Building Sales Cultures That Win

Everyone wants a winning sales culture — but few leaders stop to ask what that really means.

In this episode of Elements of Culture, Laura Skinner sits down with Ollie Sharpe, Chief Revenue Officer at Trumpet, to explore why so many teams chase results while neglecting the culture that sustains them. Ollie brings decades of experience from LinkedIn, SalesLoft, and Trumpet to challenge the belief that success is driven by pressure, competition, or control.

What if your team’s best performance isn’t a product of intensity — but of trust? What if scaling your revenue actually starts with scaling your people? This conversation will make you rethink what a “winning” culture looks like — and whether the one you’re building is built to last.

Join us weekly as we dig into the real stories behind work culture transformation.

Not theory. Not fluff. Just honest conversations with leaders and innovators who've been in the trenches.

Transcript

From Door-To-Door To CRO

Speaker 2 0:00

You can't really 'cause you're getting judged on leadership and leverage, you can't get promoted unless you're actually doing it. So it made me realise that that was my passion, that I really liked doing it. And I started getting a lot of pride from seeing other people succeed that I'd helped rather than me succeeding as an individual.

Speaker 0:16

At Elements of Culture, we sit down with experts in leadership and team building to explore the DNA that drives a thriving organization.

Speaker 1 0:24

Hey Ollie, and welcome to Elements of Culture Podcast.

Speaker 2 0:28

Thank you, Laura. It's good to be here.

Speaker 1 0:30

I'm so excited for this conversation. So obviously, I'm very familiar with your career. We've had previous conversations. Um yeah, let the listeners know where you started, where you're at now, and that epic journey of your kind of ending up as a CRO.

Early LinkedIn Lessons On Culture

Speaker 2 0:44

Yeah, I mean, I I fell into sales. I think most people fall into sales. I think every single thing is. I don't think anyone who plans when they're eight, I want to go into sales. So I uh when I left uni, I went for a job that I thought was more marketing and ended up door-to-door sales. So I did two years door-to-door sales, which taught me a lot. I I and I can't say I didn't like it. I actually liked it until I had an injury doing it, uh hurdling a wall. And so then I went into recruitment. Uh I worked for yeah, so I did I was doing sales recruitment, so uh software sales recruitment basically, which taught me about the industry. After 10 years doing that, I wanted to get out, and I either wanted my own recruitment agency or to go into the SaaS space. And uh probably a best break of my career. I started speaking to LinkedIn and LinkedIn took me on. I was the number 14 employee at LinkedIn outside of the US. Um, we shed uh we had an office on Oxford Street, which was me, 13 others, and two rats. We had rats living in it as well, which was really nice. Um so that that was I mean that was the turning point, I think. But I was I went in as an AEO at the time. I was the only new business person in Amir, um, which sounds good, but no one knew what LinkedIn was at the time, which made it hard. You can't imagine that.

Speaker 1 2:01

I'm a bit younger than you, Ollie, and I can't fathom that because like uh Yeah, it's um it does sound really weird to say that.

Speaker 2 2:10

Uh but no people didn't know what it was. We're selling talent solutions to HR people that didn't do direct sourcing, so it was it was a hard sell. So I spent 10 years there, and there I moved into leadership, and I learned so much about the importance of culture, values, and leadership. They give great leadership training there, and I learned a lot, surrounded by some awesome leaders. Then I was lucky enough to be the first person on the ground at Sales Loft, the Sales Engagement Company. So yeah, it was uh we talked just before jumping on here about lucky breaks. I had two already by the way. I wouldn't say the Daughter Door Sales was a lucky break, uh, but it did teach me stuff. So Sales Loft, first person on the ground. I grew it to uh probably I think it's around 25 million 120 people, something like that. Um was there a few years, really enjoyed it. I found my love for sales tech, and I'm I became a complete sales nerd, and it's uh most of the books behind me are either on mental well-being, leadership, or sales, which is quite boring basically for other people. Um yeah, salesloft built them, and then I left there and was sort of hunting around for my next thing. I wanted a company that was hopefully UK HQ'd, uh, somewhere that had uh probably preferably sales tech, somewhere with a good culture, and at the time it didn't really exist that aligned with where I was. So I went and did a couple of other jobs, one consulting role sort of thing, and then and I became an advisor to Trumpet at that time, and then the stars aligned, and uh, after 18 months advising them, me and Rory sat down and uh I already knew the culture was good, the product was doing a great that was growing, and the client base was that already signed Gong and HubSpot. So I went and joined them as CRO and uh not look back, love it.

