“If you’re afraid to own the mess, you’ll never get a seat at the table.”
If you’re trying to go from mid-level RevOps to senior leadership, you’ll want to listen to this.
Jordan shares his path from employee #8 to SVP of RevOps during the journey from $300k to tens of millions of ARR at Coursedog. In our conversation, Jordan proves his ability to blend the tactical with the strategic as we cover:
- Practical advice to develop the “crystal ball” in RevOps analytics
- Advice on “Maslow’s Hierarchy of RevOps analytics” (my words, not Jordan’s – couldn’t help myself)
- How to move from tactics to strategy in RevOps
It’ll be particularly helpful for folks who are tired of hearing:
- “Wouldn’t it be interesting if we could see xyz data?”
- “We need better visibility into next quarter for the board”
- “Why isn’t our new sales process working?”
Take a listen and let us know what you think!
Transcript:
All right. Hey, everybody. James from AccountAim here again. Thanks for joining us on our Aim for Excellence webinar series, where we break down strategic, operational, and career related best practices in RevOps with leaders in the space that we admire. Today, we have on a great guest, Jordan from CourseDog.
Jordan started at CourseDog as director of RevOps until being promoted to VP of Ops there. Thanks for joining us, Jordan. Do you want to show your background in a bit more detail for folks?
Jordan’s Career Journey
Yeah, thanks for having me, James Stoke, Stoke to be here. Yeah, just, brief overview of myself started my career in finance, in investment banking, and before transitioning to the kind of rev ops SAS space has spent the last six years leading rev ops at primarily two companies.
So one loom PLG, where I spent about a year heading up rev ops there. And then I spent more or less five years at course dog, vertical SAS company in the higher ed tech space. Or joined the company fairly early on, employee number eight. We’re about 200 folks now. I’ve seen revops analytics through quite a few different iterations of growth and maturity.
And yeah, hopefully I have some, I don’t know, useful perspective to lend. Yeah, for sure. And I’m excited to dive in here. Primarily from an analytics angle, I know, you’ve had some conversations with my co founder Josh in the past, and it seems like you guys have really nailed the RevOps analytics front.
You have to see a company through that scale. So we’ll get into kind of the nitty gritty there, but I’d like to start pretty high level.
Defining RevOps
Everyone has a different definition of revops, it seems like, how do you define revops? Yeah, I think I keep it pretty simple, right? It’s the sort of people process and tooling discipline or set of frameworks that enable organizations to grow, retain, and expand business with customers and hopefully in a fairly kind of predictable and customer centric way, I think there’s lots to unpack and each of those three pillars, people process and systems, but at a high level that’s how I think, and I just apply that same framework to any kind of business unit that I might be working with.
Yeah, I like that. It covers like the house of people and process and frameworks and also the goals in terms of closing new business and expanding. So I think that’s a really good kind of map to put in all the activities that you focus on from a career perspective and you started investment banking, you said we, we share that in our background.
Like what led you into RevOps post investment banking? Honestly, I’d be lying if I said anything but maybe happenstance. A combination of happenstance and luck. I joined Course Dog as I mentioned, fairly early on, I was employee number eight. At that point, we had maybe 15 customers were doing like 300 or 400 K in ARR, and so folks had titles, but we were all doing everything.
It was all hands on deck, so everyone was outbounding, everyone was closing deals, everyone was onboarding and retaining customers. And it just so happened that the kind of first week that I joined the company, we had decided to implement Salesforce. Absolutely. No one knew how to use it, leverage it.
And I saw an opportunity to assume ownership over something that I knew would be pretty intimately important to our growth. Should we continue to grow? And so I, I began spending weekends just like over time, really optimizing the system and the processes that. It brought to life and I just fell in love with, I don’t know, like the systematization aspect of it, right?
Like making, I don’t know the mess of like people in process, hopefully somewhat predictable and, making sense of it all. And yeah, so my, my, my scope just broadened from there, obviously picked up additional skill sets along the way, just as we grew. And that’s how I got into it.
That’s awesome. I don’t think I’ve ever heard someone excited about taking on a CRM implementation. I’m sure there’s some more stories there. We’ll save that for your second time on the podcast. You joined CourseDog so early. I don’t think I appreciated that. It was truly as early as, 15 customers, a few hundred thousand ARR.
