Never Follow A Sales Leader Who Doesn’t Sell (Here’s Why)

Dan Lake, Head of Global Sales at AR Insights, champions a simple but rare philosophy: if you lead sellers, you should be selling too. By actively prospecting, running demos, and managing key accounts, Dan stays intimately connected to the realities his team faces every day. This frontline empathy allows him to coach effectively, refine the go-to-market strategy in real-time, and build genuine trust with both his team and his buyers. Beyond just selling, Dan emphasizes the critical role of a coaching culture. Drawing parallels between parenting and sales leadership, he advocates for asking 'tell me more' instead of instantly providing answers. This approach helps reps build critical thinking skills and ownership over their deals. He also stresses that leaders must remember they are managing humans, prioritizing personal connections and understanding that true work-life balance is inevitably challenging. Looking ahead, Dan notes that while AI is transforming the sales landscape, the future of enterprise sales remains deeply rooted in human relationships. Complex deals are taking longer due to increased scrutiny and governance, meaning sellers must focus on delivering value, understanding organizational roadblocks, and establishing a trusted personal brand before ever making a pitch.

Discussed in this episode

Why sales leaders must actively sell to truly empathize with their team's daily challenges.
How to handle inbound lead distribution publicly to avoid team friction when leaders sell.
The importance of face-to-face meetings and authentic relationship building in modern sales.
Building a coaching culture by helping buyers buy rather than just selling to them.
Fostering team culture in a remote environment through intentional, non-work connections.
The striking parallels between parenting and sales leadership in guiding rather than solving.
The reality of work-life balance and why accepting that leadership is hard is crucial.
Why enterprise sales will remain deeply rooted in human relationships despite AI advancements.

Episode highlights

0:00 — Introduction to Dan Lake and his core philosophy
2:15 — Why sales leaders need to be in the trenches
4:30 — Balancing personal sales with team leadership
7:00 — Distributing leads and avoiding cherry-picking
10:45 — Building deep relationships through in-person events
14:20 — Culture eats strategy: Remote team connections
18:10 — The parallels between parenting and sales leadership
22:30 — The truth about work-life balance in leadership
26:15 — The future of enterprise sales and human connection
30:00 — Rapid fire questions with Dan Lake

Key takeaways

If you lead a team of sellers, you should actively sell too.
Replace immediate answers with 'tell me more' to foster coaching.
Culture requires intentional, non-work relationship building in remote teams.
Accept that work-life balance is hard; embrace the highs and lows.
Enterprise sales remains human-centric; AI cannot replace genuine buyer trust.

Transcript

Being on the front lines, I view it as my role as a seller not necessarily to sell. As ironic as that sounds, my job is to help my buyers buy. I often talk about a culture of coaching. Um, and I think a lot of orgs and a lot of sales leaders don't do a good job of coaching, right?

Somebody comes to me with a challenge and I don't dive into the answer. I say, tell me more. And I ask a whole bunch of questions around the challenge, even if I've solved it 100 times over, giving them the answer isn't going to help them grow. Welcome back to another episode of the Bridge the Gap podcast powered by Revenue Reimagined.

Today we have with us Dan Lake, who is the head of Global Sales at AR Insights, where he leads customer acquisition and retention across the globe. Dan has over 20 years in sales and consulting experience with long stint that you don't even hear about anymore. I think it's something like 18 years at space helping the world's biggest brands understand and engage their audiences. He's also an advisor, an investor, and a founder with a simple philosophy.

If you lead sellers, you should sell too. I'm going to say that again. If you lead sellers, you should sell too. We say that all the time.

This episode's about sales leadership grounded in action, culture, humanity. Dan Lake, welcome to the show, man. Thanks for having me, guys. Do do that pass your test?

Yeah. It was good. It was you're a little sick, so it's not as snappy as I know, it's a little. I'm sorry.

