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How to Build and Manage Distributed Sales Teams, with Bridget Gleason [Episode 360]

Welcome to another Front Line Friday with my very special guest, Bridget Gleason. On this week’s episode, Bridget and I discuss, among other topics, how she is hiring a sales team for her new position of V.P. of Sales at Logz.io, how far Tel Aviv is from San Francisco, and even Boston, how to accommodate account executives with relocation issues, and how complex sales need a complex infrastructure.

Key Takeaways

  • Bridget’s new job of V.P. of Sales at Logz.io has her looking for technical account executives in the Boston and
  • San Francisco areas. Her contact information is below!
  • Bridget is, once again, setting up a sales organization from scratch. Challenge number one is time and geography. Her company is a startup, based in Tel Aviv, 10 hours ahead of San Francisco and seven hours ahead of Boston.
  • Learning how to set up and manage distributed teams in a global market is something we will all have to learn to do well. Here in the U.S., Bridget is not geographically optimal for Logz.io. Boston is better than San Francisco, for time overlap.
  • The sales model Bridget is building, is an inside/hybrid role. There will be an SDR team, helping filter inbound and making outbound. There will be account executives, with some experience in SMB mid-market, looking to grow their careers.
  • The biggest challenge of remote management is where people are located, vs. where they are needed. Where should they optimize their talent? Great talent is really hard to find.
  • Great employees are requiring flexibility on where to live. Can they be accommodated and still cohere into a team?
  • Bridget looks for people who are self-directed, motivated, smart, and curious, and who have integrity, that have some affinity for technology.
  • Andy looks for big-picture ‘systems thinkers,’ for the kind of sales role under discussion. He looks at what they have done so far, and he asks them probing questions.
  • In Bridget’s view, there is one team — not a U.S. team, and a Tel Aviv team. She looks for team-oriented people.
  • Andy describes a $1B company that does not have a sales function. They have project teams that sell. That team mentality and cooperation are needed for complex deals.

Episode Transcript

Andy Paul (0:35)

It’s time to Accelerate. I’m your host, Andy Paul. Join me as I host conversations with the leading experts in sales, marketing sales, automation, sales process, leadership, management, training, coaching, any resource that I believe will help you accelerate the growth of your sales, your business and most importantly, you. 

Hello and welcome to Accelerate. This is another edition of Frontline Friday with my very special guest Bridget Gleason. Bridget, how are you today?


Bridget Gleason (1:08)

Andy doing super. How are you?


Bridget Gleason (1:10)

How are you? Where are you today? Which of your global Empire offices are you?


Andy Paul (1:18)

I am in the right coast today.


Bridget Gleason (1:23)

On the right coast. Okay.


Andy Paul (1:24)

Yeah, East Coast. We’re in Manhattan trying to stay away from the craziness that is Midtown Manhattan these days with the president elect operating from his tower.


Bridget Gleason (1:44)

Hi, yeah. That’s probably– we should just not even venture down that path.


Andy Paul (1:50)

Well, no, I wasn’t talking about the politics—


Bridget Gleason (1:52)

The logistics,


Andy Paul (1:54)

Especially at this time of year on Fifth Avenue. This is Christmas time. This is when people want to out in Fifth Avenue looking at the windows, all the Christmas displays. Ans yes, there’s some interruption going on. It’ll be interesting experience over the four years because the President has come to town. I don’t know if they do this for the president elect but once they’re in office, when the President comes to town, to Manhattan, and they know where they’re going, I think they clear the route. And if your car is parked on the side of road, it’s gone, they relocate cars. They’re quite adept at that to make sure they’re all gone. So, it’d be interesting for somebody that– because we only get the occasional visit from a president, but now for a sitting president that will come to New York very often, it will be kind of interesting to see what turmoil that creates?


Bridget Gleason (2:54)

Better get used to it.


Andy Paul (2:57)

Why do keep an eye on as much as I can. You sort of do keep an eye on the travel schedule of the president because if you’re happen to be coming into a similar airport at the same time, you’ll be waiting because they clear the freeways. And then they go down and close all the on ramps and off ramps to the freeway so the presidential motorcade can go by. I got stuck once, it took about an hour to do the trip. So anyway, I think we talked about this last time, you have a new job. And you’re now vice president of sales for Logz.io, L-O-G-Z-.-I-O. If people want to look that up. if you’re in the big data space, you need to be talking to Bridget.


Bridget Gleason (3:55)

If you are looking for a job and you’re in the Boston area.


Andy Paul (3:58)

There you go. What kind of people are you looking for in the Boston area?


