Welcome to Episode 210! Bridget Gleason is VP of Sales @ Logz.io, the startup that uses predictive analytics and machine learning to provide monitoring, troubleshooting and security. To date, Logz have raised over $45m in funding from the likes of Openview, 83North and Vintage just to name a few. As for Bridget, she has the most incredible track record. Before Logz, Bridget was VP of Corporate Sales @ Sumo Logic where she drove ARR up by a record 237%. Prior to SumoLogic, Bridget was VP of Sales @ YesWare where she increased MRR per rep by 450%. Finally before YesWare, she was VP of Sales @ Engine Yard, where she tripled monthly recurring revenue, over course of 3+ year tenure, in 3 key leadership roles.

In Today’s Episode We Discuss:

  • How Bridget made her way into the world of sales and became the sales leader she is today, having started in the world of marketing.
  • Having led and scaled numerous sales teams, does Bridget agree the best sales reps are outgoing and extroverted? How does the successful profile of a sales rep depend on (1) whether you are selling to SMB or enterprise? (2) The stage of the company? How can one stress test the character type of the candidate pre-hire in the interview stage?
  • Does Bridget believe that sales reps really are as coin-operated as many suggest? Why is that potentially an unfair position to take? How does Bridget think about structuring the right comp plans for her team? What other methods of incentivisation does Bridget believe works equally as efficiently?
  • Does Bridget believe that you should pay sales rep commissions on services revenue? Should one pay the same or lower commissions on renewals? Should multi-year deals be paid upfront? How does one structure commissions for the sales team with that in mind?
  • When does Bridget believe is the right time to hire (1) your first sales reps? (2) Your first VP of Sales? Why does Bridget believe that 70% of VP of Sales positions do not work out in the first 9 months? What can founders do to increase the likelihood of success within their VP of Sales role? Where do many go wrong?

Bridget’s 60 Second SaaStr:

  1. What does Bridget know now that she wishes she had known when she started in SaaS?
  2. SDR’s are the most important function in the sales process, agree or not and why?
  3. Sales training, what works? What does not?


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Jason Lemkin
Harry Stebbings
Bridget Gleason


Harry Stebbings: Very excited to bring you the official SaaStr podcast with me, Harry Stebbings, and it’d be great to hear your thoughts and feedback on future guests and questions for the show. You can do that on Instagram at HStebbings1996 with two Bs. I would love to see you there. But to our episode day, and my word do we bring you a conversation with a master of their craft. And so with that and my excitement in mind, I’m thrilled to welcome Bridget Gleason, VP of Sales at Logz.io, the startup that uses predictive analytics and machine learning to provide monitoring, troubleshooting, and security, and to date Logz have raised over $45 million in funding from the likes of Openview, 83North, and Vintage, just to name a few. As for Bridget, she has the most incredible track record. Before Logz, Bridget was VP of Corporate Sales at Sumo Logic, where she drove ARR up by a record 237%.

Prior to Sumo Logic. Bridget was VP of sales at Yesware, where she increased MRR per rep by over 450%. Finally, before YesWare, she was VP of Sales at Engine Yard, where she tripled monthly recurring revenue over the course of a three year tenure in three key leadership roles. I do also want to say a huge thank you to previous guest, Ryan Williams at SalesCollider for the intro to Bridget today. I really do so appreciate that. But enough from me. So now I’m thrilled to hand over to Bridget Gleason, VP of sales at Logz.io.

Bridget, it’s absolutely fantastic to have you on the show today, a big hand to Ryan Williams at SalesCollider for the intro, but thank you so much for joining me today Bridget.

Bridget Gleason: Thank you for having me, and I agree, a big shout out to Ryan for the connection.

