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How HR Can Support a Thriving Inside Sales Organization

By OpenComp


HR invests a lot of passion and resources in supporting people managers across hiring, retention, compensation and more. That’s especially true for sales teams, the revenue backbone of the modern business.

In this podcast, we talk to seasoned executive Jesse Osborne, the VP of Global Sales Development at Tipalti, about what he’s learned about managing successful sales teams in a hyper-growth environment. He’ll also share tips for HR professionals wanting to support thriving sales organizations.

Join us as we discuss:

  • How hiring profiles change as your company grows
  • Tips to develop scalable incentive comp plans and how to measure success
  • Career pathways that empower top talent



CAITLIN ALLEN:Welcome to High Growth matters, an open comp podcast for influential players in the pre IPO ecosystem. This show shares insider knowledge about building a badass business and the expert conversation you're about to hear. We'll cover everything you need to know about hiring and retention, fundraising, leadership, diversity, and more. Let's get to it. Hi, everyone. This is Caitlin Allen, your co host and VP of Marketing at OpenComp.

NANCY CONNERY: And your other co host Nancy Connery. Hello, everybody. I am co founder of open comp and principal at Connery consulting. Thank you for joining us today.

CAITLIN ALLEN: Yes, thank you for joining us. So HR invests a lot of both passion and resources and supporting people managers across a variety of different areas, hiring, retention, compensation, many more things. And that is especially true for sales teams, which are the revenue backbone of the modern business. And so in this podcast, we're going to talk to seasoned executive Jesse Osborne, about what he has learned about managing successful sales teams in multiple hypergrowth environments. He's also going to share tips for our listeners, HR professionals who want to support thriving sales organizations. So we'll we'll dive in Jessie Welcome,

JESSE OSBORNE: Dr. McCaleb. Nancy. Thank you.

NANCY CONNERY: Thanks, Jesse. So Jesse, you had quite a very amazing and interesting career, started your career in Fortune 500 companies that have led sales teams for more than a decade. And for early stage startups. We know how that goes. Some that have done amazingly well, some that, you know, it hasn't gone quite as well. You know, with that said, you know, what are you know, one or two things most of most of your co workers don't actually know about you?

JESSE OSBORNE: That's a great question, Nancy. I don't think anyone except for my dad knows that I am considered I consider myself to be the youngest attorney ever in California. At the age of seven, my dad got a speeding ticket and brought me to court. And when they said Mr. Osborn, your next step, my dad looked at him and said, Your Honor, I'd like to present my attorney Jesse Osbourne. And the judge laughed so hard. The first thing he said was case dismissed exits to the left, and my dad get out of the ticket. So I have 100% win rate. Didn't even pass the bar or anything. But I'm a really good attorney. If you have any one. You have another career, maybe? Who knows. This is just bar one.

Make sure you're paying your sales team well with OpenComp's compensation software.

NANCY CONNERY: That's a good one. Jesse, I will give you that for sure.

CAITLIN ALLEN: That is absolutely hilarious. I don't know why you ever went into sales? Or maybe I should I do understand.

NANCY CONNERY: Yeah, hi. I think it makes sense.

JESSE OSBORNE: Well, I did, I got ice cream after I got to go to the fair. And then my dad bought me ice cream. And I couldn't understand why he was being so nice to me. And I realized now I should have charged him.

CAITLIN ALLEN: It's like the first version of an incentive comp plan. So you currently lead a team of 90 for at least last week, talk to Jesse, three directors, 14 frontline managers, how have you built that team out in what did HR do to support you in that process that you do, including everything from comfort ranges, to target profiles to maybe even running an effective interview process? So

