How to Win Big as a Sales Leader!

In developing a framework, I tried to adopt a classic sort of Boston Consulting type matrix where it just made it really simple. And in my own experience as moving into a sales leader, there was the expectation that you would be primarily a super salesperson and someone who'd go in and help, you know, close and win the big opportunities. And whilst that's a very important part of what You do as a leader, it's by no means your priority. And you know that particular persona, the super salesperson, as I'll go through it, is yes, it's very effective at specific points in time, but it doesn't allow you to grow and scale the business. And so when sales leaders first get into the role, you know they're rewarded and applauded for being that super salesperson.

This is your host, Preeth Sarkar, sales leader turned top 1% recruiter. Every single day I meet really interesting people. So today our guest is Jason Leonidas. Jason is the VP for ANZ and ASEAN at New Relic. He has had a significant career in the software industry, and he leads a team of sales managers and sales reps across the region. He shared with me in a recent conversation how he coaches and mentors his sales managers, often promoting people from within, and how he has built a template around the 4 types of sales personas. They are number 1, the super seller, number 2, the business manager, number 3, the evangelist or the thought leader, and number 4, the team builder. Each one of these quadrants provides significant benefit to the manager and the team. And that's how he coaches them to grow in each of these areas. So today we get into a terrific conversation on what these quadrants are, what do they look like, and how can you grow in each quadrant. And when they come together, the magic happens. So let's jump right in. Jason, thank you so much for joining me today.

Good morning, Pri. Excited to be here.

Fantastic. Now, for context for the listeners, uh, Jason and I were having a conversation and he was talking about how he likes to coach, onboard, and develop both sellers and leaders. And he talked about the 4 types of salespeople. And I said, oh, I'd love for you to share this on the next episode of my podcast, because I think it's gonna be super useful both to sellers who wanna be leaders as well as leaders as well. So Jason, before I get into the 4 sales personas, tell me why, you know, what is it that has driven you to create some of these slides and ensure that you set up people for success?

Yeah, thanks, Priya. And I really appreciate the opportunity to share some of this stuff. The obvious thing is organizations are really good at doing onboarding and they onboard typically around products and solutions, but they typically don't onboard well around soft skills. Particularly as you develop future leaders and they get promoted from being individual contributors to leaders, there's certainly very little onboarding or structure around on how best to do that. One of the biggest challenges is great salespeople don't necessarily make great sales leaders. It doesn't mean they can't, but if they're not well equipped, then, you know, they're likely not to succeed. So as I started bringing on individual contributors and and developing them as sales leaders, I needed an easy framework in which I could share, you know, my experiences, but also help them focus on what their core priorities were.

Yeah, that is exceptional. And it's very insightful because like you said, 99 out of 100 times onboarding is mentioned, it is about products. It is about solution and value proposition. It is not about how do you get this person to operate at the next level in this role? So, thank you. Tell me a little bit more about the 4 sales leader personas.

So, in developing a framework, I tried to adopt a classic sort of Boston Consulting type matrix where it just made it really simple. And in my own experience as moving into a sales leader, there was the expectation that you would be primarily a super salesperson and someone who'd go in and help you know, close and win the big opportunities. And whilst that's a very important part of what you do as a leader, it's by no means your priority. And, you know, that particular persona, the super salesperson, as I'll go through it, is yes, it's very effective at specific points in time, but it doesn't allow you to grow and scale the business. And so When people, when sales leaders first get into the role, they, you know, they're rewarded and applauded for being that super salesperson. So they gravitate towards it. It's very natural for them. It's very comfortable for them. They can go in and help the sales lead, a sales account manager or sales representative to be very successful. But, you know, is that, are you teaching them or coaching them? And so, you know, are you doing it for them or you are empowering them to do it themselves next time? So, I frankly, when I started in my first role, that's exactly how I felt, that the pressure was on me to go out and drive and grow, you know, deals. What I didn't realize is where you get the most value is empowering your team, putting your team first. Recruiting well, enabling them, and getting them up to speed to be outstanding sales professionals. So I started thinking about, well, how do I do that? How do I create great salespeople? How do I create high-performing sales teams? And that's all about empowering them and what are the core skills they need. So I mean, so when you look at the value versus scale equation that you see on the matrix, The most value you get is, you know, leading, coaching, and mentoring a team to go from good to great. And how do you do that? Well, you instill, you know, an element of professionalism. And like any other profession, sales has got science behind it. It shouldn't just rely on natural ability. There are methodologies, there are processes in place that enable you to be far more successful at selling. So examples are MedPic, Challenger Selling, which has been my favorite and probably the most influential in my career. SPIN early on was a great one. You know, it's, you know, those methodologies are really important to develop salespeople as professionals, like any other profession, whether it be accountants, engineers, Any any profession, right? And I often have a I often have a favorite saying in that you know if engineers built bridges like salespeople sold, there'd be fatalities every day of the week. So you know I'm really passionate about you know how do you get to the end quarter end of the quarter and deliver the revenue with some science and engineering behind it. And the way we do that is by you know driving an element of profession and professionalism and pride in what the salespeople and the sales leaders do.

