The First 100 Days as a Sales Leader for a High-Growth Company with Jesse Osborne

Jesse Osborne is the Senior Director of Sales Development at Tipalti. He joins host Nelson Gilliat to share his insights for newly-hired revenue leaders and those considering leaping into the startup world. 

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The hosts:
Trinity Nguyen
Christian Kletzl

When Jesse first started at Tipalti, he knew there were opportunities to address when he discovered his CEO reading the sales outreach emails. In this episode, you’ll hear how Jesse took action and created a system to maximize SDR opportunities. 

Jesse has worked for both large and small companies in his career, and he draws on that experience to break down how to plan your career based on different company sizes. Most importantly, what to do before you start to succeed from day one.

What is Jesse’s advice for anyone transitioning to a startup?

  • First, dig into the data.
    Before I even started, I called our sales operations leader and said, is there any chance you can give me access to Salesforce before I start? I want to spend two weeks just. I want to look at conversions. I want to look at metrics. I want to look at the leaderboard. I was really curious to kind of get my head around some of those metrics and come up with some theories before I came on board.”
  • Expect the pace to be (a lot) faster.
    At a bigger company, you might say. No, I'm going to come in and observe and just not make any recommendations. And then month two, I'm going to start shadowing. And then month three, I want to start to show results. No, you got to show results month one, right? So you have to work fast.”

In this episode, you’ll learn:

  • How to make the jump from a big company to a startup
  • To maximize your opportunities with leads. 
  • The importance of knowing the “why” behind the data
What to listen for:
  • [2:05] What should you look for in a future company?
  • [7:56] Why you should prioritize your most senior SDR’s.
  • [12:03] The best compliment a CEO can give you.
  • [13:08] Advice when moving from a big company to a startup.
  • [16:58] Recap with Nelson and Trinity.
Reference Links:
Guest headshot

Jesse is an experienced sales leader with a passion for building and leading high performing sales teams.

Read Transcript

Jesse Osborne: Vol or the saying what's your 30, 60, 90-day plan. But the reality is all the stuff that you have on day 90. They want by day 30. 

Nelson: Welcome to The First 100 Days, a show for revenue practitioners, by revenue practitioners, giving you unscripted access and exclusive resources to help you navigate any new transition or initiative.

I'm Nelson Gilliat. And I'm your host for this episode today. I've got someone really special. I've got Jesse Osborne, Senior Director of Sales Development at Tipalti, an accounting software company for accounts payable special, not only because Jesse killed it on this podcast. But also because DePaul too was a former competitor of mine.

When I used to work at Western Union, formerly sworn enemies. Now we meet as friends. Jesse shares a number of insights for revenue leaders that are newly hired or thinking about making the jump, whether that's how and why you should plan your career for different company sizes, to what to do before you even start in your new role to help smash.

They want. Jesse, thank you very much for joining us, thrilled to have you on. 

Jesse Osborne: Nelson, thanks for having me great to be here. 

Nelson: Jesse, can you tell us a little bit about yourself? 

Jesse Osborne: My journey I, I spent, um, worked for a handful of startups. Some worked some didn't and about two years ago, I thought, you know, I've got this really good experience at about five years, working in software and growing teams from a team of one to two, a team of 40 at one company, uh, and putting everything in place, writing the comp plan, implementing Salesforce, documenting every single process and creating that playbook.

Building out a career path. All of that stuff was really fun to be at the helm on that, but I wasn't working at companies that were necessarily a rocket ship in that sense. And so what I really wanted to do was find a company like Tipalti record, package that up, and say, I know I've got the experience building.

Now. I want to align myself with a company that's got a really bright future. So coming on board here, I saw a company that had been doubling every single year for the past three years. And for all intents [00:02:00] and purposes was a rocket ship in the making, but it wasn't there yet, but I think that's really, really important as folks are out, looking at new opportunities to really size up, uh how's that company what's that recent trajectory been.

