SaaStr Podcast #210: Bridget Gleason, VP of Sales @ Logz.io On Why The Best Sales Reps Are Not Outgoing and Extroverted
Update: 2019-02-08
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This post is by Harry Stebbings from SaaStr
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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 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:
- What does Bridget know now that she wishes she had known when she started in SaaS?
- SDR’s are the most important function in the sales process, agree or not and why?
- Sales training, what works? What does not?
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Jason Lemkin
Harry Stebbings
SaaStr
Bridget Gleason
Transcript
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 c
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