The Lifecycle of an Operations Hire with SmartBear's Anu Krishnakumar

Sean Lane: Hey, everyone. Welcome to Operations, the show where we look under the hood of companies in hypergrowth. My name is Sean Lane. Everyone wants to say that they have a revenue operations team these days. It's trendy, right? Companies that didn't have the function in recent years are suddenly scrambling to get on board this wave and staff up with the hot new thing that is rev ops. So where does that leave the market? What are the ripple effects on both hiring managers and the candidates for rev op and sales ops roles themselves? To answer these questions, I turn to someone who isn't new to this trendy movement, but rather someone who has worked in operations for more than a decade. My guest today is Anu Krishnakumar. Anu is the Senior Vice President of global sales operations, enablement, and development at Smart Bear. Smart Bear is a provider of software development tools built to streamline your DevOps processes. And over the course of his nine year tenure at Smart Bear, Anu has risen through the ranks from account executive to customer success, to BizOps and beyond. In our conversation, we talk about the mistakes that he sees companies making as they're trying to hire for these ops positions. We break down the real ramp times of new operations hires on your team, and we even dip our toe in the water on a potential alternative to your staffing woes, hiring offshore. But let's start at the beginning. With operations roles in Vogue, what's Anu seeing in the job market.

Anu Krishnakumar: What you see in the market is companies that typically would not have hired an operations person, sales op or marketing ops, whatever, feels the urge to have an operation, their first sales op, first revenue ops person, which is great. It's good for all of us. It's good for the market, but I think there is not a lot of thought that has gone into the role, right? Most of them it's like," Oh no." I've spoken to many sales leaders and other people who are hiring for these roles. And they're like,"No, no, no, we are at size where we need a sales ops, rev ops person." I'm like," Oh, okay. What challenges are you guys trying to solve?" And they're like," No, no, no, we just have so much work." I'm like," Okay. All right." And I think that is an interesting dynamic, right? Obviously there's a lot of money in the market. It seems like we're slightly cooling off now, but we'll see. But at least as of now, there's a lot of money in the market. People want to maximize revenue. And if you look at lots of VCs and PE firms, they are pushing for these roles. They feel like that facility is very important, which is great, but then it comes with it, there's not a whole lot of clarity around what people are looking for in these roles. And on the other end, for people like us who manage teams, we have teams churning because they're like," Oh, wait a minute. When am ever going to become a director or VP or whatever? That company is offering me that job right now, as opposed to a year or two years from now." And I think the challenge with that is they are also not factoring in that what is the job going to be? Is that going to be any different? Am I going to be just managing chaos every day? And I think on both sides, I think there's a lot of urgency, but I don't think there's a lot of thought that goes into this planning. I think that's an interesting dynamic.

Sean Lane: For sure. And I want to make sure we come back to the candidate side of that a little later. To start though, you started to mention in some of the conversations you're having with people, if they are going to slow down a little bit and actually be more thoughtful rather than just it seems to be the in Vogue thing to do is to hire ops people. What is the guidance that you are giving people and what is the stuff that you do internally to be more thoughtful about how do you get the most out of that next incremental hire inside of an operations team?

Anu Krishnakumar: Yeah. No, that's a great question. I've been speaking to a few sales leaders outside who've been asking me for input on like," Hey, we think we need a sales ops person." And this is what I tell them. First of all, don't come to the conclusion because your manager said so, whether it's the CEO, whoever, or the board. Think about what problems you're trying to solve are most, especially if you're a smaller company, if revenue generation is a challenge, is that where you want to invest your money in? And okay, you've made the decision. Then the kind of talent you want to look for is not, I think many people are also confused. I'm sure you would understand and appreciate this. The distinction between sales ops and Salesforce admins and analysts, it's all mixed and confused, right? Decide what kind of person you want. Are you looking for someone who would manage your Salesforce? That's an entirely different hire than a sales ops person who's going to be a strategic part of your organization. And if that's what you've determined you want, then the kind of candidate they should look for is someone who is an entrepreneurial mindset, who is a problem solver at their core, who's ready to jump in, identify challenges, talk to the stakeholders, and willing and ready to look at the world besides just the, I don't know, Excel sheet and Salesforce reports. It's very common for people to get caught up in," Oh, this is what the number's telling me, so this is what I think we should do," as opposed to understanding what the business needs and what the solution should look like and truly become a partner. That's the kind of person they should look for. And they typically are, again, like I said, problem solver inaudible and have an entrepreneurial mindset. And on the other hand, for people like us who are trying, who are managing a team and we want to expand, and you get that precious budget to go hire that additional head. And where do you, what kind of person do you look for? And that is heavily dependent on the maturity of the organization itself.