Speaker 1 3:58

You know what's so interesting is whenever anyone asks me about like where to start in their career, I always say it either start as an SDR where you're just like relentlessly cold calling or anything like that because it will just like it'll navigate your entire career or do door-to-door sales. I feel like if you start off with one of those two things, everyone that I'm around or surrounded with, if that's where they started, they're like deemed for success because I don't think there's much of a harder role in terms of like resilience and just teaching you the fundamentals basics than you can get in front of like someone that's stone cold cold to your solution and trying to get them to purchase it.

Speaker 2 4:33

Definitely door-to-door sales, I think that's even harder than the SDR side because I mean you are literally looking knocking on a door at eight o'clock at night, and someone's like, What do you want? But also recruitment. I think that those are the three. I if I find someone that's done either door-to-door sales, recruitment, or an SDR role, and they've advanced in their career, they know how to work hard, they know to do out how to do outbound, self-gen. So, yeah, it's a good background to come from. You do learn a lot from it.

Salesloft: First Boots On The Ground

Speaker 1 4:59

Yeah, I honestly it taught me everything, like truly, it taught me everything. And I'm just super passionate about the SDR role because I feel like it can catapult you, especially in SaaS, if you get within like a rocket ship or whatever they want to call it, but it can really catapult your career, and you're kind of like one year in SDR, and then you're kind of like building a company, probably a bit like what happened in that sales loft run. But talk us through like so at LinkedIn, you're an account executive, and then at Sales Loft, did you start off selling and then build the team, or what did that journey look like at Sales Loft?

Speaker 2 5:27

So, well, at LinkedIn I started as an AE, but I spent 10 years there. So the first five years, well, first two, three years I was an AE, then I moved to relationship management. Okay. So I built teams from Fresh, etc., and new go-to-markets. Um, and then I left there and I'd basically I'd had a team of probably about 20 people when I left LinkedIn, and then at Sales Loft, I was the first person on the ground, but I was I had headcount straight away. So I was I built from the beginning, so I had seven headcounts to start with, took someone from the US, uh a sales engineer, a CS who I came up from LinkedIn, and the rest were sales and SDRs.

Speaker 1 6:08

I love it. So what I really want to dive into, because this is super interesting to me, and obviously this podcast is that transition from AE into leadership. Like, what did that look like for you? Was that just like an easy transition for you, or what was that like actual, okay, I'm I'm I'm quota, I'm hitting my number, I'm loving this, and now I've got to go and turn all of the stuff that almost like I don't know, like sometimes high-performing reps struggle to replicate how they even are high performing, right? Like there's some that just like can kind of do it. But like, what was that transition like for you?

Speaker 2 6:40

It was it was weird, it was different. It's not like you think it is, and I think that this is I I I look back and I think that because often people just go, okay, they're a great rep, they're gonna be a great manager. And LinkedIn wasn't like that, it wasn't like they just went, oh god, it's great, do it. And so what happened for me was I was a high-performing rep, I won awards, etc., number one in a Mia, and I won a few of them, but what I then started doing, so the way that they lead is on leadership, leverage, and results, what they did at the time. So leadership, uh inspiring others to reach a common goal, leverage, which is about how you share stuff, and results are your results. And because you were judged on that or you developed in those ways, I started helping other teams a lot. So I was uh the Amsterdam office open, so I helped with the training of those guys, Australia opened, and so I was still an IC, but I was helping others achieve helping them uh learn the ropes, and that made me buy into leadership, and it made me because and you can't really because you're getting judged on leadership and leverage, you can't get promoted unless you're actually doing it. So it made me realise that that was my passion, that I really liked doing it, and I started getting a lot of pride from seeing other people succeed that I'd helped rather than me succeeding as an individual, and I think that made a big difference. However, it was a lot of surprises when you go to leadership because you for some reason, if you're uh an okay performing rep, you assume what you do is just standard. Then you start managing people and you go, What you don't do that.

Speaker 1 8:14

Oh my god.

Speaker 2 8:15

It's really weird that you're just going, okay, I thought everyone knew how to pick up the phone. And it's just the basics that you didn't realise that other people did. So there was that side of it where you realize, but also the biggest thing for me, and I think the biggest thing I learned to develop was strip everything back to a framework. Because it's not about going to someone and saying, When you had that call, you should have answered and said X. It's when you had that call, this person said that. Let's build a framework for when that happens again, no matter what they say, you know how to handle it. And you strip it back to a framework that they go, Oh, this is the framework I use. And that was that was a big learning for me, and I think it's a great skill to have as a leader to be able to uh strip it back and go, okay, this is a framework or a structure that will help you in any circumstance.