JESSE OSBORNE: so that's a lot, but I'd say it's evolved over time. In the beginning, when I joined here, we had, I think we had about 12 STRS when I joined at tipalti. And I'm not kidding, you were on my very first morning on the job. I lost four people. Four people came up to me and said, Hey, nice to meet you. Today's my last day. I started thinking what did I get myself? I've missed all of this in my interview process apparently. And but it was actually a blessing in disguise because it gave me the opportunity to sit down with the remaining eight. And and those four that resigned as well to find out hey, why are you leaving what's broken here? And, and it really was insightful to see some of the areas and some of the disconnects, I think that had been in place ahead of time, which gave me a true launchpad to start jumping in and fixing things and which included the hiring profile. And and I think partnering with HR on this and, and really taking a note a dive into what we need at this stage. And, you know, thinking about when I had a team of eight STRS here, and we were still very early stage. I think we were just over 100 employees at the time that I joined we're now a little over 1000 year quality. And at that stage, we didn't need executioners. We needed builders, we need to folks that want to be creative and really wanted to test out new things. We weren't looking for robots. And that's evolved over time. And I think that's something that companies have to be aware of is that as your team scales and grows, your needs are going to evolve. And partnering with HR, who's who are the experts at this who really understand core competencies and creating interview guides that can help you lead down that path to identify some of those behaviors. Because a resume doesn't, it only tells a part of the story. And in fact, there were candidates that I would say that we hired here that that didn't look good on paper that had that might have had a few jobs, they'd hopped around. But you know, what we found is that these were some of the most creative, ambitious people that we could have hired, and they weren't afraid to take a risk. And as opposed to someone that we hired, that might have worked in one company for six or seven years, they weren't that risk adverse, right. So. So I think really understanding that not today. And I may not want that builder scrapper as much because we've got a defined playbook and we have robust processes. So we do need folks that are willing to jump in and learn and train and execute. So that evolves over time. And I think that's something that, that you can work with your HR team on really, really closely to constantly do those checks and say, Hey, are we that hiring profile? It's got to evolve. The job description is not something that's going to that's going to be staying

CAITLIN ALLEN: out of curiosity, what were the traits or characteristics that made those folks stand out to you?

JESSE OSBORNE: Extremely inquisitive. And I think I think with some of those creative types, they're going to challenge the status quo, and try to understand the why more so than others. And I think that's something when you talk about curiosity, that's something you can identify in an interview process. The part at the end of the interview, when you say, what questions do you have for me? When you hear questions like, what's the pay? What are the hours, you're not talking to someone who's thinking critically about the opportunity in front of them. And so that's something that I put a lot of weight on in the interview process is at the end of that interview, what questions do you have for me? And when it's when I hear things like, Oh, the other person answered all my questions, or I don't have any or they ask questions that, that that are that are like checkbox questions, as opposed to really thinking about what am I getting into here? And then how can I see myself being successful here? You can, you can see the wheels turning in someone's head. And I think that is so important in the earlier stages, it's still important today, don't get me wrong. But it's a deal breaker in the beginning. As far as I'm concerned, when you're when you're building that team from scratch, or from the ground up, you really need folks that you can say, Hey, what are your thoughts on this? As opposed to them coming to you and saying, Hey, Caitlin, how should I address this? Or Nancy, what should I do? It's more problem solving skills. It's actually how I identified my first STR promotion to I told you that I had a bunch of folks that had left in like in my first morning on the job. And I sat down with the remaining team. And I said explain to me some of the challenges that you see. And I heard kind of the standard the comp plan this and quotas this and process that but there was one SDR that said, she listed all the same issues. But then she said and here's how I'd address those and solve those. And I thought boom, I found the first SDR manager. And, and her name is Danielle and she's now not only became an SDR manager, she's now a senior SDR manager overseeing other SDR managers, and overseeing our entire Europe and North America inbound teams. So this is someone who was just an SDR a couple of years ago, and has just continuously been solving problems over and over again, not had another SDR manager on the team when I joined. And he is just He's phenomenal. He's, his name's Cory. And he he was the sanity check guy, where as I mentioned, these folks were coming and leaving and they were complaining, but he was like the data, the office where everyone felt comfortable going to him. And I think having this this combination of frontline leaders, that one is very tactical and problem solving oriented. And one is like the guy who can go cry on his shoulder, having that element, I think in the early stages and thinking about your leadership team, and what roles they fill and what roles and what holes they can plug is extremely helpful. One of the things we didn't have though, is we didn't have that, but I call it like the playbook dashboard, sales operations person On the team at the time, and and so partnered with HR and talked about some of the holes that I think we had on the on the STR leadership side. And they went out and fine and found the perfect guy, guy named Spencer. And they're still my team today, three years later, three and a half, almost four years later. Now, Danielle quarry and Spencer are still right beside me. And those are my lieutenants. And I couldn't do a thing without them. So this is not about about one person trying to solve every problem themselves. It's about surrounding yourself with smart people and understanding what what they're going to be drawn into. That's one of the questions I love to ask. And it is a good nugget for any leader out there to think about when interviewing. If you're looking for holes to plug on your team. I came up with this question about myself. So since this is being recorded, this can go out to the world. Ask the question, if you had an hour free on your calendar, which a lot of us don't, a lot of us were packed back to back to back. But let's say you had one free hour, what would you do? And it's not a behavioral based question in terms of how have you handled this? Or what would you you know, what have you done in the past on this, but it demonstrates what they're interested in. So for me, it might be I'm gonna go build out a spreadsheet and analyze some data, another person might say, I'm going to get the team together and do a training. And you start to see what people are drawn into. And that's where I think as you're rounding out your team, to start thinking about what are some of the holes that we need to plug when I'm looking for clones here? So that was a long winded answer to your question. But does your sales team trust your pay? Use our compensation software to find out.