A little bit out of scope of RevLabs generally, but like, how did you think about that decision? It’s like a scary. Proposition to join a company that early, like what gave you the confidence or the comfort in doing that? This is why I say it’s luck. I’ve learned so much in my time at CourseDog in particular.
And I’d be lying if I said when I made that decision, I fully understood the risk or implications of it. Obviously hindsight’s 20, 20, it’s worked out really well. We’ve grown tremendously. I’ve been here for, like I said, five, six years. We’re continuing to grow, which is amazing.
But I, again, I’d be lying if I said like at that point in time, I saw perfectly into the future and made a calculated decision, I think to the contrary, I was sitting in banking, like pretty dissatisfied, unfulfilled with my, day to day and my, the career path that I saw before me and, an opportunity kind of popped up via my network to get involved in a, something that I thought would have a lot of value.
And I knew it was fairly early on. And I just hopped at the bit. That’s great. And I’m glad it worked out. Not everyone is so lucky, so that’s awesome to see. Switching gears here to analytics. RevOps analytics can be hard, especially in a RevOps scene because it really feels like they can be endless.
I think there’s, often new requests coming RevOps way every day. Tons of ways you can slice and dice, anything. Especially when you’re running the whole funnel, basically. If we started like the most basic as you think about analytics, like how do you think about the scope for rev ops?
Like what should a company be measuring? Yeah. I think a few things this We could talk like through a whole set of basic kind of KPIs for sales marketing CS Project engineering as well, but I’m sure, everyone’s pretty much looking at, I’d prefer looking at it more from a conceptual standpoint.
So to me, it’s all about leading and lagging indicators. And if you think about, to my point earlier on RevOps being the people process and systems framework that. Facilitate the funnel, the lagging indicators would be the ability to easily identify and understand where your funnel is leaking at point in time.
Now, those are must haves. I think those are sort of foundational pieces. Just the ability to understand right now what’s happening. Ideally, you also have leading indicators, i. e. Where is your funnel likely or at risk to leak moving forward? So that’s one of the conceptual pieces I keep in mind.
The other piece, and going back to my point on making sense of the madness of the day to day Revops, I think, rightfully gets painted or tasked with being process guru or sort of data governance wizard, if you will. And so ideally, some of your RevOps analytics should help your leaders easily enforce process and hold folks accountable.
If RevOps is designed to, generate, retain and grow revenue predictably, that only happens when folks are executing a standard sort of proven game plan. So ideally you have. Insight into how well day to day, week over week, you’re actually executing at the processes that you’ve defined and iterated on.
And the last kind of conceptual thing that I think about, like analyzing or making sure that we’re tracking is anything that’s strategically relevant to the business that’s going to change company to company. For example, at CourseDog, one of the pieces that we’re laser focused on is a concept that we call attach rate, which is how effectively our sellers can sell platform, right?
We have a suite of kind of nine technically individual SKUs or modules that our customers can purchase. We believe our value proposition is in being a true platform solution. So selling as much of those SKUs up front as possible versus a kind of more traditional land and expand motion. And so one thing that we’re constantly paying attention to is what percentage of deals close in a given period can be classified as, platform deals, which to us is like anything with four or more products on it. That’s incredibly specific to CourseDog, but I think, when you evaluate your sort of I don’t know, analytical or like KPI repertoire, there should be pieces, not only that you’d find it in every company, but things that are strategically relevant to your.
Yeah, I love that framing and thanks for going through it. I love it because you’ve proven that you’ve been able to add value through just I look at your resume, like your promotion to VP of Ops more generally than just director of Rev Ops. And so often we chat with folks who are maybe mid career in Rev Ops and they have that question of like, how do I expand beyond just like the tasks of Rev Ops to get a seat at the table?
And I think even the way you frame that up showcases like the thought process and how you generate discussion beyond just the metrics. So I think that’s a great example. I wanted to like double click into each of those three things just real quick, if you don’t mind, because I think it’s like really valuable.
On the topic of being strategic, I think the crystal ball example is a really good one, and that’s how you start to add a lot of value. You mentioned can we create some leading indicators to figure out where like the funnel or the pipeline might be leaking? Do you have an example that comes to mind on that front of maybe how you did this in the past to put an example to, the higher level explanation?