Sean Lane: How are you either measuring or plotting where you might be on that maturity spectrum?

Anu Krishnakumar: Yeah. So maybe I'll give this example. So let's say this organization has a VP of revenue, op sales op in place. And they're going to hire the first person, the first IC in the organization. And that person should be everything that I just described. They have to have an entrepreneur mindset, problem solver, they're willing to talk to people, not just hiding behind a monitor. And that would be the ideal first hire you have. But then let's say you are at a maturity level where you have like five sales ops people already. Let's assume that all the title are analysts. You're trying to hire the sixth person. Now you need to evaluate what is this? It's not just about putting something in the job description that looks fancy and attractive to a candidate. What is this person actually going to be doing on a day to day basis? 60% of their job going to be account assignments and data clean up and data hygiene, right? Then have that in mind. Don't go hire someone with five years of experience who is going to get bored two weeks into the job. Or," Hey we have a lot of talent that does really good Excel, Salesforce work, works with the managers. We need someone who can bring a BI factor into this. Someone who can do Power BI, Tableau." Okay, now go hire that talent. And again, it is heavily, and you see this very often in organization, they're all just so happy that they got the budget and they're like," Oh yeah, let's get the same job description that we used three years ago."

Sean Lane: Ago, copy paste and post.

Anu Krishnakumar: Exactly. Too much trouble. I agree. I hate doing it, but still. But I think just truly knowing what this person is going to be doing. And when we think about hiring our next head, we think about, okay, what all the people here do and where do we have the overflow work? Work we think that the current resources are going to get bored of doing. Mm. And I'm sure we all can appreciate, in sales ops especially, there is this extremely crucial and terribly boring part of the job that whereas a lot of the admin work, and managing and moving accounts, and all that, that someone needs to do, but no one really wants to do it. And it usually get spread around in the team, but once your team matures and people are progressing, they want to come out of it. They want to start doing more strategic, interesting, important stuff. And your next hire, that needs to be factored in. Some of this stuff is going to go there, so what kind of candidate we want to bring in?

Sean Lane: So with everyone clamoring to add rev op or sales ops into their organization, Anu has identified a few common pitfalls that we should be on the lookout for. First, people aren't clearly defining the roles that they want. They're mashing together a whole bunch of different roles at once. Second, he's been able to put a spotlight on the traits that hiring managers should be looking for in these ops hires. He talked about having an entrepreneurial mindset, being a problem solver, and being the strategic partner to your internal stakeholders. And third, he's recognized that with each incremental hire you make, you have the opportunity to remove some of the less sexy day to day mundane tasks from your existing team. This is going to be critical in a growing ops team. And so it begs the question, how should leaders think about the life cycle of operators within their teams? It all sounds good in theory. And of course, everyone wants to grow in their careers, but what does that path actually look like?

Anu Krishnakumar: Thankfully, we have had a pretty good stable team. We haven't had to bring too many new people, but it is a fun time, right? We talk about our sales enablement team deals with our new hires we have, and every part of the sales organization, certainly the AEs is something that we are constantly expanding and hiring. We have all these ramp times, and ramp times are always just indicated. So you say three months, four months, it's depending upon person to person. But in a sales ops organization, revenue, ops organization, it's especially complicated because it's not just someone learning how to do the job. They actually have to learn so much or absorb so much of the organizational knowledge. Some change that was made three years ago has an impact on something we do now. Or oh yeah, do you remember that one time we had to make an exception and do this, this and that? And that's why this is not normal. And all these things need to be imparted on someone. And I think over the years, we've gotten very good at documentation and typically the people that we bring in, they were usually interns and so they have some knowledge of it. But it's a massive challenge, ramping them up. And what I have seen is the first three months they really add no value at all. Hopefully if they have all the basic skill sets, you are just teaching them the organizational knowledge. But usually what they tell us is two months in the organization, they feel like very comfortable and confident. And then they just hit a road block about something that's a total exception. And it takes about six months for them to really start contributing. That's when they really start adding value. And for someone to get actually good and they can kind of essentially fully hands off, it's about a year. And that's where I think we talk about all this hiring and churn and everything, and that's where the biggest challenge happens. You lose them at that one year mark, I don't think you've done yourself any favors. You could have probably gone without having that resource at all. You just wasted all your time in training someone. So I feel like, I think it matters in every single role, but in any operations role, it's all the more important you have better stickiness in the job.