NANCY CONNERY: now Jessie, you just gave lots of good nuggets in that answer. And it's very clear that you are a very successful, seasoned hiring manager, and that we would work very well together makes me think back to our early days at Salesforce when we first started hiring salespeople, and we thought, let's go after all the big guns in Oracle, you know, and then they used to Salesforce, and we were scrappy, and small, and you had to roll up your sleeves. And it was really clear that just having a No, I don't mean just they had incredible experience. But having that big company experience did not translate into success at as at a startup, and that you really need, you know, both ends of the equation and that you need to show that ability to be scrappy, that grit, you know, you will do whatever it takes, you know, and wear whatever hat necessary. So we very much speak the same language. You know, and having said that, you know, how has that early profile and process changed as tipalti has grown?

JESSE OSBORNE: Well, I think so I think a good way to think of it is, is building up a playbook. So, in the beginning, myself and my two at the time, Korean, and Danielle said, let's pull the playbook together. And we created Google Doc, and built a table of contents and said, Alright, we got our table of contents, and then we got busy with other things. And long story short, it took us two and a half years to actually finalize a playbook. And actually, in retrospect, I think that was the absolute right approach. Because if you try to over structure in the very beginning, then you're you're gonna you're gonna reduce the amount of creative element that comes into your organization. So not saying process is an important that's not what I'm saying. But it's if you if you have some gray area, then then you're then you start to hire the folks that come in and start to fill in some of that career. And then that turns into your playbook. So I think to answer your question more directly, it's evolved as our playbook has evolved. In the beginning, we didn't have a playbook, then it became a Google Doc with a table of contents, then it was like a PowerPoint deck that just had a lot of unmatching topics and themes, a little messy, but it was coming together. And now it's like this awesome. It's like it's not even a book. It's what's called a rise guide. So it's a link. It's interactive. And it's and it's very scalable, because we can make edits to it as we make little tweaks. But I think that that correlates with the team building to that in the beginning you want to have you want to be building towards that structure, so that you can start chasing the right things and focusing your team in the right areas and create repeatable processes. But if you come in on day one thing, all right, we're gonna take that playbook from IBM or from Oracle and implement it over to Salesforce back in 1999. That wouldn't have made sense, right? But evolves over time.

NANCY CONNERY: And they're with you.

CAITLIN ALLEN: I love it. Jesse in our our prep call, I believe you said you wrote a comp plan on day eight of being at tipalti. That has not changed. So I'm curious to know what is that comp plan and what are you using to measure its success?

JESSE OSBORNE: Yeah, was day eight. And the funny part is that I was sitting at the lunch tables and I saw our CFO walking through the door. action. And I said, Hey, Sarah, do you have a minute? And she said, Sure. And we sat down and wrote the comp plan in about 15 minutes. Now, I had seven days before that, to really think about this. So, you know, it wasn't just coming up out of nowhere, but But to me, it was it's about simplification. And what I found when I joined here, was out of the eight STRS, that were here, from day two to day seven. No one could think no one could explain it to me in an articulate way. And, and that made me really concerned about creating a structure that was so complicated, how to build complex, it is complicated, and there do need to be complexities built into it. But the output of it should be very simple. So what had been put in it was kind of like a half formula. You know, like, I could say, Kaitlyn, your quota this month is going to be 10 plus 20, minus 12, plus 18, divided by three times four times point two, six, or I can just say, Hey, your quarters 12. Right. So just get the output to it. So, so backing into the number, and then figuring out the unit economics that are going to support that does it make sense, is something that I was very passionate about ensuring that they had a very simple comp plan that could be described in two, three sentences. So that they could they weren't thinking about this the whole time, they didn't have to, it wasn't a complicated formula to figure out what's my paycheck, and to be wanting to be really, really simple. So that was the philosophy behind it.