The Jump From AE To Manager

Speaker 1 9:03

Yeah, it's so interesting because I honestly, when I've been coaching rep sometimes, I there's there's occasions where I'm like, I don't actually know how I got to that deal. Like I remember speaking with Mark Robert years and years ago, and I was like, what's the best like customer story? And then like when they don't know they've even been sold to because it's just like a relationship, it's just like almost like a science and a psychological conversation. And sometimes I'm just like looking at calls and I'm just like, okay, I'm either follow a playbook and a process and I can coach you, or this like outlier just is doing something, but it's working, and I can't actually replicate that. And I always found that really hard. Was like, sometimes I'd review my calls and try and be like, okay, do this, but you don't want to overcomplicate it. So I think framework processes it if you're coachable and you follow that. A lot of people in the in sales can be successful if they have that work ethic and against that framework, you know, it simplifies it all.

Speaker 2 9:49

Yeah, 100%. It's all about the frameworks and because you what you're not the more you're doing of okay, uh you uh you should answer this way, is you have to be on more calls. I mean, it's all about teaching a person to fish rather than just actually doing it for them. That if I can teach them how to handle that situation, then I don't need to be on that call. And that was a thing for me. I what I first of all did when I became a leader, I stepped too far away from sales. And I was I wasn't uh one of these purely looking at a spreadsheet leader because I couldn't even build a spreadsheet at the time, that's why I wasn't more to learn that later. Um but I probably didn't go on as many calls as I wanted, and then I realized that I was missing sales, and now I I mean um in my role currently, I probably go on I'd say at least seven, maybe up to 15 meetings a week, calls a week with my team. And I love it, and I like it. That's so motivating, yeah, and I love doing it, but I can coach the team better, but then you also see other managers that are I've had a manager who's worked for me in the past, and their area of development was not closing the deals for people because they what they were doing was they were handling the sale. Now they're purely to shut up and ask the most powerful questions and say the most powerful things, but speak the least. And I think there's it's get the getting that balance is quite hard, especially when you've been a salesperson that just jabbers all the time like I'm doing now. Um when you've been that salesperson that that had does all the talking to move to a management. I've realized if you actually just shut up and sit there, and then when it goes quiet, ask a really powerful question, you can be you can have so much more impact than leading the meeting because your rep should be doing that, and all you're doing is you're taking the power away from your rep because they're the ones that should be negotiating and coming to you and playing the game of oh, I need to ask Oli that because he's gonna be able to negotiate that discount, and you lose all of that. So, yeah, there's certain ways of doing things.

Speaker 1 11:56

I I find this so interesting. So I want to double down on that, but just going back to quickly something about your career, because I'm super interested in this, and I I value your experience in your career, and I would love to hear your feedback. But when I went from being a top performer as an SDM at a really cool company and got made into like a business development manager or SDM manager, they kept me on quota, so I remember really I was a team lead. So I went from like 12 qualified meetings a month, which were black in the den. I mean, you can do that in about a week these days, but that was quite hard back in the den on the phones. And they just dropped me down from 12 to 8 and then managed seven BDMAs globally. And like I remember speaking to someone um last week about this, but like what was kind of your approach to the team lead role? Because I actually think there's value in it in the sense if you can transition out of your role and transition in and almost like sandbag your number but all almost learn it before it's completely yours, I think is great. But I also feel like you're just gonna end up doing what you enjoy more and what's gonna make you more money at the end of the day and what you want to like get a passion for.

Coaching With Frameworks Over Fixes

Speaker 2 12:55

I don't agree with them. I don't I don't think and and it it it's hard to say that because there's always situations that you go, actually, we don't have enough team members for a manager, but we can't have them all reporting to this person because they're too busy. Yeah but and there's those situations like I still don't think it's right to have a team lead. I think you because what it comes down to for me is you're right, they'll do what they prefer or what will earn them the more the more money. So if I can still double hit 200% of my own target and not not care about any person that's under my wing, I'll do it. And vice versa, if I can do so, I don't think it works, it's like a split role. I think it works better to actually have a way of developing people, like I talked about with LinkedIn with leadership leverage and results, because what people are doing is first of all, you're building a culture that you to do your job and get a decent score in your quarterly whatever, is you are looking at how they inspire others, how they take on roles, and how they help others. So there's all of that that I think comes before making that decision, and this all comes down to your culture and the way that you structure a business. That's purely my view. I've never really seen a team leader role work well where I nearly I was off the rails.

