Michelle Benfer, VP Sales at Hubspot, on hyperscale and creating a culture to drive revenue.

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Episode Outline

[01:03] Michelle’s background

[03:12] Why you should make sure you have the demand to support your sales team before investing in the head count

[05:28] The importance of experimentation and stabilization

[07:15] The importance of cross functional partnerships and financial acumen

[09:21] How to make better decisions for your team and company.

[11:50] How to create culture within your company

[14:30] What’s next for Michelle

[17:11] How Michelle unplugs and maintains her energy

Connect with Michelle



Speaker 1: (01:05)
So today I am really excited to have Michelle Ben for on the show. Michelle was a global VP of sales at log me in currently VP of sales at HubSpot Michelle. Welcome to the show. Thank you for having me. So, you know, it's not every day that we get to chat about the kind of post startups scale phase, right? Normally we're in the one to 10 million or the 10 to 20, but I think today's episode, it would be really fun to focus on that, like real meaty scale Sage and your kind of experience in that, in that industry. So maybe we could start at the beginning. I mean, you came up through the ranks in log me in a startup within a startup. Can you walk us through that first experience with real scale? Yeah, yeah. So, so I mean the first, the first half of my career was actually a media sales and New York city, but my first kind of sass gig was at log me in, uh, where I started as, um, North America director of inside sales.

Speaker 1: (02:09)
Um, so in that position I had more of a functional role. I oversaw both new business account management and it was a pretty well oiled machine. Um, and the company at the time I want to say was about 200 million in revenue. Um, but then I pivoted over to, um, join.me specifically at log me in which at the time was their high growth product and ended up being, um, that high growth product until we, the company ended up merging with go to meeting and, you know, the collab space that we were in, um, wouldn't have happened, had it not been for the success of join me. But when I started on the join me business, I want to say it was somewhere around 11 million in annual bookings. And by the time I left, it was somewhere around 52 million in, in overall bookings and the company at about, um, I want to say 450 million in revenue.

Speaker 1: (03:04)
So, you know, it really was kind of the startup with, within, uh, uh, you know, a publicly traded company. So it had a lot of the zest of that high growth, fast pace, tons of pressure. Um, and you know, I remember scaling our Hunter team or new business team. We had had like seven reps all the way up to 30, 30 or 32 at our height within a one year period. So definitely felt some of the pain of growing too quickly, not having the lead flow to support us and having to ratchet some of that back and course correct. So there were a lot of, a lot of learnings there. Can you walk us through some of the hardest lessons in that initial sprint when you were going from, you know, the sprint up to, I think you said 52 million in bookings from seven, what were some of the lessons you maybe weren't even expecting to, uh, crop up and have to deal with that that ended up becoming big challenges you had to overcome?

Speaker 1: (04:03)
Yeah, I think, you know, when the team build out the model for that kind of hyper growth, um, when we were really kind of doubling down on the business, I think there was an assumption that if we spent the money in the market to market join.me, and this was before zoom really even took off. Um, cause that was that kind of screenshare collaboration that you find now in the zoom space and go to meeting space. But, um, we assumed we were going to spend a lot of money in the market and we thought the leads would come right back to us. And so, you know, log me in was one of the pioneers of the freemium model. And even though joined me was a freemium play. We weren't able to scale the lead flow as much as we had assumed we would be able to with the incremental investment in, um, overall, um, marketing demand.

Speaker 1: (04:58)
And so we ended up scaling up the sales team as part of our inbound channel and we just did not have the space for it. And so we had reps that were basically who were basically starving and, um, you know, there just wasn't enough business out there and, and, you know, customer acquisition costs didn't make sense for us to keep all of the head count that we had originally planned for. So, you know, we expanded and then we needed to cut it back by about 20, 25%, which that always hurts when you, you have a lot of great momentum in your sales org, but we just didn't have the demand to support it. So I think like the lesson learned there was, you know, make sure you have the demand to support the sales team before you go and invest in the head count. Um, because that was definitely a mistake.

Speaker 1: (05:42)
One. I know a lot of my peers in the industry have faced as well. Is there a system you've come across at this point for yourself in how you would begin to stress test whether or not that system is in place when you walk into a new organization or you're, you're looking at an organization and you see certain numbers they're putting up as far as demand and on the marketing side, how do you know if that's stable enough to support the growth in sales and if it's the right demand? Yeah, that's a great question. I mean, I think, um, I think what I've learned so far it's experiment, experiment experiment. So, you know, a lesson that I learned from bill Wagner, who's a CEO at log me in. I remember him saying that on any given sales experiment, you should always have a minimum of three reps involved.

Speaker 1: (06:34)
Cause if you have two reps against each other, you never know if one is good and one is bad and three kind of really gives you that equalizing factor of what the business might be telling you. And so I think one of the things we've learned is anytime you're going to enter a new market, um, if you're wanting to stress test, whether or not you have enough of that demand, you know, start with a pilot as best as possible instead of going kind of all in. And, um, you know, you definitely have to experiment and test and get to a point where, you know, you have enough demand to get the reps to at least 70, 70% of the assumed quota. Um, and so that you're looking for that overall rep productivity to like carry over the other, the other end. And then I would also say in any level of that experiment, especially with an inbound sales model is making sure there's a level of stabilization when it comes to deal size and, um, conversion rate.

