Today on #Operations, host Sean Lane sits down with Okta’s VP of Business Operations, Jake Randall. Okta’s market cap is now $9 billion…not a bad company to learn from. Together Sean and Jake discuss how to actually measure your ops team’s performance, scaling through hypergrowth, Jake’s career path at Okta, what he’s reading now and much more.
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Sean Lane: Hey everyone. Sean Lane here. Welcome back for another episode of Operations. The show where we look under the hood of companies and hypergrowth.
You know how in sales you can always tell pretty much exactly where someone is at in terms of their performance. You look at percentage of attainment to quota and by and large you have your answer, right? In a lot of other gigs though, including operations, the answer to how quote unquote good someone is at their job can be a little bit murkier. And how good an operations team is can be murkier still.
Luckily on today’s episode, our guest, Jake Randall from Okta, is going to help us clear things up. You’re also definitely gonna want to stick around for one hell of a pivot table metaphor from Jake coming up later in the show. That may be the nerdiest sentence I’ve ever said out loud.
Anyways, Jake is the VP of operations at Okta and he’s had a front row seat for nearly all of the stages of hypergrowth during his seven plus years at the company from around their series B up through when the company went public last year and beyond. By the way, Okta now has a $9 billion market cap, that’s billion with a B. During his time at the company, Jake has risen through the ranks in a variety of different finance and biz ops roles.
Now because everyone has their own slightly different definition, before we jumped in, I wanted to level set with Jake on what biz ops actually means at Okta.
Jake Randall: Yeah, it’s a great question. I think whenever I meet someone who has a similar title as myself, first question is, wait, so what do you actually do? Which is I think somewhat unique, maybe from the biz ops world So I think Okta has a slightly, maybe, different as it may be, version of it ourselves. Biz ops at Okta is really centralized strategy and operations team. And so that’s everything and really for our go to market [inaudible 00:01:56] that’s everything in how we think about building pipeline all the way through to renewing our customers. Think full customer life cycle. And then basically supporting all the teams that are involved in that customer life cycle process.
And so I think the easiest way to kind of think about it is that a big part of that particularly if you’re hypergrowth company is a sales ops function, or sales strategy. Again, that’s another role at different companies, but there’s no sales strategy or sales operations that rolls into sales, sales strategy and operations rolls up into biz ops. And then I report into our president and help make sure that that entire go to market [inaudible 00:02:34] And that’s the same for all the different ops and strategy functions, support the go to market team. So making sure that it’s all aligned and working smoothly and there’s a coherent plan.
Sean: Got it. And seven years is a long time in the tech world, at least, for being in a single place in a single company. And so you have also been someone that’s been able to grow in your role and responsibility during that time there. And so for people like me, and people who are listening, who want to try to grow their careers in ops, why do you think that you’ve been able to make those jumps and continue to grow inside of ops?
Jake: Yeah, sure. That’s a good question. First of all, what I’ll say and I’m sure we’ll touch on this is that I joke that I’ve worked at 10 different companies over the last seven years, but they all just have the same name. Right? And so that’s the fun part, but as you go through these different spurts, and hopefully no stops, just spurts.
I think I can give you my background quickly, actually. If that helps. So I started out the first four years that I was at Okta, for the first four of seven, I ran finance operations and legal for us and then transitioned over the last three years into this biz ops function that I just talked about. I think there’s a lot of different things that make you good at ops, or what’s been helpful for me, there was a lot of it that was because of the function and because it is so centralized, and you could argue that part of what ops does at Okta is it weaves this kind of connective tissue through whole business that puts you in a really strong position. You really understand the way, I guess maybe this is why we call it biz ops, the way the business operates.
And there’s been, so I tell people on my team, I think that’s certainly how I thought about it and in my career here is that I’m going to put you as someone on the biz ops in [inaudible 00:04:19] Okta I’m going to put you in a great position where you have incredible insight into the business, how it works, what are our key strategies, what’s going on, and then it’s really on you to take advantage of that opportunity. And I think that that’s something that’s for people that are in ops function. You have a unique seat at the table to understand what’s happening and it’s really on you to take advantage of that opportunity.
Sean: When Jake talks about taking advantage of an opportunity at a high growth company, I wanted to better understand what that actually means through the lens of ops roles. What does it mean to be quote good at ops? He clearly had navigated that well himself at Okta, and what he told me may surprise you. He said it’s actually not just about being analytical or good with numbers or excel spreadsheets.
