Leading The Carabiner Group With Cliff Simon

Posted on October 4, 2023October 4, 2023 by stratyve_ant2yf

Your RevOps solution is here! It lies in the hands of the Carabiner Group. Today, Cliff Simons, the CRO of Carabiner Group, shares the tactics and the actions taken to lead the organization to success. Their agility and nimbleness to turn away problems once they see them coming helped their business deal with the challenging tides. Cliff also shares his GTM success and failure story. Let’s get into this episode with Cliff today.

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Leading The Carabiner Group With Cliff Simon

In this episode, I have another great guest lined up. His name is Cliff Simon. He’s the CRO of Carabiner Group. He has a very impressive track record when it comes to go-to-market, building revenue, revenue teams, and so on. Without further ado, let’s welcome Cliff. I’m excited to have you on the show.

Thank you for having me. I appreciate it.

Let’s dive right in. How do you view and define go-to-market?

I have a different take on go-to-market and a lot of folks in B2B do in the sense that a lot of what we do in the B2B space, we’ve tried to make it fit a certain mold or what we think the traditional patterns should be. A lot of what we’ve done from a Carabiner perspective is, “How do you enable your buyers to have a B2B experience that looks and feels as much like a B2C experience as possible? What does it feel like to go through that B2C motion? How do you take away the friction very much like Amazon has done? How do you pull all that friction out of the buying process to make it easy for people to purchase?” I think HubSpot has done a fantastic job of this.

You don’t typically read through all the legal leads of a HubSpot contract because it looks like a checkout screen. If you want to read the legal leads, you have to click on the Ts and Cs. Who’s going to go and fight on the things within a Ts and Cs? You’re naturally conditioned through Apple and everything else to accept the Ts and Cs, scroll through, get to the bottom, and just move on with your life instead of doing the due diligence that most of us would do on any contract that came across our desk. It’s a little bit different from how we would think about go-to-market.

I like the aspect where you are focusing on the buying experience. I’m fully on board with you that B2B should transform itself into creating a buying experience that’s very similar to the B2C world, like the Amazons and Apples of the world. They have revolutionized, for sure. You mentioned over there the click-through and getting started on using a service or a product. There are a whole lot of activities and tons of things that happen for a buyer to come to that point.

There’s so much that has to happen there. That’s why we’re seeing such a big surge in PLG. We’re enabling them to tell us what behavior they want to walk through. They’re enabling us to understand the pieces of technology they want, how they want to deal with it, and what that experience looks like. We’ve been informed because we already know from the Amazons of the world what that experience should look like. We now have to sit back and think, “How do we take that process and engineer it for our specific use case?”

I’m sure we’ll dive deep into several of those topics in our conversation. Shifting gears and going big picture, why don’t you walk us through your career journey, what you’ve been doing, what led you to what you’re doing, and who you serve at Carabiner?

My background is about two decades of go-to-market experience selling in the mid-market enterprise. I started my career off at a Fortune 20 company, highly ranked rep there, did well, and then they took what was making me six figures a year and turned it into a $5,000 quarterly bonus. We all saw the writing on the wall and it was a pretty big exodus at that time. I have spent many years in SaaS. This is my third time doing a 0 to 10, but 0 to 15 before. That’s my first time doing it from the C-Suite.

As far as what we do at Carabiner and how I got here, most people don’t anticipate going into Revenue Operations or RevOps as a career choice. I was that sales leader who enjoyed getting into the data, understanding the why and how, and giving good data feedback to my team. Even for bringing that up to the board and the executive leadership team, this is why things are happening. I had a deep passion for it. Falling into the lucky circumstance of running as a twenty-year-old who is starting a company and getting a chance to help build something from the ground up is intriguing to me.

I got to join Carabiner in its early days when we were just a salesforce consultancy. We made the shift to RevOps as a service in early 2021. I took that very first Revenue Architecture Course that Winning By Design had put on. Jocko was leading it. It was right after the first day of class that we changed all of our positioning and messaging. We went out and picked up a couple of trademarks around RevOps as a service. This is the future. That’s what enabled us to get a decent position from a marketing rather position in the market because it is so much earlier than everybody else did and being holistic about the customer buying journey. Trying to focus on that journey and that experience has helped us stay apart from a lot of the other folks that are coming to the fore.

You started off your journey in sales at telecom companies you are at Nu-Wave Wireless and Verizon, and then you shifted into SaaS. It’s a smart move there. That’s where all the big money is. After that, you joined Carabiner, which provides RevOps as a service to SaaS and technology companies.

A lot of our clients are SaaS. We serve anywhere from series A to D on average. We’ve got folks on the outlying pieces there, some C companies, some series E, and publicly traded, but by and large, a lot of our customers are SaaS. We also work in a regulated industry and a lot of financial services as clients. We also play nicely in the higher education nonprofit space. We’ve seen a lot of folks from manufacturing start coming out and needing services.

That’s been a nice twist from our traditional ICP. When you’re doing the same things over and over again, 80% of it is the same digital transformation, whether you want to call it RevOps or something else. It is a process. How do you look at a customer’s buying journey here, a go-to-market process to it, and only then, how do you build up the technology to meet that process instead of going out and buying all these point solutions like folks have for the last many years?

When you're doing the same things over again, 80% of it's just the same digital transformation, whether you want to call it RevOps or something else. Share on X

A funny incident or coincidence was that I had a guest who made a very similar move from the other side. He started off in the services side of the house and then moved into SaaS. You did SaaS and then moved into the services side. He and I were discussing selling services versus selling SaaS are different. At least, SaaS buyers get to see “touch and feel” something versus services only after you build that trust. They speak to current customers, and that’s when they get the confidence. Otherwise, “I’m not 100% buying into what you can deliver for me.” How are you handling that challenge at Carabiner?

For us, it was building trust by building thought leadership. That was accomplished by having a lot of face-to-face interaction, whether in person or on one-on-one Zoom calls with other go-to-market leaders, finding out the pains that they were dealing with, and making sure that we were building a team that could meet that collective need. We’ve got a lot of recognition through our relationships with communities like Pavilion, RevOps Co-op, or the exclusive RevOps partners in both of those scenarios and then working well across the ecosystem.

Once you’ve proven yourself, you start building out some case studies. We were fortunate to get some larger clients very early on when we were doing some massive digital transformation projects that led to the credibility of the work that we could do. Like any small company, you leverage those and keep building. Once you’ve built up a significant body of work, it becomes a lot easier. At this point, we’re seeing 100 reviews between AppExchange, G2, and almost every single one of those. Ninety-five percent of those are five-star reviews. That’s fantastic. We want to keep that up and make sure that we’re giving that level of service to our clients.

What was the revenue ad when you joined Carabiner? That was a few years ago.

I joined in December 2020. The company was 3.5 or 4 months old at that point. We weren’t on an ARR model. It wasn’t recurring revenue. It was nascent. I wouldn’t even register as anything.

