How do you catch your clients’ attention then give them value fast? Write down the moments that matter! Vijay Damojipurapu’s guest today is Anthony Cessario, the VP, of Industries & GTM Solutions at Clari. Anthony talks with Vijay about how you need to identify the moments you want your clients to experience. Do you want them to walk away feeling good? Do you want them to come back? After you identify the moments that matter, you can proceed to build your entire strategy around that objective. If you want tips on how to build that strategy, this episode’s for you. Tune in!
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Moments That Matter: How To Deliver Value To Your Clients Fast With Anthony Cessario
I have Anthony Cessario, who is the VP, Industries and Go-To-Market Solutions at Clari. Without further ado, welcome to the show, Anthony.
Great to be here. Thanks, Vijay.
I’m super excited. I’ve been following you not a whole lot but somewhat. What caught my attention on LinkedIn is when you mentioned or responded to one of your colleagues, LinkedIn post around the importance of having curiosity. Curiosity as a differentiate or are a key factor when it comes to go-to-market execution? That post or that one comment caught my attention and I said, “I need to get Anthony on my show,” but it doesn’t stop there.
I go to your LinkedIn post. What gets me even more excited is when I read your LinkedIn summary. It talks about how you plan or how you have bucketized your time across the week. We’ll hold up on that question. I want to get your thoughts on that but let’s start off with my signature question in which my audience is eager, excited and curious to read to go-to-market leaders around this topic, which is how do you define go-to-market?
Again, thanks for having me. I keep things maybe overly simple sometimes but for me, go-to-market is that end-to-end business process of creating the desired outcome usually, revenue from a product or service offering. That’s really it and there’s a lot that goes into that but I try to keep how I think about go-to-market simple in that regard.
That’s a very simplistic definition and view. If you up-level, it that’s what it gets down to but here’s the thing. Everything that we know as a concept, we know it but execute it is super hard. That’s where the real go-to market leaders stand out. Talk to us about how you approach the execution piece around go-to-market.
At Clari, there’s a concept we talk a lot about called operationalizing growth. We think about how do you operationalize growth and that’s a lot to do with go to market. For us, it always starts with what we would call SGIs, the Strategic Growth Initiatives of the business. What is it that we need to accomplish over whatever period of time to take the company wherever we were trying to take it?
From there, when you have clear SGIs, that’s when the go-to-market starts to come in. Where now we decide, one, what are the targets that we would need to set in order to go deliver on those SGIs? What are the types of execution insights and instrumentation that we would need to either run the business in a way that we can go deliver on those targets?
You then get into the cadences and communication that needed to happen and these types of things. You get down to enabling folks on the go-to-market. That whole part, a lot of times people jump right into, “What do we need to build? What’s this LCD need to look like,” and all these things. The program management of go-to-market is important.
That starting with, what are we trying to accomplish? What are the guiding principles? What are the constraints we’re operating within? Who were the players and who were the workstream leads? All of that and making sure you have the instrumentation everyone executes against it. At the companies that I get to work with that are great, go to market organizations get all that well. They do that well and then they go execute within those workstreams across product, in sales, strategy, enablement, CS and all the teams that are contributors to the process.
When I asked you the question, you started off with those 1 or 2 lines, but then when you doubled click, there’s a whole bunch of processes. There’s a whole bunch of systems approaches, the tools and the players, the people that have to be taken into account to eventually connect the dots between, the strategy, the execution, the measurement, and how is it all lining up to what you were ever to ask the SGI at Clari. Of course, you need to build clarity around all those things and you’re doing that at Clari for sure. Switching gears slightly over here on a lighter note, how would your parents or kids describe what you do at work?
You mentioned that you might ask me this question. I wouldn’t ask my kids. I have two boys. Dominic is going to be seven soon. Daniel is four. Dominic’s answer was great. He got probably group them well. He said, “You help people solve tough problems or hard problems, and you do it over your computer.” That was cool. I try to talk to him when I’m spending a lot of time and energy on something. I want him to know that it’s important and what I’m doing is helping other people, and making their lives easier and that makes me feel better about it. How would I explain it that way? That was great that he’s been listening. My four-year-old only said, “Computers.” I said, “Danny, what’s daddy’s work?” “Puters.”
Tell your story to other human beings in a way that's going to resonate with them. Share on XHe’s on the computer, always.
