Daren Jennings: Living Your Best Sales Culture (Ep.#4)

WENDY HANSON: Welcome everybody. On this podcast, we talk about managers, leaders, cultures, and workplaces. We want you to take away ideas that you're going to be able to use right away. I've been an executive coach for 21 years and worked with many sales leaders and many sales teams, and today, I am very excited to talk to a wonderful sales leader about developing a positive culture and work environment, Daren Jennings.

Wendy Hanson: Let me tell you a little bit about Daren. Daren Jennings is the VP of sales for Interact, a global provider of collaborative digital workplace software and consulting for enterprise companies. A self-described accidental sales guy, he's now in the 20th year of his temporary sales career. More than anything, he likes helping people figure out a way to solve problems, so B2B sales is actually a really good fit for him.

Wendy Hanson: He divides his time between New York and Rhode Island, where he lives with his wife, two children, and an old beagle named [inaudible 00: 01: 03]. Welcome, Daren.

DAREN JENNINGS: Thank you for having me. Excited to be here.

Wendy Hanson: Yes, I am very excited to learn more about what you're doing in the role of a sales leader and what we can all learn from that. So give us a little background first of some of your background in your career in sales and what you're doing at Interact Software.

Daren Jennings: Yeah, sure. I think it's a great topic. And your intro was very funny, because I do call myself an accidental sales guy, because I never embarked on this career intentionally. And I think a lot of sales people have that trajectory. No one, very few people kind of set out to start a career in sales. And I was no exception.

Daren Jennings: So, my education was in political science, that's what my degree's in, with public finance as kind of a concentration, and I would really like statistics and the numbers of it. And I really wanted to be a pollster, getting out of college. And it was kind of an interesting time, in sort of the Bush Gore era of the elections, and there was a lot of [inaudible] going on, but there weren't very many jobs in that sector, especially for a kid right out of college.

Daren Jennings: So I took a job out of school as a selling to the Spanish language community, and I said, "Well, I'll try this for a little bit, and you know, see how it goes." And it turns out, I had a knack for it, and it was kind of interesting being able to not only sell something but sell something in a language that isn't your first. And I think that really kind of helped kind of guide my career.

Daren Jennings: And shortly after that, I kind of transitioned into selling into technology, and eventually, moved into management and sales leadership, because I found that I really liked helping other people to be successful. And that's kind of led me to where I am today at Interact, where I'm the VP of sales there. And what I do at Interact is I lead the team in North America.

Daren Jennings: We are a global company, and our headquarters are in New York City. So I lead the sales team here, and we've got about 15 people that go out and try to help companies increase their engagement with their employees, and improve communications and collaboration, and really just help people with a resource that they can do a better job and feel more connected to their organization.

Daren Jennings: So a lot of what we talk about in our sales process with our prospective customers kind of dovetails nicely into, I think, what we're going to talk about today, which is, how can you build people personally and professionally so that they have a much more fulfilled professional and personal life.

Wendy Hanson: Yeah. And it's lovely that your intention was really like, you wanted to help others be successful. A lot of people that are in sales may be really good at sales, but they may not be really good at being that, play that role of a manager and help other people grow. Because no matter if it's sales or anything else, or engineering, working through others is ... Humans come to work different every day. So we have challenges and things that we face in order to keep this productive work environment. So let's talk about culture. Why is culture important in a sales setting?

Daren Jennings: Yeah, I think it's vitally important, and it's a tricky thing. And I think there's this kind of perception of what sales cultures are like. And some of that is fair. I think a lot of sales cultures can be toxic, and they can be hyper-competitive with kind of subversion and salespeople stabbing each other in the back. And you've got the image of the Glengarry Glen Ross manager banging his fist on the desk, and you know, "Where are my contracts?"

Daren Jennings: And that is such a bad way to run a business and to help them be successful. So yes, I would argue, actually, that culture in a sales setting is probably as important as anything else that you can do to be successful in sales. Fundamentally, what you really are trying to do is to conduct yourself with integrity, to sell to people that have a real need and value from what that you're trying to sell them, and you want to delight them from the time that they speak to you to the time you get a contract and into their relationship with you.