Speaker 1 14:16

I was like, this is impossible. Dropping my number by like four, but adding a team of seven and still being paid the same at that point. I mean, I probably got like a five to tenk increase in my base, but like after tax and month on month, it's just like a couple of hundred quid at that point. Is like okay, so I've got four less meetings to book, but I've got now a whole seven people that all need to hit 12, was just like it honestly was just like the worst thing I could have done, and it quickly became obvious.

Speaker 2 14:41

And I think what another solution to it is hiring someone for the next role. So someone I spoke about earlier, uh Natasha Evans, who is she was at LinkedIn, she managed the CS team that worked alongside my team at LinkedIn. And when I went to Sales Loft, she came with me. But she'd she was she was managing a team of seven or eight, I think, at LinkedIn. But at Sales Loft, she went to an IC role. Interesting. The plan was we knew both knew that she would be an IC and she would grow that team, and she would it wasn't a team leader role because there was no team leader role, it was you're managing the team, but you've got to be doing IC, and she built it, she ended up actually managing CS Globally at Sales Loft. She's brilliant, she's absolutely awesome, and she she's now a hook.

Speaker 15:27

So oh that'd be great.

Speaker 2 15:29

And it's like also uh there was other people I hired that it was for the next role on sort of thing, and they knew there was opportunity and they knew my commitment to get them there, and I think that is a really good solution because they assume the role anyway, but they know they've got to be doing icy and hitting their numbers, but there's a future for them, yeah.

Speaker 1 15:46

And I honestly like when when you say about the future, it's just like if you're a leader and you can get your team to almost be on that vehicle to their next step in their career, it's like game over in terms of their motivation and what they want to do. And if you show that you actually care about that, I always say it's like a performance vehicle in the sense of like if you've got a group of people that are invested in you as a leader and you've shown them that if they do X, Y, and Z they're gonna keep getting to the next step. I mean it's just like you're making it impossible for them to ever want to leave, and then you've got like your real top performers that are just gonna want to stay.

Speaker 2 16:16

Yeah, I 100% agree, and if something, and I always with my leadership, I always refer back to LinkedIn because I learned so much there.

Speaker 1 16:23

But that's amazing. I deal with my first company. I always to SIA I'm always like, we did this, we did that. Like it's like, have I done anything else in my career?

Speaker 2 16:29

Yeah, and they they're just very structured about it. What they had was this idea about um the role of the business and the leadership was to impact the trajectory of your team's careers. And what I mean is you join at that level and sort of going on a slow hill, and then when you leave, you'll be at this level, but it will accelerate while you're there. Whether you're there a year, ten years, no matter what, you will leave on a different trajectory. And I saw that in myself. I mean, I went in as an AE with no SaaS experience, and I came out as a leader that could get a job at Sales Loft, but it's it's it's sort of a good is that they say, even if you leave after a year, I I say ten years. It's like a mind trick to go, yeah, right, you might not stay long, but it's such a good way of doing it, and I mean there's nothing nothing cloak and dagger about it, but it is very much that I knew that they were the interest of me, and I've taken that with me. When I was at Sales Loft, I said my role as the leader of this business is impact your trajectory. I want I'm more bothered about you can come to me tomorrow and say, I want to leave in six months, and I want to get ready for this role. I will work on your future to be able to get you there, and I'd rather you do that than just one day and your notice in, but I want to impact your career, and it does work.

Speaker 1 17:43

I did a whole is so funny, I feel like we're so aligned because I did a whole speech and a talk for a company once about how you know, like people can put like leaders can put their um ICs on a pip, it can be a month, it can be three months, it can be six months, performance plan, whatever that may look like. I said the best thing that you can tell your reps to ever do is if they put you on a pip, as in the sense that they're like, look, like I am ready to go, I'm ready to, I'm looking to go, I'm looking in the next three to six months. I want to be really clear about that because that comes get then gives you the time and you can also help them. So I feel like it's something that should be done, vice versa, because if it is, A, you can help them get to that next level, and then B, you can have that complete crossover and it's not gonna this whole like miss opportunity cost of the higher, the ramp and all that kind of stuff, they cover for all of that. But no one does it. But I just feel like if everyone had like the pip attitude, vice versa, I feel like it'd be quite good.