Bridget Gleason (4:01)

Sales, all kinds of sales. Some technical sales, some technical aptitude, but definitely Boston and San Francisco.


Andy Paul (4:10)

Inside or account execs? What are you looking for?


Bridget Gleason (4:13)

Account execs.


Andy Paul (4:14)

Okay, there we go.


Bridget Gleason (4:19)

This ties into the topic.


Andy Paul (4:20)

This ties the topic. You’ve done this before; you’re creating a sales organization from scratch. In this case, a little more challenging because the center of gravity in this company, which is the headquarters is actually in Israel and you’re setting up operations here in the United States, sales operations and so on. So just want to spend some time in this interview talking about, how do you do that? How are you setting that up? For the people that are have startups and aspiring entrepreneurs and maybe, first managers in the door that are setting up sales even. What are you looking at doing? What are your priorities?


Bridget Gleason (4:57)

Well, as you said, Andy, having a company that’s based in Tel Aviv, which is 10 hours ahead of me here in San Francisco. So, let’s just talk about challenge number one, which is time and geography. And for a company that is global, and we are increasingly in a global world, and there’s more and more companies that are actually coming out of places like Tel Aviv. This is a reality, that learning how to set up, manage distributed teams, is something we have to get. We have to be good at. I’m probably in some ways– for sure, I am not geographically optimal for Logz.io either, as a VP of Sales, because we are– and this was partly my decision as well, in terms of the sales organization, we’re going to have the sales—the center of gravity for the US will be on the East Coast. And I’ll tell you why we thought about it. I’ll tell you what we’re doing, and people can extrapolate when they’re thinking about it in their own circuit, our own situations. Headquarters in Tel Aviv, those three additional hours of overlap that you get on the East Coast to Tel Aviv is actually really important. That was one factor that we took into consideration. Another factor we took into consideration when choosing when and where to build up the sales team was, where can we get talented people that were looking for, I don’t want to say the price point because that makes it sound– it’s hard for a startup to compete for great sales talent in the Bay Area. For an unknown entity, we can’t always pay the same that a bigger, more established company can pay. And there’s a lot of movement in Silicon Valley, people don’t necessarily stay at jobs quite as long, which can be expensive. Well, it’s expensive for everybody, it can be super different difficult for a small company. So, that was another reason we thought the Boston Market specifically, we’ve got a good pool of talent. There are five people on the executive team. Four out of the five of us have lived in Boston. So, we’ve got networks there, which is also very helpful. Our investors are there, our lead investor with this last round is there. Just some very practical considerations that we made around where to physically locate a team. So that’s one, the second is when we’re thinking about our sales model. We’re a SaaS business. Up to this point, all of the sales has been done out of Tel Aviv over the phone with no one meeting, not meeting customers and prospects. Very technical, some very small deals, but also some very large multiyear deals. The model that we’re building is sort of an inside-hybrid role. So, we’ll have an SDR team. We get a good amount of inbound; they help filtering the inbound. We have someone work on outbound. We have the account executives. Let’s say sort of a good solid mid-range account executive, somebody that’s had a couple years of experience but it’s looking to grow their career and handle sort of some SMB mid-market but also grow. And that’s kind of how we’re thinking about is let’s start there, we know that that’s where the majority of our targets are, kind of in that mid-market space. So, we want to have the sales reps match, their experience match the customer segment that we’re going after. That’s sort of a starting point. Maybe you can ask some questions in and around that.


Andy Paul (9:28)

Well, sure. Now you know are you regretting having moved from Boston to the Bay Area?


Bridget Gleason (9:39)

Yeah, for people who don’t know I moved, Yes. I came back for personal reasons, which I needed to. It’s interesting, I will go and spend a lot of time in Boston. I could definitely move back to Boston. We will always need a presence in the Bay Area. I found also that, when I was living in Boston, I was probably there seven to maybe 10 days a month. I was back in the Bay Area at least a week, a month. And then I was traveling in other places. So, my primary home is United 22F. That’s where I spend quite a bit of time.


Andy Paul (10:20)

Well, I’m familiar with that home. I guess the question becomes, for a lot of people, it’s this issue of remote management of teams, especially a small team. At the beginning it is pretty crucial, because you got set the culture, you’re going to set the vision in place, and make sure people are aligned with what you’re trying to achieve. So, what do you see as the particular challenges right now in this early stage to make sure that all gets set up appropriately?