Speaker 1: (07:30)
So having, you know, if you're in a high velocity model, you can ideally see that within a 12 week period. Um, but if it is obviously longer term, you might really want to give any experiments, at least four months to six months would be my record. Makes sense. Um, what have been some moments, some aha moments for you throughout your career as you've grown that have helped take you to the next level and your teams and you and your performance to the next level? Yeah, that's a good question. Um, you know, I think being at a director level and above, um, I think an instinct that I always had throughout my career is how do I learn more from other departments that I may not get in my own job? So I always try to have a bit of a like part time job, just learning other parts of the business and took that on as a pet project.

Speaker 1: (08:24)
When I work with my managers today, I've, I've 13 managers on my team now and I have two directors over them when I worked with my managers and my directors, you know, I'm always asking what kind of projects are you taking on, on your own to enact change within the organization as a whole? What other departments are you meeting with? Not as just a chitchat and cup of coffee, but how can you actually implement and take action on change within the organization where you can have an impact. And so I think I was surprised at how important, um, cross-functional partnerships work and the ability, the ability to project manage is especially as you move up, it's not a skill that you learn typically coming up in a sales environment. You're not taking project management courses, you know, as a part of your professional development. So that's an area that I've come to find is actually really important as you progress.

Speaker 1: (09:21)
And then the other one is, you know, not just the importance of data driven, um, insights and management, but understanding the financials of the business and getting as close to that as possible. I think a lot of us have, have seen the trends where sales ops really is a huge, huge role of influence in a lot of sales organization. It's because they're the closest to the financials and they have a lot of skin in the game when it comes to some decision making. So, you know, I would say like having that financial acumen and savvy, and then also being able to, um, enact that kind of cross functional impact that's those are the two areas that I think are, were surprised as an aha moments for me. Where were you and, and what was the situation that you learned that lesson the first time or, yeah, yeah.

Speaker 1: (10:12)
So when, so we went through a few different organizational changes at log me in while I was there. And one of them, it was when, you know, sales was sales, marketing was marketing, product was product, and we didn't really work together. We kind of let all this, the C levels work with each other and otherwise everyone, they were just kind of functional leaderships within their team. We made an adjustment to, um, really having the VPs, uh, work with a GM to, um, drive the strategy of the business. And it was for the first time that all these departments had to work together as one. And I realized when I didn't really understand the way that the product team worked and what was important to them and how they made decisions and then the same with the engineering team and how they prioritize. And the same with my marketing counterpart, who had always worked more closely with, or the customer success team, I realized like I need to get much closer to these, these departments and how this, these businesses are operating in order for me to make the best decisions, not just for my team, but for the business as a whole.

Speaker 1: (11:15)
So I think that first aha moment was when I realized I was much better at my job. The more I knew about what was going on in the company and depending on the size of your company in the way that they're structured, that can be hard to do. So I think it was part of some of that organizational change at, at log me in for sure. And then honestly, I just feel like if I look throughout my career, one of the ways that I've always been able to kind of move up the ladder has been, um, you know, just my interest in, in lots of different parts of the business. And it just makes me, I think, more, um, articulate and a better decision maker compared to maybe some of my peers who might be interested in the same types of roles, but, um, they're a bit more, um, you know, or in the past were more sales focused as opposed to, you know, um, enterprise focused.

Speaker 1: (12:10)
I liked that a lot. So I know it from our previous conversations, that culture, and this is like almost a non statement, but like culture is really important to you. But the part that is a statement is the way that you've implemented that and become known for that. So could you walk us through examples, specific examples across any of the companies you've, you've led teams of how you've driven culture and created an environment for that to thrive and put up actual results? Yeah. Um, yeah, you know, it's funny, it's like, you know, saying you're big on culture or, you know, you are a high performer, those are supposed to be like stable takes stakes and management. Right. Um, I think the biggest indicator is you need to make sure you're surveying your people. Um, and you're doing it in a way that they can be anonymous and also write and freeform how they really feel about the culture and the environment and not just, you know, under your leadership, under their own manager and, and to get that feedback pretty consistently.

Speaker 1: (13:15)
And so I feel though I've pretty often had a pulse on kind of the overall morale and, and feel of my team. And some of that's been through surveys, but to be honest, I can feel it when I just walk the floor and we're actually not all remote in our homes, but when I was back in Cambridge and I had, you know, my sales team of, of 80 plus people there, I mean, you can feel when the energy and the buzz isn't there. And, you know, I think as a leader, you need to feel that, and then you need to listen, learn, and then act accordingly. And so, you know, some of the pieces of feedback I got from my team were, you know, we collaborate with our own team, but we don't collaborate with other teams. So we've created team happy hours with two different groups.

