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Darren McKee

Director of Growth at Wellthy

16 Insights · 6 Questions · 8min Read · 10min Listen · Connect with Darren on LinkedIn

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Sunday Nights. Social selling. Telling stories. Converting in-person energy to online calls. The power of coaching. Creating a great experience. Understanding and being content with where I am.

Here’s what Jen Allen said about Darren:

Darren McKee. He used to be at BetterUp. He just moved over to an organization called Wellthy. Darren is someone that I think is a great example of someone who is very active on social, but productively. He's not active saying like, “This is why our solution is the best.” He starts really smart conversations that relate back to what he sells. I think he embodies a lot of the characteristics I think sellers should be thinking about today. —Jen Allen, Chief Evangelist at Challenger → Listen

What are 3 ways that your team converts your market into revenue?

Yeah, that's a great question. For us, when we think about total addressable market, when we think about TAM, it's anyone and everyone. I think caregiving is a beautiful thing. One in five Americans are currently serving as caregivers. So for us, it’s:

1) Telling stories.

2) Creating a great experience for our customers, our partners, our clients, our prospects, and anyone and everyone.

3) People talk and people start to see lives being changed through what we do day in and day out.

So that's the easiest way for us. We have an amazing Demand Gen team in Kayleigh, and Kevin leading marketing, but we're out here on a daily basis. Just telling stories.

What are 2 hard problems that you recently overcame?

1) Pivoting from the industry that I was in prior. I'm relatively new here at Wellthy. I've been here for about 6-7 weeks. Pivoting from the industry that I was in prior, I spent 3 years with a PEO in insurance and benefits, and then went into the coaching world, so I was selling into leadership and development leaders. One of the things that I thought was going to be challenging was, “Hey, how are you going to pivot into selling to total rewards leaders and caregiving?” But what I come to realize is when you're surrounded by insanely talented people, your ramp time gets dramatically increased by just learning from them and watching them. So that was hard, but we overcame it.

2) I've never been at home this much in my life. I'll pivot outside of work. I think we've all had challenges with what we've gone through over the last two and a half years. And for any parents out there, whether we're talking about actual personal issues between having kids, or whatever that may be, it can be really challenging. But also, I've never been at home this much in my life. So having to adjust with a five-year-old, and a three-year-old, and a dog, and a wife all running around the house while I'm trying to be on calls was really challenging at first. But, I've learned to embrace that and love that. But, I'm not going to be one of those guys that says it's amazing every day, because it's a challenge and we have to consistently work on it, right? It's like anything in our lives. So, those are a couple of things.

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What are 2 roadblocks that you are working on now?

1) Converting in-person energy to online calls. I used to be out and about all the time. I was networking. I was at events. I was in person. I was traveling. So a little bit of a roadblock for me is, “how do I convert that energy that I have in person with someone to a zoom call like this?” What I've tried to figure out is, like I said earlier even in the first question, when we talk about storytelling, it has to be that because no one wants to see you walk through 15 slides, right? We want to talk like we're in person at an event and we're talking about Wellthy, and we're talking about caregiving, we're talking about your business and we're learning. So that was a roadblock at first, but I've been really working on it hard to try to understand how I can articulate myself and show up to myself on this little, tiny, two-inch screen as I would if I was at an event in public.

2) Just understanding and being content with where I am. I don't know if you've followed my journey at all, or anyone listening has followed my journey, I'm a builder. So where I can kind of struggle and have a roadblock is when I'm not building, which is why I joined Wellthy. I joined here because I wanted to build. I wanted to create something and I wanted to be around a team of builders where I felt psychologically safe to fail, but also create new things and succeed in certain areas. So, there’s a couple. There’s so many more that come up to mind, though.

What are 3 mental models that you use to do your best work?

1) Sunday Nights. I can be really busy in my mind. I can have a lot of things going on in my mind, and oftentimes, it's a little bit hard to focus on that key, specific area. So something that I've been doing for, gosh, since early in my career, is Sunday nights. Sunday nights I get in that mental flow state of like, “Alright. What is Monday, Tuesday, Wednesday, Thursday, and Friday going to look like?” What is it going to look like for my schedule, but it's also looping in my wife and sitting together with her on the couch and saying, “Hey, what's your schedule look like this week?” or, “Hey, what do the kids need me for this week?” And that gets me in the right state of mind. So when I wake up on Monday morning, it's not 8 emails, 6 followups, a meeting, and the kids going to school. Literally, they just walked out of the door. I normally take them every day at 8:30am, but we had this at 9am, so me and my wife had to communicate on Sunday to say, “Hey, you're taking over on this day.” So, I think that's really important.

2) Time blocks on calendar from a mental state for me. You'll see me post a lot on that. I block times for my focus. I block times for my prospecting. I blocked times for my customers. So whenever somebody reaches out to me and says, “Hey, when can you meet?” I know that my prospecting time is going to be from this, to this, to this. I have been able to really focus on that.

3) The power of coaching. From my past life at BetterUp, which a lot of you listening probably know that organization, and one that I hold deep to my heart and love everyone there, I learned the power of coaching. I learned the power of having someone outside of my existing team, helping me navigate life, and work, and career, and balance, and that's been a true game changer for me.

What are 3 techniques that GTM teams need to try?

1) Social selling. Oh man, this is going to sound crazy. I probably made less than 10 phone calls at my previous company, outbound cold calls, and sold close to a million dollars in business, which leads me to the point of social selling. Go-to-market teams that aren't focused on empowering their teams to build their personal brand are going to really wish they did that 2-3 years from now because, I think we're merging into the fact of AEs and go-to-market teams almost being mini-marketers out there, right? Because we have the ability to impact the globe with our words and a personal brand versus being in your little market where you're going to these little events with 80 people. Now I can make a post on caregiving, I can make a post to total rewards leaders, and 30,000 people across the world see that. So that's what I would empower teams to do.

2) In-person events, right now, for just teams, I think are looked over too much. We used to get that comradery where we would come in and we dabbed each other up, we give each other hugs, we'd fail together, we'd look at white borders together and strategize. Unfortunately, that just doesn't happen anymore. So, the teams that I see that are having little outings out and about, they're going on hikes, they're meeting with each other, they're having mini, little QBRs and all-teams meetings. I think those are key right now. I think it's a big retention factor as well because we all just need that. And there's some that don't, and that's fine too, right? We're all different humans.

3) Understanding your team's personal hobbies and interests and leaning into them as a leader. This makes me think of something I shared this morning on LinkedIn. The CEO of Goldman Sachs is headlining at Lollapalooza as a DJ. So it’s understanding your team's personal hobbies and interests and leaning into them as a leader because, quite frankly, we're more than our 8-5. When we can really understand who each person on our team is, we can encourage them, and build them, and make them become who they want to be. While riding alongside of them versus managing them.

Who are 3 operators that should be our next guests and why?

Great question. There's so many, but three that come to mind straight upfront:

1) Nick Kouma, who works for BetterUp.

2) DeJuan Brown, who is someone that has just encouraged me for years and years when I first jumped into this go-to-market world, or AE SaaS sales world.

3) Kellen Casebeer, Kellen's out on the west coast. Works for a firm called LEON.

Those three give you just an array of different mindsets and behaviors in how they show up on a daily basis. If you ever needed more, I could list off hundreds more, but those are three that are right top of mind today.

Work with Darren → Wellthy is hiring!

March 2022 · Interview by Chris Morgan, Host of Market-to-Revenue

Market-to-Revenue Podcast ⚡️ Lightning-fast interviews with GTM operators in sales, success, product, and marketing.

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Darren McKee
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