Sean Lane: The institutional knowledge stuff is no joke. We just did an exercise this week where we were doing an audit of a whole bunch of pretty old fields in our different systems. Don't get too excited, Anu, I know this is some sexy stuff. We were going through this, and for most of the people on my team, they were looking," Okay, this is things we can cut. This is stuff we can cut. This is stuff we can eliminate." And I have to be the one who has to have the institutional knowledge to say," This is the context of why we did this thing three years ago/ this was the partnership that brought it about, and this is the reason why that data might still be helpful to us." But it's also, to your point, whether it's through documentation or whether it's through other means of memorializing that information, we have to do a better job to make that ramp time faster. But regardless of how good you are at that documentation stuff, if you lose somebody after a year, if they've got that great documentation the whole time, it doesn't matter. You still lost them after a year.

Anu Krishnakumar: Right. And someone has to read the documentation. Nobody wants to read the documentation ultimately, right? And I completely agree. And fields is a perfect example. It's something that seems so simple and silly, and then someone who's new to the organization, even that person who spent a year in your organization would be like," Oh, we don't need these 20 fields. Who uses that anymore?" And then you have to come," No, no, no, no, don't cut it."

Sean Lane: Please.

Anu Krishnakumar: Exactly. It can't be understated.

Sean Lane: These ramp times from Anu are a good reality check. Two to three months where you're basically feeling your way through the dark, six months to kind of know what you're doing, and a full year to be a needle moving, contributing member of the team. So what then, if you're listening to this and you find yourself in the midst of this ramp period, or you're feeling as though you've hit a wall in your own growth, how should you assess either the opportunity you have or the opportunities that are being presented to you by a different company? Anu's take is not about titles, or loyalty, or even institutional knowledge lost or gained. It's about what he's been talking about all along, the core purpose of the role itself.

Anu Krishnakumar: What I try to tell people now is do not take an opportunity just because it is a bigger title than what you have now or you're going to be working for somewhere of the bigger title. And it matters in any role, certainly some roles more than others. For example, if someone is going to be, let's say we all work in sales teams. If you're a sales rep, you're going to be a sales rep for the next 10, 15 years, let's say you've determined that. Does it really matter? You go to a company and you hang around for a year, year and a half, and then you jump go somewhere else and do the same, increasing your comp every single time, probably doesn't hurt your career that much. But in a sales ops role, you do that, any ops role, you're probably not going to go down and no one's going to hire you for a leadership role, or people are going to be very wary. Because like I said, the ramp times are so high, no one wants to hire someone who would jump ship in a year or year and a half. It's too much investment. So it's important when people consider those roles, and especially if they're happy where they are, if they don't feel a compulsion, to not take jobs just for a minor comp bump or a title bump. It's better to first discuss with their manager, whoever they report to, what is their career path? And I hope, hopefully the companies especially in a market like this, they take this more seriously and discuss that more proactively. And also if you say," Okay, great. I've done the research. It's a significant compound. It's a good title. They have a plan." Then the next thing to think about is," Okay, do they know what this role is going to be? Or do they expect you to figure it out?"

Sean Lane: I think you're starting to hit on a concrete list of things that someone can actually take away from this to consider. Recognizing you and I's own biases here, you've been at Smart Bear for nine years and I've been at Drift for four and a half. And so we're probably a little biased on how we think about this. But I also think that what you're starting to provide is this concrete list of okay, if you are going to assess an opportunity, and I think assessing opportunities on a semi- regular basis is healthy, then how do you do that? And so you mentioned making sure the role is real and properly scoped. What else would do you encourage people to look for?

