The Art and Science of Sales: Balancing Data and Qualitative Skills

Lucas Price: [: 00:00:00

I've had moments where the data said one thing that seemed very different from the things I had seen and experienced at an organization. How should a sales leader think about that? We have a great revenue leader with us here today to discuss this and more. Michelle Benford is a long time revenue leader.

rica before HubSpot Michelle [: 00:01:00

Michelle, welcome. And thanks for joining us.

Michelle Benfer: Thank you, Lucas. I'm excited to be here. Thanks for having me.

Lucas Price: Yeah. Tell us a little bit about your background. How'd you get into sales? What enticed you about it? And then that transition into sales leadership.

Michelle Benfer: Yeah. I would say the sales bug was in my family. So I grew up. My mother was in sales most of my, my early years for sure. And so I would hear her on the couch setting meetings. She basically was a BDR before they had the term BDR. She referred to as telemarketer. But she would sell, she would set up meetings for other executives.

And she always had this competitive bug and I saw a working mom who whenever she needed a job could always go out and find. something to sell. And so I grew up with that. And then on the other side, I had my father who was an accountant for mass support authority in the state of for the state of Massachusetts.

s, analytical thinker on the [: 00:02:00

And that just continued on through, through college. And then when I graduated when I didn't know what I wanted to do, I said maybe I'll try. I'll try a job in sales and move to New York city. And that's how it started. I started in the sales departments at some of the largest media companies,

Lucas Price: Is there anything in that background that you'd point to that you would say, gave you the determination and drive to succeed in sales, succeeding in sales, as we know, it takes a lot of resilience. Where'd that resilience come from for you?

Michelle Benfer: my parents were really into building confident children. And telling us, if you get knocked down, you get back up. And I played very competitive sports growing up. I was in junior Olympics and so it was very much a failure.

eration. And so I really use [: 00:03:00

It felt like really leading into a product that I thought was really cool and I could get behind. And so I think it was that interest in the product paired with. This resiliency and persistence that I learned from my parents that, that really helped.

Lucas Price: You mentioned confidence in terms of what came from your parents, but a product that you can really believe in helps, I think, have confidence in that moment of sales as well.

sales department at a place [: 00:04:00

Lucas Price: So you had success as a seller and which can be very lucrative. And so some people decide to stay. As successful sellers and continue to get better at it and, sell bigger things, make more money over time. And other people decide to get into sales leadership. Why did you take the leadership path instead of, continuing on the success you had as a seller?

Michelle Benfer: you know I ask myself that question all the time lucas. No, I you know, I'm gonna say there's a part of me that really envies the Long term individual contributor. For the reasons that you said, it can be more flexible. It's certainly very lucrative as is sales management as well. But when I was in high school, I was captain of my sports teams.

It was something that always [: 00:05:00

And I also, as I mentioned with, my dad's background, I always had this kind of analytical bent. And so I really like to look at patterns and themes and understand market dynamics that went beyond just what I sold, but how do we uplift the business, the product as a whole. And so I've always had my eyes a bit more on the 360 view than just driving towards my individual number.

And then I would say the last piece is I really like to develop people. The people, the coaching that element, I think is such a gift that some leaders really lean into others overlook. It's, they find that as a tertiary part of the job. And so that piece was always compelling to me.

ngs that you'd point to that [: 00:06:00

Michelle Benfer: I dealt with a lot of anxiety during my 20s, like job related anxiety. Was never the number one seller. I was never the top, and I would say in a big way, it was also because I tended to be the youngest, I worked with people who had been selling for 20 years, 30 years, and I was really wet behind the ears.

And so that naturally I was just so much younger than some of the other sellers that I worked with. A trick that I had at a certain point in my late twenties, I. Went back and I counted every close that I had, every deadline. And so depending on the magazine, some, closed every two weeks, some closed once a month, some closed once a quarter, it just depended on, which product I was working on.

ave to stop with the monthly [: 00:07:00

And so I started to go into my stats and that movie money ball that came out really resonated with me And I really appreciated how you know, the baseball team and turn their head on how they had traditionally done things. And I started to do that and look at patterns in data when it came to number of meetings held, number of meetings created conversion rates dials.