Staying Close To Deals Without Stealing Them

Speaker 2 18:29

Well, I think the what I find the most sometimes the best people in roles are the ones that treat every quarter like it's probation anyway. Yeah. That you're you you don't sit back and you're always and there I mean there may be something more in the back of me as a person that maybe feels insecure or something that feels like that the whole time. I've got to keep proving myself. But I also think it's like when you're hiring, and there was a good thing, I think it was on the uh Revenue Builders podcast with McMahon and Kaplan that someone was talking about I think it was on that, but it was it was it was definitely a medic-focused company. And if somebody isn't working out, if I hire someone and someone isn't working out after six months, the leadership attitude is you've either hired wrong or you've not onboarded them well.

Speaker 1 19:16

Okay.

Speaker 2 19:17

And I think it's brilliant because it's not about the person that you've hired, because it's my job to hire the right person, it's my job to develop that person, and it's it's a partnership between me and them. And I think it's a really good way of looking at it. And I think too many leaders and too many companies go, is that person doing well? But really, did the leader do the right thing in hiring them and onboarding them? And I think it's just such a good way of thinking.

Speaker 1 19:41

I can't, I couldn't agree more. So I basically, like, if I'm ever going into like underperforming whatever kind of team, I look at two things. It's either a leadership issue or it's either an IC issue. If the individual contributor is coachable, takes feedback, and will work hard, it's immediately a leadership issue to me. Because I'm just like, how can you not get someone to follow a framework? And sales is hard a hundred percent, like it just is a hard career, but it's also the most rewarding and it's the most like life-changing career. Like, I was just like the worst kid at school ever and thought I had to be like a doctor and a lawyer and all of this to earn any money. I'm just like, oh my goodness, I'm just gonna be like a bumble woman for the rest of my life, like truly. And then I fell into sales classic, and like it changed my life, like I couldn't actually quite believe all it's done. But like it is a hundred percent a leadership issue as long as the rep is coachable and takes feedback because you have like the 10xs, you have like the top performers that if you just want to put more time into them to growth and make it impossible for them not to want to leave, that's great. And then the middle ones you just want to basically identify who they are and then give them a plan to get to those. But like, as long as they've got that like mindset, I just think it's I don't understand why it would ever be an individual contributor issue at that point.

Speaker 2 20:50

I agree, I mean it is down to that mindset, isn't it? If someone's gonna take on feedback and stuff, and I think that it's I think it's really important to work out how to get the best of people, and that's not what it is because a lot of managers jump straight to what do you money want to buy you? Yeah, I want a new car, and they think that is the motivator for that person, and it goes so much further than that. It's I like uh I do certain exercises with my teens wherever I've been around mental well-being, doing like a MEP check-in, which is mental, emotional, physical, and spiritual checking.

Speaker 1 21:24

We're so ahead of the game, you are so ahead of the game, honestly.

Speaker 2 21:27

But I love doing that stuff, and it came from my background because when my wife had cancer seven, eight years ago, it impacted the way I think about work, and I don't want other people to have the stresses of the target hanging over them when really there's bigger things in life, but if I can help them with their mental well-being, because let's face it, if we're not feeling good, we don't perform as well as we can. So if I can hire the right people and I can motivate them, inspire them, but look after their mental well-being, I will and develop them, then I will have the best team I can have. And it's not about putting in processes. I mean, I've got someone at the moment who openly talks about the last three companies she's worked for have been medic, and she's and she said every one of those companies it was a tick box of only just starting medic to learn medic properly now because I have it in my everyday language, I've coached them myself, I teach them how to do it, and it makes a big difference. I have this really nerdy medic deal sheet that quite a few managers in the UK now have that have shared, but it it's all of those together because you're developing them, and like anywhere else, I said to my team, if I can if if I can help you learn medic, it helps your career. And if that in two years' time you go get a fantastic job, I'll be proud, I'll have done my job. And to me, that's what it's about. But keep them happy in the in the meantime.

Why Team Lead Roles Often Fail

Speaker 1 22:43

I know 100%. The money thing's interesting, right? Because sales has this perception of okay, people are just in it because the base is typically quite high, the commission's really great, but like it honestly is like that service level, right? It goes so much deeper. And every manager that I've ever followed, and I know we've spoken about this previously about having the people that will follow you that you can almost it's almost like a free hire because you know they're gonna be amazing and you can give them, they can give you. But mine's always been about like retiring my parents, right? And if any manager taps into that, it's like game over. So it's not really about I'm not a materialistic person, and I honestly couldn't care less. I really couldn't, as long as like I can go to a nice gym and have a nice like life like that, I don't care. But like all I want to do is like retire my parents and make sure that they're all good and they've given me everything they possibly can from nothing. And it's crazy about like I've watched managers that have completely missed that, and I've watched managers that have tapped into that, and it's amazing because your motivation will just dip and increase, but it's crazier than the types of conversations you have in your one-to-ones because it's so much more vulnerable, because it's like about your family, it's about like what you actually want to achieve rather than just like I want the next bag.