In terms of revenue, you are 5, 6, or 7 figures?

We did seven figures in ARR in our first year and then followed that up in 2022 with 4.5X growth, which was incredible. In 2023, somewhere between 10% and 30%, which is not terrible considering the market and the way it is to be able to say that we are going to grow in 2023. I’m impressed that we’re going to hit that number.

For the benefit of the readers, it’s all about the tactics and the actions that led you to this point. Three things stood out for me from what you mentioned. One is being part of communities like Pavilion, which builds credibility. Something else you also mentioned is changing the positioning and improving the buyer experience. The third you mentioned is getting the big brands, the Lighthouse clients. From sequencing, let’s dive into each of those three.

At the core, the reason we’ve done well is what we call agility nimbleness. We have always prided ourselves on being able to say, “If we see a problem coming, we’re going to shift away from it quickly out, bootstrapped, or revenue back,” whatever you want to call it. We don’t have investors that we’re beholden to, which allows us that flexibility.

I don’t have to wait until I go to a board meeting and get them to approve something, which is nice. What that’s allowed us to do around that Amazon desk deal is to take a look at our customers’ journey and say, “What are the things that most people don’t like from consultants? What things do they hate about pro services? How do we take that out of the process?” For us, that means there is no SOW.

Most companies our size and with the capabilities that we’re offering have a very strict scope of work. Meaning that if we go outside of that scope of work, there’s going to be a change order, which means you’re going to have to take 1, 2, 3 weeks for that paperwork to get approved and then paid for, etc. We don’t do that. We want to be able to be very nimble. If our clients have a request, we want to be able to acquiesce to that request so long as they understand what that may do to the rest of the project from a timeline perspective and be able to adjust to that within a matter of days. That’s one thing that we wanted to do.

The other thing that we do is we annual contracts by and large. It’s very different from most of our competitors who are out there where they’re going out to the market and saying, “You’re going to pay us for this particular scope of work. It may take 3 or 6 months.” All we’re going to do is to the letter that’s scope. Because there’s no SOW and we’re coming for the long term, we’re incentivized to build systems that we’re managing that are going to work. Because of that, our Compound methodology, instead of an Agile methodology, our clients see that work gets delivered on a weekly basis and they can understand the value that’s being presented to their organization and the impact that it’s having on a regular basis instead of us going off and building in the dark.

Part of it is how we’re go-to-market and how we’re delivering the services that we’re promising. Those two things coming together create a very different buying experience. What that meant for us as a company is in that first year, we were doing a 6-figure sale on average in 28 days. In 2022, we were doing a 6-figure sale on average in 34 or 35 days. Our ACV increased to damn near $250,000. It was a very significant dollar amount that was moving very quickly.

Six-figure closing under a month is unheard of. Typically, it’s 3 to 6 months. That’s the standard benchmark, but clearly, you got something going. When you described what you guys did from a services point of view, the term that came to my mind was productized services.

That’s very much what we’re trying to do. We have four service offerings, essentially. We have RevOps as a service, which is our flagship service. It’s Salesforce and HubSpot expertise and 150 other pieces of technology that connect in those ecosystems. We have a lower-cost admin service for folks who need a little bit of help. We do an advisory service for people who are trying to understand how to think about that go-to-market, “How do I go about putting these processes in place?” We also do an audit product, which is probably our most popular product.

We do a full scope on people processes, technology, and then insights and analytics, like that data piece. It takes 4 to 8 weeks, depending on the size of the organization, but it’s a pretty comprehensive readout. On the back end of it, you’re getting a very detailed Kanban backlog of, “This is how we recommend going through and fixing your organization and the progression that we believe it should take.” It’s usually done in 0 to 3 to 9 and 18-month increments. You’re getting a year and a half worth of change laid out for you, which a lot of companies find very helpful.

We do an audit product. We do a full scope on people, processes, technology, insights, and analytics like that data piece. Share on X

I would assume that most of your clients, if they’re getting to know you and want to engage you on the first service, would start with the audit.

It’s a nice way to say, “Let’s feel each other out. Does everyone like to work? What’s a good communication style?” You start building that connective tissue just like you would when you’re bringing in a regular in-house person.

All of these that you mentioned clearly improve the buying experience, which is 1 leg of the 3-legged stool that we talked about. The second leg was around being part of communities that built your credibility. That’s Pavilion.

When it comes to the community space, it’s how you go about thought leadership and how you add value without always trying to take it. For us, it’s been very much showing up consistently and helping people who have problems. If it comes back to us as revenue or business, great. If it doesn’t, we’ve helped somebody because there are just not enough people doing RevOps.

It’s the number one job on LinkedIn. 8 of the top 25 roles on LinkedIn are RevOps functions. Everyone’s trying to figure this out. We can help point you in the right direction and you don’t have to pay for it. Go and do. If you need more than that, let’s have a different conversation. That’s been us doing webinars, writing white papers, and lots of one-on-one talks like this where if someone’s got a question, we’ll just hop on and have a conversation.

It's great if we can help point you in the right direction and you know how to pay for it, but if you need more than that, let's have a different conversation. Share on X

I’ve spent almost two decades in go-to-market across a whole host of industries with a whole host of go-to-market motions. Maybe something I know or a member of our team knows that can help you, let them help you and take that knowledge and go run with it. If that works, please let us know after the fact so that we can celebrate with you and say that it’s been well done. We did the same thing with our customers. When things are going well, tell us. We want to be able to celebrate with you because we want to earn the right to celebrate those milestones together.

The third piece was around getting the big Lighthouse clients and the brands.

That happened a little bit more accidentally, but maybe not quite as accidentally. We ended up working with the largest FP&A runner in the country through cold LinkedIn outreach. We work with 2 of the 3 largest collegiate athletic associations in the country. That was brought to us by one of our IFP partners because they needed somebody with the expertise to build up the systems.

Those systems are used by something in the neighborhood of 1,100 colleges and universities and represent the contracts between those colleges and universities and something in the neighborhood of 150,000 to 160,000 collegiate athletes every year. There is pretty cool stuff to get to do, and I had a lot of exposure because of it. Going after that has been cool, then being able to consistently work for good clients, knowing that a mature executive leadership or going after a very specific private equity or VC firm so we can work together has been good for us as well.

On a lighter note, you started your career as a salesperson, then you grew up the ranks and now you are a sales leader or a CRO. What does your family think or what do they think that you do for work? How would they describe you to others?

My wife comes from a medical background, as most salespeople, especially in the IC role or in mid-leadership. You tend to balance around a decent bit. That was a little hard for her to understand in the beginning. Now, she knows that I do something with software and I get paid to talk to people. It’s outside of her wheelhouse, but she gets most of it and respects it, which is good.

She knows it involves Salesforce and HubSpot. That’s as far as it goes. As far as my family, I’d say probably something similar, my friends all get it because they’re all in tech. Whether I’ve got guys in my hockey team who are Salesforce admins or SAP admins, they all get it. They’re developers. It’s not as far a stretch for most of them. On the family side, it’s different, especially since a lot of my family comes from blue-collar, “You help people and they pay you to do what?”