Anu Krishnakumar: Yeah. I think who they're going to work for, but I don't mean so much as what title they're going to be reporting into. What is their experience? What can they hope to learn from them? And I think most people in sales ops role, especially if someone they've always been working for, let's say someone for someone like you and me, and they're going to go directly and work for a sales leader. It's very important to see what level of appetite that sales leader has with ops. Are they just hiring someone because their CEO asked them to, and they have no interest in analytics or ops? That would be a rough transition for someone who's always worked for an ops leader. And that's important to consider. And I think the other thing that absolutely in this market goes under, is the stability of the company itself. I know of people, I'm sure of people who move to this other company because they get this big title bump, and then they realize that there's seven other people in the company and that's it, and you don't know when they're going to get the next funding, right? No amount of comp up is material if you're not going to see your next paycheck in six months. And I think like you said, you and I are... Absolutely we have been in the same company for a long time and that's not the norm, but what shouldn't be a norm is people jumping every year or year and half. And that's just not good for anyone involved.

Sean Lane: And I think even too, if we don't look at it from a leader or a hiring manager's perspective, the time and investment that you put into learning these systems, to your point about six months to get pretty good, a year to really be able to stretch your legs in a new role and understand the systems, that's real. And so your ability to then make a needle moving impact on the business, if that's your motivation for your role, you're going to need that amount of time, I think, to make that work. The only way that I've seen people accelerate that, and we've had great success with this at Drift, and I would strongly recommend it to both leaders and individuals who are thinking about this is internal transitions. We've had folks that come from sales roles, from finance roles, who, to your point understand the role that the ops team has carved out within the organization and then thought about," Does that match my own career growth goals?" And you skip over all of the company learning, the institutional knowledge, or at least a good chunk of it, to be able to be a contributing member of the team much, much faster. So I think that's the only real shortcut to that year long trajectory that I've seen.

Anu Krishnakumar: Yeah. No, absolutely. And you and I have had similar transitions. I didn't start in sales ops out of college, right? We all were in sales in some capacity and we moved into sales ops role. And you're absolutely right, that's a good, successful transition. But again going back to just the transition, the time itself, and I think, I believe you are hiring for a leadership role in your team. And when I have to do it again, I would, we all look at the resumes. And the first thing you look at is all the transitions they have had between roles are between companies. How often do you take someone seriously when someone has moved around like four times in the last five years of the career? And I think that's something that lots of people straight out of school don't realize how important that tends to be later in their career. And also, like you said, especially the transition time. And I would think if someone wants to be in sales ops, there are really good career paths. And as long as you make the right move, you give it enough time, and be thoughtful in the move that you make, there's lots of opportunities these days.

Sean Lane: Look, there's no perfect career path. And I meant what I said about bias. The career advice you hear from anyone is going to be given through the lens of their own experiences. But I think that if you take Anu's building blocks here, you assess the core of the role, you're looking at, who it reports to, who you can learn from, and you compare those to the opportunities within your current role, that's a recipe for a decision that you'll be able to stand behind 6, 12, 18 months later. For me, I ask myself three questions about any role I've ever had. Am I learning? Am I being challenged? And am I building something? Now those are my questions, and everyone needs to figure out their own. But if I can answer yes to all three of those, I'm fulfilled in my job. Okay, back to Anu. One of the reasons I wanted to chat with Anu is that in addition to these observations he's made about the market, he's also been exploring an alternative staffing solution. And he's been exploring it for precisely the reasons that we've been talking about, long ramp times, employee turnover, and most importantly, wanting to provide growth opportunities for the top performers already on his team today. And that alternative staffing solution is seeking staffing options offshore. To be clear, this isn't an alternative to having strong career paths for your team members. On the contrary, Anu says that maintaining those career paths is actually a catalyst for this offshore staffing solution. Now, this is the first guest we've had whose talked about going down this offshore path, so I wanted to learn as much as I could about Anu and Smart Bears's approach here and how they landed on this option.