Bridget Gleason (10:51)

Well, the biggest challenge, and the thing that we talked about internally right now is where people are located, versus where we want them to be located. So, I talked to somebody actually this morning, I’m looking, I’m hiring a sales ops person. Ideally, that person will be in Boston, where the center of gravity is. I’ve talked to some great candidates in the Bay Area. So, the discussion we’re having internally is do we optimize on talent? Do we keep looking? I’m sure we can find a great person in Boston as well. Like, where do we optimize? I tend to be location agnostic wherever I can, because I just think great talent, great talent is really hard to find. So, one of the challenges we’re having is, my network is here, my network is in the Bay Area. I do have a network in Boston, but I am a larger one here. So how do we balance location versus talent and known entities, and trying to create these mini-pods of people that can be supportive of one another? And I think at what rate you hire and who is always a challenge, you hire too many salespeople too quickly. And you can get everybody frustrated. You wait too long; you may be behind the eight ball a bit. So, trying to figure out what’s the right time, understanding how long it takes to get someone on boarded. And really, for us, creating a culture, we’re one team.


Andy Paul (12:44)

Well, that’s a challenge with the geographic diversity. Certainly, for someone who’s worked in eight startups in more directly, and many more that I advised; the issue of when you’re getting started is about where your people are located. That is a tough one, because I found that the most successful ones, quite frankly, were where people were all co-located.


Bridget Gleason (13:12)



Andy Paul (13:14)

It’s got to be a tough decision as you’re thinking about that. Because as you said, is finding good talent that’s not located where you’re at. Let’s say in Boston for you, and the challenges of getting everybody together feeling like they’re on the same team. They’re all the hallway conversation. It is new company, right? So many things are happening so fast and sharing best practices and experiences, dealing with customers and so on, those hallway conversations really become invaluable. And it’s hard, because we all use the technology, the collaboration tools and so on, but it’s not quite the same.


Bridget Gleason (13:53)

Well, and I think this is a challenge. We’ve got to figure it out. And I think great companies are going to figure this out earlier, because what we’re seeing increasingly is great employees are—“demanding” maybe is a strong word, but they’re requiring flexibility and where they work. And they don’t always want to live in the hubs where we may want them to live. And we’re having to figure out how to accommodate them if we want them to be part of our company. And I think about that a lot, how can I create an environment where people may be distributed? We still feel that we’re able to have some of those conversations and we’re still feel connected. And we talk a lot about this at Logz.io, because the headquarters is in Tel Aviv, and there’s no way getting around the fact that they need to be a distributed company, and that they need to have a presence here. And so, we have to figure it out. We want to minimize the friction by having these pods of people, as opposed to– I’d rather have two pods, 10 people in each pod than 20 people geographically dispersed around the United States.


Andy Paul (15:20)

Yeah. 300% on that. You’re talking about the account execs earlier; you’re really looking for someone with pretty solid technical background.


Bridget Gleason (15:36)

Well, technical aptitude. And there are different schools of thought on this as well. My first job at Xerox, my hiring manager—and the Xerox philosophy at that time was, you really screened for sales acumen, because it’s hard to teach certain emotional intelligence, how will you read people, work ethic, some really internal things, self-discipline and motivation. Those are hard to teach. They would optimize on that, and their philosophy was, if you get a smart person, you can teach them just about anything. And if they’ve got the other internal drivers, you can teach them just about anything. I largely ascribe to that philosophy, I look for people that are self-directed and motivated, and smart, and curious, and have integrity, and things like these. I feel like we can teach them a technical, but they have to have it. When I say somebody that’s been in a technical environment before, they’ll do better if they enjoy technology, if they have some technical aptitude or interest, they’ll just enjoy the job more. And it’s important to me that the people who I work with, that they enjoy what they’re doing, and what they’re learning what the product is about, and that it’s just interesting to them. So, I look for people that have some technical– at least interest, curiosity, aptitude, because I’m looking for a mid-level rep. Typically, if they are interested, they will more likely have gravitated toward that kind of sales environment already.


Andy Paul (17:39)

Yeah. What I look for in in that type of role is someone that embodies the systems thinking. If they’re not a real technical person themselves, that the least the aptitude extends to be able to understand how the whole system works together. Not just maybe the role that your particular piece of software does, but how it fits into the whole thing. That they see from end to end, that they have a bigger worldview about this problem that customers trying to solve, and the role you have in solving it. To me, that is another layer. For you, since it is a large, complex communication systems, if you have people with some technical aptitude, but they don’t really see the big picture, chances of not succeeding are much– that meant they’re more curious because they’ve gone out and learned and have this this bigger picture orientation, which to me, almost always translated into greater odds of sales success.


Bridget Gleason (18:42)

Yeah, that’s a really good point. How do you interview for that?