Daren Jennings: And if you don't have the foundation of a really solid culture, of everyone kind of pulling in the same direction, it's very impossible. It's very difficult to do that. I would say it's probably impossible. For me, making sure that my team, excuse me, know that they have the support from me and from the company and from one another is so vital to help them execute flawlessly within that process.

Wendy Hanson: Yeah. You said two words that really stick out for me. Delight and integrity. You know, we put those together on a sales team. We need to delight people, and we have to sell with integrity. If you hold those up as your litmus test for how things are going to go, wow, that's very, very powerful.

Wendy Hanson: And what would your customers and prospective customers say about your salespeople and your culture? If I were to call some of them right now, what would they say?

Daren Jennings: Yeah, I would like to think that they'd say, "I'm delighted to work with them, and they've conducted themselves with integrity." And I think we have, and we as a business are very, very cautious about how we represent our organization to the marketplace and prospective customers.

Daren Jennings: And I can give you a story about it. We, as an organization that is a SAS-based business, we sell services for a longterm commitment, and we have regular events where our customers will come and engage with one another and talk about us, and we talk about the future of the business, et cetera.

Daren Jennings: And we usually have the salespeople themselves attend these customer events and the former prospects who are now customers. It could be years after the sale is won. They're coming up and they're hugging the salespeople. They're talking about, "Oh, how are your wife and your children and your personal life?" And, "We're so happy to be here."

Daren Jennings: And they really, I think, build solid relationships throughout this buying process. And it is business to business sales. This is a professional setting. But you cannot 100% divorce the personal from the professional, in my view, especially in a highly consultative sale where you're doing things with integrity and trying to delight your customers.

Daren Jennings: So I think if my customers were to respond to this, I think they would say that one thing that differentiates our experience in dealing with the salespeople on your team is they truly felt connected to the problems that I was trying to solve. And they really want us to be successful. And that, to me, is such a liberating and wonderful thing to hear or imagine hearing.

Daren Jennings: Because we want them to be delighted and we want them to be happy. And that means that we as a business are supporting our people in the right way that can allow them to provide that support to our prospective customers.

Wendy Hanson: Yeah, and I love your example and people talking about like, how are your kids, and how is this? It's just like a manager needs to know that about their team members to check in and personally connect. It's lovely when you can do that with the clients that you're serving, and that's what builds that longterm relationship. And I bet you there's a lot of salespeople that don't do that. It's all about the sale. But it's really about who you are and what you do.

Daren Jennings: I agree. And I think relationships are so crucial to doing that, because, and then, if you run into some speed bumps or some kind of twists and turns along the way, you have a foundation where you can kind of work through them together. And it's not this combative relationship. It's something that, okay, let's solve this together. And that, I think, I do believe that in how I interact with our salespeople internally in our culture and how we deal with our market, as well.

Wendy Hanson: Yeah. There's a great metaphor for that of a treasure chest, let's call it, and you have to put things in it and fill it up, which is all those good [inaudible] relationships, everything, so that when you have to take things out, there's something in there, and that's when you need to give somebody feedback. You need to do something difficult. Then you've been able to establish something important. So we need to know that we need to fill up these banks, treasure chest, whatever it is, in order to be able to take a withdrawal later on.

Daren Jennings: Yeah, I like that.

Wendy Hanson: Retention. Boy, in the sales world, I hear many, many stories about how that's ... There's a certain shelf life that a lot of salespeople have on a team, and then it's time to go to another team. You seem to have pretty good retention numbers on your team. Tell me about that, and why do you think people stay with your organization?

Daren Jennings: Yeah, it's ... I'm proud of that. And you're right, there is natural turnover within the sales career, and you might start at a place and work there for 18 months or a couple of years, and you move onto something else, and at Interact, we enjoy a much longer longevity in terms of our salespeople. We don't have a whole lot of of churn.

Daren Jennings: Obviously, sometimes people do leave, it's part of how we work. But I think the reason people stick around at Interact is a couple of reasons. One is our product and what we're selling is compelling, and people can be successful here. And I think the other part of it is our sales culture is probably different than anything that they've experienced before.