Anu Krishnakumar: I think our thought process now is you are going to need this again, a certain pool of money to go around, and you want to make sure that you maximize that on people who are absolutely impactful. The people who have the organizational knowledge, every other skill that we talked about, right? So you want to make sure that you have these strong candidates locally, wherever your primary location is. And then you want to think about as the team expands, at least the way we are thinking about it now, is as the team expands, we want to put these additional resources in offshore locations. And I think the thought process came from you see development organizations, that's very common, right? And I see in larger organizations where many organizations have this 30/70 split where 30% of their organization, the non- revenue generating resources, sits in an expensive or the local location. And then there's 70% sits in an offshore less expensive location. And the advantage that I see with a model like that is you get to keep your strong, strategic part of your team happy. And I think the career paths are great, but if it's not accompanied by additional money, no one cares about title after a point, right? And it's not just something that you have in a PowerPoint slide. So if people want to have that career path, so now you start investing on these resources, and you obviously need someone as you start to expand all this admin work and fun stuff that we talked about, and that goes to the offshore location. And another advantage beyond just cost. The challenge I have noticed is, increasingly in the States, you could hire someone straight out of school and you could give all this organizational knowledge, they're doing all the admin work, all that. And six months into the job, they want more. They want more everything. And I'm sure you can remember this too. Like when I started, I was probably doing the same thing for two years. There was no other option. And now people are getting bored and there are opportunities, so they could simply jump ship in like eight months. Or it's completely unfordable. You're just giving... You start someone at like, I don't know, whatever number, and then you have two extra salary in less than two years, and that's just not sustainable. But in offshore locations, that money could go much further. Right. And you could keep them happy and keep, retain that organizational knowledge without going crazy on your budget.

Sean Lane: So I think I understand the catalyst for this idea. And I think people listening can put themselves in that same position, and they probably are seeing, and feeling the same things within their own organizations. Once you have that seed of an idea of," Hmm. Maybe there's an offshore solution to this particular problem," what next? What do you even do to start to assess the viability of that potential option?

Anu Krishnakumar: Yeah. No, that's a very good question. And I think it's very important to note that the 30/70 model, the 30% has to be here and you need to have strong managers, leaders, or even ICs in your core location. It wouldn't work for a company, and I would definitely not recommend it, you're going to put your first sales op person who's like in a different time zone 12 hours away from you? No, no, don't do that. That would be a disaster, right? But on the other hand, if you have a core team that is strong and you've identified good leaders, or at least people who would potentially be leaders who can mentor the people you're going to be hiring offshore, then that becomes a viable option. As long as your team, the core team is strong, again no different than what I said before, you got to identify what kind of work we need done in an offshore location, or what kind of work we need done, first of all, and how much of that can realistically go to an offshore location. There is obviously the challenges of time zones, and sometimes language or the ability to communicate directly with stakeholders. All of that are involved. So what portion of the shop job, or the role can be shipped offshore? And do you have strong resources in your code location that can ramp them up, mentor them, and even support or manage them, in the beginning, over time our expectation is we would start to develop a leadership team even the offshore. So the mentorship and at least the day to day management doesn't have to be done out of the core location. Again, a lot of this is theoretical. We are exploring our options. Maybe I'll come back in a couple of years and tell you how it worked or didn't work. But lots of companies have done this, much larger organizations with tens and hundreds of operations people do this now, and they're able to execute it successfully. I don't see any reason smaller organizations cannot.

Sean Lane: So leadership starts local, you ramp up offshore location, and then you eventually develop leadership in market. Is that fair in terms of steps of here?

Anu Krishnakumar: Correct. Perfect, yeah.

Sean Lane: You and I are both in Boston, and so let's consider for the sake of argument North America to be local and everywhere else to be offshore. That's a big offshore. Have you made it to the point yet where you have selected what offshore means for you? And how did you arrive at that decision?

Anu Krishnakumar: Well, I think in my mind when I'm thinking of offshore, at least for Smart Bear, I'm thinking of places like India or Poland, and maybe some other Southern European countries where we already have office locations.

Sean Lane: Got it.

Anu Krishnakumar: Obviously different organizations have different appetite for going absolutely nuts with this different countries. A company that is completely remote and is open to working anywhere might have more options. But also if you think outside North America, if you're going to, I don't know, UK, for example, you're not really doing yourself any favor by cutting down on the cost. So from what I see with other organizations too, usually Poland is coming up as a really strong place for offshore hires for roles like this. India always has been obviously a more competitive market. And then now lots of Southern European countries are popping up to. There are good tax benefits there. So you see lots of good talent moving there, so that's a good place to hire. And I think the advantage most companies would see with Europe is the time difference. But again, it would be slightly more expensive than some of the locations in APAC or particularly more Asia. I think for us at least, because we have offices in India and Poland, it becomes a more viable option. Again, we haven't done a more detailed talent analysis to see what kind of talent we'll be able to find, but that's what we are primarily thinking of.