“All you do is just talk.”

“You talk and you help them think through things? You’re not building something with materials? There’s no actual material cost.” That’s a fun conversation.

A funny story that you shared over there was your family members, specifically your wife and other family members who come from a non-tech background, you versus your other colleagues and friends who come from a tech background. That’s a common theme that I’ve seen. When I ask this question to my guests, it always brings us a good laugh. Thank you for that. Shifting gears here, we all know that go-to-market is not just success and up and to the right always. There will always be failures as well. It would be great if we could share with our listeners both GTM success and failure stories. Pick yours, which one you want to start with.

The success story is pretty easy, considering the amount of growth that we’ve had in the last few years. It’s been crazy. Going back to that whole, people in B2B want to buy B2C and community-led growth. A lot of what we do is community-led. In 2022, 91.5% of all of our inbound and new clients came from community-led word-of-mouth or referrals. Activating and operationalizing that program has been very successful for us. In 2023, we’re trending somewhere between 85% and 90% again. It helps drive customer acquisition costs lower and it makes for a quicker sales cycle because that trust we talked about before is already inherent in the process.

Before we go to the failure story, I want to double-click on the success story. Can you share how big your go-to-market team that includes sales and even on the marketing side and how you break the responsibilities?

We have one AE who works under me. We had gotten up to 4 or 5 at one point. On the marketing side, we had one. We’re about to hire a new marketing associate. On the CS side, we do that by committee because, unlike the SaaS company, we’re talking to our customers every day because we are on the product. It’s a bit different as far as how that gets managed. It’s funny because that bleeds into what I think is the go-to-market failure, which is an inability to see what was coming down the road. This caught everyone by surprise, but how bad it got at the beginning of the year for us being over-indexed on SaaS as a client base, which caused churn.

A lot of companies went under. A lot of people got funding cut out from underneath them and things were seen as a luxury that was previously seen as a necessity just because they had their entire budget wiped out. We ended up losing a couple of clients that way. Because of that, we had to make some head counts being a bootstrap business. For us, that would be a failure having to go through that motion. Now that we’re building back up from it, we’ve learned a lot of good lessons.

From any of your client side, you don’t need to share any confidential private information, but it will be good to share a success story. What was the institution prior to when you guys came on board, how did things change, and how did it improve their go-to-market success?

The coolest ones are probably the NJCAA, which is one of those collegiate athletic associations. They purchased another consulting firm, a product that they thought was going to help handle the entire registration process of all those pieces of tech. They implemented it. Within 30 days of the implementation, they scrapped the entire thing because it wasn’t working. It’s a huge opportunity cost and the actual dollar lost.

They were working with another consultancy to look at how to fix this in Salesforce. It wasn’t moving quickly. They brought us in within two weeks, we had shown them how we would build it, started putting together the prototypes, and they signed a very long-term contract with us in which we got to build all that out, which was cool. The success story for them is that they had never been able to uncover all of the metadata that was wide within that student body.

What they were able to do is take that metadata and bring it back to the Department of Education and get a ton of grant funding because of the way that their student body is made up. Folks, on average, are on the lower side of the economic ladder. Because of that, they ended up pulling in several million dollars in federal funding. It was a cool side piece to trying to solve the problem. They were able to turn that into an economic gain for them.

That’s a big win. You did mention the breakdown of your team both on the sales and marketing side. It looks like most of your team members are Salesforce or HubSpot implementation experts.

Almost our entire company is comprised of either Salesforce or HubSpot, what we call senior consultants or consultants, and in some cases, architects. Those folks are supported by project managers, engagement managers, scrum, and some Lean Six folks. It is very process-driven.

Another cool part of the story that we should be covering is you did mention the founder of Carabiner. What is that story like? Is it he reached out to you or did you reach out to him? How did it all happen?

He had started the company already. A quick story is he was in high school and ended up doing salesforce consulting when he was in high school for an investment bank out in San Francisco. Through that process, he ended up getting an opportunity to speak at Dreamforce before his eighteenth birthday. He was seventeen years old. He continued doing salesforce consulting through undergrad and was supposed to go work for Deloitte Digital doing salesforce consulting, but got his offer letter paused because of COVID. We ended up starting the company. A couple of months later, he and I met on Slack channel, a RevGenius of all places. We met there randomly.

The first day I signed up for RevGenius was early December 2020. We had a call and very quickly led to a series of calls back and forth. It felt right. My wife’s like, “You should definitely go forward and try this out.” Originally, I came on in a fractional capacity because we do fraction in everything, then after my first full week here, it’s like, “We should make this full-time.” We’ve built a great relationship along the way.

If you had told me a few years ago that I would meet some twenty-year-old kid on a Slack channel, we’d have a company together, and we would be building this crazy thing and what it’s become, I never would’ve believed you. It feels so unbelievable. It’s like something you read in a book or it’s in a movie. It’s serendipitous that you meet somebody on a Slack channel then Slack is the number one way in which you engage with most of our client audience. It is a great tool. I love it.

People get a lot of their networking and job leads through LinkedIn, but I think it’s becoming common, especially for more of the entrepreneurial folks who are active in good communities like RevGenius, Pavilion, and others. You can find opportunities. Did he reach out to you or did you reach out to him?

I posted that I was in between roles at the time and I’ve been interviewing for Head of and VP of Sales roles at Series A companies and some enterprise-level roles as an IC to try it out and see what was going to be a good fit. I posted on RevGenius. He reached out to me that day. We had a meeting that afternoon or maybe the next day. He was originally looking for an IC. I wasn’t interested in that. I wanted to build something, especially coming in earlier.

We were able to transition that pretty quickly because of the nature of the questions I was asking him. I wasn’t asking him about, “How much commission am I going to make? How many vacation days am I going to get?” It was, “Talk to me through all your conversion rates. Talk to me about your FP&A.” The second half of my interview process for Carabiner was building out our FP&A for fiscal year ‘21. At that point, I was excited about it. The fact that I was asking business-level questions and we were trying to get to the bottom of what it would look like to grow something intrigued him.

Something that stands out or I get a sense of is you are good at sales. That’s my sense.

I’m okay at sales. There are a lot of people who are a lot better at sales than I am.

What are 1 or 2 things when it comes to the go-to-market side that people reach out to you for like, “I have this burning question and Cliff is a great guy. I should just chat with.”

Usually, it’s a go-to-market process. They’re trying to figure out how to make one piece work or they’re new in a role and they’re ingesting all this information. They want to know my opinion on it. Maybe it’s seemingly simple as sales stage criteria or, “We haven’t necessarily thought about the fact that our mid-market and enterprise sales motions are completely different. How do we bifurcate that from an actual process perspective, and then how do we cement that process difference in technology?” It ranges a wide gambit.

