1. Library
  2. Arrow Icon
  3. Heavybit Sales Master Class
  • Sales
NOV 23, 2015 - 31 MIN

Heavybit Sales Master Class


In this Heavybit Sales Master Class, Morgan Mackles, VP of Sales from Iron.io, interviews Bridget Gleason, VP of Corporate Sales at Sumo Logic on the five tenets of succesful sales teams.

  • Introduction
  • 5 Core Tenets of Sales Teams
    • Making the Right Hires
    • Setting a Process
    • Millenials
    • Expectations
    • Team Involvement
    • Ongoing Onboarding
    • Sales Leaders and Patterns


Morgan Mackles: We are here for the Sales Masters Interview. Obviously, we are about to start up with our Heavybit Sales Masters event, our second event. But we wanted to do a one-on-one interview with this week's Sales Master, Bridget Gleason.

I wanted to just go ahead and introduce Bridget and give Bridget the chance to tell us a little bit about her background. And there's a lot of great items on Bridget's CV that really apply to Heavybit companies. So, Bridget, I'll let you go ahead.

Bridget Gleason: Great, Morgan, thank you. As Morgan said, I'm really happy to be here. I'm currently the VP of Sales at a log management company called Sumo Logic in the Bay Area. Previous to Sumo Logic, I ran worldwide sales for a sales acceleration company called Yesware, and prior to that, I was also a VP of Worldwide Sales for a company called Engine Yard, a platform as a service.

Prior to that, Morgan, lots of consulting for tech startups all around Silicon Valley around sales and marketing, sales and marketing alignment, that sort of thing.

MM: Perfect. Well, the reason that I specifically invited you, Bridget, as the Sales Master for this particular event, is because I've actually seen you present a few times. Particularly the first time that I saw you, I found your presentation to be excellent and very insightful. It resonated with me a lot.

What I thought would be interesting for us to discuss, for the Heavybit audience at large, would be to talk a little bit about the presentation itself, then get your feedback now that we're about a year later, get your feedback on how your philosophy has changed, or some other learnings that you've had in the subsequent year.

Specifically, we were at the Saastr Conference about a year ago, and there were many excellent speakers there. But specifically, as I said, your presentation resonated with me, and the name was "Fast Tracking Sales to Peak Performance," with a subheader of, "What to Focus on as You First Build Your Sales Team."

5 Core Tenets of Sales Teams

Being here at Heavybit, this is a topic that is very pertinent to companies that are in either serious seed or very early-stage Series A, which is very common here at Heavybit.

Specifically, I wanted to go through the five core tenets that you had mentioned, and we can talk a little bit about what resonated with me, initially, when I was brand new to Iron.io. And then I think maybe we can delve, in a little bit, to some changes in the philosophy or new learnings that you have now that you've been at Sumo Logic for a little bit.

First of all, the five core tenets have to do with people, focusing on A-players and the value of having really high-level hires as a part of your sales machine. Second was programs, meaning, make sure that you have an onboarding program for getting those people up in ramps, something that's repeatable and scalable.

Third were expectations, setting clear expectations with your team from day one, in a lot of different aspects of their role and what it is that they're going to be doing for you as a member of your team.

Fourth was involve the team, meaning, all the way up from senior management, CEO, buy-in, all the way down to having your new sales team members learn from existing sales team, all the way through to having ongoing trainings for your current sales team and to make sure that you have multiple means of communication and means of training. Such as, you had mentioned, "Read, hear, see, say, do," as a common pattern. Sounds pretty similar to the world of medical, actually.

A little bit about how you believe that involving the team in new-hire training can be valuable to both sides in the long term. And then last, make onboarding an ongoing event, meaning specifically, reinforcing the expectations on a consistent basis. Never stopping role plays, always trying to involve your team, but also involve other departments throughout the organization.

BG: That was really good note-taking you took, Morgan. That's awesome. I remember, I went back and looked at just at my notes because I knew we were going to be talking about this.

