The B2B Podcast Index
Sales Leadership & Management Show - For B2B Sales Leaders

HOW TO HAVE YOUR TEAM WANT TO WORK HARDER

Sales Leadership & Management Show - For B2B Sales Leaders · 2026-01-09 · 29 min

Substance score

41 / 100

Five dimensions, 20 points each

Insight Density7 / 20
Originality6 / 20
Guest Caliber11 / 20
Specificity & Evidence9 / 20
Conversational Craft8 / 20

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

7 / 20

The episode has a few useful moments—particularly the role-play self-critique test for coachability and the $7M deal process anecdote—but the vast majority of the runtime is padded with career biography, generic leadership clichés, and motivational filler that adds no tactical value for a B2B operator.

the people that give a good, well rounded self critique, they'll be balanced and say, look, I think I did these things really well. And on reflection, I think I could have done this differently
my role as a sales leader is to make the team successful and to create an environment where success can thrive

Originality

6 / 20

Almost no counterintuitive or first-principles thinking; the hiring criteria (intellectual horsepower, drive, coachability) and leadership philosophy (invest in people, have fun, lead from the front) are entirely standard. The non-commission sales model at Monday.com is genuinely interesting but is named and immediately dropped rather than explored.

Monday.com is actually quite unusual because we don't have a variable comp plan. It's a non commission sales role.
sales is bit of a creative pursuit

Guest Caliber

11 / 20

Dean Swan is a legitimate practitioner—18 years in tech sales, employee #1 in Australia for Monday.com, with stints at Microsoft and Dropbox—giving him real credentials at recognisable scale. However, the conversation never extracts the depth of strategic or operational knowledge those experiences should contain.

spent the last 18 years in sales leadership roles working for companies like Microsoft and Dropbox. And most recently for the last nine months, pre Covid, I was hired by a tech startup called Monday.com to set up the business here in the Australia region
I remember at Microsoft we had a very large deal that I was working on. There was $7 million purchase and it was down to the last day of the quarter

Specificity & Evidence

9 / 20

A handful of concrete specifics elevate the episode above pure abstraction—the $7M Microsoft deal with named system (Oracle ERP) and time-of-day granularity, plus Sydney Opera House and government bushfire response as named customers—but there are no growth metrics, conversion rates, team size figures, or any systematic data on what's actually working.

There was $7 million purchase and it was down to the last day of the quarter and it was a Friday...the appointments in the diary of the CFO for 5:30pm and my contact was standing outside his door
we've got the Sydney Opera House that use our platform to manage all of their creative projects

Conversational Craft

8 / 20

The host asks reasonable biographical follow-ups and occasionally digs a layer deeper (e.g. probing the coachability test further, asking about detecting business acumen), but never challenges a claim, never pushes on the non-commission model's implications, and closes with an openly soft question about why guests recommended the show.

Is there any techniques that you've used to kind of ferret that out before hiring them?
And you came highly recommended for the show. What do you think motivated people who have worked with you in the past to recommend you?

Conversation analysis

Computed from the transcript - who did the talking, and the verbal tics along the way.

Filler words

so63you know47right38like27sort of17kind of6I mean5actually5basically2obviously2literally1

Episode notes

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Full transcript

29 min

Transcribed and scored by The B2B Podcast Index.