Jake: Yeah. I think a lot about what makes people successful in the role is that empathy for the different people that they support and be able to communicate what at times can be hard things, either that they’re technical or very analytical or hard things in that if you’re in a sales ops role, one of the classic things is comp plans. Those are hard conversations and the ability to take that analytical mindset and translate it into a kind of empathetic conversation with your business partner, or the head of sales, or the head of marketing and effect change. I think that’s actually kind of the most important thing that you have to get out, you have to be seen as someone that can get out from behind the Excel spreadsheet as it maybe.
Sean: Right. Yeah, that’s what I was just gonna say, okay, I want to be empathetic, I want to do that, how do I do that? I think a lot of that does come from just getting out from behind your desk or your spreadsheet, whatever it is you want to say, and actually getting out there and having a real perspective on what those people are doing. And I would imagine that during those first few years when you were doing finance and legal and things like that, that gave you a pretty unique perspective that I would assume, like correct me if I’m wrong, that helps you in your job today?
Jake: Yeah, absolutely. I think that the one that was probably most important was that legal function as a caveat, I’m not a lawyer. What’s the saying?
Sean: Just playing where we got it.
Jake: What are those ads? It’s like I’m not a doctor, but I stayed at the Holiday Inn, something like that. Remember those ads?
Sean: Oh yeah, I think so. Yeah. I stayed at the Holiday Inn. Yup.
Jake: So anyways, as is the nature of any good start up, people get to do lots of things they shouldn’t otherwise be doing. So one of those things for me was running our legal team and I somehow convinced actually a really great legal team that’s still here to come on board to help me with that. But part of that was that because of that function, I would go onsite with our chief revenue officer and I was somewhat his right hand person helping to work through these complex contracts and book commercial negotiations, I actually still run our deal desk here, so pricing and packaging and deal structuring for the commercial parts as well as the legal parts to getting some of our largest, most important companies when we were in that kind of series C, series D round, when you’re really trying to get some momentum going. So things like that. Again, I think that’s probably somewhat of a unique experience quite frankly that I got here.
Sean: Building those connections that Jake is talking about, whether they be with sales, marketing, customer success, that is one of my favorite parts of my job. Let’s face it. Even if you’re not in ops, the way you’re perceived by the people you work most closely with is going to have an impact on how much of an impact you can make. Where things get more interesting though is that in ops, you can’t just spend all your time developing relationships with people outside your team, right? You have to spend time with your own team and you have to think about them as well. So I wanted to learn how Jake had set his team up for success.
Jake: So the way we’re organized is I’m actually the only person that has biz ops in my title. So I have a head of sales strategy and operations. I have a head of partners, I’ve got a head of professional services and customer success. But they all, I think what’s really key is that, I guess the point of this connective tissue is making sure that everyone understands the other parts of the business. And in turn, I think that’s a lot of what as a leader of biz ops you’re trying to focus on, but you have to really understand the sales strategies side of business and you have to understand the professional services side of the business because what you’re really trying to do is create an efficient go to market. And so finding those connection points, understanding people that have this kind of, basically having a team, I guess, that can work to find those points and figure out how to create efficiencies and how to create that kind of scale and leverage. That’s a lot of what biz ops is trying to create scale and leverage in the business. And so people that think outside of the the box and that think outside their functioning is really critical.
Sean: Finding connection points to create scale and leverage. If you take nothing else away from Jake’s team today, it’s that. Finding connection points to create scale and leverage. But I wanted to illustrate this point further. So let’s dig into an example. Pipeline.
Jake: Yeah. Marketing is a ton of pipeline build for us, but when we think about pipeline, it’s not a marketing thing. There’s partners that bring us into deals. There’s AEs that can do outbound. There’s customer success reps that can find the cross sell when they’re in there doing the QPR with one of our existing customers. And so it’s really also, it’s funny, make jokes about Excel and whatnot, but we’ve always kind of thought of it, I think a pivot table, I guess if it’s an ops podcast, ops we all know what that is, right?
Sean: Yeah, I think we’ve got the right audience.
Jake: What a pivot table is in general, but like it’s this ability to take the idea of marketing and sales and all these what historically have been at times siloed functions in their own kind of thing and how can you pivot that and look at it differently? And it’s not about marketing or sales or partners or whatever it may be. It’s about how do we generate demand in our business and that’s a much bigger, broader interesting way to think about it in my opinion. And because you’re thinking about how do we all work together, how do we all play a part in this broader concept of building pipeline or building demand? And so I think that’s a lot to what I try to think about with the team and I think how we’ve thought about it in general over time is kind of shift the lens on how you look at some of these common problems.
Sean: Yeah. So let me just kind of regurgitate that back to you because I think this is an awesome takeaway and I want to make sure that I’m getting it right. But basically you are thinking about ops as that pivot table where you can give the right lens back to not only those key stakeholders that traditionally you might think, okay marketing cares most about pipeline, but instead using that as a lens to be able to make it more of like a company metric or a company topic and get alignment around that thing.