MM: Great. That's the dimestore tour of the presentation, and now what I think would be super valuable is to get Bridget's feedback on where we stand today and what you think is worth focusing on from those five categories.

Making the Right Hires

BG: Talking about people, my thinking hasn't changed around that a lot. But that's at the core. That especially your first and early hires; you've got to make sure you get that right. It sets the culture.

A-players hire A-players, so you want to make sure that you have, first of all, an organization that attracts A-players.

Because then that person is going to go out and want to continue to hire, to hire to that.

I think that for me, it's really very much a core tenet, and culture precedes great performance. I go back to making sure you have a good culture that your A-players are going to want to come to.

Was there anything around that that particularly struck you around the type of people, or the type of profile, or you, now that you're in the role? Has the profile changed? And I'll tell you just my experience with that, but I don't know for you just over the course of the year.

MM: Definitely, a year later, one specific part of your "people tenet" really jumped out at me, which is to only hire team players. The reason being that A-players tend to attract other A-players and build to your overall culture.

Even if it seems like a stretch or a difficult thing to take the extra time to hire an A-player, or pay a little bit more money, I think that a year and a little bit later, I'm definitely seeing and understanding the long-term benefit of that philosophy.

BG: Yeah, I think especially in sales, you want to be careful that you do not cultivate a culture of mediocrity. The tenet that A-players like to work with A-players. B-players, when they do studies, tend to want to work with, not only B-players, but C-players. So there often isn't the same self-esteem, and so they hire people that are not at the same level that they are. And then you just start to see this cascading effect.

One thing that I was going to mention as I was reviewing my thoughts about people and hiring, one thing I think I talked about a year ago was making sure you have a profile, and you're very clear, not just an A-player, but the profile of the person that's going to work at your company.

One of the things that we're finding at Sumo Logic, and I've seen it other places too, sometimes we have a profile. Or let's say a job description that is aspirational in nature, but it doesn't reflect the reality of the job.

You have to be careful around that too. That this is what we want the person to be doing, but it could be the stage of the company that's not what they're going to be doing. It could be a lot more heavy lifting and things that are less glamorous, and you just have to be careful that you have clear expectations, and those are aligned, especially with your first hires.

Because oftentimes, what we think we want them to do is aspirational in nature and doesn't match what the real job is at hand.

MM: OK, so for that specific point, would you say that at Engine Yard, Yesware and Sumo Logic being at different stages, do you have to change the mentality drastically, or is it still always aligned with A-players? But maybe the details are change, adapt with which company you're at or which stage you're at.

BG: Yes to both. You have to look for the stage of the company; it's going to change. The industry of the company, it's going to change. The culture of the company. The people that I hired at Yesware were perfect for Yesware and A-players at Yesware. That doesn't mean that they're going to translate to be A-players at another organization.

I may have told this story. When I was working for Hewlett Packard's largest technical bar, I was an individual contributor at the time. They brought someone in who had been the star, number-one rep at another company. He came in, and his first year sold zero. Nothing. After a year, obviously, he was let go.

He was a star at the other place, for whatever confluence of reasons, which we don't need to get into here. It was not a good fit.

The sales motions were different, and they were different enough, the culture was different enough, that being an A-player in one place does not necessitate that you'll be an A-player somewhere else.

The same goes for when you're hiring. You can't take one hiring profile and bring it with you to any company or at any stage. Or, even as the company changes, as the company evolves, what you're going to need in that profile is also going to change.

MM: Well, that sounds super valuable and good feedback for our Heavybit members. It's very challenging to figure out what an A-player is in your particular company or at your particular stage. And it kind of speaks to the value of having somebody like Bridget who's done it multiple times.

BG: See, it's age. Age. You don't see the gray hair now, but it's here.

MM: Good. Great, well, hopefully there will be many more questions around people today when we do the event downstairs. I think it's a very important aspect of the five tenets.

Setting a Process

Moving forward with the second tenet which is program. This is an area where, I think from day one, this is a philosophy that I've always believed in, having a very specific, scaleable, repeatable system in place. Which is always going to change over time.