Hey everybody, welcome to the show. Or welcome back. Hey, this is the show where we interview the very best of sales leaders and understand first why did they get into leadership? What's the distinction there between the motives of getting into sales leadership and what differences have they found and what is working today to get the very most out of their team and have it be fun along the way. Before we get in, make sure you check us out over@b2b revenue.com where you can learn about all the stuff that we're covering as far as driving revenue in today's world. And at the very end, I'll sum it up. Let's get into the interview. Hey Dean, welcome to the show. As a way of getting started, give us a little background on yourself. Hey Brian, good to be here. So, Dean Swan. I'm originally from South Africa, so there's a little bit of a hint of that in my accent. But I've been living in Sydney, Australia for the last 20 odd years. Moved here as a university student and actually studied computer science at university. So I'm a software engineer by way of education. Yeah. But been in the tech sales industry for about 18 years now. And why'd you make the switch? Did you go engineer to pre sales to sales or straight into sales? Well, actually it was sort of graduating roundabout, the dot com bust. So perfect timing. Timing is everything, right. Really struggled to find a job in being a computer programmer. A lot of companies that I was calling at that time were having layoffs and all of that good stuff. So yeah, got into calling people cold calling companies looking for work experience and at the end of the day found a company that said, look, we don't do any programming locally but we're hiring salespeople. So do you want to give that a go? I was like, yeah, sure. So I fell into it. I can't say that there was like a sales degree that I could do. So I ended up working for a Canadian software company called Maximizer and doing phone based sales. So basically calling people and selling CRM over the phone. And that's how I got into it. And when I finally got my degree, I met up with the sales director at the time by the name of Steven. I said, hey Stephen, I've now got my comp science degree. Yeah, I'm thinking about getting back into, you know, the technology side of things. Ultimately I wanted to be a tech consultant. And he sat me down, he said, look, you know, you've been doing the sales thing for a little while now. You, you're pretty Decent at it. Yeah. What are you thinking about in terms of career choices? You can go down, you know, the technology consultant path or you can go down the sales path. And he had been a career sales guy, like, and worked in SAP sales and big ERP sales. And he sort of explained what life was like for him. I was like, okay, that sounds interesting. I'll give that a go. And the rest was history after that. You know, I spent the last 18 years in sales leadership roles working for companies like Microsoft and Dropbox. And most recently for the last nine months, pre Covid, I was hired by a tech startup called Monday.com to set up the business here in the Australia region. So that's also been a fun ride. Yeah, it's kind of weird that somebody would make the sales to engineering transition because it's always the other way around. I take it you like the variable income of sales and the control. Yeah. Look, I think for me your sales is bit of a creative pursuit. Right. So when I was, when I was a kid growing up, I wanted to be one of three things. I either wanted to be a software engineer or I wanted to be an architect, or I wanted to be a game ranger. And I mean, that's obviously coming from growing up in South Africa and going to game parks and all that sort of thing. And sales is probably all three of those. Right? So yes, the wrangling people. Yeah, exactly. The hunting, the, you know, sort of building and architecting solutions. And then at the same time, you know, it's that creative pursuit. And for me, like the drivers, in terms of what I enjoy most about the profession is really three things. I enjoy building things. It is a business at the moment where we're building a business, right. So I started here as employee number one nine months ago. And it's building a team, right? So building out a team, building the business, building the market presence, building out the market, got the GTM and so on. The other thing for me is around developing and building teams. So I enjoy that part of the profession as well is being a sales leader, is coaching, being involved in those customer and prospect interactions and sort of leading from the front a little bit. And some of the junior salespeople and showing them, sort of, well, you know, here's an example of how I would conduct a sales call or how we would do a demo, all that sort of thing. And then the last thing, it's really about securing the future, the financial future of my family. So I've got two young kids and a wife. But Monday.com is actually quite unusual because we don't have a variable comp plan. It's a non commission sales role. So it's one of those probably new breed of companies and it's becoming more popular in the tech industry where you got software companies that have got non commissioned sales roles and how do they go to market? Because it's a consumer product. Right. But it is B2B too. It's mainly B2B. 2B. Yeah, mainly B2B. But it started out, we talk about this flywheel model so people can go online, they can swipe a credit card and then they can start a subscription. And that's how you find that a lot of companies get started with our offering is it's smaller teams, individual teams that will go online and go. Right. We're going to get started with five or 10 of us and we'll start using Monday.commyteam. and our focus is well, how do we expand that within enterprises and also how do we sort of go further up market into these larger organizations? And that's a different engagement. Right. In that instance, like most recently we've signed up a couple of large enterprises where we're dealing with the leadership team and we're dealing with the C suite. Right. And it's more of a top down engagement as opposed to someone swiping a credit card somewhere lower down in that organization, we're having a conversation around well, how are they tying strategy to execution