Jake: Absolutely. Yeah. So you said it much better than I did-
Sean: No, no, no.
Jake: But that’s absolutely the idea. That there’s pillars, I’ll call it, of how you go to market if ultimately that I would call biz ops, that often is your kind of go to market strategy and operations. There’s pillars of that go to market strategy and you need to get everyone to feel some ownership of that. So again, pipeline, well that’s something that we should, everyone should feel ownership in and that we should all orient around that and not make it hye marketing, you’re not generating a pipeline, cause it’s not just marketing. AEs should do current pipeline and we should have a common framework to look at that and think about how do we generate demand across all these different business units. Similarly you can think about forecasting. That’s traditionally a sales process. You all get on call and you do forecasting. Well we’ve tried to do a lot to make it really about how does everyone have some ownership in that? How do you make sure that sales forecasting is also about building pipeline? So let’s get marketing involved. Let’s get partners involved. Let’s think about different ways to really shift that lens on these common issues.
Sean: And I think for people that are listening to this, I think you’re going to have two big buckets, right? You’re going to have people like me who are lucky enough to work on a centralized ops team, like the one that you’re talking about and I’m nodding aggressively at the things that you’re saying. And then there’s also going to be some folks who are hearing that and they’re going to be shaking their heads because either they don’t buy into this idea or they’re in a particular organization where they feel incredibly siloed and they would like to be in a world where some of these things are looked at more comprehensively and across that entire customer journey that you started the conversation by talking about. For the people in that second bucket, how can they try to enact some sort of change or shift some of those lenses that we’re talking about so that their companies can look at things similar to the way that you do at Okta? Does that make sense?
Jake: Yeah, that makes total sense. First of all, I’ll say that I don’t know what I do if the way we do or the way [Drift 00:13:10] does it is correct. So for all I know we have a much better plan. I joke at times, if it was easy, if there was a common playbook that works for everyone and every company would go public. There’s always challenges, but I think if it’s interesting, a little bit to what I talked about earlier around people that want to go and do something different and like want to expand. I think one of the things I talk about with my team certainly is that there’s tons of problems. Every company has lots of problems. God knows that the majority of my job at this point has turned into people just calling me with problems. No one ever calls me with good things. Everyone just calls to say I want to tell you how messed up this is. No one ever says, hey, I just called to say this is working perfectly. But so there’s always problems.
Sean: Thank you so much, you’re doing a hell of a job.
Jake: They’re like, yeah, this is broken, what’s happening here. But there’s always problems. And one of the things that I joke about is that everyone’s actually just looking for someone to show up with the PowerPoint and explain how we can fix it. And what you find I think, and it’s a little bit of kind of what makes someone successful in biz ops, back to the earlier conversation, people are actually pretty open and welcome to new ideas and you’ll never get, assuming you work at a good company with a good culture and a good boss, you’re never going to get in trouble for showing up with a new idea and a new way to kind of look at things. And if you can say, hey, this is a problem, here’s what I think why this is impacting us in this way, here’s a potential solution to it. Quite frankly, that’s what everyone wants. Like that’s the dream.
If you’re a manager and you walk into your one on one and someone shows up to one on one and says, hey, I was thinking about this issue and here’s my thoughts on how we could fix it. And here’s how it would work and here’s whatever. Here’s why. Here’s some fancy PowerPoint, I was up late last night putting together. For you, you’re like, yes. There is no greater moment in your time as a manager than that moment. And so I think people can be scared. Understandably. There’s this, oh, like I’m putting myself out there, I’m going to put my neck on the line, I’m going to offer up something new and different to what we’ve done in the past. But I think you should just feel, if you actually believe that’s the right thing to do you should feel confident in that and I would also just encourage people who are listening, like that’s what everyone wants, and if that’s-
Jake: That’s the whole thing. It’s like someone show up and say, hey, I think we could do it this way and like wouldn’t this be cool? And you should be, it might not work, god knows I’ve come up with ideas that were like, that’s a terrible idea. What were you thinking? But I never get in trouble for coming with it. You should never feel anxious around asking about it or proposing it. So I think it’s just really just being comfortable with that and thinking about how to, again, if you’re in an ops function, you probably have great purview over the business. You can see these issues. And so take comfort in the fact that people are actually looking to try to bring these things to light and propose new solutions.
