The Best Way to Sell Without Sounding Like a Pushy Rep

The outbound feels better, feels less icky when you know who you're talking to and that you can actually genuinely help them because you've dialed in your ICP so well.

>> Every training I've ever been in is like you got to sell hard and you got to go for the close and you got to do this and you got to do that. I don't believe in hard selling.

>> I've been in sales for 25 years. I still know how to cold call, but the easiest way to do it is to tell them from the get-go that it's a sales call and say, "This is a sales call." Welcome back to another episode of the Bridge the Gap podcast powered by Revenue Reimagined, and a little bit of Dunkin Donuts and a little Starbucks this morning. If either of you would like to sponsor the show, please feel free to reach out.

Today's guest is Ashley Beck Quir, who is the head of expansion at Seamless Roofing and founder of Salespark. She's built and coached teams in both the tech and construction sectors, blending mindfulness with performance to build high trust, high output sales teams. She's passionate about authentic human first sales practices that prioritize relationships over transactions. We're going to talk about leading with care, how to build teams that genuinely care about their customers, not the way Dale pretends to care about me, and why a shift from hard sell tactics to authentic sales works better long term. Ashley and your Starbucks, welcome to the show.

>> My Starbucks and I are glad to be here. Cheers.

>> And Adam can understand hot coffee. That's what we learned today. I don't, I just don't like it. I've tried.

>> It's okay. My best friend only drinks cold coffee also.

>> So I used to work for a Boston company and they would make fun of me. I'd be up there in the dead of winter and I'd be the only person who would walk into Starbucks and order an iced coffee and they're like, "It's negative three out." I'm like, "Great. I'll walk out holding my iced coffee, please and thank you."

>> I have mittens on, don't worry.

>> Yeah, I know. None of that either, but I just don't know. Hot liquid doesn't work for me. Welcome to the coffee show powered by Revenue Reimagined. Adam's Coffee Talk.

>> We are looking at some rebranding. We could rename the show Coffee Talk. I'm down. Bring a female co-host in and we'll have a little bit of fun.

>> There you go.

>> I love it.

>> Awesome. Well, let's jump into some sales and CS and some fun stuff about human-led sales first. So you talk a lot about human-led, you know, human first sales. What does that actually look like day-to-day for a BDR team, for example, or even a CS team? I think CS is easier, but BDRs are like, "Go make cold calls, go do all this stuff." Like, how does human first work in that space?

>> Well, so I'm going to say a thing right from the jump that is going to make everybody's blood boil. But I think that tech kind of broke the mold a little bit. They broke the model, and like super high velocity, high volume is kind of just not going to work the same anymore that it used to. There was this moment in time where it was the thing, but that's slowed down a little bit.

>> The days of 150 calls, 100 calls a day. That stuff is over.

>> And that is also a waste of time. I spend my days planning the research to make the right 10 phone calls instead of burning through 100 phone calls and hoping I hit somebody that picks up, because that then maybe it's the wrong person that picks up. You just never know what you're going to get.

>> That's hard though, right? Like, when you look at what B2B tech has done—

>> And I do think they have butchered sales. We, for the past several years, have gone on this volume mindset. And listen, I'll say it right now. I blame the outreach platforms and the sales lofts of the world who said, "Listen, go find everyone that"—and they use the term ICP much looser than I can—but go find everyone who might possibly somehow someway perhaps be able to buy your product, put them in a sequence that has no personal relevance that basically says, "Hi Dale, because you do this at Revenue Reimagined, I could solve your problem," and hope for that sub 1% response rate.

>> Yeah.

>> And listen, in the growth at all costs era, people would hire dozens to hundreds of BDRs to go execute on this, which was a whole separate conversation.

>> And now we're coming back and we're telling people, "Wait a minute, this is wrong." And with the advent of AI, you could actually do it the right way and get a lot of really good information really easily. To your point, reach out to those 10 really relevant people who could really benefit from your solution by focusing on their pain.

>> Yep.

>> But what do you say to the sales leaders that are like, "My people don't have time to do this. This is a numbers game, right? Sales is a numbers game." But what if you're looking at the right numbers instead of looking at the hundred, like the yellow book list? When I was in my previous life in automotive marketing, and when I started day one, they had just purchased a Salesforce license for everybody and basically uploaded the yellow pages of car dealerships in the entire United States. Well, that means I'm calling Bob, who is listed as Bob's Cars LLC, but really just has three cars on his driveway, and I'm also calling Pensky Ford that has 500 cars on the lot. And that is not the same conversation, you know? I mean, a BDR should not be having the same conversation with Bob as they are with Jeff, the GM at Penske Ford. And so if the people are equipped with who they are calling, then their messaging lands better and everyone—the numbers all look better because the closing ratio becomes much better when you actually are providing the right message to the right people, right?