You are good at sales. It’s not just doing part of sales but also the sales process and thinking as a sales leader. That’s what came across right when you mentioned about you and the founder of Carabiner about the FP&A process, plus people reaching out to you for sales entry and exit stages.

What’s at the heart of that is most salespeople are not trained on how to think from a business perspective. I’m trained to think about a specific problem and how my product addresses your problem. Most salespeople are only looking at that problem in a vacuum. They’re not considering the fact that that problem might not be the biggest problem that someone’s dealing with or trying to solve that problem that might only take up one to 2% of my mind share.

It might be a painful enough problem for me to care about fixing it now. You have to find out what the bigger problem is. What is keeping that person up in that area? What do they think about? What are their goals? How does that affect their career mobility? How does that affect ELT, their board, and their share price? Think about those things and how they affect their customers.

Double-clicking on some typical day in the life of Cliff, maybe it’s a week or a weekend, what does that look like?

Let’s break down a week. It’s probably easier. There’s a handful of internal meetings that I’m constantly being pulled into, whether it’s a client escalation, making sure things are going well, or just like the running of the business walking through recruitment, finances, sales, marketing, or whatever it might be. That’s probably something for 5 to 10 hours. I probably spend another 10 to 15 hours involved in sales motions. I probably spend another board five hours a week networking, talking to folks, catching up with friends, seeing what’s going on, and meeting new VCs and PE firms.

There are probably about two hours a week on professional development and learning something new. I spend anywhere from 5 to 10 hours a week vetting new technology, finding out what’s the newest of the new, what’s working well, or, “I haven’t seen this yet. I haven’t seen this in two years, let me get a refresher,” because I want to know what everyone’s using. I want to understand how well it’s being adopted and how it can potentially fit the needs of my customers.

The last piece all comes back to knowing your target customers and buyers well. We should reemphasize or highlight how important it is for each and everyone, especially you as the reader. If you want to get good at either marketing or sales, it doesn’t matter. For anything customer-facing, you need to carve out, spend time, and understand what your customer is dealing with on a daily basis. In your case, it was the technology.

I spend about the other five hours of the week talking to customers and hearing what’s going on with them. The voice of the customer is extremely important in understanding their business challenges so that we can either help stay in front of that and help lead them in some ways or make sure that we’re thinking about it. One of the things that have made us successful is we’ve got some good folks who work for us and will take the time to learn the ins, outs, and nuances of the industries and the sub-verticals that they’re serving.

Typically, I ask my guests what resources they lean on when it comes to shows, books, or community. The community definitely is top of mind for you. It’s very clear.

I lean on Pavilion. A lot of the people I respect the most in the game now are there. I went through CRO school with Pavilion. I still meet with the same cohort of people that I went through that with a few years ago. We’ve met every two weeks for the last few years. That’s been an invaluable resource. I love winning by design stuff, listening to their videos, and getting a chance to go to any of the courses that they offer. The two books that I would recommend the most for Leaders is Extreme Ownership by Jocko Willink. The other would be Matt Blumberg’s Startup CXO: A Field Guide. I love that. It’s great because you can earmark the heck out of it in terms of the chapter that you need for that moment in time.

As someone who’s helping to run a small business where I have to think from a finance, BizDev, and marketing perspective and take all of that in, and I haven’t necessarily had all of those roles throughout my career, that’s been an invaluable guide to just get into the mindset and think through the problems from the way that would particularly look at it. On the other side of that, from a sales guy’s perspective, it helps me get in the mind that much better of the people and my team’s selling to.

I don’t have those books on my list, so I’m going to add those. The final question for you because I know you have little ones to take care of in the business is if you were to turn back the clock, what advice would you give to your younger self? Day one of your GTM journey.

I would learn to be more process-driven earlier on. Don’t be late. I was bad at that when I was younger. That cost me a lot of credibility with folks in leadership. Be more process driven-early on and you don’t always have to be the one that’s right. Have a little more humility earlier on. That’s something we all tend to learn as we get older, but a 23 or 24-year-old Cliff who had been a little bit more humble would have gone a lot farther.

Be more process-driven earlier on. Don't be late. Share on X

The second one, you have clearly fixed it. You are on time or even before time joining the show, so you are not late for sure.

I’ve got one guy on my team who used to work for Jocko, who wrote Extreme Ownership. He was a Navy SEAL for twenty years. I have a daily standup for the team and he is always the first one on the call. Even if I joined five minutes early, he’s the first one on the call. He’s like, “My goal is always to be wherever you are before you get there.” I’m like, “Fair. I can’t argue with you.”

Where can people find and learn more about you Cliff?

If you want to connect with me, find me on LinkedIn. It is pretty easy. I’m Cliff Simon. There is a little cloud in front of my name. That’s the easiest way to get in touch with me. Otherwise, if you’re in any of the communities that I’m in, RevGenius, Pavilion, Wizards Of Ops, or RevOps Co-op, feel free to shoot me a Slack message. I’m happy to have a conversation.

It’s a great conversation. Thank you for sharing a lot of the tactical advice and actionable insights. Good luck to you and the team at Carabiner.

Likewise, thanks for having me on. I appreciate the time.

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Sales Forecasting As A Go-To-Market Org With Holly Procter

Posted on November 23, 2022November 23, 2022 by stratyve_ant2yf

The biggest skill you need to learn when entering the market is sales forecasting. Knowing and hitting your numbers is an important ability to possess, especially as a sales leader. You need to have the right methodologies and processes in place to achieve the highest levels of market success. This is where the company Clari excels at. They help go-to-market orgs overhaul and run their ultimate revenue processes.

Join Vijay Damojipurapu as he talks to the SVP – Global Head of Sales at Clari, Holly Procter. Learn more about her career journey before she got into this company and what she is doing now to support go-to-market orgs across the country.

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Sales Forecasting As A Go-To-Market Org With Holly Procter

In this episode, I have with me Holly Procter, who is the SVP and Global Sales Leader at Clari. For those who have been avid readers of the show, this is the 2nd or even 3rd speaker from Clari. Again, no affiliation or anything. It happens somehow by luck, faith or whatever you call it. We do have a series of speakers coming in from Clari but all in all, you will be in for a treat. Welcome to the show, Holly.

Thank you so much for having me. We appreciate your bias for Clarians. I will try to do my best even though you’ve had some good nuggets from other Clarians too.

As with every guest, I start my show with the key question that’s top of mind for all the readers, which is, how do you define go-to-market?

When everyone thinks about go-to-market, they start with the basics of how you sell your product. You sell your product through generally a handful of channels. That would be inclusive of both partners and also your direct sales team. Over the years, we’ve certainly expanded our view of go-to-market to include pretty much anyone that might touch revenue.

At Clari, I think about our go-to-market teams in our tip of the spear, what we call revenue development, which is our SDR function. Even before you get to RevDev, we think about the funnel. You are thinking about all marketers. You are thinking about content teams and people that might engage with your audience, even if that audience is not an active prospect or customer success. We have a deep sales engineering team and even post-sales, so people are responsible for implementation services. Anyone that touches revenue, which is any pre-customer and post-customer experience, we define as part of our core go-to-market team.