Speaker 2 23:44

It it is a hundred percent, but I think on top of that, it's about understanding the person as well. It's not because some people uh don't feel heard, and it it it's the there's the motivation, there's the motivation and there's the inspiration, and I think they're both different. So, motivation as in what is gonna make you what want to earn money, inspire is something that's just within us. And I think that if I can if I know my team and some of them may want to just come into work and feel valued, some of them do want me to celebrate the success, some of them don't, and stuff. Yeah, and it's those everyday things of knowing a person, how they work, and getting to know them and showing that their interests are your interests, what you are in them. Um that is so important. You've got to get to know your team, and it's not it's not get to know purely what motivates them, it's get to know what makes them tick, get to know what actually what they're what matters to them and what pisses them off and what they enjoy.

Speaker 1 24:43

A hundred percent. So talk to me about this, right? So this is really interesting because I find like sales leadership the most interesting role, like not really the CRO role, like the frontline sales leadership. So if you go into a team and say you were an AE leader or whatever, whatever, and I'm not saying that they're underperforming, but they can be better, they can be more productive, whatever. What is like we let's go back to frameworks, but like what is it? You identify that there's there's a bottleneck. How have you identified that? And then what is typically your process to get them to above their number and actually like impact their life in a positive way where quotas not this like crazy ceiling and it's actually like doable, and then as every sales rep knows, once you get into your accelerators, it's the best time ever.

Designing Careers And Trajectory

Speaker 2 25:22

Yeah, I I mean I think there's it's a very big answer to all of that because I think first of all the learning about what's going on comes from just get getting under the bonnet and really understanding going on as many calls as you can, seeing how they're doing their outbound, looking at everything. It and it depends on the stage of the business. So I've often been to early stage businesses, so it's more a case that I'm they're quite rightly they've not had the processes in place yet because that's what is the next stage for them. So that's not and but some companies are five years on and they're still not got the right process in place. So that's the different thing. I can really only talk about the area where I specialise more, which is that early stage. Yeah. What I it what I often do, I mean, with Trump hit, with other companies I've been to, it is literally just un getting getting on as many calls as you can, understanding your customer, understanding your product, understanding everything that you're doing, your competition. And that is literally like you're going that back to a junior AE role where you're learning from the people around you. I think most of the time what I find it's coming down to a lot of the time, things that I've worked on with companies is first of all the narrative. I think that what happens is a founder has built a narrative or not even shared a narrative, they've got used to all talking about their products, they built it, and it's not done in the right way. When I was at LinkedIn, I I rolled out the narrative for us to target the staffing market globally, and it helped me understand how to process building a narrative. So that's often one of the first things. Also, the demo. I think that demos lack structure most of the time. There's no I do what I'd call chaptering, where it said chapter one is show them round, chapter two is show them round the actual sidebar, chapter three is this is how you build it, etc. And integrations. So there's the chaptering and the structure to that, then there's the sales process and methodology and the CRM, and most of that doesn't have a structure because it's like being winged a lot of the time, and then there's the non-structure sales because someone may not know how to handle negotiations or anything like that. So there's a lot. I think that what I talk uh I've talked about in a few companies when doing a QBR is self-limiting beliefs, because like I came to Trump it and they were performing pretty well, but we're now doing our productivity per rep has has increased so significantly. But one of the first QBRs we did was around self-limit-limiting beliefs. Talked about Roger Bannister and about how is the four first four-minute mile when people didn't think it was humanly possible to do a four-minute mile, so we set a goal of how many records we could break in a quarter of ACV uh revenue for a month, revenue for a quarter, and I think that just breaks the mould a little bit that you just go, Oh, okay, this is achievable. Yeah, and what I find is most companies they're going into let's say 100k deals and going, I'm probably gonna have to negotiate down to 30k. I'm like, no, put 100k on the table, and if they want to negotiate, we'll talk about it. And it's it's one of those kind of things that are just your belief systems because I've come from and some experience of doing those, I'm more likely just to put the the big deal on the table. So there is a lot in answer to your question, there's a hell of a lot, but I think it is for the first short period of time, don't go with in with any assumptions. Yeah, it's true. I think people go in and assume that I'm gonna have to build the CRM, I'm gonna have to build this, and chances are you're right, but don't assume it because you'll miss the important things. Um go back to basics. It's the it's very much I can't go in and teach a team advanced things when the basics aren't in place. So get the first six months. I mean, I it does make me laugh when companies say do a 30, 60, 90 day plan, interviewing for a manager, or like, yeah, for all of that, I'm just gonna be listening and actually understanding. So the but people go in with this same listen and then do this, etc.