I usually is. You sound a little like Kermit, but um we'll we'll go with it. Um so let's jump right off, Dan. What what Adam was just talking about, like leading by example, as you as he said, you if you lead sellers, you should sell too.

Why does that matter? Uh how can you empathize with all the things your team is going through if you're not in the trenches with them at least in some way? Yeah, 100%. And and so, um how do you apply that to your day-to-day basis?

Do you end up, you know, grabbing accounts and deals and opportunities like, walk us through that process of what that means to you to sell as well. Yeah. It's it's looked different at different points in my career. Right now, though it it actually looks like doing a bit of everything.

So, I am prospecting. I'm actually making cold calls. I'm sending emails. I'm working cadences and sales loft.

I'm doing research on buyers. Uh I'm I'm holding our demo meetings for our technology and I'm I'm even managing some of our largest accounts from a retention perspective. So, I'm seeing a bit of everything across the organization. Now, as our business gets bigger, is that the ideal way to to do it?

Maybe maybe not, but for now, uh especially I'm a little over a year into my tenure at AR Insights, it's been really helpful to be able to see all parts of the business, how everything runs from our customer journey to our sales approach, uh and to be able to make modifications to it, I think I've I've got to be doing it. So, I I I don't know many leaders, um other than some very few frontline managers, um who actually get like that deeply involved in in the day-to-day. And I I admire that because I think what you said is really true, right? How how do you empathize number one, um and then also being able to see what's happening in each part of the business allows you to to shape that business.

How does that play out with with the team if like if you're prospecting, if you're running a demo, like do you take the credit for that sale if it closes? Do you give it to the top rep? Do you round robin it? Uh, do you just give it to Dale and pay Dale a commission?

Like what does that look like? Dale hasn't seen a commission in a long time. It's true. Yeah, we're pretty clear on who owns the opportunity.

So, I I try to join as many of my team's calls as I can. Uh and if I'm joining one of their calls, it's their deal. I'll contribute to it. I'll I'll aid in the demo.

I'll I'll share my perspective, but it's their deal. Uh and there are other deals where my team is not on the phone with me and I'm driving it independently. And those are mine. Those are yours.

How does how do you How does the team? Yeah. Go ahead, Dale. Please, step all over me.

Go ahead. Yeah, I was going to say, how's how's how's the friction? How's the friction work? Like, do they do they feel like, hey, Dan's cherry-picking my deals or cherry-picking the deals that are coming through?

Well, you'd have to ask them, but I I don't think they feel like I cherry-pick. In fact, I I I try often to do my best to make sure my team feels very well fed with the right opportunities. But for in large part, we do a round robin where uh inbound leads, and we don't get a ton of inbound leads. We're a we're in a small industry analyst relations that's very interconnected.

So most of our leads come from relationships. Uh But when we do get inbound leads, it's a round robin of sorts, and uh it's very public when the leads come in. They come through a a public slack channel and everybody sees, all right, you're up now. And are you part of that round robin?

He's up next. Yes. So that that that that's a fascinating to me. I I I I I love this and transparently, I hated it at the same time for for very different reasons.

I I love the culture part, right? Like I'm a big believer, and Dale and I talk about this, like you can't teach unless you do. There's so many people out there to draw a parallel on LinkedIn who are like, I'll build your go-to-market playbook for, you know, X99, and you look at their LinkedIn and they've been a BDR for six months. Like you you you can't teach that.

So, similar to leading a sales team, like I very much think you have to do. But as a seller, when my commission is based on inbound leads, outbound leads, and every deal that I sell, and I know I'm digging super deep on this. How do you overcome the, well if Dan wasn't in the round robin, this would have gone to me and I could have made X thousand dollars. Like how how do you balance that and this will tie into what we'll talk about next, which is culture, because I know you're big on culture.

How do you balance that that it doesn't erode that culture? Yeah. Uh, it's it's a challenge like anything else. I I think my team would feel like I'm doing more than just acting as one of the recipients of the occasional inbound lead, and as a leader of the sales team, I'm helping to drive additional opportunities for them.