CAITLIN ALLEN: So safe to say then that the stay away from that our listeners should keep top of mind is complexity in terms of things that ideally, a team should be able to say, a comp plan and what it means in two or three sentences.

JESSE OSBORNE: Exactly. Keep it keep it simple. Cool.

CAITLIN ALLEN: And in terms of measuring that comp plan success, are you looking at things like quota attainment, there's something else

JESSE OSBORNE: yeah, quota, we look at quota attainment, but we also change them every year. It's, when I say change, I'm not the formula, but the inputs that go into it. So we created the formula for it. And now it's just a matter of changing those actual numbers in to spit out a to spit out a quota. So if we found that we were that we were shy, for some reason, then we'll update, if we found that we over delivered, then we'll adjust it back down. So but it takes a lot of the subjectivity out of it. And I can tell you this working at working in larger companies, there was no there was no input into the quota. It was just, it was Nancy, here's your quota, your quota is x. And there was no explanation as to why it was just here it is. And so something that I that I really want to understand is walk me through the math of how you got to this number. And the first time I ever wrote a comp plan, I just came up with a random number. And so when you talk about learning from mistakes, this is going back 1012 years, when I wrote my very first sales comp plan, I just took a number that I had heard at my last company, and it seemed reasonable and just took that same number. But there wasn't thought about what are the differences in these two companies. One is a late stage has been around for 75 years, they've got a lot of marketing resources. And another one's a scrappy, early stage startup with 25 people. Right? So just coming up with the number out of thin air is meaningless, you really have to look at, I talked about the unit economics a lot. AES and STRS have to pay for each other have to pay for engineering have to pay for Red Hat pay for all this stuff. So what are those? What are the unit economics behind the quotas? And then are they reasonable and realistic? And then what are the tools and resources that you need to get to those, and that's how it all comes together. So you can't just pick a number randomly. There has to be you have to consider all the different variables and factors that go into it. And then that spits out a number that you don't have to question because you know, what's the right number? It's not a my quote is too high. It's a this is my quota, because this is what we have to do. And it's got buy in. And I think when you explain it to the folks on the team, they understand it. So it's not just hey, Caitlin, you had a great quarter last quarter. Guess what, we're gonna raise your quota because of that. Right now. Like that's like that is lazy quarter building to me. To me it should be able to to be a methodical process.

CAITLIN ALLEN: That's the worst. Yeah, congratulations, you've done a great job, you're going to be punished. No. Exactly.

NANCY CONNERY: And that happens actually. You make your quota, your quota goes up, you know, good luck next time around. And clearly you have a very thoughtful process. But you know, key takeaway also is simplicity and also being able to explain it and then your reps and your hires to really understand it. I've seen a lot of companies where they overcomplicate it, and as a result, it's actually a barrier to entry in the room. recruitment process. If you're, if your sales managers who are hiring can't explain it, then certainly the recruitment team that's not even in sales per se can't explain it. And, you know, I think as long as you, like you said, simplicity, transparency, and that that goes a very long way. That's a great one. And you also previously share, you must have this, you know, magic wand you also previously shared with us, you know, your belief that a big recession is is coming, and a reset. You know, what are you you know, doing to prepare your team? You know, for this, and what support are you getting from the HR team? Compensation software can help.

JESSE OSBORNE: But you want to hear the eternal optimist in me? Yes, I'm excited for this. And and I'll tell you, and I'll explain why I'm excited for it. For those who've been around a while. This is not the first economic downturn that that I'm experiencing. And I can say, with confidence that through the two that I went through, I went through, explosion, and then the oh, 809 real estate mortgage stuff, this is going to make your work, work differently, work smarter and work harder, and I think it makes you better. And so I think we're I think we're all going to get tested in a very good way, I think it's going to help us to think about things like efficiency. You know, if you look at a lot of startups today, it's just growth, growth, growth growth, that's the only metric that folks care about. Now, efficiency is more important. And it's going to make you think more critically, and it's going to make it evaluate some of your processes. And, and obviously, that's only going to make us better. Now, I'm not, I'm not optimistic, I realized folks have lost their jobs, and we're probably going to lose jobs. So that's, that's not I'm not excited about that part. But I think the fast four or 567 years from now, this will become an arrow when everyone's quiver that they'll be able to rely on when they go through another one. And I've got a lot of folks in my on my team that are this will probably be the first one they're going through. And I think the message to them and say this isn't the first one and it won't be the last one you go through. But take advantage of the learnings that you're gonna get from this because guess what, when you get to round two, which might be in I don't know, I'm not an economist, but might be intended 12 years from now, you might go through another one. Guess what, you'll be more prepared? I'm going to if this if we are going into one? Which who knows, right? I'm not that's not my site expertise. But what if we are going to go into one? I think it's more about the mental preparation than anything.