Harry Stebbings: Well thank you so much. But I would love to kick off today,, Bridget with a little bit about you. So tell me, how did you make your way into the world of SaaS? I’m really sales more specifically,

Bridget Gleason: Not in a direct line. Okay. So let’s start there. Just going back, but not too far back. I was actually, when I studied at the university, I was an English major, and I also taught in the engineering school. So, I’ve got both sides of the brain firing. I’m probably more of a generalist, and I started in marketing for technology division of Xerox and Harry, I was bored. I don’t know. There was something, I don’t know if it was just that I really liked the immediate reward of sales, but I moved within Xerox from a marketing position in the high tech area of the company into a sales position.

Kind of that launched my career, sold for a while, then started a company, did that for oh, five, eight years in total before I sold it. Then I did a bunch of consulting to these amazing startups in Silicon Valley. And I guess the trajectory of my career, Harry, and how I got here it just really aligned with more personal professional goals around being challenged, around learning, around stretching, around contributing to other people and the people around me to help me get better, and ended up taking a VP of sales role with a client, and that has now set me on a path for the last almost 10 years now. I’ve been in VP of sales roles, which I also really love.

Harry Stebbings: What a path is has been though. I do have to say. I do have to kick off today, though, because you said about kind of both sides of the brain, that’s super interesting element and you’ve led numerous different sales teams from Sumo Logic to YesWare to Engine Yard, and you’ve got this incredible data set of profile types of salespeople, and there’s the conventional wisdom Bridget, as you know, the best sales reps are naturally extroverted and outgoing. Tell me, from your experience and data set, is that true?

Bridget Gleason: It’s actually the opposite is true, and I’ll tell you why. First of all, people are surprised when I tell them that I’m an introvert. They don’t believe it, because I have decent social skills and relating skills. I’m very, very curious, but that doesn’t make me an extrovert. The problem with extroverts, generally, is that they want to be liked and that they tend to be people pleasers. I realize I’m generalizing, and oftentimes, in a sales environment, more times than not, you’ve got to be willing to ask tough questions. You’ve got to put yourself in a position of discomfort. It can’t be about being liked, so you have to be willing to challenge the way they’re doing something. You’re asking them to buy something new, particularly in technology, to buy something new, to perhaps think about it differently, and in that regard, an extrovert is actually not the best profile.

Harry Stebbings: I think that’s super interesting to hear the benefits there of being introverted, kind of going contrary the conventional wisdom. I mean, the subsequent question for me is, the different success profiles and, does it differ on two different elements? Number one, does the success profile differ on the market that one’s approaching, be it SMB or Enterprise, does that make a difference?

Bridget Gleason: I think it, it makes a big difference. I’ll tell you that recently, I was introduced to this company called The Predictive Index, which is really fascinating, and they did these assessments on individuals’ behavioral profiles, and the point of it is, at different stages in a company, as well as the type of sale, and SMB versus an Enterprise, you want a different profile of a salesperson. And so one size doesn’t fit all, and I think it’s really important that when you are looking for salespeople that you do understand that the stage of the company that you’re in.

Early on in a company’s existence, they need more, let’s call it a maverick profile. Somebody that’s kind of willing to go out. They don’t need a lot of structure. They don’t need a lot of rules. They don’t need a lot of process because they’re going to go create it. It’s what they do, it’s what they love. That’s a great profile. You put that profile, Harry, in a later stage company where the focus is on scalability and repeatability and predictability and following a process, that maverick profile is not a great fit at that stage of company.

So I think it very much depends on the question that you asked of SMB versus enterprise. SMB tends to be much more transactional, and so that profile, as an example, you may want an individual that has a greater sense of urgency to get it done, drive to a close. Where in an enterprise, you may want somebody that has a little bit more patience, because it’s going to take a bit longer to navigate through a large complex organization. But really, really important to think about the stage, the segment, what you’re selling ,and the culture of the company to make sure that you’re mapping who you’re hiring to those positions and segments and stage of the company.