My parents, a little different. My mom’s been working in a hospital for many years. She would say something about Salesforce.com maybe and that I’m doing an important job. She’d brag a little bit. My dad was a business leader. He had a great journey. He came up through HR. He became a VP of HR and was business-minded at MBA. He ended up becoming the President of his business by way of the HR channel, which is not something you see very often. He’d probably tell you that I’m helping grow a business now if you ask him.
Especially most of the folks within the go-to-market organization, we are all about helping to grow the business but how we do that is by serving and understanding our customers. That’s a good segue into, what prompted you to go down this path? What was your career like? How did you start and how did you eventually get to what you’re doing at Clari now?
I’ve been fortunate. I never wanted to go into sales. I thought I was going to be working in marketing. In college, I interned advertising at over in Mather in Shanghai. I loved it so much that I anticipated, I’d go down that marketing route. My brother was in advertising and things like that. I was lucky. I had a friend who was doing some sales training right when I got into college.
The trainer, the Sandler coach, was from Philadelphia like me and so my friend said, “We got to network with, you should come to meet him.” You’re looking for your first job and all that. What they were working on that day in their sales training when I went and showed up were the Pain Funnel and sales. I didn’t know anything about sales at the time.
When I went and sat in, I was super curious at the end of that because it would sound so much fun. By taking a business problem and peeling it back three layers to understand what’s going on, why and help people make decisions, I was fascinated by it. That’s where it sparked me to go into sales, even though I wasn’t planning on it. I worked for a little startup. I met a guy in that actual class who was a CEO of a company working on his sales because he kicked off the company.
I did wear a few hats for him and his little four-person consulting startup. That was my first job. Sales and marketing and a little bit of everything like you do in a company that’s small. I then went to a great company called Taleo, which at the time I was like the number two SaaS company in the world behind Salesforce.
We had HR software, recruiting software, talent management software. That’s where I got my real start in sales as a BDR. I got to learn a lot there about how sales and marketing work together. We brought a new product line to the market right when I started. It was cool to see that unfold. How do you start selling a new product to your customer base? I was on a team that was doing that job of going and selling something completely new that our customers didn’t know anything about into our customers, which was pretty cool. We’re then bought by Oracle. I got folded into this big company and probably the best decision I made back then was to know. I wasn’t smart enough to know to make a decision.
A lot of people left Taleo after the acquisition. I wanted to stay and see what it was all about and I wanted this big company. At the time, Oracle had bought Taleo as part of their go-to-market to scale into the SaaS business, going from on-premise software and the cloud software. It was cool to see that on the front lines and how you have to think about talent differently. Do you have the right people to sell these new products? Do we keep this standalone or do we integrate the code into the platform we’ve been building for years? I got to watch all that decision-making as a sales rep.
We’re selling this new platform and I had a lot of great learning successes and failures throughout that journey. That’s when I found some success and it had some leaders that were starting to tap me to help with decision-making at a higher level on, “How should we be thinking about where we go next and what things does the product need to go into new markets?” I was fortunate to get pulled into a lot of go-to-market discussions. I learned that was what I enjoyed most.
The sales part was becoming blocking and tackling. It was more the working with product marketing, product development, doing territory planning and headcount planning, and all that stuff. That was all pretty cool and fun. I thought I decided to go into the high-growth world and leave Oracle. I learned at a big company, the higher you go, the less you might get the impact in go-to-market. I knew I wanted to go somewhere in the high-growth space and help to grow a business.
I got incredibly lucky that Clari had reached out. At Clari, literally, what we do as the company is going work with the top, go-to-market teams across the globe and help them instrument their go-to-market. I knew I was going to be an MBA on got-to-market. At the very least, that was enough for me. There you go. That’s the journey. That was a lot but that’s how we got to now.
As you’re saying that, a lot of light bulbs went in my mind and something that I’m curious about as you are evolving your career, Anthony, is you started off as an intern in the advertising world. Clearly, when you’re working at a tier-one advertising company, O&M and from there, you went into a startup in sales. Of course, not only sales, when you’re like a four-person company, you are wearing multiple hats. Eventually, that led you down to the path of a BDR and growing up the ranks at Taleo and Oracle.
I’m curious how your internship the startup’s first job to the BDR, and the growth in sales and sales leadership panned out. What I want to really get your thoughts on is when you are in the advertising world, you are looking to develop a copy. As any top-notch advertisers will know, you have only a few seconds or less to get someone’s attention. I’m sure even when you go into a BDR and even enjoy a sales role, that skill is important. I’m curious. I want to get your thoughts on that.