Yeah, look, I've actually just in the last 2 weeks spoken to a sales leader who has inherited a team where the previous sales manager was a super seller. And they're seeing behaviors where The enterprise reps are waiting for the sales manager to go and do something for them, or to close things for them, or to front up to this meeting. Whereas, which means that they're probably the busiest person in the team. Whereas enterprise reps, you know, are probably more like people who are setting up the meetings and you know getting the process work done. And what they've said. is that what these people really need to go to the next level is actually exactly what you're talking about here, which is that team builder, coach, mentor. So we've, you know, we've got this slide up on the screen for people to take a look at. But so you've got, you know, at level 1, which is the super seller, but then if you go up on value, you've got the thought leader. So tell me a little bit more about the thought leader, and then I'll come back and ask you questions about business manager and team builder.

Yeah. So the thought leader is incredibly important because it's what gets you in front of strategic customers and even partners. If partners are an important part of your business, it enables you to go in and differentiate your solution and your offering. And the way you do that is because you get across as a manager, you get across a lot more accounts And a lot more customers at a senior level, and you're able to elevate the discussion into a value discussion as opposed to typically what we see the sellers and the presellers doing is a lot more speeds and feeds. So it is really important. I think the most valuable thing you can do as a sales leader is drag out the value piece when you're going through your your sales process because. Again, typical IT firms, software companies, US-based particularly, all the marketing and talk track is all around features and functions. And people don't buy features and functions. We need to link that to value. And as a sales leader, you need to be able to turn those speeds and feeds into a value statement or value statement specific to that customer. So, being able to be that circuit breaker almost or that individual that comes in and lifts the conversation is a really important part of what a sales leader does because customers and business partners, for example, resellers or system integrators, they have existing relationships, they have existing technology partners. Why would they, you know, why do they need to establish yet another relationship with you? And that only comes about by attaching to business value. So, how are you impacting your prospect's customer? If you can articulate that, then you're likely to be far more successful. And so, I see that as a really important part of what a sales leader does is to help elevate that discussion out of the technology.

And just like you said here, going back through my first 7 to 10 years as an AE and a sales leader, I was always drawn to people who can lift the conversation to that next level, you know, and then looking through a lot of the sales leadership hires again, people who can elevate the level of the conversation. You know, you've got obviously dedicated value engineering practices on one hand on the pre-sale side, but having a leader who comes in that. can lift the conversation is critical. So I think that would basically take the whole team and not be dependent only on presales or someone else's job, but basically every rep that's talking to customers, that would immediately impact them. I can see that very, very clearly. Let's transition to the business manager. What does the business manager look like? What do they do?

On the scale piece, the business manager is someone who is well across the financials of their business. So, what does that mean? You know, what's the size of the account base? What's the size of the total addressable market in your territory? You know, they're looking 1, 2, 3 quarters out to look at pipeline. They're looking at pipeline progression. They're looking at pipeline build. These are really important vital signs of any sales business. But, you know, it's really important to get, you know, that in a consistent and repeatable manner. You need to be able to get in, you know, for an hour or 2 on a Monday morning and perhaps an hour or 2 on a Friday morning and look at where the business is at and measure the business in terms of how it's performing. Why? Well, you need to be able to commit revenue, and that's a really important part of what any sales leader does is committing revenue and delivering that revenue at the end of the quarter consistently. And so what you have to do there is you have to be very disciplined and very consistent and get across the detail in your business. But again, the flip side of that is, you know, we've all had, you know, the stories about, you know, they're a spreadsheet manager, and that's because there's so much pressure brought down from Sales operations and finance to be across the detail of every, you know, of every minutia of your business that it can consume you because that's where all the pressure is coming from. So as a sales leader, you need to cut, so almost compartmentalize it into sort of short bursts, very effective focus bursts during the week to deliver on those, on that sales cadence and that forecasting cadence that you absolutely must do. But you can't let it become the predominant part of what you do because, at the end of the day, reporting internally has, whilst it is an important function, really doesn't deliver value in terms of sales and sales revenue and building effective sales teams.

