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The secret sauce to your sales success? It’s what happens before the sale. It’s the planning, the strategy, the leadership. And it’s more than demo automation. It’s the thoughtful work that connects people, processes, and performance. If you want strong revenue, high retention, and shorter sales cycles, the pre-work—centered around the human—still makes the dream work. But you already know that.
The Unexpected Lever is your partner in growing revenue by doing what great sales leaders do best. Combining vision with execution. Brought to you by Vivun, this show highlights the people and peers behind the brands who understand what it takes to build and lead high-performing sales teams. You’re not just preparing for the sale—you’re unlocking potential.
Join us as we share stories of sales leaders who make a difference, their challenges, their wins, and the human connections that drive results, one solution at a time.
Jarod Greene (00:00):
Hello and welcome to V5, where we spend exactly five minutes getting on our soapbox with some of the hottest takes and topics in all of B2B sales, go-to-market, the whole gamut. I always say this is really going to be a fun one because Kelley Hippler and I on paper might seem diametrically opposed. I'm a Falcon saying, you can see she's a Patriot saying, I'm former Gartner, she's former Forrester. But I can tell you just from the green room conversation, we are more aligned than I think I've been with any other guest in the past. So please give Kelley a warm welcome and Kelley the CRO of Briefly has a take she'd like to share with you. So Kelley, fire off.
Kelley Hippler (00:41):
All right, well Jarod, thank you so much for having me here today. And as we were chatting about STAT, I recently saw from Sales Benchmark Index talked about the fact that the average tenure of a CRO is now down to 19 months. So I think we're now shorter term than your average CMO and I want to talk about, and my mission is to really talk about people-centered leadership being the path forward to really stem that tide and to be able to build sustainable growth engines across organizations.
(01:09):
And when I talk about people-centered leadership, really talking about three things. Number one is really putting your employees front and center because at the end of the day, they are the ones who are driving the value. They are the ones who are interacting with your clients. What that also means that as a leader you have to focus on building trust. And ways to do that include being honest, transparent, and providing coaching and feedback to your team members.
(01:31):
And then the third part of that is really being focused on removing roadblocks for your team so that they can be more successful and want to stay with your team. And I know there's a lot of focus on AI right now and I think instead of the conversation being about AI replacing your team members, it should be about how does it make your team members more productive and more successful? How does it free up more of their time so they can spend it with your clients? Because the more time they're spending with your clients, the more likely you're going to be to retain those clients and grow your business. And I think the flywheel just starts to go from there. So yeah, I'm on a little bit of a mission soapbox to talk about people-centered leadership being the path forward in sales.
Jarod Greene (02:11):
That's awesome. Kelley, what do you think is in the way? Because again, we're saying in the green room, it sounds so simple, it sounds so common sense, but where do leaders get stuck on being more people-centric?
Kelley Hippler (02:20):
One of my other things that we probably will disagree on is I have a love of romcoms and in the American president. Okay, alright. We found common ground. And there's a great line in the movie where Andrew Shepherd basically says that he was so busy keeping his job, he stopped doing his job. And I think part of the challenge for anyone who comes into the C-suite, knowing that average, whether it's 19 months, 20 months, you feel a lot of pressure out of the gates. And so I think you feel like you want to just act and do things and start measuring things and you spend a lot of time quite honestly managing up. You're building decks, you are putting metrics in place instead of actually getting to know your team and what's getting in the way and understanding what can best unlock because you have that pressure. I mean, sales is pressure filled, marketing is pressure filled. And I think if you walk into it already feeling like the clock is ticking, the moment you set foot on a new job, sometimes it's going to force you to do things that won't lead to your desired outcome. And I think that's probably why. Would love to get your thoughts on that.
Jarod Greene (03:24):
Yeah, I think it's spot on. One of my bibles for work has been Michael Watkins' First 90 Days. It talks a lot about how to set up your first 90 days for success and it requires the management up, but don't forget the management down. Don't forget the management across. So you're tied up in a lot of things, but I think to our point, your people are really important. You grow your people. I forget the saying I'm going to botch it, but it's about making sure you train them and develop it in a way so if they were to leave and do successful things, they'd be phenomenal, but you treat 'em so good that they don't want to.
(03:58):
Kelley, what would you tell an emerging leader today? Maybe someone's in an individual contributor role, aspiring to be a leader or aspires to lead a bigger team and really wants to have the cheat code for kind of an ideal kind of leadership style. What would be some of tangible advice you'd give them?
