The First 100 Days of Building a RevOps Engine with Rosalyn Santa Elena

Rosalyn: So definitely the first hundred days is getting like in any role is coming in and assessing the current state. And then you're going to need to build something to handle the short-term, but always build with the idea of how you're going to scale.

Trinity: This is The First 100 Days, a show for revenue practitioners by revenue practitioners, giving you unscripted access and exclusive resources to help you navigate any new initiative. I'm your host. Trinity Nguyen from Usergems. Our guest for this episode is synonymous with revenue operations. Or some call it RevOps, Rosalyn Santa Elena has spent the last 20 years doing as she calls it all things ops with her vast experience, working at large enterprises and high growth startups, Rosalyn frequently shares content to educate and elevate the profession. Directly on her LinkedIn and via a number of operations communities like the wizard of ops genius, revenue collective, and so on.

She has been instrumental in building rev ops from the ground up at a number of companies in various stages from series B to an enterprise public company. She's now at Clari, a software company focused on driving predictable revenue, Rosalyn imparts wisdom with our audience starting first by her definition of revenue operations and what it entails.

Rosalyn: My perspective is that revenue operations have always been around, right. Somebody was doing it. With, you know, the market moving more towards a recurring revenue model organizations, you know, B2B understanding that the customer journey from the top of the funnel, being a prospect all the way through to being, you know, a customer renewing and expanding is so important, especially in a SaaS recurring model, that the rise of, you know, revenue, operations, and having sort of this end to end operational function.

That really maps to your customer journey is so important. We talk a lot about, you know, breaking down the silos between, you know, top of the funnel, marketing sales, customer success, and really driving alignment across all of those teams. And that's sort of how I view revenue operations is really its operations in the sense of it's the people, the processes, the technology.

You know, all the things that really run your revenue engine, but it's also about driving alignment across all of the revenue facing teams and making sure that everybody is aligned in terms of, you know, strategy and goals and objectives and process and data, right. And systems having everything really flow end to end seamlessly, ensuring that you're giving your customers are fricking endless process and experience.

Trinity: So, if you say it's not a new concept, per se, how did companies do this in the past? And I use DIB, I think a lot of larger organizations have somewhat of a pseudo rev ops version running. So what does that role look like and how does that compare to the start-up version of rev-ops?

Rosalyn: So I haven't seen know, even when I look at my own career and I look back at some of my titles around sales operations, right.

And you see, my title is sales ops, but the reality is, was, you know, I was running field operations. For example, at one company, I was running marketing operations and sales ops, but my title was sales ops. Right. And then we didn't have a lot of customers that quickly as an early startup. But at some point when we started having customers and the implementation team, the post-sales team needed support from an operational person.

Effective again, that sort of sales ops will have to step in. Right. And I think, um, with the rise of, you know, more tools and technology and more complex sales cycles, then marketing is realizing, Oh, I really need a dedicated operations person. Or maybe your customer success says I really need. You know, dedicated operations team.

And so we're starting to see a lot more of that. And then this revenue operations is really sort of the overarching organization of all of those different ops teams combined. Does it matter where rev ops roll up to, but 

Trinity: just for the audience here, how would you structure rev ops?

Rosalyn: Yeah, I get asked that question quite a bit, because I always think that it's, every organization is a little bit different.

Um, whether some companies don't even have a CRO, right. Or maybe they have a CRO and that person might be managing perhaps not the entire revenue funnel, they might just be. You know, managing sales and post-sale marketing and sales. I think so. And that's why the advice that I always give is it's less about the org structure and sort of who reports to who, but more about making sure that you have a consistent process and alignment around all of those different functions.

Sometimes it's simpler to have sort of one person in charge of everything. Right? So that, um, sometimes that's a little bit easier from an org perspective, but I think more importantly is just alignment because even if you're not reporting into the same organization, you're still going to partner very closely with those teams, right.

To ensure that you have that end to end process. And I think I've typically report into the CRO. Um, or ahead of sale if there wasn't a CRO, but that doesn't mean that this rule can't report into the CFO or even a CCO or even a COO, right. There's a lot of, um, supporters that think we should report directly to the CEO too.

So there are definitely many different avenues, but I think that the key takeaway is really driving alignment, making sure that everybody is talking the same language and kind of marching to the same drum. 

Trinity: I’m going to double click a little bit into your first 100 days of experience. What would be the realistic stage that the CEO needs to take a serious look at this?