It's interesting you say that because I've been speaking to some people lately where on 3 occasions sales leaders have moved someone out in the organization because they've missed forecast on 3 occasions, 3 quarters in a row. And often it was a lack of detail. It was not being the business manager. So it's interesting. I'm certain that there are people who come into sales leadership with strengths in one area versus the other, natural preferences of either being the super seller Or being the team builder, and yeah, we're going to get into that in a moment around how to you know play to your strengths, but also compensate for areas that you might be overlooking. But let me ask you about the fourth one, and then we'll come back. Tell me more about the team builder, coach, and mentor.

This is by far the most important function that you do, and you hear lots of you know TikToks and you know Instagram. you know, short videos where people talk about, you know, you hire smart people, smarter people than you. If you're the smartest person in the room, you're in the wrong room. And that's all absolutely true, but how do you put that into practice, particularly in a sales team? You know, especially if you're a new sales leader coming into the role, how do you look at other enterprise sellers, for example, and say, well, look, They've got enormous experience. How do I? How do I coach them? How do I make? How do I take them from good to great? The minute you're great, you go back to being good again, and you've got to continually improve. The market is changing. The market is constantly evolving. The expectation on sellers is constantly evolving. So how do we get seasoned sellers to become even better? And you know. You know, being able to recruit and build the right team. How do you take a person who was a brilliant seller and turn them into a brilliant recruit recruiter? How do you get them to hire well? That is probably the most important thing you do when you're building out a team is to hire well, build a you know an a world-class team with you know the right qualifications, skills, and and character, frankly. And so how do you then, when you onboard those new sellers, how do you make sure that the skills you went and recruited and hired for don't get caught up in your current culture? How do you make sure that those great skills that you deliberately went out and recruited for get maintained and flourish in their current role? So, You know, understanding, and as a new leader, they're going to come on and you're going to do a lot of teaching. But how do you quickly evolve from teaching, this is how you do stuff here, to how do you coach them to apply their experiences and the way we do stuff here to be successful in their new role? So, you know, the more time you spend in developing great salespeople, the less time you have to spend on being the super salesperson, you can— the less time you have to spend on being the business manager because they're going to do their account plans, they're going to automatically do their med pick reviews, they're going to automatically apply that med pick to the deal that they're working on, and they're going to get access to the economic buyers and the champions. They're going to understand the impact of the pain. And so your results will improve dramatically if you get that recruiting and sales Mentoring piece, right?

Yeah, I'm just thinking as you're speaking about so many different situations where the maximum number of problems which have brought sales leaders apart or is when they have probably spent time in the other quadrants. I haven't had too many people complain about being. a good team, team builder, coach, or a mentor. So that's really good. And so now I want to ask the next question. Let's say someone who's a super seller, they're naturally good, and often they get promoted because they've— you want to model your team after really good behaviors. But they've gone from being a really good salesperson, so now they're the super seller sales manager. How do you coach a good seller to become a good team builder? So to go diagonally to the top right-hand corner.