Daren Jennings: And I've heard this through some feedbacks, through some assessments and one-on-ones talking to people, and we very much have a culture where I want to communicate very clearly that my sole purpose in managing them is to ensure that they're successful in their role.

Daren Jennings: And I can help move things internally and provide resources to help them be successful. And I've got an open door if they want to bounce ideas off of me, but it's not just this kind of manager to employee type relationship, they really can go horizontally. And one thing I love when I see in our sales office, when one salesperson asks another one for input or ideas on how to do things, and in other companies, the people say, "Well, that's not my problem. That's your problem. I've got my own stuff to worry about." You know? And ...

Wendy Hanson: Right. I'm not going to share my good ideas to make your sale.

Daren Jennings: Yeah, get out of here. Go. Just go bother somebody else. But we don't do that. I see people helping each other out. And so, I want to create a culture of some healthy competition, that's always good, to kind of get a little bit of that one-upsmanship. But I don't want it to be toxic, as I said.

Daren Jennings: And so I think people really find that they are supported for across all levels of the business. And our messaging is very compelling, and it's a wonderful thing to talk about. Every single interaction with a customer is different, and so I think people really thrive in that kind of a setting, and that's why they stick around for a long time, because ultimately, nobody wants to take a job in any career to be mediocre.

Daren Jennings: I can't imagine somebody who, "I'm really excited to join this company where I can be a B player, and put a middle long, and do just barely enough to get by." People want to be successful, but they can't do it alone. I say before, it's very easy to lose a deal by yourself, but it's very difficult to win one that way. And so you must have people to support you along the way. And I think we've created that culture of support, and that's why people tend to stick around, because they're successful, and they're happy with what they do.

Wendy Hanson: Yeah. What about, how do you keep remote teams and people that aren't working? When you're in an office and you can go around and touch everybody, say good morning, it's a very different environment than when you have remote teams and trying to keep people feeling connected to the whole. What are some of the practices you do there? Things that people could say, "Ah, I think that's a good idea. I haven't even thought of that."

Daren Jennings: Oh, sure. It's really hard. I'm speaking to you now for my home office, so I'm not in the office today, but you have to constantly be in communication with people, because it's very difficult to just lean over and say, "Hey, let me ask you a quick question on this."

Daren Jennings: So one thing that I do is, I have a regular cadences of contact with all of the people that are on my team, so that there's always something on the books that is an opportunity for them to talk about things, that I can ask questions, and vice versa. And what's really important is you don't miss and you don't miss these meetings. These are really critical.

Daren Jennings: Sometimes things come up. That's going to happen to everybody. And if my team would listen to this, they might say, "Hey, hold on a second, you've missed a few of these meetings," or, "We've rescheduled some of these things." I really try not to. And I think that is such an important thing, that this is an appointment, and we don't miss, and we don't miss it ever, because if we don't connect, we have a very difficult time.

Daren Jennings: So that might be something I encourage other sales leaders to do. Part of what we do at Interact, we are an intranet company. We sell digital workplace software solutions and consulting, and we utilize our platform to provide a digital area for people to actually connect. So there's a whole section of our intranet where we have sales discussions and ideas boards and resources available to people, and we encourage people to use that, because there's not just our team of our own staff. We've got offices in New York, Denver, we've got an office in the UK.

Daren Jennings: So it's really important that people have sort of a central place to have these types of conversations. That asynchronous communication element. Email is not a good way to do it, but it's also really important, I think, that from time to time, people do get together in person. Everything that we do cannot be completely solved through a Slack channel, or an intranet, or a phone call.

Daren Jennings: So we do like to have people to come together very often. We just finished our quarterly get together in New York when we did a cooking party with everyone, and it got us a chance to socialize with people, and also have some meetings with the entire team in the same room at the same time. And it helps to establish those relationships. So that was a lot, there. I apologize for going into it, but I think there's good nuggets.

Wendy Hanson: Yeah, there's really good nuggets, because we do need that face to face sometimes, because even though we try really hard, and I love Zoom. I have people that I've never met, like you, for instance. I feel very close to you. We've never met in person, but you can get that through using a product like Zoom.