You know, one of our big strategies as a sales organization is to meet with our customers in person. I know it's flashback, 20 years. I fucking love it, dude. Like we we need to do more of it.

I am on a plane from Boston to San Diego next week to host a happy hour. Uh and we get to Long long flight for happy hour, but I like it. It is a long flight, but it's important customers who are going to be there and you just can't you can't replace that face-to-face time. And so, I'm doing stuff like that all the time.

I'm I'm I'm the most present at our live events. I'm sending all the invitations, not just to my prospects, but to my team's prospects. And it's driving opportunities for them. So, I think they feel like while I receive the occasional inbound lead, I'm doing a lot to drive leads to their book of business as well.

And so, you know, it's also when I'm gone, uh I'm I'm at a leadership meeting or I'm at a conference, which I'm at more often, the leads that come through go to the team. So, I get skipped pretty regularly. To to to level set for the audience, how big's your team? There's only five of us.

Okay. So, you plus four. Yep. Okay.

And are they all AEs or they BDRs? Like what's the what does that look like? Uh they all serve as AEs. There's there's a little bit different kind of role breakdown in how things get sold.

So, uh one of the people on our team is much more focused on account retention, while the others are focused on outbound and and selling all of our suite of software and services. Full cycle, love it. full cycle, in person. I mean, these are things I thought went away.

I thought we just use AI and Zoom. Like what what's happened here? I kind of had it a goal of mine not to talk too much about AI, having listened to the previous episodes. You know, obviously, everybody's talking about that on at every conference in every place.

Um, but to me, it's not to say I don't use AI every day. Yeah, we we stay totally away from AI. Uh it's it is every conver No, we don't we don't have to. Dan, what what I'd love to just keep it around how it enables the things that that have always worked.

And to me, that's the evolution of new technology is how do you do things that you've done in the past just better or more efficiently because we have new tools today to to do them that way. 100%. What's um what's the biggest thing that specifically in your role now that kind of being on that front line and selling has taught you that just the the strategy deck or the top level, you know, board meetings just won't. Like what what's the key takeaway that you think you've learned that's made you a better leader or allowed you to help your team be better sellers that you wouldn't have got from just like a strategy deck or listening to a recorded call.

Yeah. Well, I think my answer's going to sound potentially overly simplistic, but Bless you, Dale. Mute button. It's uh I don't have that.

I I think it comes down to uh to just curiosity. Uh being on the front lines, I view it as my role as a seller not necessarily to sell. As ironic as that sounds, my job is to help my buyers buy. And in order to help my buyers buy, I need to deeply understand their business, their challenges.

Uh not just from a commercial perspective, though that's really important, but their challenges from an organizational perspective of of they need to make a purchase. Who do they have to work with? What are the roadblocks they're going to run into? What am I seeing across the industry as things that will slow them down from getting this thing I know they really want and need?

Uh so, I have to I have to be out there asking really good questions of my clients and prospects so I can deeply understand the challenges and then communicate that back to my team and to my other prospects. So, you know, I I just have this visualization when I'm working with a prospect that it is the prospect and I sitting on the same side of the table trying to pitch the offering to their bosses. That's what it needs to feel like very soon after we meet and I earn a bit of trust. I I love it.

Yeah, go ahead, Dale. Yeah. A lot of people don't put our put yourselves in the buyer's shoes and they kind of what ends up happening after you do an initial pitch or you're having a conversation or you're going through that process, like they don't understand like, okay, now you got to go to their boss or you got to put a business case together or how do you how how does it sound in in their world? And I think what I've seen is a lot of sales reps that have been sales reps in a company or in a place for a long period of time, they forget, cuz you guys are doing this every day, all day, calling people, talking about your product or service and and it's like second nature to you.

But this person that you're presenting a value to has no idea really what you're talking about all the time. Or they have a they have a maybe an understanding or an assumption, but it's not really a a complete value chain. And so, that that is really, really important. So, shifting gears a little.