And I started to impart some of this information on others. Once I could Separate myself the ego from the work and I looked at the work is just that work I started to let go of some of the self awareness, self consciousness, like anxiety that I was creating for myself. That was some of the stuff that I definitely had a struggle on the mental side of things.

antly higher. Some of these, [: 00:08:00

And I had to get over that preconceived notion that what I think is a lot of money in a big deal, isn't necessarily what that company thinks is a lot of money or a big deal. So I had to work through some of. That mental piece as well.

Lucas Price: love that you shared that. I think that, the kind of vulnerability about sharing the struggles that you've gone through is one of the things that makes a great leader and appreciate you sharing that with our audience today. We talked earlier about what are your pillars of building an elite sales organization.

And one of the things that you talked about is making sure. That you have the right data infrastructure. Can you tell us a little bit about that?

Michelle Benfer: Yeah. I have what I think is the good fortune of having worked on large sales orgs, high velocity sales orgs who tend to focus on SMB mid market business. And so by way of that, there's a high amount of volume. And I'm actually building this out at the company. I'm at, right now.

I had a meeting on it [: 00:09:00

How do you pace week one, week two, week three, week four of the month? I like to look at that not because I want to hold someone accountable because they're down in one place versus the other. I want to understand what are the best reps do? What is that pattern recognition that's pretty consistent?

How do I impart that information on to the others? And how do I uplift the entire sales organization as a part of that? That's really hard to do when you don't have accessible data at the ready. And what I tend to find is. Companies grow and mature. Either you have an outdated set of data, or systems and you need to upgrade them.

access that data integrity. [: 00:10:00

It's funny. I wasn't a math person in college, but that is what makes sense to me and understanding how to uplift a sales organization. Then you take that data and then you can go to the individual and say, Hey, Lucas, your buddy, Pat, right next to you actually has fewer dials. They have fewer meetings and guess what?

He hits his number every single month. Do you want to know how he's working less, but. Having better yield than you are and using that to uplift people and, find a path to them for them to hit their number.

edIn. People will be talking [: 00:11:00

And that sounds like a good one too. And it's easy to go down a rabbit hole where there's all these numbers and easy to lose sight of what the important ones are for my organization. How do you make sure that when you're implementing, when you're thinking about data infrastructure, that you're able to, focus on the important data?

Michelle Benfer: That's a good question. It's one of the best things about sales is it's a combination of art and science. And so to your point, asking better discovery questions going deeper on discovery, second, third layer questions, reversing answers. mirroring your client. A lot of that is opaque and you need the quality control of a manager to get under the hood and read that part of the art.

r to assess the art. Is that [: 00:12:00

Who is learning reversing? Who is walking away from a sale because they've been able to extract the right level of pain and say, maybe this isn't the right time. And show those examples. When you can infuse that quality and what that looks like, what it sounds like throughout the organization, that's the art piece.

On the science piece my recommendation is to hire someone smarter than me who is an Anna sales productivity analyst. And the way I've seen this in some of the organizations that I've been in is analyzing everything from. Do a plot graph of, reps who achieve on consistently over a six month period, over a hundred percent attainment.

f closing meetings per week, [: 00:13:00

And so being able to have a really thorough analysis that is proactive, dynamic and consistent that again shows these are the right behaviors in. My experience the variables that have been pretty consistent as the likelihood of deals to close is number of ops created and deal size.

The best reps know how to find the right kinds of deals. And they know how to extract the right amount of value from those deals, depending on the sales organization. Again if you're highly transactional, if you're one call closes, that's where activity can, go higher on that list of variables.

the team as a whole in your [: 00:14:00

Lucas Price: The number of ops created. I'm curious about that one. Cause. I like, sometimes I hear, oh yeah, your best reps are the ones that are out there always finding new ways to create reps. They do some of their own prospecting, create their own opportunities. And also you'll also hear from, sometimes the same people, sometimes other people, the best reps are the ones who are disqualifying deals the earliest and not getting opportunities out of them.

Would expect to see fewer ops created out of those reps. And so can you tell us a little bit more about. What you look for in terms of ops created.

Michelle Benfer: Yeah so I would say it's ops created and deal size, not ops created or deal size. And so it really is the balance of those two. And I wouldn't say that ops created is the highest volume. It is that right volume consistently. That pairs with the win rate and the deal size and I know that feels a little kludgy and it doesn't sound as though there's a silver bullet in there.

hat combination. And I would [: 00:15:00

But if you take the medium and you're also looking at the consistency of ops created paired with conversion, Those are the three levers you really have to look at pretty consistently. And when you take a look at the best rep consistently compared to the others, and typically I would say it's probably the top two or three because, depending on the month, there's a different person leading again, because you have an outlier deal.