Speaker 1: (14:00)
We've created working groups. Um, you know, that actually we're, we're doing this coming up now where we're going to have four or five reps who are going to have a prompt and for them to work together on a problem that they're all looking to solve, that could be how to pitch a product more effectively. Um, and then on top of that, it's, you know, I, I do coffee chats, you know, every, every week with just a handful of different reps that are on different teams, I get to know them better and just ask them like, what can we do better? What's working, what's not working. Um, and so I just, I try to get that information from a lot of different places and then respond accordingly and then let your team know what you're doing about it. So, um, but selfishly, I, I actually would just really like to have fun with my team.

Speaker 1: (14:45)
And so we try to put together engaging spiffs and nights out and ways that we can all spend time and celebrate while at the same time, you know, working hard and, and having a great culture on the floor. So, I mean, your, your career only continues to, you know, pick up steam and, and, and you're already at the, at what seems like the top, but I'm sure you're just going to keep going. What are your own challenges for yourself? Like when you sit down and think about where you are today, what you've accomplished? Like, what is next? Yeah, I know that's what is next? Um, you know, I, this is one of the first times in my career that I feel like I'm, I'm not looking for what's next immediately. And so I think for a long time, it was, how do I get the bigger job?

Speaker 1: (15:34)
How do I get the next job, the better job, you know, all of that. I think what's next for me right now. Is there a parts of the business I really want to know deeper and more intimately that I don't know right now. So for example, you know, how do I, um, improve our overall comp plan based on what it looks like today and what are the levers that we have to pull and how can I work with the analyst on my sales ops team and the way that they might look at that, or, you know, how do we analyze whether or not like a micro territory where everyone owns their kind of like King or queen of their own domain versus team-based territory's versus, you know, um, geographic territories, which one has a better ROI. So how do I get better on kind of team structure and go to market strategies?

Speaker 1: (16:23)
Um, you know, and I was mentioning some of this as well. It's how do I work even more deeply with some of my counterparts in other departments at HubSpot? You know, HubSpot can be a bit more siloed. I think we're getting better at putting together, um, a holistic go to market team, but how do I understand, you know, the priorities of the business and how that informs really where my team is gonna go and how I can steward them over the next few years. So I'm really in this place of learning, um, and taking a look at when I look at my chief customer officer, like what are the things that she nails as an executive that I really want to work on and hone and Polish myself over these next few years to eventually, you know, be a CRO at a publicly traded company.

Speaker 1: (17:14)
I love that you draw on other orgs to further the value that you can deliver, not just focus on excellence in the org that you're in, specifically as the only lever. I feel like that's such, that's something that isn't touched on very often, and it seems like such a, a no brainer, but just a powerful approach, um, that I don't hear people talk about very often. How do you, how do you unwind, like you, you know, you have this incredibly high output, you know, you're, you're presumably a ton of type a leaders and their teams, um, and you continue to push the limits. How do you unplug? Yeah, I, uh, it's funny sometimes I don't, so I also have two kids and a puppy who is drags me all around. Uh, you know, there are some days that I'm like totally spent and, and I try not to do that, but, um, we actually have run this, this great program at HubSpot.

Speaker 1: (18:16)
That's called people fuel. Uh, I know they've, they've worked with a lot of, you know, SAS companies, and basically it helps you understand where you get energy and where you, you know, you get energy depleted and, um, and the importance of micro breaks. So for me now that we've all been working from home, knowing that I might have only 10 or 15 minutes between like sometimes all day like that really just like, I don't have many breaks, just taking a quick walk around my block with my dog, not looking at my phone, really like allow my brain to decompress. That would be the micro break that I take. And, um, you know, I try to exercise, even if I get short breaks, I do this hydro, it was like the Peloton of rowers and, um, you know, otherwise I just really like to spend time, you know, with friends and family on weekends.

Speaker 1: (19:09)
And, but I'm pretty good about knowing that I need to mentally get into, um, kind of a refresh zone when I'm, when I'm spent. Um, so yeah, I think it's just managing your energy well and, and knowing what makes you feel good and what depletes you and trying to stay away from those, you know, depleting, um, activities makes sense. I wish we all took more time to do things like that. So it's a, it's good to have that reminder. And my last question for you is, you know, surely we all have folks who either inspire us, whether they're officially mentors in our lives, or even peers that we think are doing great work and remind us to keep pushing who are some of those folks in your life? I mean, honestly, not to be, had to be cheesy, but my team, like, I feel very, I feel very, um, honored to lead the group of people that I do.

Speaker 1: (20:05)
And I think HubSpot does a really good job of hiring people. And anytime you have a group of people who work for you, who make you stand up a little taller, improve your game, make sure that you come to the next meeting, even more prepared. Um, you know, I, I'm inspired by the people that I work alongside and who I work for. Um, and specifically the reps and the managers, I just, we have a really bright group of people and I'm inspired to do my best work and feel as though, you know, it's a privilege to work at the company and, um, I still have to earn my spot, you know, and I feel like that every day. And so, you know, I, I really I'm, I'm inspired by team I work with and, um, and also, you know, the value that we can bring as a sales organization to a lot of small businesses, certainly. Well, Michelle, it's been an absolute pleasure. Thanks for taking the time and having this conversation with me. I'm sure our listeners are gonna walk away with this inspired and ready to break through to that same level of growth that you have. So thanks again. Thank you. Have a good one.