Katerina Ostrovsky: From Plans to Revenue: How RevOps Drives the Behaviors Needed to Hit Targets

Business.

Welcome to Go to Market, a podcast for RevOps, sales, and marketing leaders to dive deep into industry insights and best practices. Go to Market is sponsored by Fulcast, the go-to-market cloud. My name is Dr. Amy Cook, and I am so excited to introduce you to Katerina Ostrovsky. She is a go-to-market leader, a lifelong operations professional. She's been in both big companies and small startups, and right now she is the SVP of RevOps at Jelly Smack. Katerina, how are you?

I'm great, thank you, Amy Cook, for having me on. Um, appreciate the invite.

Oh my gosh, thank you so much for joining, and it is so much fun to connect with you. In our pre-call, I was absolutely amazed by your background and the insights that you have from a RevOps perspective. And so really excited to dive deep with you today.

Yeah, excited, excited as well. I've seen RevOps really grow up in the last few years and the field itself has, has been morphing in, in really positive ways and, and, and changing the way that it supports the various departments within SaaS organizations. And so excited to be part of the greater RevOps journey of all my other colleagues who are practicing in this space.

I feel the same way. I think it's, it's super interesting. You know, when Lean Data kind of coined that phrase in 2017, it was the first year that I started working with Simplus. And we didn't have the word RevOps that we were using, right? We were doing RevOps. And so I find it interesting to introduce you as a lifelong RevOps professional because you have been and are, but maybe didn't call it that beforehand, right?

Oh, absolutely not. I've had every title, probably the longest title, which was sales operations, which is how the field got started. But as The customer journey has expanded and people really understand that everything in the go-to-market journey is interconnected. So marketing impacts things that happen in sales and that happen in customer success, and that you really need to tie all those areas together and see them all as revenue generating and all part of one continuum, and that things that happen on one end really do impact all the customer all the way through. And so I'm excited that RevOps has morphed into this larger revenue engine that is looking at things beyond just sales and looking at the expansion revenue and retention and really bringing all of that together.

So, oh yeah, I feel like it is, it's so fun, right? Like, I am so excited. To be part of this RevOps journey during the creation of an industry. Like, to me, that's what's so, so thrilling, right? And we talk a lot about— for years and years, people have talked a lot about silos and how we need to integrate and how we need to do things differently, but we never had the technology to really be able to do that. And so I find it so exciting. Like, I feel like this is one of the most exciting fields right now and why I was so thrilled to be able to join Fulcast. But I would love to know a little bit more about your background and what got you to this journey.

Sure. So like you introduced me, I spent the earlier part of my career in large public organizations, global organizations, really working as a sales operations professional, but, you know, at scale. Dealing with companies that had a global presence, 500 to 700 salespeople, 50 different types of comp plans, major technical debt that came with the process of merger and acquisition. And when you bring all these systems together and very large instances of Salesforce and that sort of thing, and, and really kind of grew up in that enterprise SaaS space, specifically within financial services, selling to really sophisticated organizations and very complex buying processes. And then about 7 years ago, I took a hard pivot and went to work for a startup in the blockchain space, which was incredibly innovative. And it was my first opportunity to build a RevOps organization from the ground up, which, you know, once you kind of see it at scale and you see all the pockmarks of, you know, what happens when you're big and the complexity and things that you can do from the very beginning to actually improve the way RevOps and sales functions in general. So I was incredibly excited to go work for this blockchain technology firm and build out the organization and, you know, move the sales organization from being just a one-region sales team to expanding into APAC and EMEA and that sort of thing.

Incredible opportunity. Like, number one, in the blockchain space, which I find fascinating, and then number two, from the ground up, and then being able to become like a multinational organization. Like, that is incredible.

Well, the, you know, the exciting thing for me is that, you know, sometimes in the US we get a little US-centric, and, and that's okay, but we have to understand that companies in other parts of the world buy differently. Sellers sell differently. They even learn differently. And so it's really important when planning your sales team and your enablement efforts to really take into account those different cultural nuances. And that goes all the way through to pricing. You know, different regions have different pricing pressures. And so it's not a one size fits all. And as you expand internationally, it's important to take those things into account. And yeah, that was fun for me.