Sean: Right. And I think half the battle on that too is just realizing that you do have that purview, right? And taking a step back and realizing the fact that you have this exposure that is unique and you have a perspective that is unique. I feel very lucky that I get to have conversations like this as a result of doing this show. But I also think one of the reasons why we wanted to do it was the fact that I personally at least, so maybe I’m not looking hard enough, couldn’t find a lot of resources that were like this out there for ops specific people. And I’m curious, am I wrong? Like where do you go to try and get better?
Jake: This adds a great point. I’m now, I’m kind of racking my brain, like what resources are out there? I think I’ll tell you that I agree, there’s not a lot of resources out there like this. I’ve gone to happy hours or whatever. I think a lot of the resources become networking, I guess, within this kind of sub industry or whatever you would call it that we do. I think what’s funny about it is there’s, or at least my own take on it or what I’ve seen is, there’s lots of resources out there around how to think about setting like a pipe gen target, lots of resources about how to run a forecast call or what cadence you should set up as a sales ops team, how to think about different ways to affect churn or whatever it may be. If you want to think through the entire customer lifecycle there. Those are all very tactical things, which are super important, and there’s stuff out there. But I think the idea of how do you look at it more broadly, which I think is this idea of again biz ops and it seems to be more aware of the operations function as trending over time. There’s not a lot out there around that, so I think that’s a super interesting topic. I’m going to put something together on that.
Sean: Before we go, at the end of each show, we’re going to ask each guest the same lightning round of questions. Here we go. Best book you’ve read in the last six months?
Jake: I just read a book called Arsenal of Democracy, which is about the industrialization of America to get ready for World War Two, so you can tell that I like operations. It’s like Ford and the production plants, heavy operations history stuff. So yeah, there you go.
Sean: You’ve passed the test.
Sean: What is your favorite part about working in ops?
Jake: It’s, you’d probably guess this also given what we just talked about, but it’s just all the exposure that you get. It’s the people that you get to talk to and meet and the way you get to solve problems across the business.
Sean: Least favorite part about working in ops?
Jake: All the problems that there are to solve, all the bad conversations you have.
Sean: Someone who impacted you getting the job you have today?
Jake: So the way I got my job, actually, there’s a woman Julie, I was actually in Boston, I grew up in Boston, where [Drift 00:18:36] is. I was working for a healthcare startup. And when we were quite frankly winding down this healthcare startup, it turns out that there’s also failures. It’s okay to fail and eventually have success. So we were winding down this healthcare start up. And I decided that I wanted to keep doing startups despite the lack of success in this healthcare one I was doing in Boston. And this woman Julie was like, Oh, you should talk to my friend Todd. Todd’s our CEO.
And she said, yeah, you should talk to my friend Todd if you want to keep doing startups. He just kind of started this startup and she was like friends with him. And so she introduced me and I’m like, you realize your friend Todd’s like pretty smart and they just raised their A, their first crowd investment from Andreessen Horowitz and they said their B was like Greylock. This is not just like some buddy that’s kicking around in like in a garage. She’s like, I don’t know. Like she’s like, I don’t know, he’s just like my friend. We used to go out drinking or whatever in San Francisco when I live there. Right. And I was like, Huh. So probably Julie the most. Right.
Sean: That is amazing. I hope that she gets a big thank you.
Sean: All right, last one. One piece of advice for people who want to have your job someday.
Jake: Don’t be afraid to just put yourself out there. I think kind of what I was talking about earlier, again, it’s that you’ve got to take some risks. You’ve got to take a stance and have an opinion on things and come up with some solutions and just kind of own it. I think that you have to put yourself outside your comfort zone, so don’t be afraid to do that.
Sean: All right. That’s it. A huge thank you to Jake Randall from Okta for joining us for this episode of Operations and an equally enormous thank you to all of you for tuning in. I want to just take a minute and thank everyone in the seeking wisdom community who sent me a LinkedIn message, Tweeted at me after we’ve launched the first couple episodes. The response has been amazing.
Special shout out to Maribel from PI. Dennis sent me a LinkedIn message from PandaDoc, Ashley from Notarize. Matt Wood send me a video reply on Twitter, which was really cool. I’d never seen that before. All the feedback has been overwhelmingly positive.
Also good to have some critics. You know, I got a text from my mom. She wanted to make sure that we take a look at the background music again. She texted me any chance the background music could be more upbeat and inviting? So we will work on that. You can’t please everybody.
Anyways, whether you’ve got feedback on the music or you have some guests that you want to hear from or topics you want us to hear us cover, please help us make this show better. Send me your feedback. Shoot me a note on LinkedIn, tweet at me @Seany_Biz, or you can always leave us one of those coveted six stars reviews on Apple podcasts. Six
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That’s it from me. See you guys next time.