I I I want to talk about culture. Um I often talk about a culture of coaching. Um and I think a lot of orgs and a lot of sales leaders don't do a good job of coaching, right? Let's hire people.

We'll give them this document to read. Maybe I'll look at a call and, you know, send some notes like back in the call, but we don't really coach. You've talked about and posted about how culture, quote, eats strategy for breakfast. Talk to me about what that looks like in in practice.

What exactly do you mean by culture eats strategy for breakfast? Yeah. Great question. Super relevant.

I was actually just at an executive offsite last week and we brought in my former C space CEO, Diane Hesen, who's a bit of a legend in the Boston area. Uh she was there to talk about culture specifically. Uh that company had the best culture I've ever experienced, and not just from companies I've worked for, because that's really about three. Uh but I've I've been deeply involved in 100 businesses from companies that I've helped consult with and have been my customers, and and none of them built a culture like she built.

Uh there's a lot of reasons for that, but we were trying to pull apart as a leadership team what are some of the key components to being able to build great culture, particularly in a remote environment. Our our business is a remote business. We're scattered across the country and world. Uh we don't all sit in the office together often.

So that changes things pretty dramatically from a culture perspective. Uh one of, you know, one of the things that that is really important is is obviously being able to build relationships with the people you work with. So while we're not together often, we do try to make a point of getting our smaller teams together in person on a quarterly basis. We have a yearly event where we get our whole company together.

So we get everybody in the room. We do some kind of like separate, non-business relationship building stuff. Um we schedule 15 minutes before our weekly all company meeting just to come kind of hang out. This is like shoot the shit, talk about your family, talk about vacations.

Uh not super serious, not rushed. Just spend some time with people. And then it's about, you know, understanding on your team, what are those shared connections you have with people. As a leader, I think you have to obviously get to know everybody on your team and understand how you're going to make those connections so that you can a little bit more deeply connect outside of just what's the latest sales cadence and challenge we're running into selling.

So, uh long-winded way of saying it depends and and investing in building real relationships with the humans you work with is something that can't be ignored or written off as something we don't have time for. I I think that's one of the biggest keys is how many like all-hands meetings, excuse me, or sales meetings have we all gone to, um or even one-on-ones where like I'm thinking back to when I was a rep and like I I'd get on the phone with or a Zoom with my manager, um and like, hey Adam, what's up? Boom, let's get right in like not even so much like, hey, how are you doing? Like what's going on?

How was your weekend? Um I start every so we we will we'll actually lead sales teams for our clients and like we'll run sales meetings. And I start every sales meeting with like, all right, personal professional win. Let's talk about the weekend.

Like we we have to remember we're we're leading humans, not numbers. And the day that we lose sight of the fact that, you know, we're leading human beings is the day that you have a problem. And I I I tell this very brief story often, but like I used to have a rep who long story short, they were wildly underperforming. And my sales leader at the time like got on a Zoom with them and like immediately like, Dan, you know, you're not hitting your numbers.

We're going to need to put you on a pip and blah, blah, blah, blah, blah, blah, blah. Come to find out, you know, the rep's like, dude, like my wife's father just passed away. And like I've been dealing like all you have to do some remember you're leading a human. Like, listen, the dude's not hitting his numbers.

Hey Dan, tell me what's going on. Like before you even start anything else. Three powerful words. How are you?

But you got to mean it. Um and I get the sense when you talk about culture and talking to people that you do deeply mean what you say and you care about your people. And for anyone who's thinking of getting into leadership and gut check me here, Dan, not Dale, cuz Dale's opinion doesn't matter. If you don't care about people, don't be a leader.

Don't be a leader just to get the title cuz I'm telling you, it's not all it's cracked up to be. Yeah, I can endorse that. And and I think it's it's, you know, sometimes it feels like it runs contrary to the DNA of a sales person because we tend to be fast-paced and competitive and like you said, the kind of people who will join a meeting and just say, all right, let's get right to it. And I'm susceptible to that.

