Inbound Marketing

How to Avoid the Subculture | Ep. 07

Dave Shepherd is a long term HubSpot employee who joined us on our seventh episode to talk about sales leadership and building a culture with your team.

How to Avoid the Subculture

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When was the last time you were faced with a problem? How did you approach it — did you take accountability or did you point fingers? Or did you think strategically about what really was the root issue of the problem, not the obvious answer, and come up with a plan to tackle it.

We brought on David Shepherd, the country manager for HubSpot in Sydney, for our seventh episode of our podcast and what a treat it was. Dave has been with HubSpot for ten years and has played a pivotal part in establishing HubSpot in Australia and New Zealand.

In this episode we discussed Dave's journey and what attracted him to HubSpot in the first place, how he overcame difficult decisions when establishing himself in the HubSpot Australia office, and really great insights into building a team and culture. 

Some of the show highlights include: 

  • What got Dave into sales and how his career transformed over the years
  • Why Dave was attracted to HubSpot in the first place and the interview process he had to go through 
  • How HubSpot came to be the marketing and sales solution for small businesses and why Dave has such a strong connection to the mission for that reason
  • How scaling an organisation is a tremendous task and what the steps behind it are to ensure it is done successfully
  • Why your sales process needs to iterate and mirror your customers challenges
  • How Dave found and adopted a new methodology within his HubSpot branch to solve a problem he was facing 
  • Why small businesses matter so much to our economy
  • How important it is to take accountability within your roles 
  • Ask questions but don't answer them. Ask 100 questions

Links and Resources 

David Shepherd's website 

David Shepherd on LinkedIn

Extreme Ownership by Jocko Willink

Traction EOS 


Quotes by Dave

  • “I met a guy by the name of Joe Sharon, who is the recruiter at HubSpot. And I'm just like, this is the first company I've ever met that really gets it. They believe in systems and processes and they were super smart and they were driven by it a mission, it was clear that the culture was important to them.”
  • " I'm a huge fan of small business owners, I think they work really hard. I think they tend to do an amazingly good job at whatever they do. You know, whether you're building houses or you're a plumber or you're a chiropractor, whatever, like, they tend to just do a great job, right? And they really care about their customers, they care about the business, and it's really their whole life.
  • “so you got leads as the first process. The second one is probably the hiring, you got to hire really great people that can turn those leads into customers. “
  • “You got to continue to iterate on the sales process so that as things change with your customers and your prospects that you have a sales process that mirrors what is needed there. But it's also compelling and builds urgency in shows your product in the best light.”
  • “And I don't care what level of selling you're at, whether it's you know, you're selling to small businesses, or you're selling to enterprises. You have to be creating pipeline every day.”
  • “One of the things you're trying to do in life, as a business is finding people who believe in your version of the world, right? Like, believe what you believe. I've kind of said that before about the hiring. And I think that's super important. But I also think that's what you're trying to do when you're acquiring customers.”



Charles McKay  00:04

Hello, and welcome to another episode of The Beyond Business podcast. My name is Charles McKay, and I'm your host today. Today we had the pleasure to speak with David Shepherd, who's the country manager for HubSpot in Sydney, Australia. Dave Shepherd has come from the US... He started HubSpot over 10 years ago. And you know, over 10 years ago, HubSpot was a reasonably small company. You know, when he started under 50 employees and now to over 4000 employees around the world. David's had all sorts of sales roles within the HubSpot organization and pre HubSpot as well. And he goes through the journey of you know, what that process looked like to become the country manager for Australia. And then when he hit Australia and became the country manager, how, you know, it's been around for three or four years, and it did hit a bit of a subculture as such, or you know, there may have hit the ceiling, and it was fascinating what Dave found out what he thought was the problem at the time to then what really became the problem and how they went through and solved it. If you're into leadership, growing teams, and building sales organizations, then this episode is absolutely for you. Dave's got some great insights and shared some really interesting stories about the journey. Without further ado, I'm gonna hand over to Dave and myself. Enjoy.


Charles McKay  01:26

David Shepherd. What a pleasure it is to have you on the show, mate. So tell me, Dave, whereabouts, are you sitting at this current time?


David Shepherd  01:34

I'm in beautiful Manly, although it's a bit overcast at the moment. Yeah, on quarantine. I think this is week seven for us.


David Shepherd  01:45

We were a bit early to the whole game. Been some opposite times there to say the least. But this week is a good week. So your catch will be on the high.



That's good. That's good. What's been the one thing that you've been doing to keep yourself up and about in a good state?


David Shepherd  02:00

I would say two things, kind of, you know, a regular schedule of walks. Kind of start the day and end the day with at least a 20 minute walk. And then I've been cooking a lot, which has been, which has been great for being a little more healthy these days. But yeah, I just think, you know, with no commute you get a little more time to cook some food. 


Charles McKay  02:22

Absolutely, absolutely. So, Dave, thank you for joining us today. It's a real honor to have you on the show. You do seem to have a bit of a funny accent. So tell us a little bit about your accent and whereabouts you're from?

Dave's Background in University and the Start of his Career

David Shepherd  02:35

Yeah, I'm from the US. The Northeast... Grew up about two hours north of Boston in the middle of nowhere. Then spent a bunch of years in Boston, both for university and then joining HubSpot, not too long after university, and I'm coming up on 10 years with them. But somewhere in the mix there they decided to send me out here to Sydney. What was supposed to be a one year contract has been over four years now and I've totally fallen in love with, with Australia in Manly and Sydney and have no plans of going anywhere.