I knew, even coming into my role at Iron.io, that building and memorializing the process was going to be very important. I think that philosophy was definitely confirmed by what you had said in your presentation, specifically about how the value of how a program can affect velocity.

As we all know, in early-stage startups, one of the major pressures that we have from our investors is the velocity and the speed of our sales machine.

Tell us if there have been any additions or addendums to your general philosophy about that.

BG: I feel that emphatically, 10X more than I felt before. As I'm at Sumo Logic, and we're a little further along than Yesware, we're a little further along than Engine Yard, and growing at an exponential rate. Tons of velocity.

The thing to remember also, when you're in a startup that you're getting a lot of pressure from your investors, that's a good sign. Because they really believe this is one in our portfolio that makes sense to focus on. But the pressure is definitely there, and what I've seen at Sumo Logic is the company gets larger, and if good processes are not put in place early on, it is inordinately more difficult to correct them and change them.

Everything slows down when there's not good process.

I had heard a group of Intel entrepreneurs, people that worked at Intel that had started their own companies. Intel was notorious for horrendous process. People just felt choked by process.

And so all of these entrepreneurs, when they went out, said, "We are going to do it differently. When we start our own company, we're going to have less process. We are killed with process."

It turned out, what they found out, is you have to have a process that matches the stage and complexity of the issue you're trying to solve. And they found, invariably, process helps velocity when it's done appropriately.

They needed a process to help them speed up, because it's very clear what they need to do. Morgan, you heard I had a conversation with my boss just before this at Sumo Logic, and our discussion was around something we needed to move faster on. But there wasn't a clear process to make this decision. So everything slows down.

Having that defined early on, and it's going to change, but you need to have the building blocks in place. You need to have good, good culture around data: data collection, data integrity and data analytics. And how you're using that in order, and the process around it. so that as things get more complex, you can move with it and move along.

I feel that of all the things I would want people to take away, I would say you really have to start there. Hire people that are builders and are organized thinkers around that. Because otherwise, it's going to slow you down when you need to move faster.

MM: Since that is one area where you really feel that there should be a strong emphasis for everybody who's looking in on the Heavybit library, I wanted to ask you a second question, then, about how process can assist velocity. Specifically that has to do with a playbook or memorialization.

I'm really big on actually having the process in writing and having an iterative process around updating your process and making sure that it's collaborative.

It's something that we're always looking back at. Is that something that you've found to be important or successful as well?

BG: It is super important. It's important at the beginning for a different reason than maybe important later. So, important at the beginning, because you have new people who are starting, They may be involved in creating the playbook, but they need some basis just to get them started.

As you get larger, it's important because of scale, and again going back to this notion of velocity. One thing to remember, I don't know if it's different, but more emphasized today than it was a year ago, is the number of millennials coming into the workplace.


When you look at studies, millennials will be in a job for 16 to 18 months, 36 months at the long end. That creates a challenge for onboarding people for new salespeople. You have to have a way to continually train them, and also get them up to speed quickly if you're going to get the value out of them working with you.

I think the fact that millennials entering the workplace has also made having a playbook and things like that even more important because they rotate in and out of jobs very, very quickly.

And you don't have somebody that's going to be doing it for 10 or 15 years that can really learn it, and he knows it, and they've got the tribal knowledge.

We don't have as much of that, so you have to instantiate it and have a place where it's kept. Because it's much more of a revolving door. Particularly in sales, of people moving in and out. We can fight it to no avail, or we can accept it and think about and just be prepared for it.

MM: And incredibly pertinent to Heavybit companies, so, really glad that you brought that up. For the third tenet, we talked a little bit about expectations. I think item number two and number three kind of go hand in hand.


Tell me a little bit about expectations. Obviously, expectations in terms of quota and hitting your goal, but I think you did a really good job of articulating some of the less concrete expectations that you have for your sales people.

BG: I think that one thing to remember there, I think his name is John Hamm who wrote a book called "Unusually Excellent," and he talks about the rule of expectation, which is: people rise to the expectations that you have of him or her.