I'm a dad of three. I'm very busy outside of work. So when I'm working, I get in that mode where it's go, go, go, go, go, and you get on that call and you you transition from one sales call to the next sales call to an all-company meeting. And all of a sudden, you got to slam on the brakes and say, all right, it's time to be a human again and not this sales robot.

And and really listen to your people. So, you led perfectly into our next um topic, which is sales, family, and business. So, you talk openly about, you know, being a dad of three boys. How's fatherhood shaped your leadership style, your leadership process?

Well, I I think any parent uh will understand that being a parent makes you more patient. You know, the the sounds and the fighting and the things that I endure on a personal front with three boys at home make the craziness of work seem not that crazy. You know, losses sting, but they feel a little bit different when you've experienced real hardship in your personal life and, you know, just as every parent does, uh you know, endured challenging scenarios. And so, it changes your perspective for sure.

You know, just the way I look at uh everything that happens in my job. I I have a healthier perspective because I've been a parent. People buy from people. That's why companies who invest in meaningful connections win.

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If you're looking for a proven way to win and retain more customers, visit sendoso.com. Uh I also prioritize my time very differently because being present for my kids is the number one priority. Uh I still need to be really successful at my job, but I need to time block and plan and be much more intentional than I was before I had kids.

I have some thoughts around this one, but like what are the parallels between parenting and managing even if not even just a sales team, but a sales person? You're stealing my question. You're stealing my question. Your question's at the bottom.

You see the follow-up? This was my question because I I I I I struggle with this. Like, yeah, I am super curious too. You struggle with it, it's true.

This is true. Dan, this is a this is now become a therapy session. And now can you please help Adam in the parallels between parenting and managing a team? Go.

Well, Adam, are you a parent? I am. I I I I have a 14-year-old that um I I'm trying very hard to I'm going to word this my way and I'm curious how Dale words it his way. I I'm trying very hard to allow him to make more mistakes.

Okay. I would call it overbearing, but Okay, we we really have gone into therapy mode here. So, uh you know, there's a ton of parallels. And this is kind of the the meme on the internet of like how parenting relates to B2B sales.

Uh but there are there are a ton and I try to be really conscious not to not to sound like a parent to my team because that's belittling and I have parents on my team, so they'll recognize some of the approaches where you know, somebody comes to me with a challenge and I don't dive into the answer. I say, tell me more. And I ask a whole bunch of questions around the challenge, even if I've solved it 100 times over, giving them the answer isn't going to help them grow. That's the same exact approach I take with my kids.

They come to me with a problem, I try to listen. I I've been there. I've scraped my knee before. I don't need to give them all the answers.

I need to help them find a path to it. So, that's the that's the easiest one. I see him wanting to say it. Don't say it, Dale.

No, I I I what what I was going to say, I wasn't going to say anything about you. What I was going to say is, I feel the same way, but I have learned that actually a lot from my wife, because I would in my true self, I probably would rush to the answer. And my wife has always been the one that said, look it, you got to you got to like bring it through the you got to bring them through the journey and the process of it. I I was talking to um some team uh sales team just the other day and I was walking him through, you almost have to ask a few why questions.

Like, why do you believe this is happening? How do we resolve it? Like you you get to a place where they can strategically and critically think to the problem. Because the first problem probably is not always the problem or the challenge.

It's really like three levels deep. And so if you can figure out why that's happening at the bottom level, now you can solve the symptom of that challenge or problem. So, and it it ties back to tell me more, right? Like I talk about tell me more a lot as it pertains to sellers, um in sales and when a customer wants something, you know, tell me more.

Why is that important to you? And going two or three layers deep. I think as parents and as leaders, you know, we need to do that internally as well. And like I I do transparent not a therapy session, but I do struggle with that with with with Zachary, right?