Charles McKay  03:11

That's awesome. That's awesome. So let's backtrack a bit. You said you started university in Boston? What did you actually study there? How was that for you?


David Shepherd  03:20

Yeah, I was, uh, so I was one of those guys who took as long as possible to decide what I was going to actually major in. And so I picked it late and I picked economics. But if I had if... I could have picked business or entrepreneurship, that's what I really would have liked to do. And there was a new program back then you kind of get a minor. And I don't know if that all that kind of terminology makes sense here in Australia, but yeah, so did the kind of econ and entrepreneurship thing trying to figure out how to get into business. And always thought I was gonna be a startup guy, but joined on with HubSpot... just been such a great such a great run. Learned so much. I couldn't be happier with how things turned out.


David Shepherd  04:02

Yeah. So how did you know, you finish uni. How did you end up landing that job at HubSpot? Was it... did you even know what HubSpot was 10 years ago like how did that happen?


David Shepherd  04:13

It's kind of a fun story actually to tell. So I had a goal to always learn how to speak Spanish. So after I graduated, I actually went to Argentina for basically a whole another school year. So I left in September kind of came back in May. And it was, it was a great time, you know, kind of scared to kind of go overseas for the first time all by myself, that sort of thing. Didn't know anyone there... was going to stay with a host family, all that stuff. And that worked out great, made some great friends. And when I came back, I actually landed my dream job what I thought at a commercial real estate development company, so these guys were like, just the best of the best in the Boston area. They built all sorts of really big projects across all sorts of different styles of buildings, whether that was like industrial stuff or commercial or retail or multifamily stuff. And that was 2008 so you can imagine what happened I, you know, I get this great job and they were smart... They said, "Listen, you're hired, but we're going to put you on a 90 day kind of contract because we haven't really picked up any projects this year. And we're just a little nervous. Don't worry, we pick up a project, you know, you're in, you're hired. But we just want to be frank with you that like we're gonna have a hard time keeping people busy if we don't, we can't get something going here." And they knew way ahead of time that something was was off with the economy. And so I was there for about four or five months. And then obviously, that came to an end because I wasn't doing anything and kind of no one else was either.


Charles McKay  05:50

Well, what were you hired for? What was that role?


David Shepherd  05:52

Honestly, it wasn't really defined. It was more of like, Hey, we believe in you and we're gonna kind of go room you into? Yep, something and you're gonna help out and you're just gonna, you know, if you can work hard, this will work out really well for everyone. I think honestly, they had it... they were really tight knit group, and many of them had worked together for 20 years and I think that they were kind of trying to look to inject a little bit of youth into the organization, because I think they kind of remember themselves as being the youthful, you know, go getters and felt like they could, they could benefit from a little bit of that. So I basically, I don't get fired, but like, it just comes to an end. And there's nowhere else in real estate to get a job because like the banks have totally frozen, no one's giving out loans. So the whole industry just comes to a flat out standstill. And you know, I was getting some mixed advice by some mentors about you know, stick with it, you'll find something and others were just like, Well, you know, maybe need to move on. And so I ultimately said to myself, like my goal has always been the same which is to start my own company. And I was like, I've heard that you have to learn how to sell. So I, I basically took the first sales job that came my way, which was selling life insurance for a really good company, a company called Northwestern Mutual. Kind of largely considered the best life insurance company, maybe in the world. And I did really well. I won a bunch of awards and hated every single day of it. I was working as hard as you possibly work. And it just sucked. I hated it. I didn't like the way you did business. You had to like, I would meet with you, Charles and I would get to the end and be like Hey, did you get value out of this? And of course, you're gonna say yes and be like, Okay, well give me your whole Rolodex of all of your friends and family and I'll call them and try to sell them too and I just hated that. That dynamic of you having to vouch for me. 


Charles McKay  07:48

What was the like purpose behind that like other than just selling, you know, selling widgets call it anything but what was driving that? Was there anything behind it?


David Shepherd  07:59

In terms of like my motivation?


Charles McKay  08:02

No, what the business had sold into you.


David Shepherd  08:06

Oh, you like... Like what was like the... why did I take the job in the first place? 


Charles McKay  08:11

Oh more like yeah so you're young... you take the job because you need the job and you know you got the work ethic you're gonna do it, but what was the like, obviously you won all those awards, but what was the defining piece? Were you just like I hate this because something internally was not aligned with you, I'm assuming?


David Shepherd  08:29

You know, it's it was one of those funny things where I knew that I wanted to do sales but I could just tell that it was not something that was like interesting me and nor did the way the business operate nor did like the mission really matter to me. Like, I own all the products still right? I've been paying out for years and so I've had him since I was 20 something years old and who needs life insurance when you're 20 something years old. So what it wasn't that I didn't believe in this stuff. 


Charles McKay  09:02



David Shepherd  09:03

But it was... I just didn't. Yeah, I was just like, this is a no brainer. Like, if you're a responsible human, you get life insurance. This is not something I want to spend my life doing. I just didn't like it wasn't like a huge calling. So I tried to quit like 10 times, like, honestly. And I think my, my logic brain just didn't listen to my heart. And I wouldn't trade it because it was so hard that everything else afterward seemed really easy.