Rosalyn: I would say the earlier the better. And definitely, as soon as you can afford it, you should hire operations. I think as soon as you have data that you want to look at and you start to build a sales motion or revenue motion, you need operations. You know, typically I've told other Ceros that, Hey, you know, as soon as your co-founder is no longer your primary seller and you have somebody who's selling, um, and you have maybe perhaps have a couple of sales reps is time to bring in ops or these considerate at some level, no, you may not need a full revenue operations leader across all of the different platforms because you may not even have a marketing engine yet.

Or you may not have a CA you may not have any customers to support, but you should start thinking about the different areas of operations where you do need help, maybe it's setting up a CRM, you know, maybe it's just getting the data and the insights and start doing some of that reporting. Maybe it's building out your forecasting or your comp or different areas.

I think the sooner that you can afford to bring somebody in the better. And I think a lot of companies tend to hire more salespeople. Right. They use their resources in their budget to hire more salespeople. Instead of looking at hiring an operations person to help your salespeople be more effective and more efficient, and also new hires ramp more quickly.

Trinity: So you transitioned from a 4,000 plus person company, an enterprise to a startup in 2016 to build out their ops team from the ground up. What was your first 100 days priority?

Rosalyn: Yeah, I think with any company, regardless of the size of that role that you're moving into, it's always about coming in and quickly assessing the current state.

Right. And for our revenue operations. But that current state means is really understanding the people. What's the team look like you're assessing your tech stack. Right. And assessing what kind of technology do I have? And what shape is it in? Because a lot of times you have a lot of technology that perhaps hasn't been configured or implemented properly, or it's not being used properly, or at least you're not doing the right things to gain the true value of the technology that you have.

I think, assessing your tech stack, and then obviously assessing the data quality and your data availability. I like to tell everybody that, you know, everything begins and ends with data because, you know, you start with your data and you're able to make. You're able to report on it and look at insights and be able to make further decisions around how to drive your business.

So I definitely the first hundred days is getting like in any role is coming in and assessing the current state. And then you're going to need to build something to handle the short term, but always build with the idea of. How are you going to scale? Right. You're always building for scalability. And that's one of the things I actually learned pretty quick, moving from a large company to a small company, is that in a large company, we're used to building out a project plan, having all the stakeholders sign off, you know, building a communication plan or a rollout plan it’s an option, you know, all of that and sort of even the kind of post-go-live, right post-mortem and in a small company, by the time we built out, even the project.

It's changed or your priorities have changed. Things have changed. So one of the things I had to learn very quickly is to build something, to get something out now, like immediately know that it's short term, but that's where bigger sort of enterprise experience comes into play. Because then you can go out and build something that's iterative for today, but build it for scale for tomorrow, you know, so that you're not, you know, six months from now.

Tearing everything down and rebuilding, right. Instead, you're iterating and know that it's continuing to develop as the business develops. And also definitely look at places that are on higher. Right? When I first started at Clari, that was the first thing. When I met with different stakeholders was tell me what's on fire.

What it's actually burning and needs to be addressed right away. And what things are sort of the nice to have things that maybe you've had in your past. Have today. So obviously you want to deal with things, anything that's on fire, it's broken anything that's customer-facing first, and then you start to kind of build out your house.

You start to build out the infrastructure that you need to scale. 

Trinity: Usually compared to enterprise startups, so have a lot of resources. Right. But you know, people will know that they need to do XYZ because that's what the playbook should look like. You don't have the resources or the time. So what would it trade-offs you experienced and had to make doing those first 100 days?

Rosalyn: So obviously not having the resources and not in resources from a headcount perspective, but also from a budgetary perspective, from a monetary perspective. So I think. You know, the trade-offs are really, you have to be really good at prioritizing. I mean, in operations, you have to know how to prioritize anyway, because you're normally juggling, you know, literally hundreds of different things they created to kind of playing that whack-a-mole game, where you're just literally like trying to keep everything moving and keep everything down.

But you have to get really good at prioritizing and look for the low hanging fruit. Right. Look for the small wins. Look for the things that are going to have the biggest impact. Right? So when you're prioritizing, that's how I like to look at, you know, effort versus impact. Right. I think that's pretty typical, right?

Cause you obviously want to do the things that have lower effort but have a bigger impact. First is that a common thread of low hanging fruits 

Trinity: that you would recommend rev ops practitioners or leaders to consider when they start. 

Rosalyn: One of the biggest things. I think every company that I've joined has been around data quality, right.