Like I I want to give the answer and I want to make his life easier and it's not often that way. It's you have to look at it is the same way you're telling about, tell me more. Why is this important? Why isn't this important?

And well, what if you do this? What if you do that? Um I think there are a lot of parallels. Dan, when you look at like younger sales leaders, right?

Like we've all been doing this a long time. Um there's a lot of talk, especially, you know, post-COVID of like work-life balance, which is a term that I genuinely despise. Um and I'm not saying that there's like hustle culture. I don't believe in that.

I block my calendar every afternoon to pick up my kid and I I think there is work-life balance. But what advice do you give to those younger leaders who are being told or seeing on LinkedIn that like work-life balance is impossible, right? You can't be a parent and a sales leader. You can't, you know, be a great sales leader and a husband.

You can't be a great sales leader and this. Like you got to be all in and on all the time and respond to your customers immediately and never pick put your phone down. What what's the advice there? I I think it's about expectations.

Uh you can't be a sales leader, a husband, and a parent and not have hard times. I think that's a reality. And the sooner we face realities that you should expect things to be hard. You should expect to make tough decisions about how you're going to spend your time.

Some quarters, you're going to say, I need to dedicate a little bit more time to my family and that's going to come at the expense of my earnings. And that's a that's a decision, and it's not an easy one. And other months, I'm going to buckle down and I'm going to work twice as many hours and I'm going to make up for it. And that's a decision.

And again, it's hard. I I don't know that we're telling young leaders enough that work and life is hard at times. It's also really fun and really encouraging and inspiring and really hard. And guess what?

The hardest times in your career are going to be the times you learn the most from and you look back on and appreciate the most. I know I have. So, I I think what We don't want to be like this, right? We want to have highs and lows.

Like like this is not okay. And I think back to what you were saying, like, if we're if we're going through life like this, then you're missing the highs and the lows. And in fact, the lows maybe where you're learning the most to get to the highs. 100%.

And I think Dan, what you just said, like my number one takeaway from what you've said so far, and you've said a lot of good things, is it's going to be hard and that's okay. I think we have created this culture, and Dale and I have talked about this, of participation trophies and it's easy and you show up and you win and you don't show up and win. And it's okay to lose, and it's okay not to get a trophy. I think some of my biggest lessons have been on the deals that I've lost or the sadly, earlier in my career, the reps that have left cuz I'm a shitty manager or the fights that I had with my wife because I was spending too much time at work and I didn't explain it or vice versa.

When you know it's going to be hard and you have those conversations to your point, I I I think that is where you grow the most and we change this mindset of, well everything's going to be handed to me. Um, I am a workaholic. Dale will tell you like he tells me all the like time, like dude, like just last week, I was away and I was answering him and he's he's like, dude, put put your fucking phone down and go spend time with your wife. Like this could wait.

Um, so even now, I'm still learning that. Um, so for younger sales leaders coming up, the hard embrace the hardness and understand that there's going to be a balance and anything good in life takes sacrifice. Um, there are a few people who certainly have had it very easy, right place, right time, but like anything good in life generally takes sacrifice. When So, you're not buying the sales training practices from the people who were successful at Gong early on?

Um, Gong's a whole separate conversation. Um, so I we we I wouldn't call that a brand specifically. You get the idea. No, I I I I would love to go there cuz I I do get the idea.

Um, I used to be the biggest Gong fanboy. Um, I think Gong is still a good product. I think there's better. I think they have probably the best brand recognition and conversational intelligence around.

And I think folks like Udi did a really, really, really good job. Um, they are a great example of first to market, right place, right time, amazing brand recognition and a very, very, very easy product to sell then. Um, and unfortunately, I've seen companies try to hire these sales leaders from Gong, who are, listen, there's some amazing people at Gong, right? I know a lot of them personally.

Sarah Braer, Brian Lono, like there's great people there. Um, but there's other people to your point, and I'm guessing where you're going. It's like, just cuz you could sell great at Gong, don't mean you could come to AR Insights and be an amazing sales leader. It's we we talk about this all the time.