Why Dave joined HubSpot and the Interview Process

David Shepherd  09:33

Both by the hours and just like the toughness, it took for me to like, go through that. And so that kind of was the launching point. And then so I through that whole thing, I decided that I was going to look for jobs. I wanted to get into tech, and I met a guy by the name of Joe Sharon, who is the recruiter at HubSpot. And I'm just like, this is the first company I've ever met that really gets it. They believe in systems and processes and they were super smart and they were driven by it a mission, it was clear that the culture was important to them. And I was like, this is the first group of people that actually get it. And I don't know like what get it means. But it's like, I'd read a couple of books about entrepreneurship. And I tell you, I studied at university and it's just like, this is what people talk about when they talk about a great company. And I just knew it. And I get all the way to the interview with Brian Halligan, who's the CEO. And it goes terribly. I was like, it was just the worst. Like, in hindsight, it was probably a shoo in to get the job if I hadn't screwed up that interview. And I was just thinking, I've met with 400 people this year in a sales capacity, and all moved on pretty well and that was probably the worst meeting of the year. And so, Joe Joe in the recruiting team, they never quite told me no. But it was clear that I didn't do well with Brian. And so I actually had to take on another job. And literally on my six month anniversary, taking the new job, Joe calls me up and says, Hey, you should look at interviewing again at HubSpot. And I kind of played it cool like I wasn't interested, but I was totally interested. And so that kicked off the whole set of things. And you know, part of the reason why I didn't get the job in the first place was back then it was really important for HubSpotters to be what Brian would call a digital native. Meaning that you had a blog, you knew how many Twitter followers you had, and you were just doing the thing, right, you really believed in it. And I was totally a digitally native, like, I was one of the first people on Facebook. But I didn't have a blog. I didn't know how many friends I had; I didn't know how many Twitter followers... didn't know how many connections I had on LinkedIn. And so the second time I was ready, I had a blog. I've been blogging for six months. I knew everything that so I get back into an interview with Brian. And he walks in and classic Brian style he goes "didn't I already tell you no." And I started laughing and was like, "Yeah, you did, but I'm back." And so he goes through his whole spiel and asked a bunch of tough questions. And, and you know, about 15-20 minutes it goes, "alright, you're good." And he just walks out of the room, and that was the beginning of the journey. So it probably took me nine plus months to get into HubSpot. But yeah, I was always gonna try to find a way to make it back to HubSpot. 


Charles McKay  12:16

Yeah, yeah. And what was that? So that first role, was that like inside outside sales or BDR? Like, what was it?


David Shepherd  12:23

Yeah. So it was a kind of an inside sales account executive. We didn't back then... we didn't really differentiate in terms of like, who you were selling to too much. We had some slightly kind of each got... actually hired us as a pool. And then after you went through training, they then assigned you to a manager. Yeah, and so I was I had it was a regular sales rep carrying a bag. Working hard. Trying to figure out how to sell software because I've never done that.


Charles McKay  12:52

Yeah. And leading into the problems at the end of the day, because the bigger the problem, the generally the better off you're going to go. So In the early days, what was the problem that you thought you're selling to I suppose when it started to click and shift that you went "ah this is the actual problem that I'm solving?"


David Shepherd  13:12

Yeah, so both my parents own their own businesses, right. So my dad builds houses, my mom sells houses, which is probably why the commercial real estate job was like my dream job right?


David Shepherd  13:22

Not too far from home.


David Shepherd  13:26

And, you know, I'm a huge fan of small business owners, I think they work really hard. I think they tend to do an amazingly good job at whatever they do. You know, whether you're building houses or you're a plumber or you're a chiropractor, whatever, like, they tend to just do a great job, right? And they really care about their customers, they care about the business, and it's really their whole life. But I think where they struggle is to find customers. And I just always thought that HubSpot was, like, the best way to get customers in our new world and so back then we had to convince people that their customers are online. And that was not always easy to do. You know, cause this is 10 years ago, like, it seems obvious now, but back then it wasn't. And so one of the first people I sold was my mom. And, you know, I think the problem that, you know, you know, you could say that what we were doing is we were selling kind of an SEO software or blogging platform for business world stuff. But really, it was all about helping companies get leads, because most small business owners I think, like once you get a lead, like you, you know what to do to kind of get them to turn into a customer and then you're usually great at, you know, customer service and so forth. Otherwise, you just don't stay in business. Right? Yeah. You kind of fail out.

How HubSpot has Scaled with Such Success

Charles McKay  14:42

Yeah, yeah, I think too the, you know, we all know about the methodology that HubSpot built, but that was a game-changer, and it's obviously evolved a lot since then. But that core problem, at the end of the day is going to be some sort of growth of whether it's people, you know, internally or externally. So tell us about some of the like, obviously, as your roles evolved from, you know, inside to, you know, now country manager of, you know, APAC what's that shift in problems and what's you know, I suppose HubSpot, you know, they're very good at having clear focus without letting the noise come in, like, how has HubSpot scaled just so well, globally while keeping on focus and that core mission?