Data is a big part of it because I think if you ask anybody, nobody will say, Oh, my data is perfect. It's real-time. It's accurate. Yeah. I think everybody will say it could be better. Right. If nothing else, if, if it's not the extreme of it's really bad, it's at least it'd be better. Right. And I think that's sort of the ideal state, right.

Is to be able to have accurate, comprehensive data that flows seamlessly through all of your systems. They all talk to each other and it's real-time and not only real-time and available, but accessible by the right people at the right time. So I think. Every company I've joined. I think data is a big part of it.

And I think that will be probably at the top of many companies, checklists. Um, I think the data, the systems, and processes, because, um, one of the big roles of operations is a process, right? Figuring out the rules of engagement, the handoffs between teams, you know, the roles and responsibilities, and being able to have a very clear process on who does what who's responsible for, what will help drive your overall revenue engine, as I like to say because I think all of those different things feed into the efficiency and the ability to be effective and scale 

Trinity: the data piece because you managed, you mentioned it first, it’s also the hardest one to solve. As you said, I don't think I've ever worked at any company that says I'm data is great.

So if you join today to a new company, how would you improve the data? Because of a lot of time, you could buy data from certain data providers, but also a lot of it is manual inputs by reps or marketers or CSMs, but we know how it goes with manual inputs. So what are some things that you would suggest as tips to improve the accuracy of data?

Rosalyn: I think going back to sort of having those clear processes and policy is a big part of it. For example, you know, every company, pretty much every company I've joined you come in, and then you have, for example, a sales stage. Right. Everybody has sales stages in their opportunities and they look great.

They're well-defined they look, you know, look good. It looks like people are using them. And then you kind of peel back the covers and look. And if you ask a handful of reps, they don't know what they mean. There's some subjectivity everybody's using them a little bit different. Maybe some of those sales leaders within each of your segments are doing it a little bit differently.

And so that's definitely one thing within the first hundred days I've always done is revamped the sales stages, revamped the forecast categories. It's almost like just getting back to basics, right? The basic building blocks of, you know, what's an MQL, what's an SQL, what are those handoffs? And being able to drive some of those definitions as well as sort of what the process is and the expectations, and that will help you, um, improve the quality of your data.

Because if I'm a rep and I understand what is supposed to be in stage B really, it's probably getting back to being really simple as much as you can. It's basically, if it's in this stage, answer these three questions. Yes or no. And if they're all, yes, then they move into that next stage and you've got to be really clear and crisp.

And I think that's one of the values that operation Springs, and that will start to improve your data quality. Right? Those are those small wins. You start at least being able to manage what's. New being input into your system. This is just one example. Obviously, there are multiple examples of this, and then you can start going in and cleaning the existing data.

Right. And being able to sort of do that backward view of cleaning up, um, historicals and kind of what's in your current state, but hopefully you sort of, you know, kind of quote, like you stop the bleeding and the front end, right. To be able to at least start to stop. What's the bad data that's coming in.

And then you can start to work on cleaning it up. So revamping 

Trinity: the sales stages and the forecast categories, et cetera, improving the data accuracy. How do you quantify the impact so that you can talk to the CRO? If you were going to say, look, this is what I've done the last 30 or 60 days. 

Rosalyn: Yeah. I mean, I think that that's a great question, and I think the stages and the forecast category is a good example. Of course, that's just one piece, right? Of all the different things you could be doing. But I think it's one part that's very basic and you come in and it's easy to clean up. It's easy to set those parameters and then it's easy to drive the adoption of it because it's kind of in its own world.

But I think you'll definitely see the impact because you'll start to see a more improved forecast, more consistency in how you're managing your opportunities. You'll be able to have better confidence in the numbers that you're producing. And when you have these discussions across the team, everyone's talking the same.

Language and kind of on the same page. And I think ultimately that will result in better forecast accuracy, hopefully, better conversion rates, and faster and bigger wins, which is what we all want.

Trinity: So what was the number one, objection or roadblocks that you faced personally, besides that limited resources as just joining a startup, how did you handle it? What do you wish you could have done differently?

Rosalyn: I think coming from working for a bigger, more established company and then kept going to a smaller company. I think one of the things, I don't know if it's necessarily a roadblock, but I think helping the team understand that we want to move quickly. We want to move fast. But at the same time, when we build, we want to keep in mind that we're building for scale. Right. We're not just building something for today because a lot of times an early startup, they're just trying to get through the day, right.