So Well, I, I think that's so right. I remember when I was part of Infosys, we had a conversation with our sister Salesforce company called Fluido across the pond, and they started explaining to us how our US-based sales techniques would be seen as very obnoxious over in Europe. And it was kind of the first time that anyone had really laid it out. I mean, I, I had an idea that they probably would be, but it was the first time someone had actually laid it out for me in terms of like, this particular activity in sales is seen as obnoxious. This particular activity is very acceptable. This part, you know, and it's very interesting to be able to see that. So in RevOps, do you have to adjust for different kinds of cultural nuances like that?

Absolutely. It starts with pricing. It starts with the sales process. Actually, when you were talking, it was reminding me that, you know, in Europe, salespeople don't like to be called salespeople. They want to be called business development or partnership, something a little softer. Interesting. Whereas in the US, we're very comfortable with having kind of that, you know, sales in the title. So it's even things like that that are impacted culturally.

That's very interesting. Yeah, because I would like in the US, at least in the technology industry, partnerships means alliances, right? Which is a different motion. And so that would be very interesting from a RevOps perspective to try to match. You can't, you know, just match the titles across the board.

So, so, you know, after that experience at the blockchain firm, I went and started working at JellySmack, which is an incredibly interesting experience because the creator economy space is relatively new. This, you know, kind of advent of platforms like YouTube and Facebook and Instagram, TikTok, you know, we're not that old of a company, but we really focus on data and leveraging data and leveraging technology to generate revenues. And so it's the last couple of years have really been journey for me as a RevOps professional and kind of in parallel with our industry where we are starting to not only see that revenue operations spans the marketing, sales, customer success kind of horizon, but also how important it is to take the data that sits within those silos and bring it together and look at metrics that really impact the customer journey from the very beginning all the way through to the end. And sales, which has always traditionally been very much an art form, I think companies are starting to understand that if you treat revenue as a science and kind of process engineer every single part of your sales process, your marketing process, your sales process, your customer success process, and then layer on top of that the art the, the voice of the customer, that's when you have really great impact. But that, that foundation, the data that comes from all these systems, if you're able to have analytics and reporting that help drive where you use your, your limited resources, where they may have the biggest impact, I think that's where RevOps professionals are really becoming strategic in thinking through what companies should be doing to improve, you know, these small steps within, within a larger—

That's very interesting. So you have to almost look at it like horizontally, a lot like along a time continuum of the customer journey, and then also be able to segment it out in different sections to be able to make those incremental improvements across your data.

Yeah, exactly. And sometimes, you know, I, I often find, and maybe this is controversial, but, you know, large-scale change is, it, it, it's hard and it's daunting, and it's hard to build consensus, uh, across, you know, different organizations. So I find that, um, making smaller changes, smaller improvements, being able to measure those changes, it's easier to get you know, marketing and a sales leader on board for something that is small, time-bound, measured. And if it works, you double down on it. And if it doesn't work, you pivot. It's easier to make small incremental process engineer changes in that.

That makes a lot of sense. So do you find the same process, like let's say you're doing your annual planning, how do you approach annual planning? And I know we talked before about navigating both the bottom-up the top down. And it's kind of similar to what you're talking about in terms of, you know, managing a whole lot of change in different stakeholders and data.