But you want to take a look at what are those similar behaviors that are happening with the top group consistently? And how do you help others mirror that? An example, that we talked about before is the art. Is there someone who's disqualifying really? What does that look like? Are they taking out certain industries?

il, contacts that are coming [: 00:16:00

Lucas Price: You mentioned before, yeah. Talking about the art who is, who's doing the key parts? As you just brought back up with an example, when you find a rep, who's okay this is their, disqualifying well, or they're, making sure that they always book the next meeting at the end of every other meeting, or they're, doing great.

When you find someone who's doing like a key part. What do you do with that to elevate that and make and teach those skills to the rest of the organization?

Michelle Benfer: my recommendation to any team would be managers should be all over it and sharing that in team meetings pretty consistently. And so you have your weekly team meeting. You close the books on a month. You have your number 1 rep. You take a look at what have they done well. You take a gone snippet or chorus or HubSpot, whoever it is, that's, recording the calls and you share that out with the team and you have everyone dissect it based on the sales methodology.

What did you hear [: 00:17:00

I want you to understand the ease of use and how this would work in your environment and with your use case. So you want to elevate the kind of behaviors that you have shared out to the organization and do that, whether it is in a quarterly call, creating a program that you do a SPF for anyone who uses a negative reverse this month, whoever does the best negative reverse.

So there's all sorts of programmatic ways that you can recommend. That reps start to work on more of a qualitative skill that can go as far as this rep cross sells really well. This rep knows how to push for more users on the account and not a rolling rollout. So there are so many different elements.

But again, this is. [: 00:18:00

That's really the element that, sales organizations can't forget about. That's where the goods are.

Lucas Price: So it, can you give us an example of that? Like what would, if an organization's taken data too far or potentially taken data too far and taken some of the art out, what are some of the signs of that

Michelle Benfer: I'll give you an example. When we were at HubSpot, we had years and years ago we had certain reps that were selling our enterprise SKU really well. And we had some reps that weren't selling it. And if you didn't have at least two deals on enterprise per month, you weren't going to hit your number.

ally struggling with selling [: 00:19:00

And the rep Clearly doesn't know how to, and might be too insecure to say to their manager, it's not working for me.

Lucas Price: Yeah.

Michelle Benfer: the manager then has to do is go and listen to the calls and hear, was there an opportunity here? Like number one, are they qualifying the right kinds of customers? Are they large enough to get into that skew?

If they do have that customer, they're going deep enough in the questions when they're in discovery. What are the feature sets in enterprise that they should hear, listen, understand whether or not this would be a good fit, then how do they position it? And so there was a rep we had, I remember who it was really her positioning and, she didn't know how to put out the big number, the annual contract value.

was not just the positioning [: 00:20:00

It was the the packaging of the pricing that she fell short on. So we got under the hood. We understood what the why was. why she wasn't selling that kind of SKU. And then we gave her examples of how other reps position it. Then we had her manager give her a two week sprint that she had to send him examples of how she used it on the gong call.

And he could score her and say, you did a really good job here. You got out of your comfort zone. You didn't get out of your comfort zone. And they could work together on that skill. But that was an example of. How assessed prescribed, and really dissected what the problem was and worked on a solution to help up level and upskill the rep.

Lucas Price: So the data told you that there was a rep who wasn't hitting quota. And if you're jumping to conclusions on the data, then you might jump to the conclusion that the rep isn't capable. But when you go and explore the why you realize this rep just needed to be equipped with additional tools and she was very capable.

One of [: 00:21:00

Michelle Benfer: I think some organizations don't create a coaching culture. It's a bit more sink or swim. And if you haven't figured it out on your own, then we're going to put you on a PIP if you can't hit your number. And the manager might also say, you're not selling enough enterprise.

That's why you're not hitting your number. It's the what, but they don't get to the how. And organization, your people are an asset and I tell managers that your team is an asset that you are managing for the company. And so you have to measure managers on what percent of your team, turns out due to.

hurning out and they're just [: 00:22:00

That's actually an organizational problem. That's not just a manager problem. And so it's that those health metrics for your frontline managers that you've got to be looking at as well to make sure that you have a healthy organization and you're making the most of the people assets that you bring on board.

And that are interfacing with your customers.

