say, hey, we did this with it with this community member, right? That's not the spirit of community. It's not to build yourself up. It's to build up others, right? But what we would ask people for is hey as part of our normal process G2 reviews app exchange reviews if we're doing a good job cataloging the places that those things are expected to be not asking you to go out and Sing our praises on some random post on on a slack channel.
Like that's not how this works, right? You're you paid us for a service go to the place where that you can talk about that service in an appropriate forum but again, if someone asks a question or it's Prompted and you have the opportunity and the ability to and the conviction right to say that we've met the need Then feel free to go ahead and mention us.
Yeah, of course. All right 
MATT DURAZZANI: what were some of the Early tough lessons that you wish you knew before you did this. Like it's something that like, okay, we learned this one a little bit the hard way next time, if, if my brother's doing this one, I'm going to tell this right up front. 
CLIFF SIMON: Oh man. Um, don't meet your heroes.
Um, don't want to get into that one too much. Um, I would also say, just make sure that you're staying. Uh, closer to the finances, uh, at least for me personally, right? I, I don't come from a finance or econ background and I wish I'd learned that sooner on so I could have been more helpful. Um, I think a lot of salespeople, and just to sort of put that hat on for a second, tend to focus far too much on the dollars that they're bringing in and aren't thinking about what the profit margin looks like or what the cost.
of client acquisition looks like, or what's CAC LDV. They don't think about unit economics and, um, that's something I had to learn a lot early on, um, because I hadn't gone as deep down that rabbit hole as I should have earlier in my career. Um, And I think for any CRO or any executive leader, you should have P& L fluency, right?
Being able to look at a P& L and understand what's going on, being able to pull out pieces and dissect where you need to, I think is a crucial skill. Totally, totally. 
MATT DURAZZANI: Um, what was your relationship like with, um, in this case with the finance officers? How often would you guys talk on a weekly basis? 
CLIFF SIMON: Yeah, uh, we would do a exec meeting, um, bi weekly where finance is probably like the first 45 minutes of an hour and a half meeting.
Um, we would also do a weekly finance touch base and that's shifted a little bit now. We do that bi weekly or bi weekly. We do that twice a week. Um, instead of going into really big, long corporate meetings internally, we try to break that up. So it's. Yeah. Thanks. Taking small bites of the apple throughout the week.
Um, I think it's a better cadence. So we do two 15 minute finance calls a week just to say, Hey, what's outstanding? Where do you need help? Um, it lends itself a lot better. And then we do one big monthly, um, internal meeting around like what else is going in the business and working on those strategic blockers and milestones.
MATT DURAZZANI: Okay, that makes sense. I think that's an important advice to to any revenue leader because sometimes we focus so much on that go to market piece and and be always on the front line. And we sometimes don't prioritize so much on wasn't for a second. Let's let's check with people internally. Is everything on check?
Are we going too fast? Are we going to slow? Um, what are our additional budgets that we have available? How does that? What we do in it ties to the other departments, marketing and other 
CLIFF SIMON: things, so. Yeah, and what's the difference between like bookings and billings and cash on hand, right? Just because I've signed contracts or something doesn't mean invoices have gone out for that, and doesn't mean that cash is actually due to be here.
So, that's always fun. That's always fun, 
MATT DURAZZANI: fun. Um, what other type of advice do you think you want to share with the rest of communities 
CLIFF SIMON: today? If you're going to go out there, And build out this type of emotion. I think anyone can do it. You have to be empathetic. You have to show up consistently. But give it a go.
Don't try to sell yourself. Be genuine and try to build relationships, right? People buy from people. People buy emotionally. Develop friendships. Be a real human being. Um, I don't know, be a, I hate the word authentic, but just be your real self. Don't put on a mask and be the person that people think you should be or that you think people want you to be.
Show up and do a good job and act with integrity, like all the things that you were told growing up, right? Like, follow the golden rule, treat people like you want to be treated. If you do those things, things will work out one way or another, right? It might not be at this role, but yeah, there's, there's a, there's a whole career in front of you and people are gonna remember the things that you did, the things that you said, and the things that you didn't do that you said you were going to do.
MATT DURAZZANI: That's a great advice. Thank you. That was really, really good. Um, what's next for you here? What's your next, uh, challenge that you're hoping to solve 
CLIFF SIMON: for? Um, I'd like to grow our EBITDA significantly. So that's, uh, that's my challenge going into 2024. Um, yeah, no, I, I think that that's been a fun one, uh, to be thinking about, uh, the challenge for this year was to diversify away from SAS a bit more just because of the way the market is.
And we've done a really good job of that as a firm going back to our other. core industries and Now we sort of just keep going with the build. Right? That's 
MATT DURAZZANI: right. Well, listen, um, this has been a pleasure. I, I'm, I'm just going to try to quickly wrap up a couple of thoughts here with regards and maybe you can help me keep him straight if, um, if you may, um, if, uh, you are an operator listening to this podcast today, one of the things that I think it stands out is, uh.
Um, whether you are on the frontline or you're working internally, your customers are your internal people in the organization and the same advice of not trying to sell yourself, but trying to really show empathy and support the people and help them have a win, that's probably the best way that you can go about building your position and, but at the same time, providing that value that will keep people coming and ask for your help.
So that's one thing I think it stood out from what Cliff has said. Um, the other one is that I think from, uh, Um, if you're a revenue leader, whether on the front line, like a CRO or internally, um, it's really important to be able to understand, um, what. Makes your customers take in in in the good way. What makes them really feel like they're feeling that value and find ways to measure that.
And I think bringing that information to on a regular basis, just like Cliff was saying, showing up and bringing that information to the forefront of the leadership would allow the leadership to constantly feel where they need to. Pivot a little bit to stay on the right course. And so I think, um, if you need to start today, uh, maybe put in practice some of these early principles that Cliff discussed.
And, and I think, um, uh, Cliff will be happy to connect with you via LinkedIn or some of these other community and you can find them online. And, and I'm sure his, him and his team will be able to support you in, in your, uh, 
CLIFF SIMON: challenges. And if you have any like additional questions that you want to ask me about how we did it, some of the more granular stuff, feel free to reach out.
I'm happy to have a conversation and share. Awesome.
MATT DURAZZANI: Cliff, it's been a pleasure. Thank you so much. You're a great addition to this community. Uh, we'd love to have you and keeping up with, uh, uh, your story and your success. And, uh, for everybody else, we wish you a great day and thanks for joining.
CLIFF SIMON: All right. Thanks so much, Matt. Take care.