Yeah, I think the most basic example that comes to mind would be on the top of funnel side of things. We actually use a custom object in Salesforce that we call the discovery call object, which for all intents and purposes, you can think of as a mini pre opportunity. These are records that get automatically created whenever our SDRs sort of book a discovery call under an account.
They have a set of stages that move linearly as an opportunity would that our SDRs manage and they, their close winning or coming to fruition is the creation of an opportunity. So at CourseDog, besides just assessing overall pipeline coverage, for example, Getting a sense of even further up funnel, what our discovery call pipeline looks like, i.
e. like potential to create discovery calls or how those discovery calls are progressing, how long it’s taking us stage to progress them, i. e. Pre discovery call to post, to how long it takes to set up a demo, to between how long it takes to have a demo and actually qualify the opportunity.
As well as those conversion rates are some of the ways that we can get ahead of what pipeline generation is going to look like in a given period. If you can get ahead of what pipeline generation is going to look like in a given period, you can probably get ahead of what bookings are going to look like.
It’s not always perfect, but to me, if you can like Just begin to live in the data as upstream as possible. You open up the opportunities to identify leading indicators that, hopefully make it so that all of your lagging indicators aren’t so much of a surprise. Yeah, that’s awesome. I actually haven’t heard about a custom object for kind of pre op creation.
I think it’s a really cool idea and exactly like the board cares about, right? The board cares about seeing into the future, understanding that you’ll have the pipeline to hit the bookings goal. And so it’s pretty hard as like a marketing or DG leader to say with certainty will we hit that pipeline that we need?
And I think what you described is a great way to build some comfort. So I love that. Yeah. From what I’ve heard, just I think it’s all iterative. It’s not perfect. And I don’t want anyone listening to this thinking like course dog has a crystal ball and they. They forecast perfectly and it’s completely predictable.
It’s just things that we’re trying to improve at or focus on day in and day out. And we nail it maybe 10 percent of the time. Fair enough.
RevOps Analytics and Data Governance
Another thing you mentioned at the end of your kind of three examples was around enforcing process and data governance. I think one big challenge in the rev up seat is you can create dashboard after dashboard doesn’t get looked at.
And so it sounds like that’s not necessarily the case. Of course, Doug, like you actually have. Sales managers, sales leaders in here making sure the sales process is being followed. How does that process work for you? Like, how do you ensure it’s being actioned? Are you bringing this up in meetings?
Like, how do you generate like the productive discussion based on this to make sure that like those processes are working? Take a few things. Yeah, cadences are absolutely a part of it. You should make the dashboard that you’re building should be a part of your operating rhythm. It should be used by the leaders of the business and should be viewed as genuinely valuable by everyone.
So like. Individual contributors and managers and execs should all want to see the dash, the dashes that you built because they, they believe that they’ll help them do their jobs better. I think the other piece that comes to mind is like getting as ahead of that conundrum that you described as possible, i.
e. Being thoughtful about the very real possibility that you build things that are never useful. To me, the best way to do that is to actually collaborate extremely closely with the people that are going to be using the dashes as you build them and then iterating on them over time. So I think another common pitfall is just like setting it, forgetting it or making it a one time exercise.
We try on an annual basis to revisit all of our sort of core ops stamp of approvals views in our BI tool. And we vet those with the leaders of each vertical across the business to make sure that they have what they think they need to run their business units. So yeah, I guess high level takeaway, it’s like cadences, build them, build using them into your operating rhythm and then as far upstream as you can,
you shouldn’t be building dashes in a silo. They should be the output of like pretty close collaboration between RevOps or Ops and each exec or each leader. Yeah. And are you pushing these out into the field, like to the leaders saying Hey, we need some clarity on if these processes are being followed or is this more of a pull from like the functional leaders saying like they want the clarity?
I think it’s push and pull, right? It’s in an ideal world, you craft the process or the optimal processes or SOPs alongside the leaders. And then you say, Hey, we should also hold ourselves accountable to holding everyone accountable. And the best way to do that is. To have visibility throughout the year on how well we’re doing against this process that we’ve defined.