Speaker 1 29:26

It's honestly so interesting about the mindset thing because like I find this crazy because I don't know whether I just have an insane amount of self-belief in everything that I've worked for, but when I actually like put a big number on the table and it gets questioned, I then question them why they don't see the value. I genuinely think it's like comes down to a value thing because like I believe it's worth them. So if I believe it and I'm the rem and then I'm questioning them on what they their value, then it becomes a really authentic and honest conversation, and that's what I've always done. But like remps want to hit number and then scale it to miss and all that kind of stuff. So then so they'll probably drop, but all of that, like Mindset limiting belief. I feel like if you've got a rep that's coachable, that will follow a process that'll execute and work hard, and then you add that like element of like high performance on their mindset and do everything that you just spoke about in terms of coaching them. I think you can make any average sales rep like straight up to an A player, which everyone always struggles with, right? Because there's just so little A like proper, proper A players out there. But like I feel like the combination of those two is just killer.

Speaker 2 30:24

I agree, and I think there's there's something I read or heard about quite a few years ago, a few years ago, that was about where leadership spend their time. Yeah. Because your A players you don't spend much time with, your B players you don't spend much time with. You spend your time with your C players, which tend to be the people that dra sort of drain your time. Oh. And really that's not the best thing to be doing unless you see uh see something coming from in the future. But I think that because to me, what my attitude here is that if we run uh I believe that nowadays your sales process is a differentiator. Yeah, the exper the buyer experience that some you're taking some, especially when you sell to sales leaders, is a massive differentiator. I love it. It's a massive differentiator. The amount of times you sell something they go, your sales process was fantastic.

Speaker 1 31:15

Yeah, I love it. And I used to sell sales excellence, so I was like, I'm the product, I'm literally the product because I'm selling sales excellence to your company.

Onboarding, Ownership, And Manager Accountability

Speaker 2 31:24

Yeah, and it's I think that is so important. That's how I saw it at sales loft, and that's how I see it here. And really, if you're if I'm teaching my team properly and we're finding a pain that we can implicate, not just identify pain, but for implicate it properly and find the metrics and go to the EB and position it in the right way, when that conversation comes up later where the guy, well, your competitor is half price. You're like, yeah, yeah. And the number one, they remember the sales process, but you know how to implicate that pain. And if you've also built their decision criteria that only you can fix, so it comes back to the science of selling, and it's it's not rocket science, it's just a great way of doing it. And this is I mean, I think medical is fantastic, I've Andy White's courses and stuff like that, I think they're brilliant. So it's um I think it's important to have that. It is the mix of process and structure that you put in, but then there's the art of sci of selling as well. Yeah, um, and the art, it's actually insane.

Speaker 1 32:24

You need all three a hundred percent. I honestly say to all of the reps that I've coached, if you get to the end and there's any objections, you should have done a job throughout the process that you can like knock that objection gone. So anything that happens, you need to build for anticipating those objections. And if you've done a great job, you won't get any objections right, but that's just like not inevitable with environmental factors. But a lot of the time you've done a great enough job not to get objections anyway. And then any objections like that where you just go back, okay, well, you've got all those metrics in discovery for this reason to then go and implicate the pain. You did all this stakeholder engagement for this reason. And once reps make that, I feel like that's like the like almost at the light bulb moment.

Speaker 2 33:02

Yeah, 100%. Once they realized, and one of my team did a post about this just uh today, I think it was uh this yesterday or today about this big deal, and it was all around the the belief in medic and using it properly. And once you do use it properly, and we have compet competitors that come in and do offer free or ridiculous low low price. This is what happened with this one. They offered a free and we still won the deal. Yeah. And it's it's when you when that happens, you go, okay, yeah, we we we're doing this properly, and um yeah, that's why I'm gonna be able to do it.

Speaker 1 33:32

It's like they offer it for free, but then how much time do you want to spend? Like uh just like all the other stuff that you can tie to it. I just want to talk to you forever, but the final thing that I want to ask, because I know we're over time, but I'm genuinely super curious, is that leadership on terms of like spending their time on different areas, right? Because I'm of an opinion that there's like three categories. One, you've got like your top, top performers that if you just like help them grow, because they're just gonna continue to continue to grow, and you make their comp plan really attractive that they never want to leave, and you really focus on the fact that you're growing their career and never wanting them to leave. And then you've identified the people that can get them, that they've just got almost like not a development plan, but a process to get them. And then you've got like your smaller bucket that either you need to transition out and help them get a new job or within the company or something like that, and then you end up with this like killer team. But I would just love to like wrap up with kind of like your thoughts on that because you mentioned it, and I was just like, I I'm so passionate about kind of like where you should spend your time because leaders are gonna want to spend their time with A players because it's like that's the more fun, that's the more revenue and stuff. But yeah, I'd love to hear your thoughts on that.