Don't hire the sales rep from Salesforce or Gong, uh, or Zoom info to come be your sales leader at your startup. It's a wildly different skill set. Um, still some of the best branding of all time. Agreed.

Let's talk about enterprise sales for a second. Um, the future of enterprise sales. So, enterprise sales leadership, I think is very different than SMB transactional sales leadership, right? It's, you know, much slower, much more in-depth.

I don't want to use the the A word, but where do you see the future of enterprise sales leadership over the next call it 6 to 12 months. What what what's going to change and how like buyers engage with vendors and how you as a leader have to coach your team? Well, let me start with what's not going to change. Enterprise sales is is still going to be about relationships.

Uh This is a bigger buying decision. This there's more people involved. The stakes are higher. The procurement teams are larger.

The security assessments are longer. It's still going to be about relationships. So, you need to build really strong relationships with the right people. Uh What's going to change is it's taking longer.

So, you've got to plan that into your in in into your rev cycles. You've got to forecast appropriately. You got to account for the fact that it's you're just going to spend more time per deal. I I think that's the case now, even with all the tools at our disposal.

That's not that's not compensating for the fact that I'm dealing with AI governance councils who come in and assess all of our AI tools and that's a separate procurement process. And sometimes it takes months. I think So, enterprise sales to your point is personal. AI is not going to replace enterprise sellers.

I do think AI could replace some SMB sellers where it's super transactional. Go online. But, you know, as Dale and I buy millions of dollars of software a year for our clients, um and I can tell you for those larger deals, like I'm not buying it without having a relationship with that person and speaking them and deeply, deeply trusting them, um because it's my ass on the line. Um, you know, generally speaking, you know, I I'll use Gong.

Very few people have ever got fired for purchasing Gong, right? Like it doesn't happen. But as you have all of these new technologies, and as you have all these competitive things, like every six, seven-figure purchase becomes so increasingly important that there has to be a level of trust that no AI, no bot, no automation is is going to, you know, be able to build and create. Well, and if we talked earlier about asking these asking the questions of buyers, you know, beyond what they come to you looking for.

So, a buyer comes to you and says, I want this kind of software. I want this conversational intelligence software. You need to understand why, because everything as much as every buyer says, I want to be able to make my purchase entirely without dealing with a human or a sales rep, they need it. And and and in every purchasing decision they've ever made for a a significant spend, they valued the seller who can come in and help them feel like their solution is truly customized for their need, because every enterprise need is unique in some way.

Sure, you might be buying a product off the shelf. Gong may not look that different, but the implementation of it could be different. Uh, how I train which reps and share which case studies so that you get the most value out of it could be different from buyer to buyer. These are the things we have to understand on an enterprise level that sure when you're doing a more transactional SMB sale, less critical.

You can get away without it, but that's not changing. I I think where enterprise, there's two things I want to say on this one. I think from an enterprise sales perspective, um when you're selling, you almost have to educate the buyer to something they do not know. Like they have a list of things that they know and it's like, have you thought about this and why this is important?

And like if you can get that moment where that's like a a change in their mindset like, oh, I haven't thought about that. Now you've just your trust proxy has just went way up because they're like, now and they can bring that back into their organization and they can look smart on on that conversation. And then the second thing, and I think this goes beyond leadership, but and I was just having this conversation with a client, sellers and sales leadership, the one of the most important things from an enterprise perspective, in my opinion, would be having a brand and understanding what your brand your personal brand is and how you can bring that personal brand to an organization. I think we've shifted in most cases where they like social selling or being on LinkedIn and doing these things and being a thought leader in a thing or whatever you call this thought leadership thing.

