Posted on 

May 30, 2022

How to build a sales culture that makes reps thrive and perform

Mikkel Boris
Director of PR & Communication

There is more to a great sales team than just reaching targets. A great sales team is profitable. Sure. A gong-hitting, deal-closing growth machine. But it’s more than that. It’s also a comfortable and meaningful working environment - with great team spirit, interesting career opportunities and a fun social dynamic. It’s a place where sales reps grow and thrive. A place that supports the entire company and collaborates well with marketing, product, customer service and every other department. 

So a great leader of a sales organization shouldn’t just focus on reaching this month’s targets. They should also be focused on building, scaling and maintaining a holistic sales culture that makes sales reps thrive and perform now - and in the long run. 

Finding time for that is hard. Time is a precious resource nowadays. But time you can win by optimizing workflows - like automating your sales contracts with Contractbook for example.

Finding expertise can be even harder. But we’ve also got you covered here. We organized a webinar on the subject with seasoned experts such as Rory Brown from Kluster, Tom Lavery from Jiminny, our very own Alexander Irschenberger, and Jenna Rogers.

Jenna Rogers is VP of Growth in Sales Assembly. She is also the founder of Career Civility - a consultancy firm helping sales organizations build culture through communication. In other words, she knows a thing or two about cultivating a comfortable and efficient culture in a sales team.

We sat down with her for a quick Q&A on how to build, scale and maintain a successful sales team. Here is the result: A conversation about finding a common why, avoiding toxic competitiveness and hiring the right people.

So how do we go about this? How do we foster a great sales culture? 

So one of the exercises that I do is making sure that we all have a shared mission statement, some shared values, or a shared why. So when we wake up in the morning, and instead of going to an office, we now just open our computers, we all do it for a reason. When you are cultivating your team, you must be able to uncover what everyone’s why is and then cultivate that energy to a shared goal across the team. 

So it sounds a bit elusive, I guess. But when you sit down and really uncover their background, how they grew up, any challenges or hardships that they’ve occurred in life and why they’re working so hard towards their own quota or their own attainment or their own commission, that is really golden information. 


So how do you go about it practically? Do you ask people every morning before they open their computers? That sounds time-consuming.

It’s not time intensive, but from a management perspective, getting to know each person on an individual basis is really important. I think the easiest way to do that, especially in the sales world, is to have weekly standing 1:1’s with the direct reports and your team. So you don't need to go above and beyond, but really just having a standing meeting on the calendar every week, every other week, and making sure that you have 10 minutes to say: What can I help you with? What was hard this week? Both at work and outside work. Because one of the manager’s goals is to remove obstacles for people. So making sure that you're checking in both personally and professionally helps you uncover those values, those hardships, those why’s. And obviously, it takes time.

But how do you then create a common why based on these individual conversations? 

The first step is getting to know people. The second step is cultivating that comradery. In the sales world, I think that is done - or at least in the old school way - through happy hours, dinners and team outing events. In this “new world”, I think that it needs to be a little bit more intentional. So one of the activities that I've facilitated in the past is creating a shared mission statement as a team. So your individual team, in this organization that has hundreds of people, what does your team of six to eight people want to be known for across the organization?

The other thing, in terms of career development and career progression, is really giving your team members a platform to stand on. Sometimes people are shy and they don't want to be known as the large loud person in the room, even amongst salespeople. So give them another responsibility. Like, are they going to be able to run the team meeting? Are they going to be able to forecast for the week? So that way it gives them more purpose at work. 


I assume that method could work in many organizations and teams. What do you think makes sales teams different?

In my personal experience, sales professionals and sales organizations are very outgoing. They're very energetic. I've used the word competitive in the past. They're very determined versus other professions. You know, in a lot of jobs you clock in and you clock out. There isn't that drive to go above and beyond. In sales, the work you put in is the work that you get out. And in other professions, the work you put in is the work that is expected of you.


It’s interesting with the competitiveness. How do you manage that so it doesn’t become toxic?

Yeah, healthy competition. I think you can harness it in a couple of different ways. So in a SaaS environment, you do have very clear and established roles and expectations. I have worked for organizations where it is kind of a dog-eat-dog world, and you had a “territory setup”. Those weren't really productive. So I think in order to cultivate healthy competition, you have to create an environment of shared learning. So how can I learn from you and how can you learn from me?

That way you're consistently levelling each other up. That's kind of taking this competitive nature, and instead of it being dog-eat-dog, it's more of like: I'll help you up after I've learned this mistake. Or I've I won this really big deal, so I want to make sure that you're winning other big deals as well.