Sean Lane: So if you're considering an offshore staffing path, Anu and his team have started by first identifying which roles and functions you want to consider. He's also has this general guideline of a 30/70 split with 30% in the local, more expensive location. Now hearing this for the first time, 70% of the team being offshore sounds like a lot. So how does Anu and his team think about standing up a team offshore and making sure that they have the support that they need?

Anu Krishnakumar: We had someone in our team move from our North American location to our location in Europe. We are trying to put more resources in as many places where we have offices as possible. In those cases, obviously it becomes much easier. Now you have someone in that zone, in that time zone. And you start to hire more people, now it's easier for them to start to ramp up people in that location. But you're not going to have people ready to move to Poland or India from North America that often. But if you don't, then the most important thing is, okay, are there parts of the job, and when you're planning, there's so much more work going into the data cleanup, identifying accounts, and just grouping them, and all that sort of fun stuff than the actual planning itself. And a lot of that could be managed offshore. And as long as someone has experience with the tools like Salesforce or Excel or whatever, that's a much easier place to ramp up on. And then over time you can start to, throughout the process, you can start to input some of the other organizational knowledge.

Sean Lane: So if I'm trying to play devil's advocate here and I'm trying to take the other side of this argument, I think one of the things that would give me pause about this strategy would be the amount of time and investment in the documentation, the process, the training that you would probably need upfront in order to pull this off. How do you think about that particular challenge, particularly during the transition time?

Anu Krishnakumar: Yeah. No, you're absolutely right. I think it's obviously easier to hire someone who sits right next to you or at least in the remote environment, in the same time zone. But if you know," Hey, we are not going to be hiring another person for the next, whatever, call it five years, seven years or whatever," then probably it's not worth going to this model. On the other hand, if you know that there's going to be a lot of expansion, you want to have a sustainable team, then the initial effort would be worth it. The first hire offshore is obviously going to be the hardest, because that's where we are. Lots of trial and error are going in. Like you said, the documentation and all of that. But once you have the first person, the second and third becomes exponentially easier. And again, this is all built around the belief, and obviously there's to be enough research to say," Okay, we know we are going to need, I don't know, four more people over the next two, three years. And it's not realistic or sustainable to do that in the core location." Now you prepare yourself for this grind of getting that one person ramped up first. But no, I completely agree with that. It's more about the trade off of the short term pain versus the long term benefits that we're going to get.

Sean Lane: Before we go at the end of each show, we're going to ask each guest the same lightning round of questions. Ready? Here we go. Best book you've read in the last six months?

Anu Krishnakumar: The Five Dysfunctions of a Team, I think highly functioning team. I'm probably butchering the name. I loved it. It's such a fun read. It's a short book. They take this fictional scenario and talk about all the things that could go wrong in a team and how you avoid it. And it's one of the most fun, not fully fictional books that I've read in recent memory.

Sean Lane: Love it. Your favorite part about working in ops?

Anu Krishnakumar: New problems every day.

Sean Lane: Flip side, maybe it's the same answer, least favorite part about working in ops?

Anu Krishnakumar: Well, I guess you answered the question. Yes. New problems every day. I want a break sometimes.

Sean Lane: Someone who impacted you getting to the job you have today?

Anu Krishnakumar: Oh, lots of people. So I don't want to leave anyone out, but pretty much every manager I've ever had.

Sean Lane: Got it. And last one, one piece of advice for people who want to have your job someday?

Anu Krishnakumar: Be patient, know what you really want, and think about what your next, not your next job, but the job after that should be.

Sean Lane: Thanks so much to Anu for being our guest on this week's episode of Operations. If you liked what you heard, make sure you are subscribed to our show. A new episode comes out every other Friday. And if you learn something from Anu today or from any of our episodes, make sure you leave us a review on Apple Podcasts or wherever you get your podcasts. Those reviews really help other folks to find our show. Six star reviews only. All right, that's going to do it for me. Thanks so much for listening. We'll see you next time.