And that's precisely the point of the matrix, Priyank. It's very easy to talk about it, but if they've got something simple and, you know, salespeople generally are fairly coin-operated fundamental, and I found this a very useful, simple tool to To help, you know, give them direction and where they want to take their own careers. So, you know, being able to build out a team and getting that team to scale is is something that they've never had to think about before. They were rewarded previously for being a super salesperson, and then, you know, they might have been pretty good business managers in their own little in the way they manage their own territories. They might have been really good thought leaders. You know, great AEs earn their seat at the table. They understand their space, they understand their customer, they understand their solution, their competitors. That's what helps them become great salespeople. But they've never had to mentor and grow the next generation of super salespeople. So when you're doing that recruiting, it's really important when you're, when you're promoting them out of the field, it's really important To pressure test their mindset around: Are they going to cut it as a coach and a mentor? Are they going to be able to make the hard decision? Are they going to try and be the salesperson's friend, or are they going to try and be the salesperson's leader? And so I put a lot of emphasis into understanding that mindset before we even think about or contemplate promoting a salesperson into a leadership position. That's the first thing. The second thing is when they're in the role, you know, you gotta spend time with them doing one-on-ones around how, you know, how are you doing? How are we doing? What do you need? Typically, the biggest trap we fall into is going straight to the operational cadence. Where are you at with that deal? Where are we at with this account? And it gets very operational. When you're talking about career development, you have to have you know, specialized career coaching sessions at least once a month, preferably in the early parts of their career, probably once a fortnight or once a week where you're working again on the business, not in the business. And on the business in this situation is on the people that you're entrusting with the leadership of your team, you're entrusting with I think, you know, the majority of info, contact and the majority of relationships with your key customers and prospects, right? So, you gotta make sure that you're across that. You gotta make sure that what they're doing is, you know, maintaining that the culture you wanna build and you're getting the results. So, in the same way you are coaching your new sales leader to be a team builder, coach and mentor, you need to be practicing exactly the same behaviors.

Yeah, and I think that, you know, the pressure that builds through the quarter, you know, from the start to the end, will obviously now start dragging people into different quadrants of operations. So is there a recommended flow, you know, depending on how things like look like on the first week versus the 13th?

Yeah, of course, of course. Yeah, look, um, I call it the rubber banding, where you rubber band between the 4 quadrants. And typically the first weeks of the quarter, you're well and truly on the bottom right there as a business manager. You're preparing the forecast, you're doing your mid-figure reviews, you're working out what are the deal stages, what you can commit, what's in best case. You're in that detail in the very first weeks of the quarter because you've got to submit your commit at the beginning of the quarter. You then have the opportunity to get out and meet some of those customers that you're committing deals for. So, hopefully, you've met them in the quarter before, but you might be meeting them within that quarter. So, in sort of month 2, you're out there meeting executives within your customer base with your salesperson, and you're spending time doing your one-on-ones with your team. So, that's when typically in the middle of the quarter, You elevate on the business and you're looking at your customers and your team to make sure that everything is as expected. And then slowly but surely as the quarter creeps in, you start getting sucked back down to the bottom left there as a super salesperson. So you're in there daily deal review calls, meeting customers, handling last-minute objections, getting legals across the line, negotiating MSAs. And you're in super salesperson mode. So that's typically how the quarter would rubber band, I call it. And when you— and it's really important at the end of the quarter, at the beginning of the next quarter, you sit down with your FLM and say, right, take me through your previous quarter. Where did you rubber band? How much time did you spend on the business versus in the business? What changes are you going to make this quarter to ensure that you improve on that? How do you spend Less time in the business next quarter than on the business. So again, it's about understanding the fact that look, business pressures hit. You are going to have to be fluid in how you move around, but you need you need to be aware of where you are at any point in time, and you know you have to be effective in each one of these. That just because you don't want to be a super salesperson all the time. Does not mean you stop being a super salesperson when required. That's just nature of the business.

Yeah, that's fascinating. And, you know, at first glance, when you look at this, I think this is a really good format and framework for people, um, from working on taking care of the current quarter To actually building a sustainable multi-year growth plan across their you know team and organization. So how do how does one what would you say? How does one actually improve if they were if I was to ask someone to say give me on a score of ten, ten being the highest, one being the lowest, I'd actually get them to do a self-assessment. You know how do you see yourself as a super seller on a score of one to ten business manager one to ten events? 1 to 10, and then Team Builder 1 to 10, and then obviously get them to develop a plan wherever they were below maybe a 6 on areas that— so what are some of the things you'd suggest? How do they develop their abilities across the different quadrants, self-driven?