That’s more expansive than what I’ve heard from others. Not from my show guest specifically but from others in the industry. Again, you can clearly make out the provision that they like by asking this question. What I’ve seen is that folks who are in sales think go-to-market is sales and nothing else. Folks who are in marketing, and especially those who are in product marketing, think they own go-to-market but lo and behold, sorry, you are in for a rude shock. You clearly don’t own product marketing. Customer success, I’ve seen off late the connotation shifting to include customer success, which is good. One gap that I saw in your definition or your perspective, Holly, is how come you left out the product.

It’s a great point. I love our product leaders. If they are reading, I hope that they will take my apology. The product is massive. What I would say, and part of the reason why I didn’t include them, is that we probably haven’t yet figured out how to crack the code on incorporating them as a close loop in our process and how they play a role in touching the customer experience outside of building a great product but no question. That informs everything we do. I will give you an active example.

We are now going through planning for 2023, as most companies are. A big part of our planning process is figuring out what product features we are going to announce and launch in 2023. That will deeply inform how much and how many accounts I can assign based on what new open accounts we might unlock in line with the product roadmap functionality. It’s such a core part of the way that we build the business and product go-to-market.

That’s the thought process. That’s what I’m seeing. That’s a shift happening in the industry, which is product also becoming a core part of the go-to-market. Even within the product or outside of the product, there is a design that has a big impact on user experience that translates to the sales and how quickly you can go close and customer acquisition costs, and so on.

Anyway, enough rant on the go-to-market piece. I would love to hear your story. What has been your journey? I’ve looked at your LinkedIn profile. You had a very blessed career and a very interesting career path. You started off as an employee at the university you graduated from, then now you are the Global Sales Leader at Clari. Walk us and our readers through that journey.

I’m from Nebraska, originally. I got both my undergraduate and graduate degrees from Nebraska and then decided to work for the university under the guides that we had an asset that was a facility. We were trying to figure out how to monetize this facility. It was this huge rec facility, and we were trying to figure out if there was a path to monetizing both access to the asset and the building. Also, what else did we have?

We had access to a population of people, and that population of people was a student body that made purchasing decisions on a regular. We created this event called Get REC. It was called Get REC because it was held at the Rec Center and basically allowed every business in the town to come in and put up a booth that wanted to sell to college students.

They ended up paying us several thousand dollars to come in and do that. Figuring out a healthy way to monetize our assets and get additional funding for the university was awesome. A great first job, and then I moved to San Francisco. I was tech robust and eager to move West. My first job in San Francisco was at Gallup, the Gallup World Poll. The thing that I was so excited about with Gallup, I don’t know if you follow any of their research but they are an academic company. It’s stewards of research.

A big part of what Gallup does is sell both employee engagement research and customer engagement research. I fell in love with the company for many reasons. One of the big things that they talk about with their leadership development is that the employees join companies and leave managers. It was this big, huge part of the thing we were consulting around. It was where I grew fond of leadership, education and development, the process of being a student, and becoming a great leader. I got some deep education on how to be a good boss. This was before I became a boss. I then was eager to go into tech, so I joined LinkedIn.

At Gallup, you were leading what BizDev or was its sales?

It was biz, and I was a seller. Our motto was fewer larger relationships. At the time, McKesson was one of my biggest customers. I’m spending a lot of time with them on leadership development and employee engagement. Incredible experience in consulting because you get to go wide. Not necessarily deep. Lots of exposure to different business processes across tons of different business types and unique companies. It was an incredible experience there over years. Living in San Francisco and not in tech, which felt like a misnomer, so I decided to move to LinkedIn. I started with LinkedIn right before we went public, and then I left LinkedIn, and we were owned by Microsoft.

A lot of things happened over that six-year window. My role inside LinkedIn changed almost every year. I led pretty much every customer segment, so from our smallest customer all the way up to our largest key accounts and in a couple of different lines of business. Both our talent solutions business and the sales navigator product when we launched that product, which is now over a billion in revenue.

It was incredible to be able to build something from the ground up based on an amazing asset, which is the LinkedIn network. I learned a million things from LinkedIn but one of the things that fueled the next phase of my career was selling into sales leadership, which is what a selling sales navigator did. As go-to-market professionals, there’s something meta about selling to sales leaders. I wouldn’t trade it for the world.

As go-to-market professionals, there's something sort of meta about selling to sales leaders. Share on X

I get to talk to my peers all the time. It’s probably how you feel getting to talk to other experts. I learned from my customers regularly, which is incredible. I fell in love with sales leadership. Not just being a sales leader but working with sales leaders at LinkedIn. As I mentioned, I led all different customer types and in a couple of different lines of business. I felt like I had deep exposure to lots of different parts of go-to-market orgs.

The other thing I will say about LinkedIn, outside of it being a phenomenal company, is that it demonstrated to me how it should be done, how a business should be run, how to take care of your people, how to build a sustainable business, how to build a moat around your product and how to inspire a huge audience of a global talent pool. Best in class across many vectors that matter when building a sustainable business, so forever grateful for my time at LinkedIn.

I took all those learnings, decided to gamble a little bit of in the startup world, and went to WeWork, where we could spend the entire episode on that. Maybe we should grab a beer to do that. It was quite the run. I spent a few years at WeWork leading up to our at Ben failed IPO attempt and just wild run. I was running our mid-market business across the US and hired over 70 people.

My last job was to eliminate them all. It was a wild experience but if LinkedIn taught me how to lead in peacetime, WeWork taught me how to lead in more time and a major benefit to both. I learned a lot and worked with some incredible people at WeWork. I was there in the Adam Neumann era but I would say one of the things that I learned the most about WeWork was how to pressure test growth and ask yourself the question if something could be done faster, bigger or at a lower expense.

Challenging the status quo of, “If we can do that in six weeks, what would it take to do in two days?” It’s asking the question of pushing the boundaries of what you think is possible. Whenever I got a question from WeWork that was like, “I need you to do X, Y, and Z.” I always thought it was insane. Most of the time, we delivered.

There was something to that, which is that if you can apply enough pressure and enough resourcing, what you are able to accomplish is pretty incredible. I learned a lot there too. The next up on the rung for me was that I was eager to get back into the software. I was eager to get back into the ecosystem. I mentioned selling into sales leadership and so moved to Clari. Clari was, at the time, mostly an enterprise product. They were overhauling forecasting. It was their bread and butter.

Over the last few years, it has been incredible to be a part of a team that I deeply admire and respect. Our leadership team is phenomenal, led by Kevin Knieriem and Andy Byrne, which is so strong. Working in a space that has blown up when you think about revenue and sales tech is exploded, which is awesome to be a part of for lots of reasons.