Harry Stebbings: I mean speaking of correctly mapping, I’m super interested. You said there about kind of those different character traits. You’ve built many incredible sales teams. How can one really stress test to determine the character type of the person in the interview? Are there core questions that you find maybe most revealing of their character, be it that kind of transactional urgency that they have, or the kind of more patient tenderness to engage in a longer enterprise sale. How does one determine that pre-hire?

Bridget Gleason: I think that is the million dollar question, and and actually this company, The Predictive Index, because that is so hard to assess, they have these assessments that oftentimes companies will ask a candidates to take to try to address it. So, outside of that, because I have not used them before, we’re looking at deploying them here at Logz.io, I find the best way is to dig in to examples. Ask for very specific examples of a time when they exhibited whatever the characteristic is that you’re looking for, whether it’s a sense of urgency or if it’s, if you need someone that’s very thorough and detail oriented. Or if you need someone who’s intrinsically motivated. You want to ask them for examples of that and then really dig into those real life examples of, it’s not them just talking about it, but how they demonstrated it in the past.

Harry Stebbings: Yeah, absolutely.,and I totally agree with you there on the examples and really kind of tangible ones, but you also mentioned the mavericks and those profiles at the very beginning stages of a company. I do have to ask the common question that I always get, Bridget, and it’s super hard for me to answer in a generic way, and so I’m going to ask you, which is very unfair of me. When people are thinking about adding sales reps to the team for the first time, how do they know when’s the right time as conventional wisdom of a million ARR or how do you think about the right time to add your first sales reps?

Bridget Gleason: I think you want to add them when you feel pretty good about the product market fit and that you’ve got some initial traction where you’ve gone beyond friends and family, you’ve gone beyond the people in your network and you really want to test it to people that are outside of that inner circle. And there’s no magic bullet, Harry, of when or how much or who or, but I would say when you’ve got some initial, some traction, the CEO or co-founders have kind of exhausted their ability to participate in any meaningful way, because early on the founders and early team is so intimately involved and they’re doing the sales. But then after that, that’s a good time. There’s not an ARR amount. There’s not a time. It really depends on the company and the product. The other thing I recommend though is don’t hire one. I would hire a minimum of two, maybe three, so that you can eliminate, if it works or doesn’t work, that it has to do with a specific person, you know, you want to be able to eliminate some of those question marks in some of those variables.

Harry Stebbings: Can I ask, how long does one give one to really prove themselves in that role and really test their effectiveness, so to speak. Is it kind of a three month, or often in the enterprise sales role, obviously because of the long sales cycle, it can take quite a lot of time. How do you think about kind of the right time to really kind of prove some form of tangible kind of milestone movement?

Bridget Gleason: Yeah. Wouldn’t it be great, Harry, if I can say in weeks, is the amount of time. As you pointed out, it does depend on the maturity of the product, the maturity of the market, the market that you’re selling into, whether it’s a large complex sale that is six figures, seven figures, so some of those things make a difference. I would say there are things you want to look for and monitor. So you want to be able to see, are you getting traction? Are there opportunities that are being created? Are we uncovering opportunities, and are we starting to see those close, and is that pipeline growing, and is there conversion and closes, are they growing?

Because sometimes we set targets that aren’t realistic, and I think that’s another really tricky one, but you want to look at the traction. You want to be realistic about kind of the market and product market fit. You want to be realistic about “Did I get the right person and the right profile in this at the right time?” I think if you have more than one, it makes it easier. So for example, if you hired three, and two of them are clearly sort of in the same category of selling and opportunity creation and closing, and there’s one that isn’t, that makes it a lot easier, but if nobody’s getting any traction, that may lead to a different problem that isn’t the salesperson himself or herself.

Harry Stebbings: Absolutely. That’s a challenging time indeed. I do want to discuss a little more granular. Now we’ve got these reps on board, say we hire these two reps, and the often, all this criticism may be positive towards salespeople, is that their kind of coin operated, so to speak. And I’d love to ask, from your experience with multiple different teams and personas, are sales reps truly is coin operated as many suggest?