Get through this deal, get through this meeting. And so that's why a lot of times for operations, you'll see that train of thought in the processes, you know, and I use that word very loosely, but in the processes that are, you know, that are in place. Um, so I think taking at least a moment to. You know, stop and take a step back and think about how you're going to lay the infrastructure long term.

Maybe it's not today that you're going to build all of that, but you've got to think about as you're building, how this will scale when we get to, you know, 20 million or 50 million or a hundred million AR and beyond. And I think that's something to work with, like a co-founder or somebody who just has, you know, kind of, they have this brilliant idea of what they're trying to do, but helping them understand that, Hey, we're building this so that we can scale.

I think in a startup environment, oftentimes if you're only if you've only worked in a startup, you're very smart, very talented, and you're great at what you do. But oftentimes if you don't know what it looks like when the company is a billion dollars, then you don't really know how to get there, or you just have more trial and error.

Right. You'll try different things to get there, versus when you've done it before you at least have something in your toolkit that you can pull from, right. You might be able to say, Hey, I seen this work in this scenario, but maybe this doesn't work in this scenario. And I think one of the mistakes, or maybe not mistakes, but challenges that we have in a lot of the smaller companies is you might have a group of individuals who haven't seen, you know, what it looks like at that, you know, at that scale.

So you have a little bit of a, you know, you have more of a challenge to make sure that. People are thinking about that and making sure that they're considering that as they're rolling out whatever the process or project or anything that they're working on. So we sort of keep that in mind that what is that going to look like?

You know, even three months from now, or six months from now, five years from now, right? Because the last thing you want to do is build something very comprehensive that you have to tear down and rebuild from scratch.

Trinity:  So once you recommend that startups or businesses that set up rev ops for the first time hot bringing on someone who's very seasoned, who've seen it all to kind of guide the team through basically future proof.

Rosalyn: It's oftentimes, you know, we have a sort of a set budget for what you want to hire and you don't want to over-hire because sometimes you don't need a VP level person, potentially you may only need a certain level. Um, the trade-off with that is you bring in somebody at a certain level that will get the job done for today but may not build for scale.

Then I think at some point, you know when their company might be in their series C or maybe they're just about to really see a trajectory of growth, they hire in a more senior leader, then that person comes in and they start to, then that first hundred days start to unwind some of the things that have been built and start to lay out the infrastructure that they need.

And I think that that kind of goes back to, you know, making sure you hire her right hire early at the best quality that you can because there's just going to be less work less rework later down the road. 

Trinity: If you were going to create a cheat sheet for a first time, rev ops leader, building the team and process from scratch, what would be on it?

Rosalyn: Definitely the data piece that we've been kind of harping on her. I've been harping on building processes. Try to think it will be some policy start to drive some policy that will be iterative and it'll continue to move. Definitely setting up, you know, looking at the. Just start to really dissect the data that you do have.

And part of that, as you're cleaning it up is really being able to, you know, look at your data. What insights is it telling you what decisions can be made from it? Also, one thing that I don't think I've done a good job of, and many times when I've joined a company is hiring quickly. Um, you know, kind of raising my hand for help and asking, really pushing to hire ops people sooner and others, I'm not taking my own advice about hiring faster because I think, you know, we are very lean in the companies.

We tend to be very lean and I think with more and more, you know, leaders realizing the value of operations, I think that's a much easier sell because you can really build out the ROI. You can kind of show what. Value and what lifts you'll be getting by bringing in operations sooner. Um, so that would probably be in my checklist to start building out that plan and start socializing.

Then starting building your ROI and your business case for bringing in your, yeah,

Trinity: a lot of revenue, new practitioners, and revenue Gators. Uh, also be more present on 

Rosalyn: social media, building out their personal friends, but also like applicating forward. The 

Trinity: cost, right? In your case, that's rev ops community and I've seen you've done extremely well because when I think of wrap-off, I think of Rosalynn.

So I'm just kind of curious just for the audience is beyond the standard advice of like, you gotta be helpful and post frequently. What have you learned from this process that surprised 

Rosalyn: you about this whole personal branding? So, I don't know if it does maybe not surprise me about the personal branding, but really about just the revenue operations.

Right. I think I've shared with you in the past that, you know, when I started out this year, I really made it a sort of a personal mission, right. A personal objective to really help, to elevate the revenue operations function. As well as really try to help elevate the professionals. You know, it started out with me just wanting to share more experience and share some of my, you know, my knowledge and experience with others.