Have they been growing what's that growth look like who's in charge of the company. And the last thing that I looked for that I thought was so important was what customer churn looks like. Sometimes you can get a little lucky, right? You, you gotta, you got a product that. Uh, the, the flies off the shelf.

It doesn't matter if you've got good processes, you got good leaders, you got good people. Sometimes you've just got a hot product. Now, what I was able to quickly identify, in my opinion, as a faulty was there was a lot of room to put structure and organization into the SDR team. All of the sales leaders here said the same thing.

We need more pipeline. We need more pipeline. And in my head, I just kept thinking, how do you scale then? Right? How do you scale this, uh, with, with the current processes? So I think if I, if I were to give advice to anybody, looking at joining a new company, taking on a new department, uh, the first thing I did was sick my teeth in the data.

That's the very first thing I did before I even started. I called our sales operations leader and said, is there any chance you can give me access to Salesforce before I start, I want to spend two weeks just, I want to look at conversions. I want to look at metrics. I want to look at the leaderboard. I was really curious to kind of get my head around some of those metrics and come up with some theories before I came on board.

Nelson: If you can remember, I know it's probably been a while since you started, but what were some of the data points that stuck out to you and, or what are some of the things that people should be looking at? And then what are some of the solutions you recommend that they, you know if they do see certain common data points that would raise a flag and say, okay, that that needs to be addressed.

Jesse Osborne: So with, with leads, I think every company needs to know what is the ratio of inbound leads per SDR. No, I think that's a really important ratio to make sure, because I, at the time our marketing team was generating about, I think it was close to 2000 leads a [00:04:00] month, the inbound team. So they were getting these 2000 leads.

So that's about four or 500 leads. A piece is what it worked out too. And, and the question is, is that the right ratio? Is that a, is that too many or is it not enough? And, and the reason I say is it not enough? Uh, the first thing that I did was I wanted to dissect. Let's break. These leads out, not every inbound lead is the same.

Sometimes an inbound lead is someone who's raising their hand and saying, I want to get signed up right now. And if you wait more than 20 minutes, in my opinion, to respond back to that person, you're dead. Cause they're going to call your competitor. They're not just going to, they're not going to reach out to you.

They're going to reach out to you amongst others and. So the question is, how many of those do you get a month? And, and do you have the capacity to make sure that your, that your SDRs are, are able to respond accordingly? Uh, so when, when I first heard the number, the ratio and someone on our marketing team said, that's a really high ratio.

And my response was, well, I don't know if that's a high ratio or not because what I want to see is how many of those are actual hand-raisers. So what we did was we broke out the leads, into two different buckets. And, uh, we called one group, uh, what we called high intent. And then I called the other leads, low intent.

So high intent, uh, these are the leads that, that are proactive. They filled out a form online, the proverbial like I want to hear more. The low intent leads might be someone who went to a webinar. That doesn’t mean they're interested in buying to Baltic. So you can't say that lead is the same as somebody who is currently using one of your competitors and the contract's coming up and they're looking to evaluate new companies, then they fill out a form on your website and they want to hear more.

Those are two totally different types of leads. So what we did was we broke those into two. I had built our ratio, our headcount ratio. Based on how many of the high intent leads do we have and then how many inbound SDR is do we have? And from a planning standpoint, that's why I say it's important to understand the data.

We could go back in time and they weren't tracking high and low intent back before I started. So I was able to look back in the historical data to separate. Okay. What is the high intent? What are the low intent leads? How many inbound SDR did you have in that particular month? And then how many opportunities did you create?

And w there was no surprise therein, in the month where there was a high volume of low intent leads. Uh, there weren't as many opportunities, uh, but it, it really slowed the inbound team down because they were treating every lead the same. So there were months where SDRs were just cherry-picking and going, yeah, this isn't a good lead.

I'm not going to waste my time, which is not good because. Some of those low intent leads may actually be good. Right. So it's really about trying to science that ratio and look at what is the optimal ratio that you're looking to try to get. So right now we've got, we've got our ratio down to about 200 high intent leads per inbound SDR.