To your question, I would say probably, even higher level, what Ogilvy did for me and especially in China, and getting to work in Shanghai, what I realized was one, that it was fun helping companies solve business problems and I can make an impact on them. When I was a sophomore in college, that lit a fire. I wanted to do more of that. I couldn’t get done school fast enough at that point because I wanted to go like, “I can do this now. Let’s go do it.” That was the biggest thing I would say.
I didn’t care where I was doing it. I wanted to go as fine. That’s what intrigued me about the startup when I went to work for Starr with Darren Starr, he was a smart guy. He came from the VC world and AEye from Kleiner Perkins. He was standing up this Salesforce Consulting Firm. I realized that I was going to get to wear a lot of hats and create marketing copy.
Write your own call scripts.
Also, product summaries. I knew I didn’t know what I was going to learn but I was going to learn a lot, that was interesting to me. Again, back to curiosity, I was curious on like, “What I was going to learn and what it’s like to be out of business at that stage.” When it comes back to the copy and the marketing stuff, I always joke, “I’m a marketer in a sales guy’s body who thinks he’s a product guy and wants to be a strategy guy.” That marketing experience, I had played a profound role in shaping how I think about communicating with anybody but, especially with businesses.
My brother was a successful Creative Director before he became a wanted entrepreneur. You can look him up online. I’ve learned a lot from him as well and how to communicate with people and how do you keep it human and how do you keep things simple. That stuck with me certainly from Ogilvy, going into sales and thinking about how do we tell our story to other human beings in a way that’s going to resonate with them. It’s been something that’s helped me a lot.
I’m always curious. I always look to read up and also follow a lot of these practitioners around how to communicate in different formats, in different channels and how do you get someone’s attention in the shortest possible time span? That’s one, but once you get that attention, once you get a follow-up meeting, you got 30, 60, 90 minutes or even half a day. How do you then deliver value because they have carved out time?
There’s a concept that my sales teams put the work a lot that we call moments that matter. For every meeting that we have, for every pursuit that we’re going after, we’ll write down, “What are the moments that matter?” What that means is, what do we want the people that we’re interacting with the walk away saying, thinking or feeling after our interaction about Clari as a company, our product, us as individuals. We write it down. In this case, it might be, my moment that matters for this would be Vijay walk away saying, “I enjoy that time with Anthony. It’s going to be helpful for the audience. I hope to have him back again someday.” Those might be the moments that matter, and we’ll build the entire strategy for the meeting around that.
That’s something that, again, I learned from advertising where you back into the experience that you’re trying to create. Similarly, for companies, it’s an important thing to think about, “What is the experience we’re trying to create for our users, for our customers? What is the perception we want them to have of us?” That dictates a lot. That dictates how you build a product. What is the type of insights you want to surface in your product and things like this? It dictates how you communicate, the type of salespeople you hire, the marketers you hire, all of that, you can stand back from, what is the experience that you’re looking to create for your customers?
I’m sure because you’re in sales and you’re a lot in the customer-facing roles and interactions but eventually, you need to get those insights and learnings inward to the product teams. You are clearly communicating and working very closely with the product marketing organization and even the tech support and others. How do you bring that, as you said, moments that matter, MTM? That’s what I’m going to call it now MTM. How do you work with the product marketing team and the product management team in building or incorporating those insights into the product?
In my opinion, it’s so crucial to have product management and product marketing very closely interwoven to the front lines. There’s a great body of research out there around something called ONA, Organizational Network Analysis. Back in my HR days, it was a trendy hot topic in HR. How does work get done within companies? With all the technology out there now, Zoom, Slack and email, you could imagine if you were to look at the patterns of data on who people spend the most time with over Slack, over Zoom, over email, you would see an interesting web that has nothing to do with the org structure of the company.
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I would argue that with great go-to-market teams, you would see a tight-knit connection between product marketing, product, growth marketing and sales. There’s an important feedback loop that has to be happening there in a machine-like way or machine actual way. That’s how we think about it. Different companies take different approaches. Product marketing can be the glue to help connect a few of these pieces. Sometimes it’s hard to translate directly from sales to the product development team. Product marketing can maybe play that intermediary a little bit. That’s not always the role that they play in companies.
Sometimes product marketing might be more content-focused and things like that. For me, that’s the formula, keep a close cadence. At Clari, we build programs around this stuff. For my business, I’m building our market expansion into new verticals. We have an entire program around it where, as I mentioned, we have our program charter. What are we trying to accomplish, guiding principles, how we make decisions, all that stuff but then we have a roster and we have, who owns the product marketing workstream, who from the product, we have engineering involved? All the way down to HR and talent.