First and foremost, as a seller, our function is last to evolve. Almost every other function had innovated and supplied its employee base with new technology to become more efficient and smarter in their work, except for sellers. We are finally getting our moment. Our moment is here, and we’ve invested, and you are seeing a huge amount of not just venture capital but excitement from investors.

A seller's first and foremost function is to last and evolve. Share on X

Analysts are all over the space. It’s blowing up. If you look at sales tech similarly to the way that you looked at MarTech of the 2000s, it is hopefully going to follow a similar thread, which is lots of investment, tons of companies, and ultimately consolidation. It will be interesting to follow the space over the next ten years or so to see what happens.

Clair has expanded from being a forecasting platform that could help people overhaul a process to going into tons of different workflows. How do a company and a go-to-market org run their ultimate revenue process? How do you inform a rep to a manager one-on-one? How do you inspect opportunities? How do you spot risk? How do you ensure that your pipeline has enough coverage? Ultimately, how does a CRO define to the board and the leadership team if they are going to meet, miss or beat their number? It’s a very exciting time for us to be a part of.

Two things stood out for me. One thing you talk about is being meta, going back to LinkedIn, and selling to sellers. It reminds me of my time at SugarCRM, where we are selling to sellers and marketers. We need to be great at doing marketing and selling. That was a big eye-opening experience for me. You are preaching but are you doing the right things where you can lead by example?

I always say to my sales team, “We are demonstrating a sales process to the sensei, to the people.” Their inspection of our sales process, you can imagine, is going to be diligent. The way we show up in these moments is so critical. I would say that one of the things that are so incredible for me as a sales leader is the number of outreaches that I get from a head of sales or CRO complementing my sales team and asking if they can hire them. It is the best compliment because I know they are a tough critic.

There’s something that I want to pick your brains about clearly, you are an expert. You have been in sales, from a sales rep to leading a sales team, to now you are technically a business leader representing sales at the board level. How did you master or how are you continuing to master forecasting and prediction? That’s the biggest skill to learn.

From my personal experience, I have been at startups and worked with sales leaders. More recently, when talking about forecasting and missing the forecasting, here is a big miss where we forecasted $800,000 in a quarter, and eventually, sales closed at $30,000. I don’t want to go in there but clearly forecasting and being able to hit the number is a huge skill. What advice would you give to our readers on that?

It’s massive, especially as you move into sales leadership. As a sales rep, you are generally responsible for calling a number but very few orgs hold a rep accountable for their accuracy around that number. Part of that is because they don’t have a lot of diversification. If they miss one deal, it could throw their number off by several hundred percent, and that’s tough. Not a lot of accountability at the rep level. A little bit more so once you move into frontline leadership.

Naturally, when you get into executive leadership and sales leadership at the highest levels, the forecast is the thing that you are expected to get right. It’s table stakes to be effective in the role. If you don’t have a good methodology for how you get there and you have to put a good process in place, you are screwed. When you go into a board meeting, you are going to get eaten alive, and you need to be able to defend your call.

All that to say that there’s so much that is unpredictable in our environment that there’s no amount of machine learning, AI or fancy software that’s going to call COVID or the current downturn. Even the rise of PLG businesses is much harder to forecast in that environment because you are responding to market factors that you may or may not be able to predict. Velocity is all over the place. To get to the root of your question, there’s a handful of things that are core to getting this right. I’m going to walk through some very specific examples here, so forgive the granularity.

That will be the most useful for our readers, for sure.

One of the first things that you have to get right to get a good and predictable forecast process is sales stages and forecast categories. The terminology that you use inside of your sales org to call the way a deal is represented is critical to getting the overall process right. What that means is that you need defined stage criteria. This is what must be present inside of your deal for this to be considered a stage 2 or 3 deal however you have laid out your stages. Most companies have 4 or 5.

Within those stages, from qualifying to pricing and negotiations, however, that is enabled for you that it is crystal clear to a rep and impossible to argue when something has moved into or out of a stage. For example, in my world, we might say, “To move to stage three, we have to have been named vendor of choice.” This means we have to have gotten from the customer, the prospect, an indication that we are the partner that they want to partner with.

We might still need to get through security. We might still have an outstanding MSA but they have said, “We would like to move forward with Clari,” and now we know we have to move towards our paper process in getting a deal done but we have been named vendor of choice. That is a requirement to move into stage three. The requirements associated with stages and forecast categories are critical, and ensure that you’ve defined them. All of your leaders are managing to it is so important.

Now when you look across every single deal, you know that you are looking at the same set of requirements. You don’t have one deal that’s being represented differently than another deal with a different set of requirements. It’s foundational to getting a forecasting process in place. Second, there is no silver bullet inside the forecast. Therefore, you need to have a set of data that you can triangulate against.

For me, what that is, first, I have a rep roll-up. The rep roll-up is inclusive of all of the outstanding inventory. A lot of companies will do a bottoms-up view, which is deal by deal. They will say, “This deal is either in or out, or this deal has X amount of probability.” You have this bottoms-up view to informing one point of your triangulation process.

The next is you have a manager override or a manager commit. You have your leaders pressure test the rep-level forecast to see where they would agree or disagree based on how they might be called a deal. For me, the third layer is using AI. Specifically, inside a Clari, there’s a module called Pulse. Pulse is looking at historical data, and it’s making a prediction on how that quarter or a next quarter might shake out, looking at conversion rates and the amount of pipeline that we have to see how we might land. That means every single time I’m calling a number, every week, I’m triangulating between what the actual inventory says at the rep level, how my leadership team thinks we are going to shake out and what the machine says. Between those three, I’m landing somewhere in the range.

The first point you made is supercritical, which is my takeaway from that is defining very clear entry and exit criteria for each stage, where there’s no argument. There’s no ambiguity. Seller A can argue, “This is how I see it,” versus seller B will see it completely differently.

It’s black and white.

You use Clari, obviously in-house, and shout out to Clari. For those of you who are reading, if you are curious, check out Clari. Going back, if you have to go back in time and pick either a GTM success or a failure story, can you share one from your most recent time? That will be a great eye-opener for us.

I’ve got lots of both. Do you want me to share one of each?

Yes, absolutely.

There’s obviously recency bias here but I will share a failure. I will use one at Clari, which is we initially set up our go-to-market org to be geo-specific. We were going to have these little hubs. The hubs would be like if you owned Minneapolis, you were the CEO of Minneapolis Clari. Your job was to map out all the businesses that resided in Minneapolis, to get in with the Chamber of Commerce, to set up local events, and to create a community across companies that might sit in Minneapolis. You owned that geo. That’s how we structured it. This is pre-COVID.

You moved to a world where geo is almost completely irrelevant. I remember the moment when I knew this was a failure. I had an incredible rep who I very well love and still with us, who sold our first logo in Toronto. He said, “I planted a flag in Toronto, and it happened to be a relatively small deal.” You love getting a deal. A deal is a deal. I will never not celebrate a win but the win was that we landed in Toronto.