So next year when my marketing team says, Hey, we're going to [00:07:00] double the number of leads. Then we sit down and say, okay, what percent of those will be high intent? Right? And then I go, and then I take that number. Uh, it's usually about half roughly, uh, so if half the leads are high intent. And then I divide that by 200 and that gives me my target headcount if you will.

So that's how we can be a lot more prescriptive in how we grow the business. You don't oversaturate, you don't have too many resources on low intent leads, but you also have enough on there to where you're not losing out on good, hot leads that are coming through. 

Nelson: Did you guys make any tweaks? Uh, in addition to headcount around like the nature of these leads to make sure that they were working different types of leads.

Were there any changes there as well? 

Jesse Osborne: Yeah. So this was another really good data story. So what I did is at the end of last year, I looked at, I looked at all the leads. I went to all the SDRs and I broke out every SDR. How many high intents, how many low intent leads did you get? And what I found was on the high intent leads.

The more [00:08:00] senior SDRs, we're converting those at a much higher rate at the low intent leads. No matter what the tenure of the STR was, they were all converting around. It was like, it was like 0.8%. It was less than 1%. So what thought would that made me stop and think about it all right. I'm trying to get the most opportunities out of this pool of leads every month.

So what we did was we created two teams. So we have a low intent team and then we have a high intent team. And the idea is that the high intent team they're going to make more, uh, out of these leads because they're more senior. They, they have a better eye for like when that lead comes in to know, okay, it's not just high intent.

This thing is smoking hot. They're faster, they're more efficient. So they jump on that quicker. They also are going to have more intense conversations with inbound leads to the product. So what we found was having new folks get those high intent leads. Yeah. They converted some, but they were converting somewhere around 3%, three or 4% were converting to opportunity.

Whereas, whereas a senior SDR, they got a high intent lead was converting about eight or 9%. So in layman's terms, it's kind of like, you want all the good leads to go to this group. Cause they're going to get more out of it. So what we did was I thought this was genius. We created a career path for inbound SDRs and said, when you start as a new SDR, we're just going to give you low intent leads.

These are the, have the least chance to convert, but we also have the least expectation out of these. And it's a great way to have a new person come in, learn the business, not have as high of a quota, right. Because there's not as much pressure to convert these, but they're competitive and they're driven and they want to try to get as much as they can.

So that's generally about three to four months. If they just work, these lower intent leads. And then, then we turn the spigot on and give them the high intent leads after that. And they're converting better because generally for us, it's about four or five months or so that it takes someone to get fully ramped up and running full speed.

So I'll put it like this, I'll leave it at this. We're getting about the same number of leads every month that we got a year ago, but we're getting twice as many opportunities out of those today than we were when I started. And after a year or so of working on the inbound team, that's when we moved people into the outbound team by then, uh, they've spent a year on the inbound team.

They've talked to every inbound, you get all shapes and sizes, right? You get, you get to in our world, we're selling to the finance world. So we'll get CFOs that submit a lead. And we'll get finance interns that submit a lead, right? So we're talking to all spectrums of the org in all different industries and all different parts of the world.

So from an optimization standpoint, that's, that's where the data really helps to try to science. If you've got so many resources, how do you put your people in the right place to get the most out of it? How do you get the most out of the inbound leads and how do you most effectively position your outbound team? Ultimately we're all trying to support the account executives and get them more opportunities.

Nelson: So when you looked at this data and you came up with these insights, what was the response when you, when you sort of peel back the layers a bit and you wanted to implement these changes and reverse course, were there any hurdles that you had to overcome there? 

Jesse Osborne: A few, but again, that's why data when you can present data to an exec team in an articulate way and say, say, look, we've got, we've got new outbound SDRs that aren't generating ops for their first three months.

They're getting nothing. It takes them three months to get that first opportunity. That's two full months where you've got someone on the books it's producing nothing. So being able to present that data. It was actually, it was, I wish I could say, yeah, everyone looked at me crazy, but being so data-driven and presenting that data in a meaningful way and then saying, here's what I would project that we will do by flipping it.