We have all the stakeholders. We all are putting in our program updates on a regular basis. Everyone’s invited to our weekly meeting and a lot of people come and participate. When you keep everybody narrowly focused on this business outcome that we’re trying to accomplish together regularly, it’s cool. The information naturally flows well.
I love that concept of again, MTM, moments that matter, and incorporating that into each and every function. It’s not just about the customer-facing functions but even within HR. HR and talent team has a big role in figuring out and hiring the right talent, who can get that concept. Not only get the concept but put it into practice on a daily basis.
It’s massive. I always remind my HR business partner that the B should be extra capitalized. That’s what this is. You’re my business partner. She comes to our team meetings, our QBR. It’s not only an HR function. It’s a business function, especially in the tech world where talent now is such a scarce resource across engineering and sales. It can be your biggest differentiator or incompetence as a company. If you’re not factoring the talent piece into your go-to-market, you’re probably in trouble.
Two questions come to my mind. One is I would like you to share a GTM success story. You and I talked earlier about how you helped increase the ACV in the whole enterprise sales motion. Perhaps you can shed more light into what is the challenge, what are the hurdles, and how you and the team overcame the entire go-to-market sequence to increase the ACV? Let us start off with that question first.
Again, I think it goes back to SGIs. When I came into Clari, one of the things our CRO brought me in here to do was to go further upmarket. We started getting into some larger enterprise pursuits and felt like the value that Clari provides is so massive. For those who don’t know what Clari is, we help companies predict revenue. We make the revenue process more connected, efficient, predictable. When you get into large enterprise companies, driving more forecast accuracy, week 2, week 3 in the quarter for publicly traded companies is a massive and value add.
For me, that’s where we started when we looked at this SGI and how do we go further upmarket. We wanted to think about what is the value story there? How are we going to communicate the impact that we can help make at that level? What we saw how massive the opportunity was, especially in large software companies and things like this. That was the first thing we did. We validated. Is there a valuable story to tell? We can’t ask for more money from our product if there’s not a value story there.
How did he do the validation? That’s a very important piece within the go-to-market machine, when you said that it’s a big market and there is potential.
This is an important thing that a lot of companies get wrong. The very first thing we did was a prioritization exercise. There’s a concept that we talked about a lot at Clari called focus capacity. How do you focus the capacity of the go-to-market teams on the right motions? For us, that can mean different things for different teams.
If you’re looking to go upmarket, you need to prioritize your accounts by way of ICP, Ideal Customer Profile. Are they ICP? Are they adjacent ICP? Are they secondary? Priority 1, priority 2, priority 3 type approach. You have to start with that baseline to understand, what is the TAM and SAM of accounts that we can go after if we want to go further upmarket?
In our case, if you’re trying to drive more revenue incrementally, you also need to understand, what the maybe addressable revenue is for that account? Come up with some of the formulas. For us, it’s not too hard. If you’re selling to go-to-market teams, you can get a sense from LinkedIn and things like that. How many sellers, how many marketers, that do they have in the company. We broke our business down by ARR bands, priorities and said, “There’s this many companies worth this much revenue to us. Call it $1 million plus, $500,000 plus, $250,000 plus, and so forth.”
Once we had that segmentation, then we could validate that there’s a worthwhile market to go after there. Two, it helped us drive everything from territory planning and coaching the reps on where to focus their time, building equitable territories by way of those revenue bands. Everybody gets these many million dollars plus accounts, $500,000 plus accounts.
That first piece of getting the planning right allowed us to have a more predictable execution because we knew that everyone had similar books, focused on similar size accounts. That changed not only the size of the deals that we were doing but the efficiency at which we were selling. We needed our pipeline. Our conversion rates went way up with more focus. That was an example for us. As you mentioned, we went from, let’s say for number’s sake, average enterprise deals of $100,000 to $300,000 or $400,000 quickly by way of focusing the team further upmarket.
I liked the way how you called out around double-clicking and doing the homework, the due diligence. One is, you can say it’s a huge addressable market but what does it mean? The way you guys did the exercise of breaking it down by segments, you can do your homework and due diligence on the number of seeds or potential seeds. Of course, you know your pricing. You count with the different bands. After that, it’s all going in. It’s almost like ABM account-based marketing, but then very targeted into maybe a top 50 or top 100 in different regions or bands.