But you have perspectives that people then will follow and have conversations around are super important when you're talking about the enterprise sale. Now, you want to make sure that you don't just have there's a lot of brand people on LinkedIn that couldn't sell ice to an Eskimo. So like there is a a a a validation you need to have, but this personal branding piece is super important because it brings tons of value to an enterprise, um, that people don't really realize. Yeah, I like that, Dale.

I and I think you raise an interesting point about what should that brand be. You know, one of one of my top priorities as a sales leader is uh to to create a brand where I think my greatest opportunity as a sales leader who interacts with not just my own customers, but my team's customers is to be a really curious listener. So, I'm I'm hearing from 100 different buyers what their challenges are, what their boss is asking them to solve for, what success looks like in their business. If I can't go to the next person and share something succinct that helps them improve the way they run their own program, what good am I?

That needs to be my brand, is that the value you get from me is that I'm I'm as connected or more connected than any of your peers. And so if you ask me the right questions, I can give you real value before I've tried to pitch you anything. That's always my goal is how am I delivering value to a buyer before I've asked them for something? Yeah.

Number one, like if you're if you're not delivering value and solving pain, nothing else matters, right? Right. We are at that time, um and as someone who's listened to the show, you know what comes next. Um so it's time for a little bit of rapid fire.

Uh the goal is 10 words or less. Um every word over 10 is $5. Dale has to pay me. So, feel free to talk as long as you want.

Um, all right, here we go. Dan, what's one sales cliche you wish would disappear? Time kills all deals. Ooh.

I would love yeah, rapid fire. I would love to go deep on that one. I like it though. I was going to I would say always be closing.

Um, but I like time kills all deals. What's uh your favorite activity to do with your boys? Anything outdoors. Hiking, biking, climbing.

Nice. In Boston. I love that. One of my favorite cities.

I spent a lot spent a lot of almost 15 years working for Boston-based companies. I think it's a very underrated city. Dale spent some time in Boston too. Uh, Dan, what's the most underrated skill in modern sales?

Listening. Truth. Mhm. Mhm.

What's one leadership belief you won't think will survive in the next decade? A leadership belief? Yeah. It won't survive in the next decade.

Hmm. I think right now we're hyper-focused on the role of technology. Mhm. I see the pendulum swinging back.

So, whether or not that's going to survive, it won't thrive the way we think it is that leadership requires everyone to have such a hyper-focus on the tech they use. Maybe an engineering, but in sales, I don't I don't think it's Hmm. No, you're good. Last one, I'm going to steal Dale's.

Favorite or dream vacation destination. All right, I'm going to break 10 words on this one. Let's go. Because it's it's it's on my mind.

Uh uh when my oldest son turned 10 a couple of years ago, I took him fly fishing in Montana. Uh we had the best trip I've I've had in my life. And my my middle son turns 10 next year. So, we've been talking about what his 10-year-old trip is going to be cuz now that's a thing.

Uh he is he's the most curious human I've ever met. He's obsessed with the with space, the universe. If we could go to Mars, we would do that. Uh outside of that, he loves animals.

So, we're talking about safaris. We're talking about the Grand Canyon. We're talking about going to Scandinavia. Clearly, we haven't narrowed the focus.

But what it's a dream vacation because I will be traveling with somebody who is soaking up every second of a new space. So, it's not to me about where I go. It's about the feeling that the people around me have when we're traveling. And so, we could go down the street, but if it was the place he so desperately wanted to be, it's going to be a dream vacation for me.

So, I'm really looking forward to that. I love that. It's just you two are going to go. Oh yeah, it's just the two of us.

Yeah. That's super cool. Thanks to my wife for allowing me to do this because it's uh it's such a luxury. That that time I spent one-on-one with my oldest son is something I'll treasure for the rest of my life.

So, I'll do it with all of my kids and and maybe even, you know, schedule in a 13 or a 16-year-old trip as well because it's such a such success. I love it. I I I agree with Dale. That is definitely the best answer we've got to that question.

Dan Lake, thank you for joining the show, man. Thanks for having me, guys. This has been fun. Thank you.