It's expectations in their work ethic. It's expectations in how they conduct themselves. It's expectations around being a team player. It's expectations, like you said, around quota and achievement. But this also goes back to the people-piece of it.

Champions are champions long before you see the results. You know they behave like champions before the results even come in.

So that's what you want. You want to set the bar, that this is a person who can excel, that they're going to be a leader. That they're going to be mentors for other people, and I think if you have high expectations of people on your team, they'll naturally rise to meet it without intentionally doing so. It's human nature, it's just a law of nature that we rise to meet those expectations.

MM: OK, rule of expectations, very interesting. I like that a lot. So, in keeping with the premise of expectations, I think again that's a good lead-in to the next tenet, which is "Involve the team."

Team Involvement

I think that, a year ago, I definitely understood the first half of this tenet, which is, make sure that you have buy-in on your sales strategy, in your sales playbook, from the top down.

What I think is resonating with me more, a year later, are specifically how to involve your team in best practices and setting those rules and expectations, guidelines for your team, and how to help them be a cohesive unit to really drive this sales team forward. Have there been any findings or anything to support you in the last year on that front?

BG: No, I feel the same way about it.

That you need buy-in from the top, and that's really important that they've got their fingerprints on it. Because then they feel more invested. They feel more invested in sales and in the program.

Because we're all interrelated. Everybody's really in sales. You want as many stakeholders involved and feeling invested. The reason from the bottom-up, and to have them be participants and creating a playbook or training other reps, is again, when people have their fingerprints on things, they're more invested in it. It helps them learn it.

When you say, "You need to go teach this person how to give a demo," the teacher, the new teacher, often has to go learn it themselves to the point that they can go explain it. One of the things we do at Sumo Logic is we have brand new reps go and give the presentations and demos at the onboarding classes.

Some of them, we do them every month, they may have only been there a month. And they're having to go train the new people. Initially, they are stunned. But what we've seen is it accelerates their learning very quickly when they are required to go be participants in teaching the next class, which is just a month later.

We again, talking about velocity, that helps the velocity, because it's a forcing function for them to learn the product, or the demo, or whatever it is.

Then it also creates good camaraderie, a connection and a bond. And those bonds are also really important among the team.

MM: Yeah, that's great. And yet again, an excellent segue into the fifth item on the agenda, which was, "Make onboarding an ongoing event." I think you're alluding to, in your answer, "Involve the team." You're alluding to the fact that you want your sales team to constantly be learning and growing, but it sounds to me like what you were able to articulate in this presentation was that involving the team and having onboarding be an ongoing event are very closely tied.

Ongoing Onboarding

It sounds like your key takeaway is is making sure that your team is involved in that process so that they're constantly learning and constantly stretching themselves, and then taking that learning and passing it on to other people on the team.

BG: Definitely. We've got an onboarding at Sumo Logic, we did this at Yesware and Engine Yard as well, but we had a one-to-two-week onboarding program. Some of it, at Engine Yard, there was a lot more of it that was self-service with speakers, different people from within the company coming in.

Sumo Logic is a very formal one week. They're in a conference room, and people are coming in and out. But it's a much more formal one week. After that, the education can't stop there. We do weekly, we call it "nerd time," and we have the sales engineers talking to the team about different technical topics.

We do something we call "audible ready" at all of our sales meetings. We believe that you have to be ready at any moment in time to be able to answer a question about the competition, or the value proposition, or a sales methodology.

We want our reps to always be on their toes, because that's the reality of a sales situation.

You have to be able to think on your feet. And so that's something that the reps do with one another, and they practice. And then we do what we call audible ready. "OK, Morgan, audible ready: what does MEDIC stand for?"

And then we make sure that we test peoples' skills there. But we have a lot of ongoing training and learning, and it's also creating a culture of learning that's really important. Everybody really looks forward to it. We have people that we share books. We read. We listen to Audible.