For sure, startups and later-stage startups with VC funding are often working within models that their VCs hand them or strongly recommend that they within. A lot of times, those models are very top-down and that’s important. It’s important to go top-down and start with the TAM, SAM, SOM and all that, especially in the enterprise motion to go bottoms up. That’s what you do there when you get to that prioritization exercise.
You can do a bottoms-up analysis and start to look at we’ll map out things like we call it path the plan like, “What would it look like to do X million in revenue? How many accounts of which size revenue bands do we have to close to get to this number?” That focuses on all the go-to-market teams.
If we need to go way up, if we’re going to do twenty deals over a million dollars or something like that, we have to sit down with the product team and say, “What do we need to deliver in the next couple of cycles to go service accounts of this size?” We’re going to go down-market to SMB. That might change something. We’ll say, “Do we have the product cycles to deliver what we need to do and go after this revenue?” That prioritization exercise becomes a great foundation, like a bottoms-up foundation, to get all teams on the same page on what their responsibility will be if they’ll execute.
I think a couple of points, one is when you’re doing or growing mid-market or upmarket. Mid-market or enterprise is one but when you’re going into more of the SMBs, potentially it can be like a self-serve. Product-led growth, which means is a product ready and do you have the right like the free trial? Was this the conversion of the whole journey mapped out? Not from the internal company point of view, not from Clari’s point of view but for that end-user that you’re targeting versus if you go into an enterprise, it’s more of an ABM play, a targeted account play.
Now you’re talking about having the right content. It all comes about having the right experiences to be delivered. It can be maybe a half a day or one-day event at those specific company’s enterprises. You also have the community. Anthony, there’s something that I’m grappling with and I’m testing broadly with the go-to-market leaders is the concept of what I call it as three pillars. Three pillars of a go-to-market engine, which is one, it’s content. Two, are the experiences, and three is the community. Broadly speaking, we are talking about content, experiences and community.
Have these three pieces in your go-to-market? That’s the Holy Grail. What role did specifically content play when you are looking or going to increase the ACV from 100 to 340? Can you talk to us about that the role of content? What does that versus what needed to be created maybe by the product marketing team, the brand or the content marketing team?
There were several roles. One is, we had to take a deep dive into the side. Again, back to moments that matter, who is the audience that we’re trying to serve and what do we want them to think about Clari? One of Clari’s superpowers is that we’re loved at the board CEO, CRO type level, you can imagine. Revenue predictability is important to these folks.
That’s something we think is special and we take seriously. One of the things that we started thinking a lot about from a content perspective is, is our content ready for that audience? Is it ready for the CROs, presidents and CEOs of the top companies in the world and is our voice coming across that way? This is a busy space that we’re in sales technology and things like this.
A lot of people have different voices. I would argue most of them aren’t tailored for an executive audience. They’re more operationally driven and things like this are for the functions themselves. That was one thing we thought a lot about from a content perspective and made sure that we had Polish. Good guiding principles around was that we were communicating in the voice of our most special customers, which are the executive teams and things like that. That was one piece.
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We built content around things that mattered. You think about it, it’d be easy for us to build content around forecasting but that’s not a CEO-level topic. We would build content around things like transitioning from hardware to software or going from SaaS to product-led growth or these are the topics that these folks are thinking about and how they think about go-to-market.
The more we can speak up there, build content in the world that they’re living in, the more relevant we were. That was helpful. That whole value story, I’d say that was the other one. Building out a valuable service, not only content. We built out a whole business unit around it and building the content that needed to serve that. Again, it’s your value engineering or value services, and you think ROI. “I need an ROI calculator show.” We would argue that. There’s a lot of content that comes with that.
Having someone believe that you’re going to help them run their go-to-market better. A lot of that comes in the form for us of content around SGIs, helping them understand that we’re going to help them accelerate their go-to-market. The product-led growth or their go-to-market into SaaS revenue streams for the first time from on-premise or something like that. We built a lot of content in that regard. That gave us credibility to go command higher prices in some of those enterprise cycles.
I love the bear you emphasize and touch the point of content pedagogy role. In that whole go-to-market execution and up-leveling your ACV for you or for your target audience, which is the executives, the CEO, and the board to connect with the value of what Clari can do, it starts with, how is it going to help them as they’re evolving their business model? Be it an on-prem to SaaS or a PLG Product Led Growth. First of all, understanding that and then building content around it. Would you agree that content, community and experience are key pieces between the go to market machine?