Wendy Hanson: But having somebody personally sit down next to them and have a conversation, that's incredibly important. And you also onboarding people when you're remote, and you have people all over. That's another challenge that I think you've taken on very well, it sounds like. What are some of the tips you have for onboarding new staff when they're coming into a sales team?

Daren Jennings: Oh yeah, this is great. So, this is some feedback I got through a 360 degree survey, which I know we'll talk about in a minute. But I think we struggled with our onboarding a little bit, and getting that excitement on the first day. And we talk about a lot in my own career about the risk around new starters.

Daren Jennings: And it's usually the first two weeks before they start their job, and it's that two weeks after they started their job, where they might be questioning whether they've done the right thing, and then they start, and their engagement is really, really high. And then you kind of have this gradual decline because they're starting to realize, "Wow, I've got a lot to learn," or, "It's going to take me a long time to do this," or, "I'm not gelling as well with my colleagues as I thought I might."

Daren Jennings: So it's really important to focus, I think, on that four week window. And so some of the things that we've done is just basic stuff. Like on the first day, we try to clap our new people in. So we just kind of applaud them on the way in the door, which is kind of cool. And then at their desk, we have just a set up of swag that we've kind of set up in advance so they know that we've been thinking about them ahead of time.

Daren Jennings: I think a lot of companies throw out tee shirts or coffee mugs at people, but if you're rummaging through the supply closet and digging out and saying, "Hey, what size are you?" It's a different experience than having things kind of set up and folded nicely, maybe a little welcome card signed by the staff.

Daren Jennings: But I think just when you set the tone with something like that, it really makes a difference. And that's something we've done at Interact, and that's been really cool. And if it's a remote worker, obviously, you can't do those things. But we make sure we send a care package to their office, whether it's a regional office, or if they work from home, that arrives and it's waiting for them the day they start.

Daren Jennings: And it includes some of those things, like a welcome letter. Maybe there's a gift basket with some goodies in it, or some of the tee shirts and stuff like I talked about. But just because you're remote, it doesn't mean you're not part of the team. And that's something that we need to be to be mindful of. So ...

Wendy Hanson: I've never heard that, the care package. I love that because that's really what ... I've always heard that a person's first day at work and their last day at work are their most important days. What happens in the middle is what happens in the middle. But how we welcome somebody in and how even when somebody leaves, how we do that, are really important, and that's where people are going to talk about.

Wendy Hanson: That's what, when they go home for dinner and they're talking to their family, or they're talking to their friends, that's the vibe that's going to be translated. So you create such a good vibe. Because I've heard so many people that go in for their first day of work and oops, there was a little snafu. We don't even have a laptop for you yet. Where are you going to be sitting? And talk about getting off your game first day.

Wendy Hanson: So, good work. That's a great takeaway for people to really put into action and make something happen. Hmm. Now, I have to have a little full disclosure here, that I've had the pleasure of coaching you. We'd been working together for a while. We've had four coaching sessions, and that's how we met. That's how I got all excited about what you represent, and what you know as the sales leader.

Wendy Hanson: And part of our process at Better Managers, we have a 360 that we do, and it's part of our coaching process. And I loved how you just took this on, and you got feedback from your team, from peers, from your manager, and what was the impact of this? Because you really made the most of this 360, in my estimation.

Daren Jennings: Oh, that's good to hear. I found it to be incredibly valuable. I remember when we first started talking, I kind of had this general feeling of being overwhelmed. You might recall that. It was just, I have too much going on, there are too many things to do. I've got too many reps. I'm traveling all the time. I can't focus on the right things.

Daren Jennings: And we've coached through some ways that we can correct that, which has been very valuable. But one thing about the survey, the 360 assessment, that was so valuable to me was knowing that I got some really good feedback from my team. And I know this isn't the same for everybody, but I think a lot of us, especially in leadership roles, are very harsh critics of ourselves.

Daren Jennings: And we tend to think that the way we think about ourselves and our own shortcomings is the same way everybody thinks about us. And I found through the assessment that that wasn't necessarily the case. It was not to say that the assessment was all just flattery and talking about great, there was really good, important constructive feedback for me to take on.