And then, and then getting the green light to say, okay, well, let's go that direction. But that's where the pressure is to execute. Right. Cause if you don't show those improvements, then someone above you is going to come in and say, Hey, your plan didn't work. But [00:12:00] I, I don't have anybody here, uh, telling me my plane doesn't work.

In fact, my third day on the job, the third day, the first email from the CEO. Hey Jesse. Welcome to the team. Next paragraph. By the way, I've been reviewing inbound SDR emails that they're sending. They're not very personalized. They seem to be just kind of spamming people. Can we work on this? And in my head, I went, wow.

My CEO is spending his time, reading SDR emails. This is broken. I talked to him a couple of months ago. We had a one-on-one, our CEO and I, and, uh, and I said, Hey, are you still reading STR emails? And he said I haven't thought about SDR emails in a year. Thank you so much. And that was like the best compliment I could get back.

Nelson: Another question. I think the audience might want to know who is making this transition from the big companies to some of the startups and then eventually to Tipalti, who was maybe in the taking off phase in that sort of transition, is there something that the audience should note when you're [00:13:00] thinking about making a move from a big company to a startup or some challenge there to kind of keep in mind and how to handle that?

Jesse Osborne: Yeah, the best advice I'd give somebody who's coming from a big company into a startup. I expect the pace to go three times faster. And I say three times faster because at a big company if we've all heard the saying, what's your 30, 60, 90-day plan, but the reality is all the stuff that you have on day 90.

They want by day 30. So, uh, at a bigger company, you might say. No, I'm going to come in and observe and just not make any recommendations. And then month two, I'm going to start shadowing. And then month three, I want to start to show results. No, you got to show results month one, right? So you have to work fast.

You have to work and, and, and working, working with tools that are gonna help you to be more productive in making recommendations. Now I'm not saying come in with a pre-packaged plan. I think that's. Uh, that's, that's the opposite of, of a good approach to coming into a new company and saying, here's what we did at a big box company.

It'll work as a small startup. Uh, you gotta, if you're coming into a leadership role, I got to get buy-in from the team you got to get. Uh, you have to pick their brain on what's working. What's not debit as far as delivering and executing that that's, that's gotta be a mindset, uh, right away. 

Nelson: Things move three times as fast in the startup.

Right? So being able to come in there and deliver much faster, you don't have the luxury of time, 

Jesse Osborne: but, and our resources. So I remember, uh, not this company, but a different company. I had to build collateral and, uh, I was going to send out this big email and I wanted to build some collateral to go with it, but there wasn't any pre-built collateral.

So. Uh, in order to get this, this email blast out on time, I had to build the collateral and then get the email blast out. Right. So it's a, it's three times faster because you're doing a lot more yourself. I've been at the startup game now for. I guess what eight years now? Seven, eight years now. And I've just, I've seen [00:15:00] a lot of people come in from the big companies and, and not to say that they can't succeed because I came from a big company, but it is a transition.

It's a, it's a transition, not just in pace, but in mentality I had the mentality of, there is no way you are, they now you've got to own everything. 

Nelson: Was there someone or something that helped you kind of navigate that? 

Jesse Osborne: So my first startup boss, if you will, uh, He, he really opened my eyes to, to I'll say, to understanding the why behind certain data.

And this was, this was opening. And this is probably going to sound very sophomore to a lot of folks that are listening to this, but at a big company, your boss, if you're in the sales world, they're going to tell you to make X number of calls every day. Why? Because if you don't, you're going to show up on a report and you're gonna be in trouble.

My first boss, when it was just me and him started at this company, he was like VP and I was sales manager. Right. And we were a two-man show. Right. Uh, but we worked out theories about how many calls and all that stuff we should make. And we [00:16:00] backed into the number from the result we were looking to get to.

And, uh, and it really bought me into, okay, this is why we have to do this type of volume. This is why we have to do this. And I've taken that with me to every team that I've built, that I want everyone all the way down to the SDR level. I want them to understand the why behind, why we're asking them to do this, not just, Hey, you need to make X number of calls every day.