Look, we use personal development plans, and, and I think where you can get unstuck is by trying to boil the ocean and doing too much at once. So what I typically do is, you know, exactly what you've just described. You know, you're a, you're a, you're a green, green, amber, red. Let's focus on the red. Let's try and move the needle on that. What are the 3 key things you can do over the next 6 weeks, 12 weeks to go from being, you know, You know, unacceptable, acceptable, great, right? So, and it's just about, and this is where the business manager piece really comes in. It's about the discipline and the consistency. And as much as forecasting and opportunity management and cadence is super important because that's what your sales and finance want, the cadence you provide around people is just as, if not more important. If you've got heaps of pipeline and you've got heaps of deals that are going to close, the business management forecast piece becomes delightfully simple, right? It's nothing like pipeline to cure all forecasting pressure, but you don't get that if you don't have your entire sales team performing at an optimum level. If you've got one or two weaknesses, all of a sudden that puts pressure on your ability to forecast and close revenue. Right. It's, it's that simple, right? You're, you are a factory production line. And if you've got a team of 8, you've got 8 machines producing product. And if 2 of those machines are not producing product effectively, you're never going to meet your production targets. End of story. So the team leader, team management piece is the most important piece. And you need to use the same disciplines you put into forecasting as you do around people management. Everyone needs a personal development plan. You need to sit down in your one-on-ones and work on that personal development plan. And like everything, it needs to be some something that you can bite off and chew. And it's the old analogy: How do you eat an elephant? One bite at a time. And so you just got to say, right, how do I get? How do I identify one potential growth area or opportunity to grow? And you work on that consistently over a six twelve week period. Tick it off, move on to the next one. But this is where one of the most important attributes of character, I think, is in people you hire, is coachability. If you can't get someone to understand and identify that that is an area of development for them, you've got the wrong person in the job, right? Coachability is probably one of the most important things I recruit for. And that's being able to sit down and go, how do you think you're going here? I need you to self-assess. Can I provide you some input? I think you did really well in these areas. I think you probably need to start working on these areas because they're holding you back. And their ability to take that on and go, you know what, that's absolutely what I want to do, I agree, here's my plan around how to do that. Um, then, you know, you've got to question whether they're the right— they've got the right mindset. You cannot change people if they don't want to change.

Brilliantly put. Before this, uh, conversation, we were talking about F1 for a moment, but I remember saying to reps whose, you know, quarter after quarter, the activity was just shockingly below where they needed to be. And I'd say, it doesn't matter if you think you're a Ferrari, if you don't have any fuel in that tank, you are not going anywhere, right? It doesn't matter how good you think you are if you're just not, you know, bringing that motivation. And it's the same with— I think with people, it's a skill versus will job. Do you want to be a good leader? Do you want to go from being a successful seller to a significant leader? Because one thing I find with good leaders is that they have been able to change the, the focus from themselves to others and that they're finding their success now through enabling others. And if that doesn't happen, it'll show up in so many different ways where they start— it becomes a toxic leadership relationship. So yeah.

Well, certainly one of the early lessons I learned in my leadership was one of my former, you know, leaders pulled me aside and said, listen, it's not about you anymore. It's about your team. And I was not taken aback, but I was like, it was a bit of an— I'm allowed to say, oh shit moment. And it's all about putting your team first. And if they— if you have a really high functioning team, it reflects really well on you. No one told me that. No one, no one plucked me out of sales and put me into leadership and said, you need to focus on building a team. For me, it was all about deals, deals, deals, right? That's It's like a footy player. You're there to get possessions, right? And so, you've got to go from this get possessions, kick goals mindset to how do I go out and recruit the best players? How do I structure my team? What's the game plan? Great players don't make great coaches and vice versa, right? So, it's a skill you have to learn and you've got to want to learn.

Fantastic. Jason, this has been Such an enriching conversation. I, you know, you've you've created an incredibly good quadrant with the sales leader personas. I am absolutely certain I'm going to get calls and messages as and when people come across this episode and see it because there's so much value here because you can really structure and build a career. You can build a year. You can build the quarter.

Yeah, I really hope so. I mean, as I said at the top of the session, I'm really passionate about our profession. I I have a a lot of pride in what we do. You can't just walk off the street and become an enterprise seller or an enterprise sales leader. And there's very little industry standard around what we do. So, I value the brand a lot. It's your personal brand as a sales leader or a salesperson. And I think we undervalue that a lot. So, yeah, let's put some engineering and science behind what we do, and I think we'll be far more successful.

Jason, thank you so much. This has been an absolute masterclass, and I appreciate you so much for doing this. Thank you.

Absolute pleasure. Thank you.