One Hundred percent. If I had to pick, if you were to talk to Clari’s customers about what makes our company so special, I would argue that you’d probably hear 1, 2 or 3 of those things about what makes us special. Whether it’s the content that we provide that is valuable at the highest levels of the business or the experiences that we obsess over and think deeply about, and hopefully deliver on for our customers or if it’s the community that we’ve created.
This community is across our portfolio of people. We have CROs call us and tell us that, “I interviewed for my next job and I told them, I won’t take it unless I have Clari.” That’s a community. These are raving fans that when you build a community like that for us, we talk about the double moat at Clari. That’s the second moat. That community is that moat. When you build, it gets wider.
It all starts with the content and the experiences of once people get attracted towards those components, that’s what will grow that whole, the second moat, which is the community piece. Let’s switch gears and go more into the forward-looking. What are your big initiatives or focus areas for 2021 and 2022?
That’s what I’m doing now. To your point earlier, I’ve run sales teams for a bit now. This 2021, I stepped a little bit more into go to market strategy role to kick off 2021. As Clari sets our sights on IPO here, we had a big SGI as a company of what we call it expanding strike zone, which is, how do we go with a great TAM opportunity? How do we create more SAM and SOM we can serve as our platform gets used by more go-to-market teams? We started off having sales teams use us a lot.
Marketing teams started coming in, customer success teams and now finance teams and product marketers. As we look at expanding our strike zone, there’s a couple of key motions that we think about and how do we serve more vertical markets? Where are markets out there that are looking for visibility, rigor and predictability across their go-to-market motions? We think there’s a lot of interesting stuff there. We think about personas. Who are the people that are stakeholders in the go-to-market process? How do we create experiences for them that would delight and add value inside of our platform?
Business models, you mentioned a big one. We’re a big believer in the move to product-led growth. We think that’s a major shift that’s happening in the market. We want to be able to serve our customers that are making those transitions. As you can imagine, it becomes much harder to predict growth in a PLG, Product Line Growth landscape. We’re thinking deeply about that. What I’ve been doing is helping us build to go-to-market and in those motions. Now as we get into the second half of 2021, we’re now double-clicking and I’m building out the vertical selling teams and things like this that are going to go serve the strategy that we set up in the first half of 2021.
I will be looking forward to maybe having more conversations with you. I’ll be studying and tracking you guys on how we are executing the go-to-market and growing into more territories, personalized, verticals. In that regard, obviously, you got a big chapter for 2021 and 2022. What do you think are the 1 or 2 barriers that might affect your plans?
It’s whether or not we can keep our focus narrow but while still looking, seeing the forest and the trees and all of that. Can we keep our focus and accelerate velocity? It’s a good problem to have, a big TAM to go after but you have to be focused to do it. Any executive team at a high-growth startup will tell you, the number one thing the board asks about is hiring. “Can you hire fast enough?” In a company like ours, we have a cool company. We have AI machine learning that works and solves real important business problems. That helps while you’re still battling for engineering talent with the who’s who of Silicon Valley and things like this.
That’s one thing. “Can we continue to hit our hiring targets?” which we’ve been doing. As you grow and scale, we passed for the 400-employee mark as you get to 500, 700 and 800 employees. Can you continue to hire world-class talent at scale? That’s probably the one we’ve been executing on for sure. You want to like, “Can we keep doing it? Can we keep bringing in world-class people?” That’s one thing. If you were to talk to people in our company, they would tell you what they love about clarity is the culture.
We have this special culture. It helps that we’re still founders run and you want to keep scaling that. You don’t want to lose that over the next stages of growth. That’s one of the things that help us keep high retention rates on our talent. I would say that some of that stuff, can we continue to hire in a world-class way across product, go-to-market and can we retain the talent that we have? I know we can execute it. It’s less on the execution side. I know we’ve got the strategy right. It’s more about, can we keep the resources we need to go to deliver on the strategy that we’ve built?
That’s one of the biggest challenges, especially in a high-growth world. It’s all about talent and then culture. It’s not just about getting the right talent but will they fit in within our culture? You also mentioned maintaining focus while not losing the big picture. Those two are big areas. Besides that, let’s say if you were given a 5, 6 or 7-figure budget, where would you invest besides people?
Again, I’ll double down. I’d invest in engineers. I don’t think we could ever have enough great engineers. One of the things, one of the skillsets that I’ve had to learn here and it’s been great, and we’ve talked about a little bit is world-class program management. I can’t speak enough for what that’s done for our business.