Yeah, I think annual planning is one of the most critical activities that RevOps plays. And of course, we work very closely with other parts of the business, finance specifically, but also product. And so we have this unique perspective. And I think that the organization relies on the RevOps professionals to kind of bring that data to make decisions. So I think regardless of the company that you're in, large or small, annual planning, the earlier it started, the better, I think, because it actually takes quite a while. But it's a, it's that combination of bottoms-up planning, meaning, you know, what's in your pipeline? What kind of pipeline coverage do you have going into next year? If you have short sales cycles, you may not have a pipeline that goes out, you know, all the way through the end of 2025. You might have to extrapolate one quarter of information into further quarters versus organizations that have longer sales cycles that are, you know, a year, year and a half, they may have longer timeframe pipelines, but that are kind of chunkier and big deals hit. And then, you know, so I think there's, there's the initial understanding of the metrics that, that matter. What are those metrics? So think about what is the average length of your sales cycle? How long does it take to sell? What are your win rates across your various products? What is your current pipeline coverage by region, by product? What are the conversion rates that happen within every— from lead to opportunity and then within every single sales stage? So you kind of have to understand all of those mathematics and metrics to be able to say, based on our win rates today, our conversion rates today. This is, uh, what we think we can accomplish next year. But that, that's your kind of bottoms-up approach of what do we have, what do we think we can do if everything stays as it is today. Then RevOps has to really work with the leadership to understand what are the goals, what goals coming down from the board, what are the growth expectations, how is finance looking at this and what numbers, you know, no one's going to accept kind of status quo as it is. We're always looking to improve, looking to grow. And so there's that top-down pressure. And top-down doesn't just include what are our growth goals, but what are we doing with our product? Are we adding products and services to our portfolio? Are we, you know, improving things in different ways that will allow us to charge higher prices for our products? Are we increasing pricing? So there's, there's not just the sell, the marketing and selling effort, but there's the directives from the board and the new products and innovations that are coming out. And those two things eventually meet up, right?

And you've got, and you've got, you've got the CEO saying, hey, I want to grow 50% this year. And you've got, well, the historicals of, you know, what I'm projecting is 20%. And then you have to negotiate, like, how to decide what what it's going to be, right?

Yeah. And that there's, there's always kind of that meet in the middle. But I think the, I think it's important for revenue operations professionals to help the organization understand what it's going to take to meet the goal. So the answer isn't necessarily that's a completely unreasonable goal. We're setting our salespeople up. We, we, we can't put quotas like that. They won't be able to— I don't think that's the answer. That— but the real question is, okay, if we're going to grow by 10%, how do we do it? And, and that's where the real, I think, strategy comes in, is, you know, you have multiple levers. You can increase the input that happens from marketing into sales, right? So you can increase funnel, giving salespeople potentially more opportunity to close deals. You can get better at every deal that you have. So what does that mean? It means, you know, if you can increase your conversion rate from demo to negotiation by 5%, that can mean a lot of dollars at the end, at the end of that sales cycle. And so there are all these levers, including, you know, how are you going after your existing book of business? In theory, an existing customer should be easier and cheaper to close than a net new logo, right? And so if, you know, if you look at you know, how much expansion is happening within your accounts? What's happening with retention? Are you, you know, is there a way to increase the retention rate? So there are all these different levers. And I think that's the real conversation that needs to happen. You've got the figures of what does it look like today? You've got the board directive pushing the organization to be better. And then it's more about, yes, we can if, if we do this, if we implement this action, if we, you know, potentially hire more people, but not always. Or let's say we make them more efficient, or we implement technologies that allow us to predict our customer behavior so that we're not chasing as many opportunities, but we're chasing opportunities that have a higher propensity of closing. These are all act— small actions that compounded can really impact your growth rate.

I love this. So with you kind of being the nexus point between all of these different things, obviously you are very, very strategic. How do you negotiate the conversations between all the different stakeholders? And do you work especially closely with the CRO to make these decisions? Do you work closely with the CMO? Do you work with the CEO? How does that typically work in terms of like negotiating the comps with the salespeople, talking with the CEO about what needs to come in the funnel and what we need to increase? Are you the one responsible for having those conversations?