Bridget Gleason: I don’t think sales reps are coin operated at all. And in fact, I bristle at the term. You know, it makes us, us, we, my people just sound so simple and heartless, and there’s been a lot of different studies really on that. That money is more of a motivator, and you’ll find individuals being more coin operated if it’s a mechanical task. I think Dan Pink has done a lot of research on this.

But if it’s something that is more cognitive, then money’s a factor, but there are other factors that are more important and will drive an individual to perform better, whatever metric you want to use. Some of them include autonomy, so, people really lIke to feel like they have some control over what they’re doing. A mastery. So, am I getting better, am I improving? And then I think everybody wants to feel that they’ve got a purpose, whether it’s a purpose in, on a team, whether it’s a purpose in a company, whether it’s a purpose in a market, and I think it’s not that money isn’t a factor, but to simplify it, to say that it’s only money that’s gonna make the difference, I think is grossly incorrect.

Harry Stebbings: I totally agree with you there on the pushback against the coin operated mentality. If we do stick with the kind of compensation plan though, so to speak, I do get asked by, again, a lot of founders about it. For you, as we said, having constructed many teams, how do you think then, especially with the kind of not coin operated approach, how do you think about constructing the comp plan for early sales teams and what’s really worked well?

Bridget Gleason: Yeah, so a lot of times early sales teams I have to build in, in addition to sort of a traditional comp plan that is based on a certain percentage that you get per dollar that you sell at its basest level. Often I put in MBOs around things that are important to the team or the company or the learnings that we’re trying to get at that stage. So for example, to early on here at Logz.io, growing very quickly, I wouldn’t say bootstrapped, but we’re still, you know, we’re, we’re careful about our spend.

One of the MBOs I had for some of the early reps were around training and helping one another and just making sure that that was a part of what they felt was important is to help other people get better. Sometimes it’s around the traction that they’re getting. So it may not be closed deals, but it may be what opportunity are you creating? I t may be conversations that they’re starting. There’s a whole host of things. But, I typically, early on, like to put in some MBOs because I don’t often know enough about what, kind of what’s realistic to expect in terms of closed revenue. So I look for other things that I know are important to the team and the company that sales are the right people in position to contribute because they’re the ones that are often closest to a prospect or a customer.

Harry Stebbings: A couple of kinds of nuances and intricacies that I always get stuck on. Should one pay commissions on services revenue, do you think?

Bridget Gleason: Yeah. Okay. So another way to think about it is let’s say for example, Harry, that there’s services revenue around onboarding and training, and maybe it’s not going to make a lot of money for the company, period, but here’s what I know. That every company that gets onboarded and trained well, that their lifetime value is 40% longer than if they’re not, and that they are more likely to upgrade and our ARR will increase by 30%. I’m making up the numbers. Every company, it could be a little bit different. In the case of Logz.io, we do know that. We do know that good onboarding and training does increase the growth of the company.

They’ll tend to to grow more and faster and that they, they’ll stay customers longer. It’s stickier, so in that regard, it would make sense to pay some commission on services because that’s a really, really important factor in the overall value of a customer, and it may be that I don’t want to build it into, let’s say an annual compensation plan, but I may want to create a spiff around it, or an MBO around it, or some way to indicate that this is important. And while salespeople aren’t coin operated, comp plans are the guide for what you want them to focus on, and so you want to make sure that your comp plans are well aligned to the goals and the priorities of the company.

Harry Stebbings: Totally agree with you in terms of kind of that alignment, and leads me to a more messy question around the psychology of sales, which is how does one create an environment where there is an aggressive culture of goal setting that really aim to strike those company targets without the fear of maybe a disincentivized sales team, if they don’t hit those numbers? How does one create that very nuanced and balanced environment?