Another thing I see done very often is sharing wins. So whether it’s in a month in review, a quarterly business review or a year-end, recognize the rookie of the year, the MVP, and all those accomplishments. Another thing is setting up mentorships, pairing reps who are successful with a rep that isn’t as tenured. 

The hard part is time. It's such a valuable commodity for sales representatives. So it's hard to take them off the floor for traditional enablement and learning. 

Sales teams tend to be very metrics focused. So if you had to measure a successful sales team, I guess you would always look at if you're reaching your targets, but if you have to talk about sales culture and whether it's a comfortable place to work. Do you have any tricks on how you can measure that?

That's such a great question because, in a lot of sales organizations, the toxic culture is overlooked based on performance. Because if you're performing well, who cares? 

That's not a great recipe for longevity or for sustainability. So what one of my mentors and former managers used to say is: follow the process. If we have a sales process and you're following it, the numbers will come, the performance will come. So you need to define what your process looks like. What is success to you? So we can talk about processes like prospecting and how many calls you're running a day. Or the discovery questions you're asking. All of that goes into the process, but then there's also a part of the process as to are you respecting your peers? Are you playing for the name on the front or on the back?

Those are all questions or pieces of your process that you have to think about because if you're following that process, the numbers are going to come. As opposed to focusing on the numbers, not caring what goes into that number, that's kind of where the toxic culture is created, in my opinion.

How much do you think is defined in the recruitment process and the people you're getting in and how much is defined in the work you do to actually cultivate the culture?

Yeah, we had this discussion in a peer group at Sales Assembly last week. It is very top of mind for the marketplace that we're in right now because hiring is so difficult. Add five years ago you could have hired someone very green and then coach them up a lot quicker than you can in a remote world. With soft skills, I really think it comes down to coachability. How much can you coach this person? It depends on the resources you already have on your team. Ask yourself: Do I have the time to be able to coach this individual up? Do you want them to be 50%? They have all the skills and 50% you can coach them. Or if you don't have that much time, then it's 80% skills and 20 % you’ll be able to coach them. Then you can start to understand the give and take of the type of candidates you hire for. 

So I think it's very contextualized. But I would say look for 50 %, 60 % hard skills and don’t turn great candidates away because a lot of candidates just need the right manager and the right environment and they thrive.


Yes, it seems really hard to recruit nowadays? That should make your culture even more important? 

I think one of the reason it's so tricky is twofold. Number one. Especially in the world that I'm working in - SaaS/startup/B2B tech companies - they're growing exponentially and they have a lot of open headcount. They need more bodies, but they also need to make sure that these bodies are a right fit so the culture scales appropriately. I think that that's a really big challenge right now. 

Many organizations are focused on numbers as opposed to process and the culture they want to create, so all of a sudden they get all these heads in seat and they look back a year from now and they’re like, where did we go? This wasn’t the organization. 

What do you think is the most overlooked aspect of building a well-operated sales culture?

I come from a communication mindset. My mission statement in life is that if we could learn how to communicate better, a lot of our problems would be solved. Everyone knows communication is the skill of the century. It's what employers look for in their employees. It's what therapists taught you to have good relationships with your friends, family, your significant other etc. And yet no one actually knows what good communication looks like. So I think the most overlooked aspect of a sales culture is having transparent, effective, productive communication amongst the team members.

That makes sense. But what kind of resources would you point people to if they wish to improve their communication skills?

Well… my consulting firm. No. I think it's a great question because again, like no one knows how to do it. You know, you can go to a class on negotiation. You can go to a class on prospecting on cold calling, but there's not really material built out to learn how to become a better communicator. So I think that that's a huge opportunity in the marketplace, which is one of the reasons I'm so passionate about it.

But then I do think that there are books, there are articles written about it, but I also think asking for feedback helps in your day-to-day. How did that meeting go? How did I communicate our product? Or how did I communicate with you? I know that we were in a heated argument but do you have feedback for me there? So instead of going to a class or reading a book or reading an article, get it in real-time, ask your manager. Or tell your manager, Hey, this is typically how I communicate, and this is typically how I like to be communicated with. Know your communication style and ask to get that feedback. I think that is a start. 

Check out the full panel discussion on how to build, scale and maintain a sales culture where everyone thrives and performs via our on-demand webinar!

Industry insights you won’t delete. Delivered to your inbox weekly.