Yeah, I think that's why RevOps is, is so much fun and so cross-functional because, you know, in the day-to-day, we're typically working with our CRO, CMO, sometimes CSO. And also finance, like those that is happening throughout the year, not just annual planning where, you know, when you're the CMO and you're really focused on your area, you're really relying on revenue operations and that communication of what does that funnel look like? How is that translating? Are we closing the right kinds of customers? You know, we're saying our ICP is this, but then we're noticing that our closed won deals might look different. So I think that type, those types of relationships should be ongoing throughout the year. During annual planning season, I tend to work with each individual leader to get to the, to get to the numbers. And then, you know, it's a series of meetings where you come together. I think that an important point that I didn't mention in your earlier question is, you know, this concept of, okay, we're going to grow revenue because we're launching a new product, right? And everyone's sitting in the room, marketing is going to do a big launch, there's going to be PR, sales is really excited, they have something new to sell. And these are all actions that we believe will grow, will help us hit our target. And I think the one thing that everyone in the room needs to be aware of, including the product people, is the concept of timing. And we tend to overestimate how fast we can get these new products and services into market, how, how fast we can ramp our salespeople and then get the information out to our client base. And then the time it takes to actually sell. If your average sales cycle length is 90 days, I mean, I think we've all made horrendous mistakes where we said, oh, we're launching a new product on January 1st and we start ramping the revenue for that new product.

January 2nd.

Or January 2nd, exactly. Or by March. And in reality, the process of marketing, communicating this new product feature service to the market, leads coming in for it, sales getting enabled and understanding and being able to talk about it and then being able to sell it. Really, that time lag, just like there's a time lag to ramp new hires, I see the same thing in annual planning. Oh, we're going to hire someone in January and they're going to start, you know, they'll produce 50% of their quota by XYZ day. And there's always— I tend to find we're overly ambitious in those estimates.

Yes, I think that makes so much sense. And just from a marketing perspective, as a marketing leader, one thing that I'm so excited about with RevOps and the way that RevOps has developed is I am starting to be asked questions like this in annual planning. 3 years ago, it didn't ever happen. Nobody asked me, and maybe it was, maybe it was me, but nobody ever asked me really important vital statistics like what you're saying, like How long, how long does it usually take a cycle like a marketing campaign to develop? How long do you need to ramp up a PR campaign? How long, you know, those kinds of things are not typically something that a sales operations person would ever ask, right? So this new RevOps function for me, I'm so excited as a marketing person who has also on occasion had to do my own RevOps because that function just didn't exist in the business. It's so exciting for me to meet people like you who have it dialed in, who understand the complexity of the business and how every single stakeholder needs to be part of that annual planning. This is just really exciting to hear.

Well, and it's a shame because I know in the past, you know, there's always been that kind of marketing sales friction. And I think it's It's so misplaced because the reality is these teams function together and they're here to help. And that's another— you bring up a good point because a lot of times people say, well, we need more top of funnel, we need more leads. And I think the organization needs to decide if they want quantity or if they want quality. Because in an environment where you can't just hire more salespeople and you have to be more efficient. Marketing being able to identify leads that are ready to buy, and I've seen lots of AI applications in this, you know, that are being predictive about where in the buying journey that particular prospect is and really narrowing down where sales puts its efforts. You know, you can really change the quality game and make every at-bat that much more impactful and have the ability to actually close. And so I think these things are conjoined. And the more that an organization understands that their expansion revenue, so the share of wallet within an existing account becomes more and more important, the more I think the collaboration of marketing needs to happen because marketing isn't just about acquiring new logos. They're— I believe they have significant impact on the existing customer base. So, so how do we make that part of the customer journey, which isn't linear in any way? How do you identify and market to existing customers I think that's an area that we can do better at.

I love what you're saying. I so agree. I know this is about annual planning, but just to follow up with your point and emphasize it, you know, we come in with marketing with case studies, right? That's the customer journey. I've been on, I've been in opportunities, especially recently, being at Fulcast, we, we live what we preach about the integration of the go-to-market, which I'm super grateful for. And so I'm sitting in opportunity conversations, and I am learning so much about the opportunity itself, about the questions that our prospects have about, you know, all those things. We're not— because if you look at things very linearly, marketing sits at the beginning and then comes sales and then comes customer success. And if you don't merge some of those activities, marketing will never know what it's like to have to, to handle objections. Right? And sales will never know on the customer success side if they would have only addressed something sooner, then they could have avoided a problem. So I'm just preaching to the choir, I know, but I love meeting people like you who have already got it figured out, are seeing it as a kind of like a center of the wheel, and you're reaching out to all of the stakeholders.

