Michelle Benfer: 5 Tips for Remote Sales Management

How do you build a healthy sales culture?

Why is it important to create balanced sales territories?

How can you transition to a remote workforce more easily?

On a recent episode of the Reveal podcast, we connected with Michelle Benfer, VP Sales at HubSpot, for answers to these and other questions that are top of mind for revenue leaders.

Key Points to Remember

1. Your culture isn’t “set and forget.” It’s living, breathing, and organic. 
2. Create a psychologically safe environment to help your reps manage anxiety and stress.
3. Well-designed territories help create an equal footing for your reps.
4. Clear communication and expectations are critical for managing remote teams.
5. Designing an effective coaching program starts with defining success, and then holding yourself accountable.

Building a Healthy Sales Culture

HubSpot is famous for our company culture. Sales is a microcosm of that. But when I first arrived at HubSpot over two years ago, one of the pieces of the sales floor culture that I was really impressed by was how helpful everybody is to each other.

So if you’re a new rep and you start at HubSpot, everyone around you wants to help you. And I know in some sales organizations, there can be lone wolves. Or people don’t want to share best practices because they feel that it takes away from their own selling time. You never really find that at HubSpot. It’s a very giving, helpful culture, which I really like.

And I would say that our sales team thinks of culture as living, breathing, and organic. It’s not like “set it and forget it, here are our values, let’s hope this all works out.” So, one of the things I try to do as a leader pretty consistently is get feedback from my team through surveys. What could we do better? How can we enhance the culture? Does it feel like an inclusive environment? 

And you get pieces of feedback from your team like, “I’m a parent, and it’s hard for me to go to team bonding events after work. Can we find something that happens in the afternoon?” Or, “I don’t drink alcohol. Can we come up with events that don’t have alcohol as a part of our entertainment?”

And so we just really try to have a pulse on what people want. I think you can listen to your people. You get to create a culture that they want, understand what the gaps are, and try to lead to address those to create a healthy, fun, vibrant, energetic, and inclusive culture.

I grew up in a sales environment that was in some ways Machiavellian. I had some leaders who led by fear. The “Sunday Scaries” were just a part of life, and it was kind of this sink or swim environment. It wasn’t healthy. 

A lot of sales managers will come to me and say, “Hey, this rep, they’ve really been struggling. They doubt themselves, or they have imposter syndrome, or they’re really stuck in a rut like they’re doing all the right things—it’s just everything’s not clicking yet from a revenue perspective. Do you think you could have a chat with them?” 

Probably the highest number of one-on-one chats that I’ve had with reps in the last few years has been about their own personal anxiety and stress that they’re trying to navigate. You know in sales, that pressure is just always there. You’ve got to hit that monthly number. You’re stack ranked against your peers. For a lot of people, it’s the first time they’ve faced professional adversity. It’s either their first sales job, or they’ve been in sales for five or six years.

But for a lot of people, they’re really struggling with how they face some of these personal and work challenges. It affects their daily work. It affects teams being able to hit their number. 

And so we try to create a psychologically safe environment where people can talk about their mental health. They can talk about needing a break, whether it’s to go to appointments with a therapist or something like that. Instead of brushing it under the carpet, we really tried to build a healthy work environment that supports the needs of our people. 

We’ve had a few reps who have had to take a leave of absence. Mistakenly, I thought, “Okay, this is probably their first foot out the door. They’ll be looking for a job because this isn’t the right fit for them.” And then we’ve had people return, and it’s just unbelievable, the turnaround. They just really needed that life pause, that professional pause, and they come back recharged. It’s done wonders for people.

Creating Balanced Territories

When I first arrived at HubSpot, everyone had their own mini territory. So you might have Boston, you might have western Massachusetts, you might have Alabama. There are these little micro-territories. 

What ended up happening was there was a lot of territory disparity. So some of our strongest reps might have San Francisco or New York. The conversations they have had, and the level of sophistication that a lot of the buyers had, was very different than more rural communities. Areas of the country that just aren’t as much of a hotbed, whether it’s tech, eCommerce companies, or manufacturing.

We realized that it really did a disservice to a lot of our reps. If you started in the territory that wasn’t as high performing, you had to close a lot more deals. The deal size was much lower.

So last year we moved from this kind of micro-territory model, where everyone was kind of a CEO of their own domain, to a 100% lead rotator. We had an east coast team, a west coast team, and we had a Canada team. And everyone received equal distribution of leads based on our model. 

We didn’t end up seeing the lead quality that we had hoped. So you’d have one rep that would receive 30 leads in a month. Another rep would receive 60 leads. Well again, they were at the disadvantage.

So we moved this year back to territories, but we moved into team territories. And what we did is, we broke out each territory under a manager. We had tier one, tier two, tier three territories. So for example, that might be New York City’s a tier one, tier two might be Delaware, and tier three might be Louisiana.

So every team has a combination of a really hot territory, more medium, and maybe one that doesn’t yield as much revenue. And those leads get distributed equally among the reps. And they can prospect into that full territory, which really expands that total addressable market for all the reps on the team and the team as a whole. 

So far, so good. The reps seem to love it. It gives them exposure to all different types of conversations. They learn a lot, and they feel as though they’re on equal footing with all the other reps on their team.

The New Remote Workforce

We have a super flexible work from home culture. My team probably has the lowest number of remote employees. The reason why it’s been like that is because so many of our sellers are very new to their sales career. And we really like the learning from osmosis and having your team around you. That said, we’re in the process of building out our work from home playbooks and remote employees playbooks. 

We’re really looking to not only allow our current employees to work remote more often, but also how to start building teams from scratch that are going to be fully remote teams. And a big perk is you get diverse employees from all over the country. It isn’t just Boston-centric. And you can tap into levels of diversity that we may not have in just one singular market.

I think the most important thing is really communication and setting expectations. We’re building this playbook out right now. But we have our sales managers making sure that the expectation is that constant communication needs to be agreed upon—not only from the manager, but the rep as well. Sales management software can help transition to remote selling.

One of the recommendations we have is, a manager might have a one hour one-on-one, but also two 15-minute check-ins a week with one of their remote employees. That might be a little bit different from the employees they have that are sitting in seats. 

And then also giving a remote employee two buddies. If their one buddy’s on a call or their manager is not available, they have at least another person who is dedicated to them. If they have an immediate question, the odds of them getting a response back pretty quickly are high.

We also do remote happy hours on some of the teams. How do we create a culture that is inclusive and fun? You can kind of relax a little bit and get to know some of your team members doing some good ice breakers. And also surveying people—what’s working, what’s not working, how can we make this better? 

I think if you work in tech right now—or really in any industry—you have to be able to adapt. The people who adapt are the ones who survive and thrive. 

Coaching and Accountability

We actually have a coaching framework that we use to help our reps improve their skills. But you need to know, if you put together a coaching plan, is it effective? And how are you measuring it? And so I think that’s the first piece. And then the second piece is accountability.

My leadership team, when we chose what our core values were going to be as a group, they wanted to hold themselves to a higher level of accountability. And so, if you’re going to coach your people and your organization to be more effective, how are you going to hold yourself accountable to make sure you see it through? And what are the metrics you’re going to measure, the success criteria, to see that you move something from point A to point B? 

I think it’s really that self-reflective accountability. We all have a number to hit, and sometimes you can hit that number. But that doesn’t mean that you’re doing your job as effectively as possible. And so we’re really trying to double down on coaching effectively. 

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