We've really created a culture of people that learn and share. We learn from each other, some formalized, some not so much.

MM: Right. That's so fantastic, and I think a lot of us in the program aspire to be there one day. I would be really interested in your feedback, having worked at startups in many different stages. How would you translate that advice for companies that are at a much earlier, maybe their sales team is only a sales leader and a few other people?

BG: How would I translate in terms of what they should do weekly, or just onboarding in general? Putting together a program: how do you build the foundation for a culture like you have at Sumo Logic, like you originally referred to?

MM: I think some of that comes from whomever the leader is. My team knows they can never have a conversation with me without me saying, "You know, that reminds me of a book I read," or "That reminds me of something I listened to in Audible or a podcast." So, I'm an aggressive learner.

I think part of it is, that comes for me. This rule of high expectations, these all are intertwined. My expectation is when you want to be the best, that you too are going to go seek out these opportunities. And creating a culture of people that want to work together, they want to then go and help one another do it.

It's everybody, all of us, wanting to get better. What are our different parts? Even if there are just two or three people that are participating, I think it can start really small, and then it just scales as the company gets bigger.

It really starts from the top and having the leader that really believes in continuous learning and continuous education. I think it starts there.

Sales Leaders and Patterns

MM: A year ago the number one, most asked line of questioning from everybody who signed up for the Heavybit event tonight, across the board, people want to know, "When is it the right time to bring in that sales leader? When is the right time to bring in a VP Sales, and how do they know that the signals are there, that they need to start making that job hunt?"

BB: Bringing in a sales leader and a VP of Sales, those two are different. Those are different, because your first sales hire doesn't need to be a VP of Sales. Your first sales leader doesn't need to be a VP of Sales. So, I think that's one distinction. Bringing in a VP of Sales and a sales leader, I would think about those two differently. This could be a long topic, so I'll try to keep it short.

The signals. So, the signals: sometimes you wait for signals, sometimes you've got to go out and make the signals. I would advocate hiring a few at the beginning, like, a strong, entrepreneurial, ambitious, couragous, smart individual contributor who also is a builder, has to be analytical. And the two are not mutually exclusive.

I wouldn't sacrifice one for the other on the first hire or two, and it's usually good to get a couple of them, because you get different input back.

Once you start seeing, and you can identify, a good product-market fit, and you flushed out a little bit, "OK, we know that there's a market for this. We know we've got a good product market fit. We know the personas of who we're going after." And you feel ready from a product-and-customer-support standpoint.

Then I would say, "All right, bring in a sales leader." I don't know that I would necessarily hire a VP of Sales first. Bring in a sales leader, and let's go test how far we can go, because the first round's going to be friends, family and extension, and you learn some.

But then when you want to step on the gas, then you might say, "Now we've proven we can go out to a certain level." Every company could be a little bit different. Maybe it's a million in recurring, whatever it is, depending on if it's a SaaS model or not, and then you may go out and say, "OK. We see the pattern."

It may not be perfect, but we see the pattern. Let's go bring someone that we think can step on the gas.

That person, though, has to be, again, entrepreneurial. Willing to fail fast, good at recognizing the signals that are coming in.

There's a lot that they have to be good at as well, and somebody that's used to being in a startup. I think that's really important.

I guess that the last thing I'll say, just, again, because I could go on for a long time, is I think it's unrealistic to think that the sales leader you have from zero to a million has to be the same as the one from one to 10, as the one from 10 to 50.

It's great if it is, but the company can also change dramatically, and I think everyone just has to be comfortable with the fact that there may be changes along the way in who that sales, who that sales leader is. And just be OK with that. The company can change a lot.

MM: Right. Great advice, great feedback. Thank you very much. I'm looking forward to diving deeper with you once we're at the actual event.

Again, I'm Morgan Mackles, VP of Sales from Iron.io, and this was our Sales Master for the second Sales Master Class, Bridget Gleason, who is VP Corporate Sales at Sumo Logic.

BG: Thank you so much. Nice to be here. Thank you, Morgan.