In a startup, things like program management, it might be someone like me wearing that hat. If I had a lot of budgets, I’d probably put some into program manager across each of the functions and be a dedicated program manager within the revenue team or something like that, tooling and instrumentation to help serve this stuff.
I know big companies do that and have that. Have a budget to do that stuff. Whereas there are trade-offs, you have to make at our stage of growth. I’d probably put some investment in program management and making that machine actual. We’re getting machine-like now as a company. A little bit more human level, I’d like to get people together more in this environment. I think there’s a lot of barriers to that.
I feel like if we had a couple of cobbles of budget, we could probably come up with some creative ways to get folks together in a safe environment. I miss that. It’s this remote world that is awesome but we need to find ways to get everyone together. Again, with an unlimited checkbook, maybe we could design something where everything gets folks together more often in a safe environment.
Again, you talk about experiences but in this case, we’re talking about employee experiences. It’s tough. Let’s search and transition more into the closing section. Who are the 2 or 3 people that if you look back played a pivotal role in your career growth?
There’s a lot. If I had to pick 2 or 3, the first would be Kevin Knieriem, our CRO at Clari. We met at Oracle. As a rep, he put me on a formal leadership development plan and it always told me I was a leader. Told me that to manage people to be a leader and gave me the opportunity to lean into that. Kevin’s the guy who brought me into the high-growth world. He had left and did a company after Oracle on a high-growth company. Kevin, for sure. I’ve learned a ton from him.
My CEO at Clari, Andy Byrne. Andy is a phenomenal leader, phenomenal human, phenomenal entrepreneur. I’d say what I’ve learned from Andy is how to think about the big picture. More importantly, than not even is becoming a more human leader. I’ve always been pretty execution-focused and Andy’s helped me think about the human side of leadership and what we’re doing and the impact that has on people’s lives and things like that. He’s been remarkable in that regard.
That’s definitely the two. There’s a guy named Mike Hogan at Oracle that had started bringing me into a lot of the go-to-market stuff, which was great. Letting me get exposure to that and contribute to that. That, again, helped me realize how much I enjoy that stuff. My kids probably be the last one. My kids keep balanced and humble and forced me to think about what’s important. They played a big role in it, too.
I love the way you included and mentioned kids. It only clearly shows the human side. Let’s say, if you were to turn back time, the clock and go back to day one, if you go-to-market journey, what advice would you give to your younger self?
Become a more human leader. Share on X
Maybe it’s me building off our human chat here but it would be that. I would tell my younger self to be more human and practice mindfulness and be more aware of the present in your surroundings. Early in your career, you can get execution-focused and hard-charging. I was definitely in that bucket. I probably missed a lot of great experiences being narrowly focused on executing and not realizing all the great humans around me and how I can help play a role in their lives and the role they were playing in my life.
Mindfulness is something that Andy brought to my life as well, which has been helpful, meditating and things like that. If I would’ve done that, have been more human, being more mindful earlier, the journey may have been the same but I may have been a little bit more peaceful and helpful than others along the way.
Be more human and you’re using tactics, specifically meditation. That brings me to my last question but a very important question. My question leads to the topic of why I wanted to have you on the show, which is going back to the LinkedIn summary. You mentioned how you break down your time or a week. Talk to me and the audience about the importance, what is the motivation behind doing that and what does it remind you of or how does it help you become more human and mindful?
First, I always tell my sales team, “Unless you’re applying for a job, your LinkedIn is your resume for your customers.” That’s who’s looking at you when you’re going to the meetings and we’re going to look you up. I try to be pretty transparent on who I am, what I think about and what I care about from a business and a personal perspective so when people meet me, they know what they’re getting, good, bad or indifferent. You can go check it out.
First, that whole exercise is it’s as much of an exercise in thinking through planning what you’d like your week or your time to look like. My week doesn’t look like that every single week but that’s certainly my intention. When you write down a plan, write it, it makes it a plan. Not just like a thought. That’s where it started was, “If I write this down, maybe I’ll live it more weeks than not.” It then comes down to me to thinking about, “You only have so many calories and hours in the day. Where do you want to invest those calories?” When I write it down and I realized like, “I’m a big Fred Kofman fan.” If you haven’t read Fred Kofman’s Conscious Business book, it’s the best book on leadership there is.
Fred talks about, there’s no such thing as work-life balance because if you’re saying it’s balanced, that means when you’re working, you’re not living or when you’re living, you’re not working. That’s not true. When you write it down, I’m spending maybe 50 plus hours a week doing work. When I write it down on paper, I’m spending maybe 40 or 50 hours a week with my family.