Daren Jennings: But the reason I felt overwhelmed was because I felt that I had to do everything myself. And what I learned from my assessment was that not only did my team like working for me and for the company, it was that they were ready to help me with more things. It was such a liberating experience. I can't tell you. It was just like I felt this weight coming off my shoulders, that they want to help me with the very thing that I'm struggling with.

Wendy Hanson: Yeah. And you probably wouldn't have had that insight if you just kept going on a day to day basis the way you were. And this was a big aha.

Daren Jennings: It was a huge aha for me. And you're right, and it's not only knowing that they want to help, but look, they want to grow their own careers as well. So gathering that information, it's such an important thing. And there's also great feedback I got from my manager as well.

Daren Jennings: And so what I took away from it was that, I have the support of the people around me, who all want to be doing the same thing. Again, everyone wants to be successful. Everyone wants to grow their career and whatever trajectory they have.

Daren Jennings: So for me, it was very liberating, and it allowed me to have confidence to execute some of the strategies and the tactics that we laid out through further coaching sessions, and relinquish a bit of control, which a lot of people struggle with. But it was really good, because it's liberating and allows me to help my staff grow and it also helps me to focus on things that I think will be more impactful.

Wendy Hanson: Now, you took on a few new practices after getting this feedback, of, "Wow, they do want to play. They do want to help me." Things about staff meetings. Can you give us some ideas of what are the things that you shifted that really did take that burden off your shoulders and helped other people grow? Talk about a win win. That's a great combination.

Daren Jennings: It was a great combination. A couple of things come right to mind. One thing is just general kind of sales advice, or, we have a lot of people in the office. Some of them have been there relatively early on in their careers at Interact, and some people have been there for a number of years.

Daren Jennings: And some of the feedback I got from the team was, "You, Daren, don't need to be involved in every single one of these areas where people ask questions. Let us tap into some of those resources horizontally from our peers and empower them to make some decisions and provide some advice."

Daren Jennings: And it was one of those things that it sounds like a duh, but sometimes it's not right in front of you, and until someone connects those dots. So that was really good, and it helped me not only to free up some of my hectic days, which of course, I'm here, I'm happy to support people, but there are other resources that can provide that same level of guidance.

Daren Jennings: It allowed the other people within the organization to feel empowered in growth and that I have confidence in them. And so that's been a really important, key thing. And you know what? A lot of times, people have better ideas than me, or a different way of thinking about something. And I find that to be very useful. So that was one thing.

Wendy Hanson: Yeah. Giving people that space to share those ideas and brainstorm, and not just, "Here's the download for today, here's how we're going to handle things."

Daren Jennings: Yeah, yeah, exactly right. And I wanted to encourage that. I realized that this was something in culture that I was very much in favor of, but just hadn't actually implemented it. So that's been quite freeing.

Daren Jennings: Another thing is on our weekly meetings, we have sales meetings across the team, and in the past, we had done them, and it was a lot of just me talking at people, and going through numbers, and some various things, and pipeline reports, et cetera. Kind of your cliche sales type meetings. And nobody was contributing.

Daren Jennings: And we just got rid of doing them, because there wasn't any value. And I just started doing one-on-ones instead. So we brought them back. And one thing we've done, and part of this is I've been now tapped into, one salesperson per week is actually responsible for running the meeting. And it's been really well received, because I think it forces at least one person to be prepared, and to talk about things that maybe I haven't been made aware of.

Daren Jennings: And they can collaborate with their peers ahead of time, and because we do it on a rotating basis, everybody knows that one week, their time is going to be up. So they really tend to help each other out, and I've found ... We just rolled this out a couple of weeks ago, and it's been really cool, because they set the agenda. They talk about things that are important, and I can kind of chime in, or I can allow the conversation to just take place.

Daren Jennings: And of course, there's things that I talk about, but it's been such a great thing, and I think people have really embraced it, because now, they are in control. This is a meeting that is valuable to them. It's their meeting. It's not just me talking about numbers and boring them to death for an hour.

Wendy Hanson: Yeah. Yeah. And I would guess, too, that you learn a lot, because there are things that wouldn't come up if you were kind of orchestrating the path of that meeting, that wow, I had no idea people were thinking about this.