So I, at least personally, in my experience, I’ve seen it be collaborative from the very start. And I don’t really think about it as, in terms of them asking for it or me pushing. For it, it’s more like symbiotic than that in an ideal in the world of my experience. Yeah, it sounds really healthy.
I think that’s unfortunately not always the case. Sometimes get, sales leaders who are so deep in deal management, they don’t want to think about process, but it sounds like, you have like pretty good relationship on that front, of course. Yeah, kudos to our CRO and also some of our other leaders who I think are fairly operationally minded and, are invested in doing things like scalably and predictably.
That’s great. Next kind of question here, we can go as deep or as shallow as you want to on this, setting up the analytical infrastructure at CourseDog, there’s a lot of things that can be done here. There’s CRM native reporting, there’s gathering data sources. Some people will bring in a data warehouse to crunch what they need.
Like, how do you think about what you would recommend, at least from your experience at Coursedog, is like the Menu of tech or processes or structures that you need to have in place to do a RevOps analytics. The first thing that comes to mind, and this is maybe like a getting around the question a little bit, but I think people make the false assumption that standing revOps analytics up in and of itself is going to be a crystal ball into how.
The business is doing or how things are working, if you think about ops as a sort of pyramid that builds upon itself to me at the bottom, you have, and these are prerequisites for one another, right at the bottom, you have what I would call core operations, which is just like in plain English, what are our processes and how are things supposed to work?
Then you have the tools that bring those processes to life and automate them where possible and enforce them. And then you have the RevOps analytics that sort of are layered on top and provide insight. So I think 1 sort of false assumption that folks make is like implementing a tableau or a looker or whatever.
It’s just like instantly going to give you a whole bunch of insight that. You didn’t have that could be true, but the fundamental prerequisite is like really clear process that people are following that you’re actually and that you’re collecting the data that you want in such a way that you want to that’s going to allow you to answer the question that you’re after.
So I think a little bit less about I don’t know, foundational I think any, there’s lots of text acts in a ways of getting at pretty. Like advanced RevOps analytics course dogs for one, and this could just be a function of our scale and nuance of our business, which is like we are definition, like low volume, high ACB, like we don’t use a data for example, so that, that sort of presents it’s sets the challenges as far as like snapshotting data, and like pipeline management.
But it also makes it easier to wrangle fewer systems, if that makes any sense. It does. It makes total sense. I like the pyramid idea or framework a lot. Any advice for folks, let’s say if they feel the need to start at that base level, like how would you advise people to go about figuring out that kind of base level of SOPs or kind of operational procedures?
Is there a mental model you have of if we’re starting with a blank canvas, like how we can get to that? Yeah, interesting. There’s, there are lots of in the sales world, for example, there’s lots of proven methodologies or whatever in the context of sales. I just think a lot about like linear stages.
What are our entry and exit criteria? And what’s the sort of like perfect balance between. Our internal business processes, the I’s and T’s we need to dot and cross balancing all of that with the, our customers journey. If we have this perfect process, it doesn’t really matter if all of the logic behind it and the wording of it means nothing to the, to our customers or to our prospects.
And so it’s a balancing act there. I, the other thing that comes to mind is I think lots of folks aren’t starting from scratch. And so I think a really good way to know if. You have good process besides, your, the ability to analyze the underlying data is to literally just ask an IC in any function, how they do a certain aspect of their job, ask like six of them.
And see how different their answers are. The more similar they are, the better your process is. And the more that they diverge, the probably the worst it is. Yeah. I love that. I think you always have to pair that qualitative insight with whatever you’re doing quantitatively, to make sure you fully understand what’s actually happening beyond just the numbers.
A hundred percent. Yeah. Any specific, and I don’t want to, spill too many details on CourseDog, their internal secret sauce, but any RevOps analytics or analyses that are super important for you guys, as you think about like the customer journey, like anything you guys live and breathe by.
I know you mentioned leading indicators on pipeline earlier, which I think is really interesting and sounds like probably guides a lot. Anything else is on your guys Top of the kind of pyramid, a different pyramid than the framework you gave of what’s really important for you guys to be tracking day in and day out, or what actually drives the business forward.