So I started posting and I think I was surprised by the. Huge appetite for this kind of information and how much it resonated with other operations professionals, as well as revenue leaders, who aren't ops, maybe their sales leaders, or marketing leaders or customer success leaders, and realizing that there's really a big gap.

In the information where somebody could go and read a book and figure out how to run revenue operations, right. That doesn't especially exist. So I think being able to share more of that has been just very rewarding for myself, but very impactful in terms of all of the people who have contacted me as a, Hey, can we have a conversation?

And that's the part that I really enjoyed the most is being able to really meet with other operations leaders, be able to answer questions that they might have been able to share best practices with each other, and learn from each other. And as I shared with you, I would call it a little bit of ops therapy also because I do find it very therapeutic to talk to other people.

Because as soon as you start talking, you're talking the same language, you have the same issues you've met with the same challenges. And I think that's very comforting in a lot of ways for other operations leaders to know that they're not alone, they're not the only ones faced with this, that other people are experiencing the same and being able to really leverage each other.

To learn versus having to try to do everything on your own. And as we've been talking about throughout this conversation, a lot of ops teams are very lean, especially in a smaller company. And sometimes you're the only ops person, or maybe there's only two or three of you. And so you don't have as many resources.

Internally to ask for help or asking sounds even bounce ideas off of. So being able to go outward, you know, go outside of your own company and be able to, you know, whether it's through different communities or just through networking or even on LinkedIn and being able to reach out to people who seem to be in the, sort of the same.

Spaces you and just reach out and have a conversation. Have a 30-minute conversation. You'll learn so much in that short dialogue, whether it's over Boba or coffee or anything like that, you'll learn so much. And just even walking away with the computers or at least, like I said, feeling at least satisfied that you're not the only one.

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you like me. When you now think of rev ops, you think of Rosalynn and her hashtag ops therapy. Christian joins me to break down the insights that Rosalind shared. 

Christian: The first thing that stood out to me is, is actually unrelated to like her first hundred days there. The interesting thing about revenue ops is I guess that you have something that you can work on immediately.

Like it's obvious you want to look into like, what are, what is my 80 20, where can I make a strong impact? But I think, for revenue operations, the good thing is that that the data is never as good as it should be. So as she said, the first place you can make an impact is by looking at the data and improve it. And then this means that you can get started on the first day. And then what, while you're doing this, you can now then have these conversations figuring out what are the other important elements for the organization that I should be working on in the near future. 

Trinity:  I think she mentioned a lot where she said revenue operations is essentially the alignment of the company. Like how you set up revenue. Operations is how well aligned your organization is. And it's funny because revenue operation is a relatively new term, even though everyone has been doing. Different types of opposites marketing ops sales off customer success ops, et cetera. Um, the concept of bringing all that in together to bring the whole company together is relatively new.

At the same time, we've been hearing a lot about the conflict between sales and marketing and also the handoff between sales to customer success. So I think it ties to her recommendation of hire early, as much as you can for the talent that you can afford at the time. Because as sooner you have this layer of full-cycle revenue operations to get at the earlier your processes for sales and marketing as CS will be built in a way that more aligned rather than everyone goes off and just build their own ops specifically for their own departmental KPI.

Christian: And I think in this case, she obviously points out how important this alignment is between the different sales, marketing customer success. But I think a little bit the good thing is, and I think that's why she said like hire earliest that you can. Influence how well they work together by hiring the right people into these roles

Trinity: So we hiring a revenue operations person, right. Christian,

Christian: what does the face you talked about that you should start 

Trinity: focusing on. She said hi at early, 

Christian: early, once you reach serious D 

Trinity: now that is not true. That's not what she said. No, but I think, yeah, depends on the business needs. Depends on the products and the processes you have in place. Um, don't neglect ops, because what usually happens is you end up hiring an ops person too late to clean up the mess.

That's already blowing up. Maybe that's the culture that you aiming for, but if you can think ahead of what you do differently as a business owner. 

Christian: I agree. And I think these operations roles have a huge multiplier in making everyone a bit more effective and therefore quickly pay for themselves. 

Trinity: Are you going through a major transition within your organization or your career?

Do you have a first 100-day journey to share recently on the past? If, yes, I want to hear from you email me at podcast@usergems.com. And if you're looking for the ultimate revenue leader, cheat sheets, sign up to receive them at usergems.com/podcast.