David Shepherd  15:35

Yeah. So, you know, I think the secret to HubSpot is kind of what I first sensed in some of those first interviews, which is, you know, they, they certainly hire the very best people. We hire the very best people, but we believe in kind of doing things that can scale and kind of building process and so if you just think about, like a sales funnel, for example. You know, you start with how do you generate leads, and then a whole bunch of steps happen before then. But really, that's the first step in the process in order to grow sales. And so for us, we built out the whole inbound methodology and we followed it to a tee, right? You create content; the more content you create the better... you socialize it on all the different social media sites. You build a community by commenting, and by interacting with people whether that's on your own blog, or whether that's on social media sites, and you just like that stuff... It builds it's like a tidal wave, right? 


Charles McKay  16:44



David Shepherd  16:45

Yeah, compounds. Yeah. And so that's how you generate all the visitors, and then you got to create really great content and turn those into leads, you know, I probably don't need to go through each step of the inbound process. But yeah, you know, then you turn that over to the sales side, and then you have a couple of other processes you have to kind of figure out, so you get leads as the first process. The second one is probably the hiring; you got to hire really great people that can turn those leads into customers. Then once you hire them, you got to figure out a way to onboard them, get them set up in your culture, get them set up in your ways and your processes and how you do things. And then the last part is you got to continue to iterate on the sales process so that as things change with your customers and your prospects that you have a sales process that mirrors what is needed there. But it's also compelling and builds urgency in shows your product in the best light.

Why Finding the Right People for the Right Seat Matters

Charles McKay  17:39

Hmm. So I want to dig into this a little bit on the people component, especially the sales component because that's one thing that I have, you know, I'm not trained in sales. I didn't do sales. As you know, it wasn't my first job. And the thing I found about nearly everyone that deals in sales at HubSpot, you wouldn't say they're the traditional salesperson. And, you know, some of your best have been introverts... don't like public speaking, like, just totally off your traditional playbook. So tell us a little bit about how and when that sort of happened that you saw the, you know, alter ego sales rep.


David Shepherd  18:18

Yeah. Man, so where there's so much to go on. Okay, so I think the first step to finding great people is to work out what are like the fundamental values or attributes that someone has to have in order to be successful? And I think as you're a start up and you're growing, you don't really know those things. You start out, you try to figure it out, but then you end up hiring all sorts of people and you realize that all sorts people can be successful. 


Charles McKay  18:53



David Shepherd  18:54

But there's some common core that is the same across all them. So you know, some of the things that that house looks for is like curiosity, commitment to win, being coachable among many others, right. And when I think about that sort of stuff, like you're really what you're really doing is you're trying to find people who view the world in the same way that you view the world. Now they can come from all sorts of different backgrounds, they can have all sorts of different, you know, shapes and sizes, be extroverted or introverted. But like if you're an introvert or an extrovert, just because you use that as a label... Both... there are people in both those groups who are just dying to win, right, and who are super curious and who are super coachable... those... their outward way that they deal with the world introvert or extrovert, or how they kind of gain their energy that doesn't really have any to do with any of those things. And so I think we build a very long interview process to try to tease out what exactly is this person kind of made of? And do they, do they think about the world in the same way we do? And do they have those kind of those attributes that we're looking for? So I think that's step one.


Charles McKay  20:18

It's fascinating, and I couldn't agree with you more. You know, you get that mission-aligned and you get the right person in that seat. It doesn't nearly matter what they do, and have done if they've bought into it and a passionate, curious, coachable. I was listening to something yesterday actually on especially in this current time, like think of elite athletes where the dates have just disappeared from their life. So there's, there's no Olympics, there's no football, there's no tennis events. So the ones that are actually going to come out of this period stronger are the ones that actually treat it as a process every day they get up, they do their work, there's no date. And would that be something that's quite common or a common theme too? That and, you know, it's all about the process, not necessarily the result.


David Shepherd  21:10

Yeah, I think there's I mean, it's, it's, it's hard to give you a full on yes to that one. You know, s a salesperson, there's, there's nothing I like more than a deadline. Right. And I know, you know, as a salesperson, you always have a bit of a weird relationship with quota and end of the month or end of the quarter or whatever it is. And but I do think that does help us take action. But I agree. I think that when I look at our best sales reps, it's the ones who are consistent on a day to day basis. You know, they don't have they don't necessarily have good days and bad days often, right. They have steady days. They don't let themselves have a bad week they figure out how to course-correct if things get off to a bad start, or they hit a hiccup in the middle of the week, and I just I do think that the process and especially for sales reps, like so much of it comes down to just creating a pipeline. 


And that, that can't be a sporadic process that has to be an everyday thing. And I don't care what level of selling you're at, whether it's you know, you're selling to small businesses, or you're selling to enterprises. You have to be creating pipeline every day.

How Dave Approaches Issues 

Charles McKay  22:31

Yeah, no you are, you are spot on. What' a classic story that comes to mind where it's been an epic failure?


David Shepherd  22:43

I can go a couple of different ways with that.


David Shepherd  22:48

I think maybe one of my most, I don't know, one of the stories I'm most proud of, I guess. So this was more recently, maybe a few years back. I had been a director for maybe about a year... I finally kind of figured out what that was, like, having kind of managers sit between me and the individual contributors. 