Well, I mean, every problem needs help from lots of different departments. One of the things that One of the ways that I've worked, as just an example, at JellySmack, we had some conversational intelligence tools in our, in our tech stack. So we're able to listen to many, many conversations with, with our clients and customers. And, you know, we were really seeing a drop-off during our negotiation stage, which is not a good sign because it costs so much money just to bring a prospect through the funnel and all the way to negotiation just to lose them. And so we started focusing on what were our customer objections, why were we losing deals? And through the help of AI, we listened to hundreds and hundreds of these conversations and really narrowed down the issue to one objection question.

Really?

This is really where you can, you know, when you get down to root cause, sometimes the you tend to think, oh, well, if we're losing deals in negotiation, maybe our sellers need negotiation skill training. You could come to that.

Of course, it could be that. It could be the deal itself.

It could be, you know, it could be, yeah, it could be the commercial structure is not competitive. It could be the product. It could be a myriad of things. But in this particular example, we did figure out what the objection question issue was that kept coming up over and over and over again.

What was it? Do you mind my asking?

It was a term that we had in our contract that was really important to us as a company but wasn't necessarily—

Interesting.

Agreeable to our customer base.

So you had the whole thing figured out and it was just in the contract, that one thing, huh?

It was, but the answer wasn't— part of the answer was relooking at the contract and the importance of turned to us relative to how much business we were losing and working with the CFO and the chief legal officer on that, that, that was part of the answer. But the other part of the answer was I went back and I worked with my marketing team because part of the customer journey is setting the right expectations. Expectations. And so when we changed the way we talked about the services we were providing and we worked with marketing on kind of surfacing this objection right from the beginning, addressing it early on in the sales cycle, in our decks, not shying away from it, it became a non-issue by the time we got to negotiation. And we really brought in marketing to figure out how do we explain to our customers why this is important to us, why it should be important to them, and what they can expect with us as a partner, it really, it really changed that kind of just the gotcha that our customers felt previous. And so I think marketing can really help in many areas of the sales process, not just, not just filling the top of the funnel. And that's just an example of how I love that.

Well, thanks for making me feel better about that. I love it. Well, I know that I've taken up so much of your time and I really appreciate it. Great. So for this last question, I just have to ask you, you know, clearly you're at the top of your game. And what do you do to stay there? It could be anything from your favorite drink to a favorite book that you read or what?

Yeah, honestly, I— be in touch with your community. And what do I mean by that? I really spend— I attend a lot of revenue operations events. I make sure that I network within my community and that I, you know, I'm in a couple of LinkedIn groups where people, or even Slack channels where people share their challenges and then how they overcame them and talk about the newest RevTech technology that's coming out. I sit on a lot of demos because I'm always curious. You know, I really enjoyed looking at the Fullcast product, you know, because You don't know what's out there and the landscape is constantly changing. This is a really fast-paced world, so, and field. So if you're sitting in your job and you've been there for quite a few years and you haven't seen how other companies are doing this, your best bet is to get out into the community. There's so many, you know, revenue operations forums, alliances, meetups that are happening. Go to them. Talk to people, see what's the latest and greatest. And sometimes some of the smaller startups are really doing innovative things, and the companies at scale are doing things, you know, differently. And so to me, it's networking, getting out, knowing the community, and keeping on top of things.

I love that. And I think that that is so insightful. And it also resonates really well with what a couple of other people that I asked said about that is the importance of community and the importance of especially in this nascent industry that is, is really coming together right now, the importance of leaning on each other for that growth. So thank you so much, Katarina. I really appreciate your time, and congratulations to you and all of your success.

Really appreciate it, and thank you to Fulcast for having me on, and, um, I look forward to talking about these topics again. Likewise.

Is that business?

Business? Is that business?