The only thing that comes to mind is a little bit specific to course dog and maybe I don’t know, enterprise vertical SAS, which is we pay a lot of attention to our deployments. So we have a long sort of enterprise sales cycle and then long complex deployments. And we have found that our implementation experience.
And our ability to implement and deliver value quickly and effectively is more or less the only thing that matters as far as retaining and growing our customer base. And so we pay a lot of attention in terms of the utilization of our professional services team time to value, we’ve begun to pay closer attention to the margin profile of each of our implementations or each of the functions involved in our implementations.
Yeah, again, this is very specific to CourseDog, but unless I think broadly applicable. So I might have to get back to you on a better answer. Yeah, no, I think it’s super helpful, actually, what I was looking for. Because I do think you guys have a small ish team. I’m not sure how many universities there are in the U.
S. Maybe 5, 000, if that, yeah, if that, yeah. And so I think there are other industries like that too, where I think Reynolds has like unique set of challenges that aren’t as well evangelized because it’s not like the high velocity model or the PLG model. That’s all the range these days.
So I think deployments is like a great example of how you might be really focused on the big accounts. I always say our TAM is a blessing and a curse. It’s a curse. Cause. Obviously it would be nicer if it were double, triple, quadruple the size. There would just be more, more territory to go carve up, but it’s a blessing because it means we can be extremely intentional and data driven and insightful with every part of the customer journey.
So yeah, pros and cons. Yeah, that’s great. This is super interesting. I know we’re almost at time here.
Rapid Fire Questions and Conclusion
We like to finish usually with a rapid fire, one or two word answers just to a few questions. Sure. Take through it here. What’s the biggest myth about RevOps? Biggest myth about RevOps is that it’s just sales ops.
I feel like that’s probably the most common answer you get to that question, but I think it is the biggest myth. I think there are genuinely cases where sales ops teams have been just simply rebranded as rev ops. To me, there is a fundamental difference though, between sales and rev ops, where rev ops is a centralized operations function responsible for stewarding.
Again, that people process and systems framework that informs the entire customer journey. versus sales ops, which is a part of it. But yeah, I think the biggest myth is that RevOps is just sales ops. Yeah, that is a common answer. It’s probably second to that RevOps is just a CRM jockey. Although I think that’s.
RevOps more, which is great. Nice. Next question. Biggest sales rep pet peeve? I love working with sales people. I don’t, I wouldn’t say that I have a sales rep pet peeve per se. Like the only thing that really comes to mind is, and it’s not, I don’t think it’s even unique to sales folks, but it’s just, it would just be like people asking for things or tools that they don’t actually wind up using or needing.
RevOps is I think always, we’re fundamentally a cost center. Obviously, there’s ROI. We deliver value, but we’re not a directly revenue generating team. And so Where we tend to be staffed a little bit more thinly and so I think you know when it’s easy for us to get stretched in tons of different ways and so when people are asking for things that they don’t really need that can be frustrating How do you describe a great relevance leader in three words?
I think someone who’s like really empathetic can relate to people and understand their pain points Extremely well, someone sort of word of the day, who’s like analytical, wants to genuinely understand how something works and how they can improve it. And then maybe like resilient. I think oftentimes people are only going to come to rev ops when things are going wrong, when there’s a problem to solve.
And so you’re probably not the first function to be celebrated. And so being able to just be the calm in the storm is a huge asset. And last one, one piece of advice you give to someone starting out in rev ops today, maybe starting their career. Just based on my own experience, I would say, get your hands as dirty as possible.
Don’t fear ownership. My experience has told me or taught me that RevOps strategic value lies in its intimation with the tactical day to day and the ability to operate at all levels and bridge that kind of strategy to execution gap. And so early in your career, if you can become a true subject matter expert on the day to day functions and like what makes them work as you grow and assume more ownership,
you’ll be able to flex back into that role while also speaking for the business at a more macro level. So I guess, yeah, takeaway is, or TLDR is assume as much ownership as possible and just get your hands as dirty as you can. That’s fantastic. I don’t think there’s a better place to end than that and clearly it’s worked for you jordan This is super interesting.
I think really valuable. I’m excited to get it out into the world Anyone listening if you have questions for jordan, Feel free to funnel them my way and i’ll run them by jordan and get back to you Of course, if you have any questions about accounting you can reach out to me at any time jordan.