and how can we help them as an organization achieve the organizational goals? And that's where we engaged at. Cool. And so you have a lot of experience that from Dropbox, which had a similar model. Is that true? Yeah, that's right, yeah. Land, expand, build up to the enterprise. Now from the outside looking in, people would think that's an easy sale. Is it? Yeah. Is it an easy sell? I don't think there's such a thing as an easy sale. And especially in the current environment. Right. It's just different challenges. Right. So if I look at the way our business operates, it's 99.9% inbound. Right. So the team are responding to people that are signing up for trials and downloads. The biggest challenge is actually how do you bridge that gap? So how do you take a conversation that started in a very small part of the organization and how do you broaden that out? Right. And I think that's where the skill comes in is really sort of understanding not only that individual's particular challenges or opportunities that they're trying to go after, but actually sort of broadening out that scope and having a conversation. Well, how does that impact the team? And what's the team trying to achieve and then going out broader from there? Well, what's the organization trying to achieve? And then the skill again is then being able to navigate the organization and get sponsorship through the organization until you're at a level where you're talking about an organization wide opportunity and solution. And have you found common use cases across organizations or is it all over the map? Well, I think it's a function of our offering because it's what we call a work operating system. So the use cases are far and wide. Right. So we got here in Australia, we had one of the government organizations were using our platform in fighting the bushfires. Right. And they weren't throwing software at bushfires, but they were managing it. Yeah, yeah, but managing their resources and their teams in the field and the workshops and so on through to then, you know, we've got another company that would be a creative agency. So for instance, we've got the Sydney Opera House that use our platform to manage all of their creative projects and their digital marketing and so on. So the use cases are quite varied. Right. And so from, you know, first response and critical operations through to creative use cases. Which means I think, you know, for our team you got to be quite agile in your thinking. I think it you do rely on the skill set of being able to think fast on your feet, be able to ask, you know, questions that really open up the conversations and then understand. Exactly. Well, how would we fit into that? How would we bring a solution to bear for that particular problem? And you moved into leadership because you like building stuff, is that. Well, yeah, I enjoy building things. I enjoy developing people and teams. You know, if I think back to when I started at Maximize, I was, you know, inside sales rep, banging up the phone calls and you know, doing that high volume work. And a little bit later on I got promoted into leading that team and that was fun because that was, you know, was at the same time as being right at the coal face in terms of engaging with customers. You also thinking about crafting? Okay, well what are some of the messages? What are some of the challenges that we're seeing? How do you solve for that? How do you define a go to market strategy? How do you open up new markets? How do you hire great talent? So all of those things are quite enjoyable and it's just been a repeat of that through my career. And you have a pretty good knack for picking companies too. Yeah, there's some Good ones. Microsoft, Dropbox, Monday.com, all exciting companies to work for. A lot of trust in the market as well. Well known, good brands. Well known, good brands. I mean, I had a stint there in, I started my own tech startup and. And you really get an appreciation for power of a brand. Right. So when you're engaging with people and you needing to explain who your company is and what do you do, it's a different type of challenge, but that of itself also sharpens the saw. Right. And what are you looking for in reps now for companies like this where there's, it's a seed and spread, trying to work up the enterprise? Yeah. So there's a couple of things. I think there's definitely intellectual horsepower, looking for people that are very smart, that can think on their feet. You know, because the engagement is a consultative style engagement. You need people that can really understand the problem at a deep level and then be able to think on their feet and think about, well, okay, well how could we architect our solution? What are the elements of what we do that can help you solve that problem? So intellectual horsepower, but also just the variety of industries that you're dealing with. So one moment you could be having a conversation with a local government council, another moment you can be talking to a marketing agency and then you're talking to a retailer. And so in some instances their challenges are similar, but in many instances it's just different domains, different industries. So how do you adapt to that? The other thing I look for is people that are driven, you know, people that really have that drive, that ambition because they have the get up and go, they will get it done as well. And it's that resilience as well that comes into play. And you can pick that up. You have a look at people in terms of what are their pursuits, what are their hobbies or what challenges have they overcome in their lives or you know, what, what's their career trajectory? And you can just see, see that thread. And then the last thing is, which is, you know, and trying to get that combination is pretty tough. Is someone that's humble, low ego because, you know, translates and yeah. Sales. Well, yeah, it's. And that's a, it's a, it's, it's looking for a bit of a purple squirrel sometimes. But when I say humble, someone that's really coachable. Right. So someone that is open to feedback and they constantly learning. Right. And that's the thing I think that's when you know that you're working with someone that's going to grow and they're going to be able to adapt and fit in with the rest of the team as well. And