Uh, what I'd rather position it in terms of, Hey, here's, here's, here's the volume of activity that we've seen people do, uh, that have been successful. I'll show you how they got there. Let's back into it, and it gets a lot more buy-in from those folks. And I think it becomes less of a do it because I said so attitude.

But like who wants to work for that person? Not me. And I've run a mission together.

Nelson: That was Jesse Osborne from Tipalti. What did you think Trin? 

Trinity: I love that episode. I think a lot of the details of stories he shared are so helpful because he got into the details and he was very specific. I absolutely love the part where he said, the first thing you gotta do when you start a new job in sales is just to look into the data, dig into the data, slice and dice it.

And I think it's, it speaks a lot to the statement that people usually say sales is part art and part science. And we, we all heard of the art side, but he really double-clicked on the science and I was awesome. 

Nelson: Yeah. I thought that was really important too. You shouldn't wait. Until you like day one to get access to the reports and to the data and to the metrics, you know, try and get early access before even starting the role.

So you can analyze come up with some recommendations and then come prepared with a plan and recommendations on day one. So, you know, first of all, You know, you feel more confident because you know, what's up and then you're really excited because you have some cool ideas to share and you make a big splash and that's what leaders want.

Right. You want to make an impact and [00:18:00] instill confidence and that right. The first impressions matter, you come in the first day or so. And you're like, uh, okay. No, I'm not really sure what, you know, people are like, Hmm. All right. You know, but you come in like that people will be like, wow, this is great.

Especially as a leader, as, as your people are, you know, especially above and below, right. You have to manage up and down. They're all kind of looking at you, you know, and they want to make sure that you have your head properly on a swivel. So I love that recommendation. That's 

Trinity: a good point. A lot of times people talk about finding the next rocket ship and men one out of millions of startups fail at some point because it's just so hard.

So his advice of looking at the customer retention, or you say like customer churn rate helps you identify whether the product has found its product-market fit. And if that's the case, then at least your decision is now backed by. Some kind of data instead of just, Oh, I feel like this company is going to be the next rocket ship.

It's now like the market has spoken, there is a need for this product. So this startup has a higher chance of success in the future. So I think that's good advice that he shared.

Nelson: Yeah exactly. It's like relationships. If you see that someone's not lasting the relationship for very long, it's kind of like raises some questions you want to see long-term right.

Trinity: If I had to sum up for Jesse, I think I love his approach to solving problems. So he's very structured. Like the way he thinks and his approach to everything, like he wants to optimize everything and he wants to use data to optimize them in his methods are so structured. And the thing, if I wasn't gonna listen to like an episode of podcast or listening to someone adviser.

I always think about what's in it for me. Like what can I take away from? And the weight hate approach, even though it's in sales, it's just so relevant. Even other professions, right? Like, just look in the data, don't use any kind of like anecdotes look into data and then you find gaps. So now you have data to back your recommendations.

And then from there, you can optimize it. Like we usually say like what's measured can always be improved. What's not magic will never be improved. So he. Always set out to measure the baseline and then make improvements based on that. 

Nelson: I don't know Trinity, I measure my waistline, but there's no improvement ever.

And then the other thing. It is for the people that you're leading. He said because of my data-driven approach because I look and try to understand the why behind doing things and back into things and say, okay, we have these goals. How are we going to get there? We need to take X, Y, and Z steps. He then communicates that to the people.

On his team for them to, you know, to follow. And he doesn't just say do it because I say so, but he says, you know, here's how I arrived at this, and that instills confidence. And I think people that we’re more likely to follow you in and do what it is that you're asking of them and everyone's then hitting their goals.

Everyone's aligned. So I, I think. That as someone who can emulate Jessie's approach, I think you'll find those type of feedback, that those type of benefits at the end of the day,

Trinity: are you going through a major transition within your organization or your career? Do you have a first 100-day journey to share recently on the past? If, yes, I want to hear from you email me at podcast@usergems.com. And if you're looking for the ultimate revenue leader cheat sheets, sign up to receive them at usergems.com/podcast.