David Shepherd  23:11

And we, you know, in Australia, December and January is a bit of a tricky time to sell, because, you know, you have Christmas and just the way the culture is, you know, people take at least a week, sometimes 2/3/4 weeks off at that point in time. You know, kids are out of school, it's the middle of the summer. The weather's great here. It's, it's a good time to take time off. And so everyone kind of goes into what they call this like, you know, silly season, kind of somewhere in November to kind of late January where things just kind of slow down. 


Charles McKay  23:50



David Shepherd  23:51

And we just do really poorly in January and February, and it's not looking like it's gonna go well in March. And so we jump in, we do a whole bunch of analysis. And the analysis basically comes back that essentially our reps, our sales reps just didn't go to work. They didn't do that consistent daily pipeline creation. So if you looked at the graph, it was like, October and November, are up here, December drops in half, January drops in half, and then you're like, Okay, well, what's gonna happen in February. And February is like a small uptick. So you basically have like, December and January are the same amount of activity to create pipeline as just one month in November, or October, right. And so now you're already behind the eight ball because we're on monthly quotas. And because we're an American company, the end of the year, December is a huge push to get some extra deals in. And so you pull deals from January into December, and so January, February, just absolutely terrible. And I'm sitting at the, you know, first week of March being like, what's going on, and so you do the whole analysis and you know, in some ways, luckily, it wasn't a change in the market because that's a lot harder to fix. But to discover that, it's just because your team is not putting in the effort, that is a... that's just a kick in the gut. And so I'm thinking about it and we've done a whole bunch of things to try to stimulate activity and stimulate pipeline generation because we know this is a tough time of year and it's all just falling on deaf ears. And I have this I have this little ephiphany right. And by the way, to give you the level of failure that this is like me worrying about whether I'm going to be able to continue as a sales director... This is like a total face flop as bad as it gets, that's how bad the results were right? 


Charles McKay  25:51

Yeah. Oh, cuz and you guys too, if you run two months, not hitting there are red flags flagged, yeah?


David Shepherd  25:58

Yeah. And it was such a bad miss both months that it was like total red flags high alert. Everyone in the company is talking about it. Lots of scrutiny from all sorts of people across all sorts of divisions, like not just sales that's worried about this. Because, you know, the Sydney office has a meaningful portion of the global revenue. So this is an all hands on deck. And, you know, one of the key stats we found was that when BDRs are creating deals, right, they were going through the sales process, just as well as if a rep created a deal and so that was a good signal for us. So there was nothing really wrong with our sales reps, there's nothing really going on in the market. But the whole level of activity in terms of just like, creating ops and creating pipeline was way down. And so now I got to figure out what to do about this. And you know, the worst thing you can do is just say, hey, the reps are lazy. 


David Shepherd  27:00

So the Epiphany I had was, what the... just a single question, what if the low activity is not the problem? What if that low activity is actually a symptom of something bigger? And so I started to kind of ask people questions and, and kind of work with that in my mind a little bit. And basically, where I came back to was at that point, I think the Sydney office was maybe three or four. Probably, yeah, somewhere like that three and a half years old, or something like that. And I started to think back about the guy who, who founded the office, another American guy, Sam, who you know very well. From the original team almost all of them are still with us today. And the mission originally was to put Sydney on the map. Right. They had a mission to prove that they were as good as any other team. And for two years in a row, which basically ended in December, they were the best team in the globe, right, like highest performing. And I think what started to happen towards the end of that year was like the mission of putting Sydney on the map and to proving to everyone internally at HubSpot that Sydney could do the job had worn off. And now you had a whole bunch of people who were looking for the next steps in their career. And they hadn't lived that high growth scenario before and they didn't know what was to come in, you know, six months, 12 months, 24 months or even beyond that. And so what I really decided was that we had an identity crisis in Sydney. That like our identity as an office was, you know, tied to something that was in the past, and no one really understood where we're going or what was ahead or what the opportunity was. And so I sat down with that point, just the sales managers who were the majority of the office but not the whole office, and we decided on trying to figure out a bigger vision for the company. And we saw... we did some quick modeling, and said, Okay, if in five years if we just do what we're supposed to be doing, we'll be at X number of revenue... what's what's our big stretch goal? And so the managers, you know, being sales managers picked a really big number. I remember going home that night and I remember just being like, what have we done? Have we just... have we just way over committed?


Charles McKay  29:26

You haven't shared this with the rest of the company yet though. You've just done it in Sydney?


David Shepherd  29:31

No. And so I was looking at the Sydney office like it's kind of its own little business unit. Because we kind of take after the whole Australia, New Zealand market. And it was really about trying to paint a picture about what it was gonna be like for our team to be HubSpotters over the next five years. And we settled on a revenue number, I don't think anybody was happy with that. I think we much would have rather have settled on something that was like, you know, customer impact or impact on our employees. But the only thing that we could have really... we knew we were going to be able to measure was revenue, because there were so many things that were changing within the business. And if we went back two or three years, you know, we couldn't have possibly have determined the metrics that were super important to us at that point in the business. So we're gonna pick a five year goal, there's just no way we're gonna be able to pick the metrics that are going to be super important at that point in time. And so we went with revenue one. And I basically prepared a whole TED Talk, like 15 to 20 minutes, no slides, talked about the problems, talked about the future. And it was a pretty emotional talk, to be honest, but we launched it a few years back and I don't honestly know how it was received on day one. My guess is there was some people were just like, this is total BS. You know, I got this American guy who were doing a little bit of the rah rah thing, which is, you know, slightly frowned upon in Australia, not terribly but slightly. Yeah, less so with my Irish friends. Irish guys are way more skeptical I feel like.