Kelley Hippler (04:14):
Yeah, I mean think when I think about people centered leadership and what folks can do who want to be good leaders, I think part of it is just if you're already in a leader role, get feedback from your team. And it doesn't mean go and ask them, it means conduct an upward feedback, have a trusted third party or some anonymous way to get feedback so you can get really good feedback on your leadership style. And I think sometimes people forget that as a leader you are in a position of power and people may be afraid to share that feedback with you. And so I've learned sometimes the tough way that having, whether it's your HR team or your sales ops team, run it, you will learn things that people won't tell you directly.
(04:53):
Another thing is there's no replacement for actually spending time with your team in the field. Anytime I would visit offices, I would try to schedule and ask me anything session, I would meet one-on-one with our leaders and high potentials just to hear what's going on, what's working well, what are obstacles that we could remove?
(05:11):
And then again, as you think about tools or programs and things, really making sure that your goal when you implement a new tool or a new process is to help drive productivity. We used to reference it as being, taking the sand out of the gears and how do we take some of that friction out of the system so that our sellers can spend more time with their clients and then measuring the impact of what we are doing. And so instead of measuring things like dials and emails, which are just activities and not outcomes, we actually used to stack rank our managers looking at what percentage of your reps got to plan and what's your attrition rate as a way to see who is being effective as a leader.
(05:50):
And so I think if someone's interested in moving into sales management, just recognizing it is a different job than selling. It is about enabling other sellers to be successful. And I think where a lot of high potentials go wrong, and they don't mean to is I think in their minds it's like, well, I was a successful seller, so if I can get my team to do what I did exactly the same way I did it, they will be successful. And that's just not how management or leadership works. Everybody is an individual and you really have to take the time to understand their skillset, their motivations if you want to effectively coach.
(06:27):
Oftentimes what we would do is have people mentor somebody first before putting them into our emerging sales manager program as a way for them to see is this really something that I'm interested in doing? Because I think a lot of sellers think, oh, it's the next step. I'm top performer at the company, so I have to become a sales manager. And some of your best performers as ICs can be some of your worst leaders as sales managers. Dunno if you've ever seen or heard that. And then it's an awful situation because you've lost a top performer, you've probably turned over an entire team. And so it's a nobody's best interest to do that. So I think really being transparent about folks of what does a management and a leadership role mean and how is it different from being a successful seller? I like to say to some of my folks, when you're a top rep, the spotlight and the sunshine is on you. When you become a manager, it's about putting the spotlight and the sunshine on your team members and really elevating them to their career best. And if people aren't comfortable doing that, then totally fine, stay where you are, but a leadership role is probably not going to be the best next move for you.
Jarod Greene (07:35):
Yeah, I love that. The analogy we use is, I used to work at an enablement company and the analogy we used was, you take a manager from the field, you take an individual contributor who's phenomenal, you make him a manager. And the analogy was, there's a reason why Michael Jordan wasn't a great coach because a lot of times it's like just do. Just get the ball, go by everybody. Jump over everyone and dunk it. We didn't have the same routine. We are not the same. But it would be akin to that, just do what I've done and look how easy I made it. And it's just like you are the greatest of all time. I don't know if that's the debate for us, Kelley, who the greatest basketball player of all time is. You might say someone else, but...
Kelley Hippler (08:17):
Nope, nope. You're not going to get a debate for me on that one. I am Michael Jordan all the way as far as that one goes.
Jarod Greene (08:23):
Alright, there we go. These always go super fast. I'm sure we could talk for five hours, but really appreciate the time you spent with us today. Kelley, if people wanted to get in touch and talk more about people-centric leadership, where would they find you to do that?
Kelley Hippler (08:37):
Best place would be on LinkedIn and more than happy to connect with folks and continue the conversation. As you can probably tell, it's a topic I'm extremely passionate about and happy to help any new leaders or new leaders stepping into a new situation. Anything I can do to help folks out, just love to carry the message forward.
Jarod Greene (08:56):
Awesome. Well thank you. We appreciate that and people do reach out, so please take Kelley up on her offer.
Kelley Hippler (09:02):
Thank you. And thank you so much for your offer today. It's been a great conversation.
Jarod Greene (09:06):
My pleasure, great time. So thanks, Kelley.