NANCY CONNERY: Yeah, no, I I completely agree with you. I've been through the same downturns the you have as well, and turn them into opportunities to really learn. And, you know, when it comes around, again, which it seems to be knocking on our doors, you know, how are you prepared? And how do you come out stronger on the other end? And also having a team where many or maybe all of them have never seen a downturn? How do you turn that into a positive positive learning aside from of course, like you mentioned, the folks who have lost their jobs. What is it, I

JESSE OSBORNE: think acknowledging it that it's in the moment, it's terrifying. I mean, I remember in the oh, 809 downturn, the company I was working with, at the time, they had a, they had a conference call every Friday. And this was terrifying. And every Friday, they would announce the names of the people that had been let go. And, and if you got invited to that, you are so happy. Like, oh, great, I got the calendar invite. I'm not one of the people getting cut, but oh my gosh, my friends might be or my peers might be in it. So it was in the moment. It was It was horrible. But but you know, like my, like, some good advice I've had is maybe thing things are usually worse in your head than they are in reality. So things can be a blessing in disguise, you never know.

NANCY CONNERY: Yeah, no, I hear you on on all of that. And I wholeheartedly agree. You know, during during previous downturns, you know, where have you seen HR miss in supporting you and your teams?

JESSE OSBORNE: So sorry, I worked in HR. Back in the Oh 809. When I was in talent acquisition, my manager was the director of HR. So I was very involved in some of those conversations. And so I felt very supported. But I think I think that's the opportunity for HR is to is to is to convey some of that. The sense of calm that they can that they can bring out there without sugarcoating things, right? Because it's a very dig tricky time right now. I mean, I I'm glad I'm not an HR trying to figure out COVID protocols. I mean, that is going to be just a nightmare trying to figure all that stuff out. And because you're never going to make 100% of the people happy. Whether you're whether you're doing a hybrid environment or remote environment, you require mass vaccinations, all that stuff. You're not going to get to 100% of Belize. I don't think so. Out of your of your population all being happy and saying, Great, we're all making the right decisions, you're always gonna have people second guessing you. And that's where I think HR can really step into to provide that that sound calmness to say, hey, we don't have it all figured out. We're we're just people. We're trying to figure this stuff out, too. And I think if we can humanize it a little bit, I guess that's why it's called Human Resources. is I think I think that's the win for them.

NANCY CONNERY: Yeah, very well said.

CAITLIN ALLEN: It is just a thank you for this conversation. It's been wonderful. The examples in particular have been very evocative. As you know, we're talking to HR leaders, if there's one thing that you could ask them to remember from something you said or that you want to still say, what would it be?

JESSE OSBORNE: Encourage your team to keep it simple? You know, I think even when it comes to hiring, I think sometimes we try to overcomplicate the interview process, or the interview guides are the competencies and sometimes it doesn't resonate as well with the field. So I think trying to try to stay in touch with your frontline leaders to to bridge to build that bridge. While they want to keep it simple, you might want to make it more complicated. So trying to find that middle ground, I think is key to good partnership there.

CAITLIN ALLEN: Keep it simple.

JESSE OSBORNE: There you go. Well, thank you just like the comp. Exactly.

CAITLIN ALLEN: Well, thank you, Jesse, we have really enjoyed,

JESSE OSBORNE: thank you.

CAITLIN ALLEN: When top talent while strengthening runway with open comp 1000s of the world's fastest growing companies use our compensation intelligence platform because it offers the most competitive benchmarks and insights available. To learn more visit app dot open up thanks for listening to high growth matters and open comp podcast. Stay connected with us by subscribing to the show in your favorite podcast player. And if you like what you hear, give us some five star love so we can keep serving up the latest info to help you keep building a badass company. Until next time.


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