Lucas Price: You brought up coaching culture. Can you tell us a little bit about what that means to you? I've

Michelle Benfer: Yes. Yeah. I think I gave you, a couple of examples there, but again, you have to assume like your people are your assets and it's up to you to get the most, the highest return on the investment of your assets. And the highest return are they happy? Are they culturally additive?

Are they bringing energy to the organization? Are they hitting their number? Are they beating their number? And are they setting the pace to bring the bar to a new level? So that's like. Foundationally the kind of environment that you want to set. And so I just, came on board with bill about seven months ago.

I had my first meeting with [: 00:23:00

And. I think in general, in sales, there's a lot of blame game, right? I didn't get this deal. I didn't hit my number because marketing didn't give me enough leads. I didn't hit my number because none of the leads were good enough. I didn't hit my number because the macroeconomic environment, I didn't hit my number because I have reps on my team that shouldn't have been hired in the first place.

And so they shouldn't have been hired in the first place. That's the manager's fault for hiring them. Number one if we did hire them, what did you do? What were the manager's actions to make them successful? And so my directors who oversee managers, I'm asking them, what are you doing to make that manager successful?

alitatively and from a stats [: 00:24:00

Really you have to create that culture of expectation.

Lucas Price: heard some people say that they think like the processes that you've set up and the coaching culture. One of the signs of that is how big your middle tier of reps is and whether their performance is improving over time. You have a top tier. Who, is probably like they've gotten to a point where hopefully they're getting better, but they're not relying on the coaching to succeed.

r time, I've heard is like a [: 00:25:00

And whether you have the right processes in place, do you agree with that? Or how do you think of that

Michelle Benfer: I totally agree with that. Yep. 100%. If you know a sales as, a sales plan, an organizational sales plan when you take a look at a rep by rep basis, it has to be well balanced,. It's like a bell curve. And you'll have fewer people that are a hundred percent, 110% and above.

You'll have ideally fewer people that are below 80%, and you want that 80 to a hundred percent to be the bulk of the organization. Most sales organization plans are built that way to assume 80 percent attainment some 90 percent attainment, but totally agree. It's that middle group. You want to strengthen.

Lucas Price: in your history as a salesperson and a sales leader, is there something that you've seen that has really made you point to like coaching is really important?

o you want your, if a BDR is [: 00:26:00

The longer reps are on board, the more productive that they are. So if you can retain your people, they're happy. You have that institutional knowledge. They also offer mentoring to, and help uplift the people that are coming up the ranks as well. And so you really create this really nice engine for talent.

And so it is in an organization's best interest in my belief to To have a really robust coaching culture purely for the retention purposes. And selfishly, I like to develop people. I think that's one of the most it's one of the biggest benefits of a role of a leader is to be able to develop people, who they work with.

th that. I've met with other [: 00:27:00

Lucas Price: When you're looking for, maybe at the top of that funnel, when you're hiring reps. You're going to coach them, but how do you make sure that you're hiring the people that are going to be coachable?

Michelle Benfer: yeah. Love that. So we actually at HubSpot, we had we did a study. We had a intern from MIT business school program who came and analyzed all of our hires, 12 months, 24 months after we had hired them and they looked at a scorecard of attributes that we had attributes were like a commitment to winning.

ellectual curiosity. And And [: 00:28:00

It's also you need people on board who are willing to take coaching. They are willing to fail and get better. They're intellectually curious. So that ideally, and this is something that I did throughout my entire career, they're going to get better. actively seeking how they can be better, whether it's reading sales books, listening to podcasts, it's asking, some of the veterans on the team.

So it really is, you need to get the right mindset on board. And that's what I've seen in terms of hiring the right kinds of people that help fuel growth within an organization.

Lucas Price: I love that. When you think about the things that we've talked about today, two or three takeaways that you have for our audience.

Michelle Benfer: Would definitely say the role of a frontline manager cannot be underestimated. It is. Integral to an organization in two parts, one, I would definitely say the hiring, making sure you're bringing the right people on board who are intellectually curious who want to win but they're also coachable.

[: 00:29:00

It's not just art. It's not just science. It really is a combination of two and understanding which levers are the right ones to pull.

Lucas Price: That's good. I love that. I also love how you shared with us, your early career struggles with anxiety and how you turned that into, and there's a lot of people out there listening who might feel some of that right now. And, you've, you put just something together that helped you get over that.

you enjoyed this. Episode of [: 00:30:00

And if you have any feedback from us, you connect with me on LinkedIn. Thanks for joining us today.