Thinking about that, it allows you to put sufficient calories into both of those buckets that you should. It’s a realization moment. Some of the other things like health and mindfulness and fun night doing things that you enjoy. Realizing how little time you get to put into some of that stuff, it’s a helpful exercise to go through and think about.
I got exposed to that concept. I think from Brian Tracy. This whole book and concept around manage your time, manage your life. If you manage your time, you’re going to manage your life. When I dug deeper into that, if you look at the table of contents over there, he breaks down the time categories into 7 or 8. Things like relaxation, reflection, family, work, income improvement, strategic it’s all of those.
I had that book. It was on my desk, and then I looked up your LinkedIn summary, you practically broke down your time in those several buckets. I wish more people do that. That’s the best way to manage your life, after all. Manage your time, that’s how you’re going to manage your life. That’s how you become more human and that will translate to being more mindful.
It’s something that from early in my career I’ve done is set goals in each of those areas and it changes. When you start the year, you think about, “What are the roles I’m going to play this year?” I remember early in my career it was boyfriend, coworker and peer. Now, it’s father and son. I have to think about, as my parents get older, the role I play there, financial stability and health and all these things.
Being intentional, setting goals around those things and checking in on them regularly helps. It’s not like it’s not that I don’t want to call my parents and say, “Hi,” but if I don’t put intentionality around that, it might not happen for a couple of weeks. If you set goals around it, put them on the calendar. Like you said, manage your time. Even if you only get 60% of it done, it’s probably way more than you would have got done if you didn’t write anything down.
Wonderful conversation, Anthony. Where can people find more about you and learn more about Clari?
You mentioned LinkedIn. LinkedIn’s a good place. I keep on top of LinkedIn. I think it’s a great social network. Clari, get us on Clari.com. You can follow us on LinkedIn. We’re hiring like crazy across every department and go-to-market. Come check us out. As I said, I’m building out a verticals business now. If you know anybody that comes from professional services, financial services, healthcare and things like this, that they want to come to join a good go-to-market team, give me a shout where we’re hiring.
Good luck and good stuff. I’ll be cheering from the sideline for your team and Clari also. Wonderful conversation and good luck once again.
Thanks, Vijay. This is great.
Important links
- Clari
- LinkedIn – Anthony Cessario
- Salesforce.com
- Kevin Knieriem – LinkedIn
- Andy Byrne – LinkedIn
- Oracle
- Conscious Business
- LinkedIn – Clari
About Anthony Cessario
There are 168 hours in a week. Here’s what mine looks like on a regular basis.
For 50+hrs each week, I get to create/problem solve/strategize with, and learn from, some of the most truly amazing people you could ever want to meet. Together we’re helping companies of all shapes and sizes grow and predict revenue in remarkable ways. It’s fun, challenging, exciting, and I wouldn’t trade it for anything in the world.
45-50hrs of my week is spent sharing the most quality of my time with the loves of my life, my wife Anna and perhaps the two most incredible little boys in the world, our sons Dominic and Daniel. We split our weekends fairly evenly between relaxing at our home in Walnut Creek, visiting family, traveling, wine tasting in Napa and enjoying the quiet life in the town of Truckee (Just outside of Tahoe).
4-6hrs weekly goes to exercise; mainly Brazilian jiu jitsu, but also some boxing, lifting, running and muay thai from time to time.
2-3hrs goes to reading.
10-20min daily goes in to meditation/focus on mindfulness (arguably my 2nd most quality time all week)
In the spring, 2hrs weekly goes to helping middle school students better prepare for their futures through the Junior Achievement program.
If I can carve out a few days every few months for fly fishing, I am a very happy man. In football season, a few hours each Sunday goes to watching my beloved Philadelphia Eagles.
The last 40-50 hours weekly goes to the rest needed to manage all of these other commitments day in and day out.
Life is great and I am very fortunate.
Specialties:
Go-To-Market (GTM) Strategy
Predictable Growth
Market Expansion (Going Up-Market, Industries/Verticals, Point Solution to Platform)
Customer Led Growth (Driving Net Dollar Retention)
Business Model Expansion (TCV to ACV/ARR; ARR to Usage Based/Pay-As-You-Go)
Revenue Operations (RevOps)
Sales Enablement / Sales Innovation
Product Marketing
Talent Management
Building High Output, Diverse & Inclusive Teams
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