David Shepherd  31:09

So yeah, we get the kick off but then we make it a part of our regular cadence. And you know, I had a coach at the time and he was just like my worry is not whether you can execute on the vision my worry is not that you can't do the presentation. My worry is not that you can't get people bought in. It's can you get the rubber to meet the road. And so we implemented this thing called traction.... EOS entreprenuerial operating system, which I know you're a huge fan of. And that's been how we've kind of be able to keep the vision grounded in the day to day, week by week, quarter by quarter thing. It worked. So we now have this huge goal, right and we've talked about it in terms of revenue, but you know, similar to our flywheel, which I actually have like this little thing here, in case people don't know what the flywheel is. We've kind of you know, said that the goal is the middle orange part and that, what that means is that we're going to have to be more innovative in Sydney, than anywhere else in the world in order to hit our goal, because it's such a big stretch goal. And what that does is if we're innovative, we do that right, we'll be able to get more customers and have a bigger impact on our customers. And if that goes right, then there'll be even more opportunity in Sydney, for our people. And so, you know, there's more opportunity that leads to more innovation and on and on, and kind of equal kind of spin. And it's worked out great. It's exactly what's happened like we've been able to build a brand in Sydney that we're willing to test things and do innovative things. It's also a nice sized market for HubSpot as a whole. And so we like to test things in Sydney and the team here is, you know, most of the time, you would say that sales reps don't want to test things. They just want to like, Hey, leave me alone. Let me sell, let me get to quota, let me get the President's club, let me make a bunch of money. But that really hasn't been the case in Sydney. We've really had a really fantastic adoption of some of these innovative projects, or tests experiments however you want to think about it. And it's going really well. So that actually fixed our activity problem. It was really a vision problem in the end. The people didn't know how they end. And, you know, I would have to say that over the last couple years, we've iterated on it, but activity has never been higher than it is now. And it seems to be getting better quarter to quarter. 


Charles McKay  33:25

It's fascinating, especially too with a business that has such a good vision and has all of those things. But in a branch or a sub branch, how subcultures can exist, and it's like, well, how do you get that buy in? And it just shows vision, at any level in any office, having worked in businesses that have multiple branches too like, there is a subculture within those branches for sure.


David Shepherd  33:47

Yeah, I think it's such an important point to make Charles. If you were to say like, O"h, we don't have a vision or mission at HubSpot," like that would be crazy, like, you know so well, like that's like everything to us. And so when we set when we settled on this idea of what we call this a vision for the Sydney office. I was, I was actually really surprised. I didn't think that was going to be the answer because we have a great culture. We win all these awards as best place to work and, and it's everybody, every HubSpotter can tell you what HubSpot's mission is. But really the gap was, what does that mean for me on an individual level, and I felt like the missing gap there was like having something that was just for the office that would, you know, break down that big global mission into something a little bit more meaningful to them. And then from there, we could we could start to tell the stories about individuals and how their careers were moving forward and all of that. And it worked. It's again, it's worked out great. And I think it was really the missing piece though, that people fill in their own stories and really understand where the boundaries were and how they can make a life for themselves within this big global mission, you know, with 4000 people, I think now at HubSpot or something like that.


Charles McKay  33:51

It's amazing and so empowering for people as well, like you're giving them their own purpose and setting their own little mission within the company. I love it. So, wait, so that was like three and a half years ago that you did that. And probably a pretty defining moment for you too in your career where you've just gone and said, you know, you've always wanted a business or you've always wanted, but you've literally said, Oh, this is my business now or I'm going to just treat it like it is. Which I think is a really good thing to do. Like at the end of the day, every business is your own business. You're dealing with people, you're building relationships. What, you know, that vision that you set to the journey, it's been like, and you said that they probably thought you're a bit crazy initially, but you know, we all know that it takes seven to 20 times for it to actually sink in and eventually, you know over your quarterlies it's gonna get more exciting, more momentum. Everyone buys in harder. Has the vision exceeded or like, you know what, what has happened from where you initiially set it.


David Shepherd  36:13

Yeah, we're basically right on pace.


David Shepherd  36:17

Although the way we did the plan, the first two years, were going to be the easiest two years to be totally honest. And so, you know, this third year is now really the first really tough one. But the truth is, we're right on pace. You know, I haven't looked at the last maybe a month or two of data yet. And so, you know, COVID is probably put a little bit of a dent in that. But we'll you know, I think we'll largely get through that. But it hasn't actually been the way we anticipated it. So the way we did the modeling was we have to hire X number of reps per year. We have to have a certain amount of MRR retention. And then we had to improve the productivity of the reps in the last three years of the plan. And so without getting into like all the numbers I went over, it was really only three metrics. And, you know, we've we've largely been able to figure out so far, how to improve those metrics and kind of stay on path. So we've actually hired more sales reps than we thought. Our retention has been pretty good, but not maybe exactly where we had wanted. And now we're gearing up for that productivity piece. And so, you know, we're really looking into like all of the moving parts that really can impact that from attrition to... because our more senior reps sell more than the newer reps, to products to innovative sales, you know, processes and making things simpler and all that stuff. And so that's that's kind of the big challenge in front of us now is like, how do we just improve the productivity of the reps because we've hired more. And so that can be a huge leverage point for us to kind of continue to scale and grow. 