Bridget Gleason: Yeah. I don’t want a team to feel disincentivized, let’s say if a target isn’t hit. At the same time, I don’t want them to feel okay that a target was missed, so you’re right, it is a nuance, and I think a really important quality for any salesperson is resilience, and resilience, one place where thIs shows up, it’s the ability to look at the reality of missing a target and having that sense internally that I can feel a sense of accountability and responsibility for missing it, but not so much that it’s going to knock me out and I can’t go back after it. Typically, if I hire the right sort of person in profile, that loss or that not hitting a target is going to drive towards a greater desire to make sure that they do things differently or look or investigate. They sort of come back with a vengeance, and have more energy to go get, have a different result in the next quarter.

Harry Stebbings: I love that. Coming back with a vengeance. I do want to talk for second, you said there about kind of aligning incentives and ensuring that maybe training and onboarding as effective as possible and how that adds kind of LTV overall. I do want to discuss that core, a starting day, so to speak, especially in the sales and rep world. We had our mutual friend, Ryan Williams on the show, and he said 70% of VPs of sales do not work out. Can I ask Bridget, what do you think most often goes wrong to lead to such a high failure rate?

Bridget Gleason: It could be higher than that also, and it depends on what you say about not working out. I don’t know, remember what the statistic is, but I think the average VP of sales an early stage company…nine months, 12 months. I mean it’s short, and so, I would consider that not working out. First of all, it’s really, really hard. Okay. Because you are in the really early stages, the company often doesn’t know enough and doesn’t have realistic expectations and is not hiring the person that’s appropriate to the stage where they’re at. The most common mistake that I see is they hire a VP sales that is really good at, let’s say, scale when they need a really good VP of sales, somebody who’s really good at building. And if you hire the wrong time, the wrong profile, somebody who’s great at scaling, and you bring them in too early they don’t know how to build, they haven’t done it or they haven’t done in a long time, and if you hire a builder and it’s too far along, they don’t have the skills or experience to scale.

And it also depends on how quickly the company is growing. I think sometimes if a company’s in hyper-growth, the right VP of sales for the first 12 months may not be the right VP of sales for the next 12 months. And it takes a lot of humility and honest conversations and just looking at reality to be able to have those conversations and like look at what’s really happening and not feel badly about it. Very, very, very few people can go from builder to grower to scaler to, like, very few people can do that. It’s hard to do, and I think it’s hard to get right, but how many CEOs have experience hiring salespeople, much less VPs of sales, or even executives. Believe me, sales people were great at interviewing and presenting a pretty picture, but it may not always be what the company needs.

Harry Stebbings: No, I totally get you there on that kind of flexibility to move with the company and I’m so pleased you said that about the example of someone who’s maybe a scaler and they maybe need a builder, on the flip side there’s maybe someone who’s maybe a little too junior for the role, and you’re taking that risk on them hoping they can scale into the position. The big question for me is what are the signs that a stretch VP is maybe a stretch too far.

Bridget Gleason: Yeah, I think first of all, just results. If you’re not getting results, I would think I would say that’s probably a number one. If you’re leading versus they’re leading, like are they coming to you or to the CEO with ideas and experience and things they had done in the past or how they’ve learned it, and like you said, there’s a lot of people haven’t done it before and can do it and stretch and grow, so you want to look at what are they bringing to the table, and are they able to bring things to the table either from direct experience or sort of adjacent experience that they’re able to move the business forward in a way that you feel confident you definitely want in that initial person, I guess a red flag would be if they’re not coachable or they’re defensive or they’re not aggressive learners.

If they’re not looking for other ways to do things. And if they’re not humble or if they’re secretive, like you just, you want it to be open so that everybody can sort of look at it and then make a more honest assessment about what’s happening or not happening.

Harry Stebbings: Absolutely. Jason always tells me, “Harry, beware of the micro-manager.” That’s always the big sign for him. I couldn’t agree with you more in terms of that transparency. I would though, Bridget, love to dive into my favorite element of any episode, being the quick fire round. So I’ll say a short statement and you give me your immediate thoughts. Does that sound good?