Daren Jennings: It is unbelievable the little things that come out, and just something that maybe I thought it was in the back of my mind, or I hadn't even considered, as you said. It turns out it's a really big issue for them. And it might not just be this one person, it's the whole team. But now, they own the agenda. They can raise it, and then we as a business can address it. So it's been phenomenal, and we're going to continue to do it, and we'll see.

Wendy Hanson: Great. Well, we're hearing a lot of great practices that not only if you're a sales manager or leader, but if you're a member of a sales team, you can bring these ideas back to your team. Like the idea about the onboarding. Make sure that, when people get onboarded, that they're taken care of, they're welcomed in.

Wendy Hanson: I love the clap, and I love sending people a care package. Taking these meetings and having rotations of who leads that meeting. What's another takeaway that you want people to practice that we're going to create positive cultures on sales teams?

Daren Jennings: One thing that really comes to mind, this is very much similar to what we've talked about, which is, we now have, I've kind of asked, anytime we bring somebody new on board is, I assign them a sales buddy. So this is a peer of theirs that is going to help kind of usher them through the training process, and getting them acclimated to our culture and everything else.

Daren Jennings: And it's really great, because again, it not only empowers the person who is the buddy and says, "Wow, the company has confidence in me, to kind of participate in this." But it also gives the new hire a resource, a horizontal resource, a peer, to go to, ask questions that sometimes they might feel dumb, or they don't want to come to their manager with this. They can ask those questions to their sales buddy.

Daren Jennings: So that's something I would really encourage. And if you're in management, roll it out. If you are an individual contributor, maybe suggest that, I think, to your manager, as one of our listeners tonight. But yeah, suggest it. It's a really vital thing, and I think it's been part of ...

Daren Jennings: It kind of establishes from day one, again, we're trying to benchmark people's experience and understand what our culture is like, and it benchmarks that we are all in this together. And that really, you have to live that culture, and you have to implement things that do it.

Wendy Hanson: Yeah. And really, what I've learned from you, Daren, is that you're aware of this all the time and keep thinking of opportunities. How do we create this culture that's positive? How do we share the load in terms of when you share something, you can then use your skills for something else? And it's such a win for the people that you get to delegate to.

Wendy Hanson: And I love this horizontal buddy system, because there are, you go into a company and you never learn what the rules are until you break them, normally, because there's just secret things like, "Oh, we don't do that here." That you get to learn if you have a buddy, and you can ask questions, and your buddy can say, "You know, this is the practice that we do here." So that's great. Great advice.

Wendy Hanson: So, if people want to get in touch with you to learn more, or, I think this kind of information is great for people to understand the culture in a company, and when they're looking at what kind of sales company do I want to work with? It's very important to understand a company's culture. So could they reach out and chat with you, or look you up on LinkedIn? How can they get in touch?

Daren Jennings: Yeah, I would love it. I'm all about the network, so please do connect with me on LinkedIn. I'm on Twitter. You can find me that way. You can always get in touch with me. Well, those two are probably the best methods, I think we'll probably share those.

Wendy Hanson: Okay, great. And it's Daren Jennings, and @DarenJennings on Twitter?

Daren Jennings: Yep. It's @DarenJennings. Daren with one R. Thanks Mom and Dad for that.

Wendy Hanson: Thanks for clarifying that. Yes, that's important when they're looking for you on LinkedIn.

Daren Jennings: Yes. Yeah. Look for me on LinkedIn, Daren with one R, and yeah, @DarenJennings on Twitter. Hit me up. I'd love to chat with you. No strings attached. There's so much more we can talk about other than just the time today.

Wendy Hanson: Yes. Good. Well, thank you so much for sharing your wisdom today. Lot of really concrete takeaways that people can use to make a positive sales culture, and I have fully enjoyed our work together, and look forward to staying in touch. This is a longterm relationship.

Daren Jennings: Agreed. Yes. I love it too. And thank you for having me. This has been a lot of fun.

Wendy Hanson: Great. All right everyone, go off and make it a very productive day, and be positive. Take care.