I was like, “This is one of our best reps. He is trying to crack into getting a small deal in Toronto. Why do I care if we are in Toronto? Do you know what I care about? Revenue. Why do I have him focused on these geos when there’s much bigger fruit if I were to distribute, let’s say, the market of New York?” We made this decision to move from a geo-based model to an account-based model a few years ago and never look back.

It was such a better distribution of our opportunity. Also, it allows us to hire pretty much anywhere and so we can get better talent without needing to focus on the geo. That was one, and I learned that way. A success, I will say, is that we were a pretty enterprise-focused company when I started. Most of our customers were enterprise customers.

There was a lot of trepidation to go down-market. People were fearful of the impact on ASPs. People were fearful of not having the support resources to support the velocity business. It took a lot for us to go down-market. One of the things that we did was pilot it with a handful of apps and gave them our smallest potential customers to see what they could do. This small team, we call it emerging. They exploded. It was all the fish that were jumping into our boat.

We decided to take that as a signal and say, “If these are a bunch of leads that are coming our way, what if we put capacity against it?” It did something with it instead of letting them come to us. It started with a small team and let them run wild for a quarter before we knew that this was a no-brainer place to invest based on the interest that we got and the success of that team. My regret there is that we should have done it sooner.

One question for each of the scenarios there. For the failure scenario, you mentioned you moved from geo to account level. I’m going to take a hypothetical example over here. Let’s say it’s Home Depot. That’s the account you are trying to break into. Were you assigning a rep to break into, let’s say, Home Depot in Michigan State versus Home Depot at any location? Is that the shift they are talking about?

We organize the account by HQ location. If Home Depot were headquartered in Minneapolis, then it would be owned by the Minneapolis rep but wherever the HQ location is would dictate ownership.

I had a question regarding your success scenario, which as you can clearly relate to this moving upmarket. Our down-market is super hard for any organization. What is the thought process for you and the leadership team at Clari on how you define the success criteria? Was it verticalized or how did you think about framing the team? Can you share some more insights about that?

It is a tough and big strategic decision. We operated more as an enterprise-grade company. We had enterprise customers. Most of our market position was geared toward the enterprise. That start there, which is how do you tailor your messaging and your market position to be attractive to different segment? Something we had to face in something we still deal with a little bit is you will see the SMB customer ask us, “Are we big enough for Clari or is it too soon for us to find value and benefit out of Clari?” If they are a former user, they never ask that question because they know what the value is to them.

For the general population, that’s where you need to start. Reeducate the new population of people that you are going after and why you are right for them. That was the one. One of the big changes that we went through as well is that naturally, at the market, you see enormous complexity. Both in the buying persona and the number of people involved in a purchasing decision and also for us technically. You are integrating with data.

The way that data is structured can be very complex. Nuance for that unique customer. How do we simplify our process so that we could move through complexity at a different speed when we go down-market? We had this internal hashtag that we talked about. There’s a guy in my team named Adam Wainwright, who I will credit with this.

He labeled it supersonic. Supersonic was the charter for that team, which is, how can they move through a process quickly? If somebody said, “The average sales cycle time was 45 days, how could we get it to 30?” Everything we did was through the lens of supersonic. Taking what was a cumbersome process upmarket for a complex cycle and trying to figure out how we remove friction to get to a supersonic process.

I got some more follow-up questions for you on that. When someone goes to your website, you get the messaging, everything directed at the person who relates to like an enterprise customer, the ICP, versus when you are looking to go midmarket or down-market in your scenario. There’s the messaging, pricing, also other different aspects which we won’t get into. I’m sure you will share. Again, how did you think about that or how did you attract the initial set of your target midmarket customers?

Specifically, do you mean in the messaging that would be attractive to that?

It might be outbound because, obviously, you won’t be driving a lot of inbound or maybe you already have those in your pipeline, in your list somewhere, and then you segment that as the potential midmarket. What strategy did you use for those?

Firstly, we had to make a decision on what we would use to define segmentation. What was the best marker to signal that this type of company was indeed different from this other type of company? We ended up using just employee count. There’s a good debate on whether or not we should use sales employee count. The reason why we didn’t use sales employee count is that it’s harder to get that information and also different by industry.

Employee count is generally representative of the size of a go-to-market org that would be attractive to Clari. That was the first thing we aligned on. Not revenue, and that was by design. Employee size is the place that we started, and then we drew a line in the sand for us around a thousand employees. The other exercise you had to go through was, where does a cycle become differentiated? What is the line in the sand that says, “When you are below a thousand, you operate like this. When you are above a thousand, you operate like this?”

Those two things require a different sales motion, a different set of resources, a different market message, and a different price. Therefore, we are going to treat them differently. That is an intellectual exercise that should be run with product marketing. Hopefully, you have an ops function that can help support the data around that suggests, “You should stand up a motion that looks fundamentally different for this customer than that customer.”

After we went through the academic exercise to come up with an answer, then you go to trial and see if that’s, in fact, right. I will say that as our product and our go-to-market org have evolved, we have made some type of change to our segments most years. We collapse and expand. As we add more skews to the product, the way that we think about supporting them is different.

I will give one other example, which is in the presales side of the business. When we sell to a prospect, we segment by employee size, as I referenced. As soon as we sell that and it passes to the customer side of the house, and it’s going to be run by an account management team. They segment by revenue. Not by the revenue of the company but by the size of the deal that we did with that prospect. For them, the way that it makes sense to organize is how big of a deal it needs to be serviced and, ultimately, ensure that we can make that customer successful in a different way for different needs to segment.

Especially for customer success, it’s more of an expansion opportunity. Clearly, that makes sense. That is super helpful. Did you allocate six months or a year for this “experiment”?

We had prepared for six months and ended up making a decision after three. The reason why we decided after three is because it was so obvious that it was successful. We had done twenty new logos or something in a month. It was clear to us that applying resourcing there made sense. The other thing is that you get feedback anecdotally from your prospect base.

The number of customers that we had spoken to that appreciated got onboard with our supersonic approach and appreciated that they could move fast but it didn’t feel like a clunky, stodgy enterprise process. The feedback I got from many CROs in that space was aligned with the process we had put in place. It was very clear that we were going to make the investment. If you know that you are going to make the investment, why not move fast?

Let’s switch gears. We are coming to the final segment over here. What are 1 or 2 or 3 things within the go-to-market arena that you are curious about? What’s causing you to go deeper into research and shift your thinking from a go-to-market perspective?

There’s a ton. In no particular order, I will say the things that have been top of mind to me here. One is around intent. There are so many amazing new signals that we can incorporate into our sales process to try to find intent which means that we are going to use so much better at attaching the right accounts to the right resources. If we know the accounts that are warm and we put them with our bestsellers, we should be able to do all kinds of things. Not least of which is increase our revenue.