like, how do you tell that when you. I'm sure you've hired people that you know or have worked with in the past, but you don't because everybody does pretty well in the interview. Yeah, yeah, yeah. And it's a skill, right? I think 18, 18 years in the industry. I wouldn't say that I'm expert at it. Still make hiring mistakes from time to time. The way I test for that is in our interviews, we do a role play. So we have someone and they'll come in and they'll do a mock sales call, they'll do a demonstration. And for me it's pretty tell. And how they self critique themselves. You know, I normally ask them so, well, how do you think you did on that and that go through? And yet the people that give a good, well rounded self critique, they'll. They'll be balanced and say, look, I think I did these things really well. And on reflection, I think I could have done this differently next time. I could have done better here. And then how receptive are they to your feedback as well? So, yeah, I have an opportunity to also give them some feedback and some coaching. Think the people that do it incredibly well are the ones that take that feedback and they'll give you a replay straight away. They'll go, oh, that's interesting. Can I try that again? And then they'll give it a go. So I'd say that's like a 10 out of 10. Someone in the middle of the ground will sort of go, okay, yeah, that sounds good. Thank you for that and whatnot. And then I think a bad signal is someone's super defensive and dismissive. Right. And do you see that the most often? Because that's. Everyone kind of rationalizes, well, you know, I'm uncomfortable. I really don't do it this way. But I mean, that first example is perfect. Yeah. I'd see the middle of the ground the most often. Right. So most often people like, yeah, because you're in an interview situation, it's a bit of a contrived situation. People are really polite, they're nervous and so it's probably the middle of the ground. Yeah. If I see someone that's really defensive and pushes back and you can see that pretty quickly and go, okay, well, that's a red flag. I don't think we're going to move forward with that person. Yeah. And that business acumen, that first item that you mentioned being able to have the intellectual horsepower to talk to a diverse group of people about a diverse group of topics on their feet. Right. You just can't take notes and get back to them. You have to have it interactively. Is there any techniques that you've used to kind of ferret that out before hiring them? Before hiring? Yeah, look, I think it's. I like to have a conversation and just understand how conversational is someone. Sometimes I'd ask an interview question around something topical. Right. So what technology do you think is having the most impact at the moment? Or what are you most excited about when it comes to technology? A technology or an application that you use in your day to day life the most and then really sort of unpacking that. So I think that brings out the ability to be conversational and not just be too one dimensional in the conversation and then from there just get into different topics. Right. So tell me about a customer that recently won or what's a win that you're most proud of? And then out of that you'll get a sense of, did they really have an understanding of the business problem or the challenges that we're trying to solve for what sort of conversations were they having with that organization? Who are the people in the organization that they were engaged with through that sales process? And then it becomes pretty clear whether it's someone that has that business acumen where they have the ability to engage with the C suite and get into the boardroom and carry a conversation. That's a great question. I remember a manager asking me that. And then he asked, well, how did they administratively purchase? And I told them. Exactly. And he goes, you're the first person I ever interviewed who knew that. Yeah, yeah. And that's, yeah, it's interesting because that's a skill in. Of itself. Right. Understanding the procurement path and especially with large complex organizations that. Yeah, that's a significant scale. Yeah. Just near the end of the quarter, what happens, you know, they don't know where it is, you don't know where it is. And the manager's like, is it even real? Yeah, yeah, you know, it's kind of black box. And you, you got to. And look, I think with, with our team, we ask those questions. We, you know, we're, we're scrutinizing every engagement that we're on, engaged in and understanding, well, who's the economic buyer, who's the decision maker, how these decisions being made. Is it decision by committee or is it one person understanding, well, where does that budget come from? Who needs to sign off on it or sometimes even what. What system do they need to, like, what do they need to do at a, at a system level? I remember at Microsoft we had a very large deal that I was working on. There was $7 million purchase and it was down to the last day of the quarter and it was a Friday. And basically this one deal was the make or break for the team for the quarter. And we literally had the appointments in the diary of the CFO for 5:30pm and my contact was standing outside his door and he had an appointment to go in and just sort of have the CFO push the button in the Oracle ERP system to release the pr. So you had to get down into that level of granularity and detail to get it done. And if we hadn't done that, we probably would have had a deal that would have slipped into the next quarter and be pretty painful. And what's it like to be. You're probably the first person they hire in Australia, usually. Is that true? That's right, yeah. And you know, I've been kind of that person in a certain market that no one understood. Yeah. So you're kind of, you know, not black sheep, but you're the distant cousin down in Sydney. Yeah. How is that? How do you manage that? How do you. You get the time zone, you got the language, you got. It's a new market. Yeah. You got it. You treat it like a business. Right. It's my own enterprise. That's how I look at it. So setting up this business here in Australia, it's a startup within a startup. Right. And it's super scrappy. But that's fun as well. Right? I enjoy that. I mean, my little home office