Charles McKay  38:11

And I, like I can bet you that January productivity was down anyway, just because, like the fires like it was a full on. We found it really hard too. You know, you got to have so much EQ and empathy and just want to talk to people but, and then the COVID stuff, but I actually think now with COVID, I can bet you if you looked at your internal metrics, your activity would be through the roof the last six weeks. 

How HubSpot Helps Small Businesses 

David Shepherd  38:35

So it's been it's been odd actually, we've had like moments in the last six weeks. It's been really up or really down. So last week was our best week ever, of all time. We do measure on a weekly basis. But we went back like five or six weeks ago, it was one of our worst weeks ever. I think it was kind of the week when everyone started to go work from home. It wasn't quite when everything shut down, it was like maybe the week before or the week after, but there were there was a two week span in there where just like people just didn't even show up to their meetings. And I think it was just like, people were doing the awkward commute from office to the home life, and probably didn't have the systems and their schedules were all out of whack all that stuff. Yeah. So yeah, I think now we're on the up. And I think I think people are more willing to talk and maybe they have some more, I don't want to say free time, but like, they've maybe settled down, they're now thinking a little bit more strategically, Hey, how are we going to deal with this? And because we're a business that helps people grow, I think that's on everybody's mind right now. And so it's, you know, and our job is to try to how do we interact in a way that is, you know, polite and empathetic and really centered on helping people and educating people as opposed to being you know, opportunistic, and just using a bad scenario to our advantage. And I think that I don't think it's actually hard to get that right. But it's, it's certainly when you have a quota easy to try to solve for yourself as opposed to your customers.


Charles McKay  40:11

100%. And I think everyone at the minute is too... assessing everything like, is this what I wanted to do... is my business where it was taking me... like what is important to me? Which, you know, I think is a good thing as well, because, you know, like everything, you can look at everything in two situations, either bad or good. And, you know, I'm optimistic, I will look at everything in a good way and what can you learn and what can you come out better from that scenario, which sort of leads into the next point. You know, HubSpot redid their mission of we want to help millions of organizations grow better. You know, I think I think that's a... it's a really, it's a strong mission. And you know, at the end of the day, that's what this whole podcast and conversation is about is... organizations trying to do things in a better way. So what are some stories that you've seen and what HubSpot are actually doing to not just, you know, we can sell millions of software licenses, but how is that actually going to make the place better, and shed some light on what that means.


David Shepherd  41:19

So I think that... so there's a couple things in there. So one of the things I mentioned was like, one of the things you're trying to do in life, as a business is find people who believe in your version of the world, right? Like believe what you believe. I've kind of said that before about the hiring. And I think that's super important. But I also think that's what you're trying to do when you're acquiring customers. And, you know, yes, you do have to evangelize what you're doing at times but that's that's ultimately what you're trying to do... you try to find people have a similar view of the world. And I just think that we largely sell to small businesses, right. Companies under five hundred employees like we have, we have loads of customers that are more than that, but that's that's generally our group of customers. And that's really the backbone of every economy. And, you know, both my parents owned their own small business. I have just always loved the idea of helping folks like that.


David Shepherd  42:21

You know, my mom has, what, 12/15 employees, something like that. And I just know what it's like to be that business owner having grown up in that household. And I just think that... I think they're doing a great job for the world. Like, they employ people. They give people a place to... a community. They give people a mission and give you a purpose. They're helping their customers, they're really doing everything they can. They're trying to do everything right. And so like I said before, I do think that one of the hardest things about business is getting customers and I think HubSpot helps with that and so I just see those small business owners, and I think if we can help them, I find that to be a really noble cause. So I really identify with the small business owners or the CEOs of companies, and just... I know how much effort they're putting into things, and really all of the leaders in these companies. And so for me personally, I just think that this idea of helping millions of organizations grow better, is actually a really noble cause. You know, I think, in aggregate, there are definitely people out there that think that growth at all costs is a really negative thing for our world.


David Shepherd  43:38

And I I totally understand that. I think most of you know, those folks who'd be more upset with big business as opposed to small business. And, you know, I just, I don't know if I'd be as excited about our mission if if we weren't targeting or we weren't working with small business. There's something very special for me about that group.


Charles McKay  44:04

Yeah. And I think too in this current environment, things are going to go more local, like globalization is going to be there, of course, but things are going to localize with consumables. 100%, it just makes sense. You know, we've all done it, who hasn't got a fruit box from their local grocer in the last six weeks? And how many people are gonna keep doing that because the food's better, it's locally supporting farmers, like all of that stuff. So I think it's really compelling. And when you guys shifted to it, like at the end of the day, you look at your partner community and your apps and like, who is connected with you? And it's without a doubt true that there's a value alignment and there's a mission that everyone seems to be aligned. Subconsciously or consciously, some probably don't know. And I think you would find the ones too that don't last; there's a disconnect. So and I've talked about this a few times... in every relationship there's balance and as soon as it becomes unbalanced, it'll break. So, you know, what's that guiding mission to keep the balance right? And I think, you know, as you've grown and evolved, it shifts, it shifts and pivots. But at the end of the day, it's keeping that balance. And I think you guys have done that really well.