Andy Paul (18:51)

That’s good question. I think back some of the interviews that I did. But in some cases, it’s just talking about what they’ve done, and how they approach solving an issue for a previous customer. And for me, that was one of the things I really wanted to dig into is, give me examples, hard examples of things that you have done. Start at the beginning, take me through the thought process, how did you arrive at the solution? And if you really spend time really digging in on that, and not taking answers necessarily at face value all the time, but, prodding, probing, you’re going to uncover this person, “hey, they couldn’t have lived without the technical engineer next to them, sales engineer next to them”, or, “what could they really do on their own and how are they able to drive this?” And you’ll begin to uncover that pretty quickly. But it just takes some probing, and the hiring managers don’t ask the superficial questions, but it’s better to go deep.


Bridget Gleason (19:59)

Yeah. Really good point. I’m going to add that to my list of qualifications because I agree with you. I think that’s a really important one, somebody that’s able to see the big picture, and is a systems– I like that phrase, also a systems thinker. The other thing that’s important that Logz.io, and I’m sure it’s important in other companies as well is the cultural fit. When we’re trying to build one team– when I was at Reinvent. Last week, the big Amazon conference in Las Vegas. And there’s a couple new members. A US sales higher, a sales engineer, and one very senior account executive, myself, and my sales director from Tel Aviv was over as well. And she’d said to me, “okay, I want to take a picture of the US team”, and I said, “no, we’re one team.” I don’t want to start thinking about us, this early, as the US team and the Tel Aviv team. Let’s think about us as a single team. And it’s a little thing, but it’s also a very big thing, we’re one team. And hiring people that are of this mentality, the two that I that I hired I’ve worked with before, and I know how they are, I know that they are very team oriented, they’re super hard working. There are people who say “yes”, whenever they can. That’s a good cultural fit, and being a good cultural fit is as important as any of the other qualifiers that I’m looking for.


Andy Paul (21:53)

Well, I think that this whole idea of teamwork and being on the same team is really important. Because too often, especially in tech startups, the technical team and the sales marketing team, and even the sales marketing could be separate teams. And yeah, having a culture that says, “look, we’re all one team”, they do different roles, but we support each other, without all of us working together on the same goal we’re just not going to make it happen. This week at the airport, I run into former colleague from a company that started small, they’ve gone public, and they’re a pretty big company now. But one of the things even back then, this was 20 years ago, we didn’t have a sales function. And the company is well over a billion dollars in revenue, and they still really don’t have a sales function, and kept making these really large deals.


Bridget Gleason (22:54)

How do they do that?


Andy Paul (22:55)

Well, because they bring together the team of people that have to work together to make it happen. From all the disciplines required to work with the customer to make it happen, and this guy was telling me about a 350-million-dollar deal that he had worked on the closed. There was a big team that was doing it, but there was project managers, and there was a lead, sort of, quote unquote, business development person, but who was also very technical in their background. But that’s the way they handle opportunities. We bring together the right disciplines and we are able to do it, but they’ve grown to the size where they have one division where they have some people that is formally labeled “sales”, but for the bulk of a company, no.


Bridget Gleason (23:42)

You know, this is a discussion that we’ve also had internally. We were just thinking about designing comp plans and quotas, and that sort of thing. On the big deals, it really does take a village, and not to take anything away from the salespeople because they certainly are huge in what they do, but it often requires this team. It may be a product manager, the CEO, somebody in development, product, sales development rep, so many people that came together to make that deal happen. And how do we make sure that we recognize appropriately? All the different people, especially in big, large, complex deals, that come together to help bring something to the close. It certainly is bigger than just people on the sales team.


Andy Paul (24:43)

Yeah, absolutely. So hopefully try to find someone from that company to bring on the show to talk about how they do it without sales.


Bridget Gleason (24:56)

I’d love to. I’m always curious about that.


Andy Paul (24:58)

They are selling, there’s no doubt they are selling, but how they do it is a different model than a lot of companies. So well, Bridgette we’re going to wrap up this episode right now, as always it is a pleasure. We’re going to spend a lot more time in the future as you continue to grow your organization to talk about this. But as always, a pleasure to talk with you.


Bridget Gleason (25:20)

Likewise, and good luck with that traffic jams out there.


Andy Paul (25:24)

Yeah, we’ll keep everybody updated on that as well as we go along. So, Bridget, friends, thank you for listening again on this episode of Frontline Friday, and we will talk to you next week.


Bridget Gleason (25:35)

Have a great one.


Andy Paul (25:37)

Thanks for listening to the show. If you like what you heard and want to make sure you don’t miss any upcoming episodes, please subscribe to this podcast on iTunes or stitcher.com. For more information about today’s guests, visit my website at andypaul.com.