Motivation, Inspiration, And Knowing Your People

Speaker 2 34:32

Yeah, I think that there is a I can't remember what it's called, something curve, leadership curve. Some leadership curve. What it does, it takes you through the four quadrants of taking it along. Because I think there's two answers to what you're talking about. I think there's because you've got to work out, and you can use the Eisenhower matrix or whatever you want to actually work out where you spend your time, but you've got to remember that every person in your team, or most people in your team, are at a different stage in their journey with you. There's that side, and then there's the where do I spend my time? The first side, there is this uh quadrant that talks about it's got uh basically consciously capable. So you you come in and you don't know what you don't know. So you need to teach them everything. Then they know what they don't know, and they move into the next quadrant, and when they know what they don't know, it's a different style of leadership, and then they're do they are conscious and they know what they need to do, but they the last quadrant of it is where they actually are unconsciously competent, i.e., they are so competent they don't even need to have to think what they're doing. That's when you start using them to help others. Yeah, so if you take them through that curve, but also on the other side of that is what happens if everybody is rampant and there, where do you spend your time? And I think it comes a lot of it comes down to what's the ROI of spending your time because does some is someone curious, is someone listening, all those kind of things, and a lot of that is their personality and their mindset because if if you've got someone with so much potential but they don't listen, you're like, why? Um whereas if you've got someone so I do think that you should be spending more time with this middle ground that you know if you invest the time, they will listen, it will have an impact, etc. The ones at the bottom, you're right, uh, but I think that that is only when you inherit. Because to me, if I've got people in this bottom bit, I it's my I'm accountable for making them successful.

Speaker 1 36:33

Yeah, it's that to me is just so interesting because it's just like you can miss higher, and then you're just in a position where you're just like, Okay, do I really go all in? And this is gonna be pretty draining on my time, but I think I can get there. And then I think the talent that doesn't get spoken about that that much is identifying the difference. If you've inherited like a huge team, identifying who you think you can spend the time in to make it and who you don't think has, and being able to identify that within personality traits and stuff is huge.

Speaker 2 37:03

Yeah, I I think that, and also I I do have a little bit of a bugbearer with um if you go into a business, I I do think I mean we're all human, and there is a way of handling a pit situation. And I hear horror stories. I hear horror. It's uh we're that that person that is being treated like that is human, they've come to this role, they're maybe they're hopefully trying their best, and I think all of these things that happen, some leaders may not think about what happens after that because it does come back, it does bite them later, as in that rep when they go for another job, they may have lost their confidence, and nothing's worth that. And I think that to me a pit conversation is look, let's work out whether this right this role is right for you. These are our expectations, this is not and it's just that grown-up conversation. You don't need to treat them like shit on your shoe just because they're underperforming, um, unless they've done something against your values or something like that. But I do have an issue with that because I think we should all be in it for to help other salespeople, whether they're not performing or not, and we should help coach them, develop them, and treat them like the the humans that they are.

Speaker 1 38:10

And ultimately, if you give them that, it's pretty life-changing. Like it really is. Like, if you can nail sales, like and I say this to all of my friends, like, yeah, being a lawyer, being a doctor, all that stuff is incredible, but like, and sales has this like negative reputation when when you look at like my parents' generation, right? But it's just like insane what it can deliver if you kind of like can follow it, so it's like almost like down to the leader to do that, you know.

Speaker 2 38:32

Yeah, and it's I mean, sales is stressful enough as it is. We don't need to as a as a manager. I think we can be supportive, we don't have to wrap them in cotton wool. I'm not saying that for one minute. We can be supportive of them and we can hold them accountable and set expectations, but treat them like a human and make sure that they're not impacting their mindset in the future. That's a huge thing for me. I think it's uh it's broken in many places.

Speaker 1 38:58

100%. Honestly, Ollie, this has been incredible. I feel like we're super aligned. I would love to work for you, honestly. You sound like you sound like you could transform my career, but I really appreciate your time. I'm looking forward to seeing the next couple of quarters from Trumpet, and thank you so much.

Speaker 2 39:13

Thank you. It's been good, thank you.