Lots of exciting companies. We happen to partner with 6sense. They are phenomenal on this front. Lots of intent resourcing here that changes the game for us. That’s number one. The other is around business models. The other thing you are seeing a lot more of is consumption use cases and usage-based models, and PLG motions. There are all these new ways outside your standard license-based model to structure the way you capture revenue from a customer. That’s super interesting to me. We will only see more advancements in the way that pricing in packaging is structured, especially in software. Those are two that are hot for me now.

There are so many ways outside of standard license-based models to structure the way you capture revenue from customers. Share on X

The first one is intent, clearly. There’s a lot of talk in the industry about how you define intent. It has always been there in good market teams. You need to identify the intent signals but there has been no clear black-and-white way to identify them within the sales stack and marketing stack. That has been the biggest gap. Of late, I’m seeing more companies like 6sense.

There are others as well who are helping. They are also adjacent solutions that can say, “Plug this. Stick stack into your solution, and you can see the intent signals.” That’s from a tech perspective. I would like to get your thoughts on within the go-to-market team. How will you define whether this is a high-intent versus a low-intent account?

We use the signal that we are getting from 6sense primarily for us. We also use some G2 data, so we layer those on. The other thing for us is diversifying the leads. Not all leads are created equal. How do you ensure that you’ve got the right lead scoring so that it gets the right urgency that’s required? Naturally, a demo request or referral for us is high intent. We want to ensure that the speed to lead is short and that we can get connected to the buyer as soon as possible.

For us, that meant we instituted. I will give you an example. A product called Caddy. We are new to using it. It is the ability to book. If you book a request for a demo on Clari’s website, you would be directly connected to the AE that owns the account instead of bifurcating and moving away, going through all the other channels like being to an SDR or someone to do a qualification step. If it’s a named account, we already know that that’s somebody that’s already qualified by default, and we want to ensure that there’s as little drop-off as possible. That’s some of the mechanics that you have to optimize in the go-to-market.

One other topic, I have been coming across this topic also, and I speak to other go-to-market leaders. There has been a constant debate as to who owns the SDR team. Is it sales or marketing? What is your thought process around that?

I’ve seen it in both different departments. It obviously works in both places. At Clari, Kyle Coleman owns our SDR org. He is like LinkedIn famous.

He’s an SDR champ. I see him on LinkedIn. He is a true champ.

Deep expertise in the function, and so we are lucky to have him for lots of different reasons but that’s one of them. For me, he’s probably one of my biggest partners. There’s nobody I spend as much time with as Kyle in orchestrating a sales motion for us. Where it lives is much less important than the alignment between the two orgs.

Even if it lived in sales, naturally, so much of the lead flow you would hope your SDRs are responding to is generated by marketing. If it lives in marketing, it must be responsible and accountable to sales. This is why there’s no obvious answer to this. Either way, there are tradeoffs. It’s not a perfect answer, no matter what. The alignment between the 2 orgs and, arguably, the 2 leaders is the most important thing.

Moving to the last couple of questions here, who would you credit if you were to go back in time? Who have been your code mentors and sponsors? Who have been the role models that helped you get to this point in your career?

I’m so lucky because I have many. You said 2 or 3. I will start maybe in logical order. The first time I ever went on a sales call like as an adult with a full-time job and going out to see a customer. I was with a guy named Aaron Nadolza. He and I both worked together at Gallup. We were going to our first big sales meeting.

It was his meeting, and I was just shadowing. He took me under his wing and taught me how to sell. Everything from how to set up a good meeting, how to follow up on the meeting, and the real basics of customer engagement. That’s like the least exciting thing he’s taught me over the years. I have now worked with him at three different companies. I followed him on LinkedIn. When I went to WeWork, I brought him over to be my boss.

I’ve worked with him for many years. I’ve learned a million things from him. The big thing outside of sponsorship, as you mentioned, is that he certainly sponsored me but he just deeply invested in me to teach me everything he knew. I was afforded his life experiences. I didn’t have to go through them myself, which was so incredible. Aaron has made a massive impact on my life.

When I went to LinkedIn, I worked for a leader that didn’t just change my professional trajectory but changed me as a human. His name is Peter Kim. Pete was the best boss that I have ever had. I remember specifically a one-on-one we had where I was asking him for some career advice. He basically said like, “Holly, I am yours. Use me however you want to use me but I believe in you. I’m here to develop you.”

What changed in the course of our interaction was that I did start to use him. A mistake that people make is that most people want to invest in high-potential talent. Where there’s often a mismatch is that the talent also has to go and engage and make good use of their resource. I took Pete up on his offer. I used him for everything, and honestly, I still do. We got to a place where he could give me advice about my whole life, everything from how to structure my mortgage to which job to consider or not.

Ultimately, it’s still your decision. It’s still your life but to have people that care deeply about you and therefore are interested in you making the right decision is so important. The last one is my current boss, Kevin Knieriem. He’s the CEO at Clari. He has invested in me in lots of different ways. One of which is to empower me to make my own decisions, build out an org, and be able to stand up for something that I knew was right.

I feel so empowered in my role now. Having limitless belief changes the way you operate. When you know that the person above you is in your corner and rooting for you in every way changes the way that you show up at work every day. Back to the comment, I made earlier about Gallup and that people join companies and lead managers.

For all the leaders reading, it’s a deep responsibility that we have as people leaders at any level. Whether you are leading leaders, managers or reps, someone’s happiness depends on the way that you approach them. You, as their boss, get to empower them. You get to ensure that they are going to have a good day or a bad day. That’s something that we shouldn’t take lightly. I have been lucky.

As a leader, someone's happiness depends on how you approach them. You have to empower your people and ensure they will always have a good day. Share on X

That’s a great piece of advice there. For all readers, it doesn’t matter if you are a people leader or someone who’s reporting to a boss. You will have both up and down for most of you there. Hopefully, someone will take this as an inspiration to sponsor and grow someone’s career and vice versa. Ask and take, go full advantage of your manager because they sincerely care for your growth. That’s the message. Last question here, Holly, which is, if you were to turn back the clock and go back to your day one within the go-to-market career journey of yours, an amazing career journey for sure. What advice would you give your younger self?

One of the biggest things I have learned, which is so critical, is that much of the career decisions that we make can be convoluted when you start to add in title and comp and roll scope. You can get attracted to those things but one of the things that probably has the biggest impact on your return is the quality of the company. You are picking the right horse to bet on.

If you pick to be the assistant at the right company versus the CRO at the crappy company that goes nowhere, the fact that you have a big title, a big comp or whatever but the company doesn’t succeed. It ruins the whole game. Picking the right horse is 90% of the battle. If you take what is perceived to be a lateral move or even a step back in title and comp is so insignificant in the grand scheme of life and a long career. It’s so much more important to pick the right company and invest in the right company that you believe in over the long haul. It’s a big learning for me.

I have nothing to add to that. That’s a great piece of advice, for sure. Thank you so much, Holly. It has been wonderful speaking with you. Thank you for sharing all the wisdom and insights. Good luck to you, your sales team, and the folks at Clari.

Thank you so much. I appreciate you having me on the show. It’s great to spend some time together.

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