David Shepherd  45:21

Yeah, I think you could look at our mission and just be like, Oh, that's just a really... you know, that's a thinly veiled way of saying, we just want to grow because like, if we get more customers, and we have millions of customers, then like, HubSpot will grow. But, you know, I think, you know, anytime you try to boil something down to just like, the most succinct thing you know, it does get a little bit maybe close to a cliche, but that's just the way those things are. But I think it's more about your actions. Right. And I think we do an exceptional job at HubSpot trying to live out really solving for our customers. And, you know, I think in this time, I think that's really kind of come out in spades. And I couldn't be more proud of our executive team and some of the top decisions they've made to really support our customers and our partners like yourself. I've been honestly I've been very proud that we've, you know, maybe not necessarily taken the great like, the thing that would help our balance sheet or our PNL in the short term. But by kind of thinking about the whole HubSpot customer ecosystem and our partner world as being part of the business and part of the group of folks who are trying to help over the long term... I think that will pay off in in the longer term. I just, I'm so proud.


Charles McKay  46:55

I couldn't agree more and I actually watched something not that long ago, from Brian Halligan around, you know, lots of people in the world are trying to buy or build and sell stuff, like fling it and sling it, and they're in it for the long game. And they want to be... the decisions they've made will get them to... get them through the long game like massively and especially in the last few months. So yeah, I couldn't agree with you more. And you've sort of touched on it throughout, you know, the last 20 minutes of this conversation, but what's the tip, one tip that you would like to share with the audience? You know, if you're a growth or, Chief revenue officer, you know, car sales manager, marketing manager, like, what would the core tip be?

The Number One Tip

David Shepherd  47:46

I think I probably have two. So the first one, I would say is like, take accountability. I think a big difference as we will move up any organization is every level that you go up requires a new level of accountability of taking responsibility for things that are really outside of your control. So, you know, don't point the finger and then I think, I think the next one is like ask yourself questions. Like, don't search necessarily for the answers but the way I got to that epiphany with that question was like, I literally was just sitting down I was like asking myself, I was trying to get to a point where I was asked myself 100 questions without answering them, you just ask the question. And that honestly, like you do learn stuff, by not answering the questions but just asking them and then that really kind of was like I said, like the epiphany that was like the moment where everything changed. And then it's very easy to figure out okay, like, what have you learned from this? What's the next step? What are you going to do about it? But I really think if you if you don't take accountability, and you don't do a kind of a proper reflection and asking all those questions. If you become reactive and you... my experience is you just tend to do the same shit over and over and over again, in different flavors. Yeah, and you get the same results. Exactly right. And so yeah, one of my favorite things is like, you know, if you want to get what no one else has, you have to do what no one else does. And, you know, I don't know, like the story we've been telling this whole time is exactly a perfect example of that, but it does kind of fit in with my recommendation.


Charles McKay  49:29

Yeah, yeah, I totally agree with you. It makes a lot of sense. And I suppose to share your, you know, last 10 years at HubSpot and what you've achieved and all of that is your most you know, biggest success story. Is it actually setting the vision or is it actually getting the rabbit out of the ground and making it come to life? 


David Shepherd  49:50

Yeah, so I have a hard time distinguishing those two, like they are one in the same for me, but I would say yeah, I would say like the biggest win of my leadership career for sure is that whole scenario. 


David Shepherd  50:07

You know, I couldn't be prouder of my team of leaders. I couldn't be prouder of my team that are kind of on the front lines on a day to day basis. Like, they're really the ones who do all of the great work. But I do think that leadership matters. You know, like going back to the accountability thing. One of my favorite books about that is called Extreme Ownership by Jocko Willink. And man like, I think... there's a... he has a quote in there that there's no such thing as... there's no such thing as bad teams, only bad leaders. And I think that's a really, that's a really tough thing to say out loud when you are the leader. But ultimately, I think that is really true. And so I do think leadership matters in a big way.


Charles McKay  50:58

I hundred percent agree with you. The amount of you know, obviously, a lot of people may or may not have watched the current Jordan Netflix documentary, but when it clicked for them too like, you're not it's not about you Jordan, it's about the team, like how do we make the team and that leadership that Phil had that, you know, it's phenomenal and the amount of sports. Like I love actually relating back to sport because it's, you know, businesses and sport are so aligned in my eyes. And, you know, champion teams, are team, like a champion team, not a champion. So a team of champions. So fascinating. Fascinating. Dave, this has been awesome. We better start bringing it to the ground. So 10 years at HubSpot amazing journey that you've done, you know, congratulations on all the work you've done. Thank you for all the work you've done as well. How to you know, you said you started a blog and built some content. So what is your blog and how do people find you these days?


David Shepherd  52:02

Ah, that's a good question. So I'm, I'm in the process of launching a new one. You can find me at that should be up in the next couple of days. So my guess is by the time this gets launched, that will be up and ready so you can kind of find me there.


Charles McKay  52:21

Awesome. Love it, Dave. Well, thank you again. I really appreciate it, it's been a great conversation to learn about your journey. Until next time, we'll chat to you soon.


David Shepherd  52:30

Charles. Pleasure, as always.

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