Bridget Gleason: I love it. Yes.

Harry Stebbings: Okay.

Bridget Gleason: It sounds great. I’m ready.

Harry Stebbings: That is an incredibly enthusiastic response to my quick fire round. So do you agree with Lars Nielson, that SDRs are the most important function in the sales process and why?

Bridget Gleason: I think I used to agree with that more. I think because buyers are entering, they’re entering the sales process and being introduced to a sales rep so much later in the game, that I think marketing has a huge role for creating a big catchall at the top of the funnel and creating this sort of honey pot of information that your prospects are going to want to go to that you can then kind of move them along the funnel. So, I would say second to that would be your SDRs who are often doing a lot of outbound to try to bring people closer, but I kind of changed on that. I think marketing is taking on a bigger and bigger and bigger part of the funnel as buyers are–their buying habits are different now and they’re much more, they’re doing a lot of the research on their own, so I think marketing is starting to take on a more and more important function in a sales organization.

Harry Stebbings: Sales rep productivity, what’s good, what’s bad?

Bridget Gleason: Sales are good. Churn is bad. I think in an enterprise rep it can take a year before you’ll see a payback period. In an SMB rep we see payback periods within, gosh after training four months. In an SDR, we start to see payback periods, gosh, within eight to 10 weeks, so I think you’ve got to know your business as best you can and determine it depending on the role, the size of the deals they’re going after, the complexity, that sort of thing.

Harry Stebbings: You mentioned training there, sales training, what works, and what maybe doesn’t?

Bridget Gleason: I think sales training needs to be ongoing, continually reinforced, responsibility held, not just with the trainer but at a manager level, at a team lead level, so I think it needs to be constantly reinforced. Lots of role play and requires participation. It’s not sitting back and absorbing information or listening to an audio book. What I think doesn’t work, let’s say a two-day seminar that you send people to, expect that they learn it, they come back to an environment where people are not practicing it regularly and they’re going to lose it, and I promise that will be money well wasted.

Harry Stebbings: I love that, so money well wasted. Finally, Bridget and I saved probably the hardest till last. What do you know now that you wish you knew at the beginning of your sales career, and maybe your VP of sales career 10 years ago?

Bridget Gleason: To be okay with failure, and to not have a stigma around failure, and I think why that’s so important, I think failure can be, or the sense of failure. It’s not really failure if you go learn from it and again, when you can come back from a, let’s say a setback, however you want to classify it, with a vengeance and a fire and learning that makes you better, it’s not a failure. And I think what I wish that I had learned then was to be able to more quickly reclassify any setback as this amazing opportunity to learn more than I would ever learn when things go well, and I think that’s what we miss the lesson. And I always tell reps when they, let’s say they lose a deal, I say, “Fine, you lost the deal, don’t lose the lesson. Grab a lesson, and never, never miss that.”

And I think there’s just such a great opportunity for all of us to learn when things are good or bad or up or down or going our way are not going our way. And, I wish I had really sort of embraced it earlier and not just beat myself up for it because it doesn’t, that doesn’t do–It’s not super productive.

Harry Stebbings: I mean, my word that is such a good note to end on. I absolutely loved that, and don’t lose the lesson element. Ryan told me it’d be an incredible episode, Bridget, but you more than exceeded my expectations. So thank you so much for joining me today. Honestly, it’s been such a pleasure to have you on the show.

Bridget Gleason: Well, Harry, the pleasure is all mine, and a big hi to Ryan and it’s a privilege to be on the show. Thank you so much.

Harry Stebbings: What a phenomenal guest and such a great discussion there with Bridget. If you’d like to see more from Bridget, you can find her on Twitter at Bridget Gleason. Likewise, I’d love to see behind the scenes here at SaaStr. You can do so on Instagram at HStabbings1996 with two Bs, it really would be great to see you there. As always, i cannot thank you enough for tuning in and I’m very excited to bring you another brilliant episode next week.

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