here, it looks like a little bit of a post office. I've got all the IT equipment piled up and as we get a new hire, I'm getting a courier, I'm sending a laptop out and a monitor and I'm doing that. But at the same time, we're working on these larger enterprise customer engagements and projects and everything in between. But it's fun, it's scrappy. And again, coming back to my why. Yeah, I enjoy building things and for me, that is a creative enterprise. At the same time, there are sort of certain things that you just got. It comes with the territory. So dealing with time zones, we're having this conversation at six in the morning and I'll be meeting with someone just after this because they're in New York. And then later on this evening, I'll Be having calls with people in Tel Aviv, and then during the middle part of the day, I'll be engaging with, you know, customers and team members in Australia, New Zealand. So, I mean, but ultimately, you just got to manage your energy as well. So at an individual level, you've got to make sure that, you know, you taking time out to look after your health and, you know, get a little bit of sunlight and exercise. So, yeah, I do that as well. And you came highly recommended for the show. What do you think motivated people who have worked with you in the past to recommend you? Well, that's a. That's a good question. I think I enjoy having a connection with people like the people that I work with. You know, I'm invested in their development, their success, you know, so I think that shows also in, like, having fun. So, you know, the people that I work with, you're with them for the most part of your day, more so than, you know, you might spend time with their families. You know, how do you. How do you work with people that you enjoy working with? How do you make the work environment, you know, an exciting, motivating, fun place to be? So I think that's a big part of who I am. That's sort of my approach to leadership in general. And yeah, I think that's, you know, the people that recommended me, obviously, it's. That's resonated with them and hopefully they've grown professionally, but also had a good time as we work together. And how do you do that? Is it just events, open communication, getting to know them as people, not just as employees or team members? Yeah, I think it's all of that. Right. It's understanding, well, what are people's personal motivations? What do they want to achieve for themselves and their lives, and how can you help them do that? Right. I think, you know, my role as a sales leader is to make the team successful and to create an environment where success can thrive. Right. So. And I do that in a number of ways at an individual level is understanding, okay, well, what, what's your motivation? What's your drive? How can I help you get to that? Yeah, and sometimes the conversations are broader than just, you know, work. I think, you know, sometimes it's, it's. It's. It's giving people on advice and other things or sharing your life experience. You know, I am quite open and, you know, can be vulnerable with people as well, and I think that that establishes that human connection. Right. So people understand, you know, what's my background, what's my Drive. Why am I doing this? What are the things that I'm challenged with being, I think as a leader, just also being vulnerable and just having a go and showing people. I think with one of the sales folks that I was working with, he had a really tough role, like he had to make phone calls, cold calls into enterprises and it was just getting knocked back. Knocked back, knocked back. And I was like, hey, well, why don't we just go sit in a room for half a day and I'll make the phone calls and then you listen in. Right. And I'll get in the trenches and I'll make the call, the cold calls. And we did that for a couple of hours and you know, so just willing to sort of walk in his shoes, show them how it's done. And I think that resonated as well. And then you come back to the. Having events, having fun. Yeah, I think it's, you know, just creating an atmosphere not only in the office but outside of the office where you connect as a team and you feel like you're doing something as a team as well. Like you've got a shared vision and you're building out something that's just bigger than yourself. Cool. Hey, I really appreciate your time today, Dean. Where can people go to connect with you and learn more about you and your work? Yeah, so you can go onto LinkedIn DeanSwan and can find a little bit more information about myself there. And yeah. Monday.com. so if people are interested in looking at what our startup's all about and what our platform's about, you can just go online. Hey, what a great guest. I really enjoy talking with other sales leaders, understanding their motives, their differentiators. And I think you get a lot out of hearing how other people are solving these particular problems. If you or your team is looking to up your game, check out our training courses over at b2b revenue.com the letter B, the numeral 2, the letter B. And then the word revenue.com is not a beautiful word. Revenue. Also, if you'd like to support the show, please put a rating, a review or even better, tell another sales leader or even your team to check us out. Either this podcast or we got several others. We got the brutal truth about sales and selling, which is interview based about the very best reps in the world and what is working today. Sales questions, brutally honest answers. A daily Q and A type show talking about the questions that people are asking today and the answers that I have for them. Also the B2B Revenue Leadership show where I talk to CEOs, CROs and CMOs about what is working today. Oh look at all that content. And if you happen to see my videos, pass you by on LinkedIn. Brian G. Burns Give it a little thumbs up. Whether it's comedy or content, I try and break up the day with a little sales comedy as well as some content about what is working today. Little tips, tactics, techniques that have been working for me, different ways of looking at the sales world and how to get people's attention, get conversations started and keep those deals moving. Appreciate you listening and we'll see you next time.

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