And I think to the CS part of it, Dale, I think client success is massive and it is something that gets so overlooked. And where do you mine revenue? From the people who are already paying you. So those people are incredibly important to keep your people happy, keep that trust there. I just had a conversation yesterday with 15 people in a room and the conversation basically boiled down to this: my best client was based on trust. They trusted me to make a decision. I trusted them to give me the right information and the right feedback. So it's that trust level, and the CS is what does that. That's what keeps the clients and scouts around, you know.

>> And so on the CS side of the world, it seems a little bit easier because you already had that relationship a little bit. Now, your product or service has to deliver exactly what you promised. Do you know what I mean? Like, you can't just—it can't just be all human first. Like, your product or service has to deliver. And I think in the growth at all cost mindset, there was a world where that was not happening either. That's why a lot of products fail or services fail just because you're not delivering on what you're saying you're delivering in the sales process. But I think on the front end of this, what we have seen work is more human first understanding your buyer. That's why a lot of times when we're talking about it, we talk about building a stable foundation of what we call go-to-market foundations: value proposition, ideal customer profile, buying persona, competitive analysis. If you know that basic piece, then you're going to be much more effective and efficient at who you're reaching out to. So I'd rather you have one meeting set after 10 than one meeting set after 100. It just doesn't make sense. The numbers are much better.

>> Yeah. And I think the outbound feels better, feels less icky when you know who you're talking to and that you can actually genuinely help them because you've dialed in your ICP so well.

>> 100%.

>> And to speak to the fact that I'm attempting to build a new vertical over here in my own little world, I learn every day. I learn every time I sit down and do outbound that maybe I'm refining something a little bit more. Maybe I get big eyes and I'm like, "Oh, I want that Fortune 500 company. I'm going to go after them. Look how many facilities they have. Oh my god." And then I'm like, "But wait, if I really look at it, it's those owner-operated homeboys that got the checkbook in his hand. He can write the check."

>> It's those that are really where our sweet spot is.

>> And so you just learn, you know. You go about it and you learn. And it doesn't mean you can't go after the big guys. It just means your majority of the outbound, or wherever you're going from a sales perspective, is in your ICP. And you go for a couple home runs once in a while. But like, do you want to spend four months trying to close something or do you want to spend four days? And it's like, if I can spend four days, I can go through—

More and provide more value to more people. At the end of the day, if you are in a company that you believe you can provide value to more people in a faster way, that should be our mindset. Not like I want the big commission check.

Well, and especially as you're building, right? As you're building, it's like get some of that low-hanging fruit so that you show value and you provide value and then people know your name a little bit more and then you can start to have more case studies, have more examples, have more to show for what you've done. And then that helps you get to the bigger ones, too.

But it's a fundamental shift, right? The other fundamental shift that I think we're seeing and where people are struggling is this kind of what I'll call soft sell versus hard sell, right? And historically, in every training I've ever been in, it's like you got to sell hard and you got to go for the close and you got to do this and you got to do that. Whether I was working full-time for a company or even in our business, I don't believe in hard selling. Listen, I'd love to partner with you. I think we have an immense amount of value. I think this could be a really symbiotic relationship. But I'm not going to push you.

Yeah, like if I haven't shown you the value, me being pushy isn't going to do it. "Oh, we only have one spot" or "the price expires tomorrow." All of that is what I call used car sales.

Yes. Which is what soft sell is, right? But people are afraid to soften it up and just be human, right? I often will start sales conversations with: listen, we're going to have a chat and if it makes sense to continue the conversation, fantastic. Maybe we could work together and if not, hey, it's a great networking opportunity and we could find a way to help each other out in some other ways. No problem.

Absolutely.

I think that takes the pressure off. That honesty takes the pressure off. And even in cold calling situations, right? I'm doing cold outbound and I've been in sales for 25 years. I still know how to cold call. But the easiest way to do it is to tell them from the get-go that it's a sales call and say, "This is a sales call. My name's Ashley. Do you have time for this right now or do you want to hang up on me?" I make it a joke. And every single time I have yet to have somebody not say, "Go ahead, let's talk about what you called for." That's the way it goes when you're pushing that honesty and not, like you said, Adam, not the hard sell like I have to sell three more today at $500 off.

You know, that type of thing is not because it makes people feel like you're being pushy and they don't want that.

Yeah. And I think that there's also this big thing, especially because of AI, there's a lot of like we can do personalized at scale. And I'm like, okay, but if you actually personalize, can you do personalized at scale?

Oh, you can't, but really, you kind of can to some extent. So, one of the things that I do, and that's part of my process, is once I've decided that a person inside the building is the contact that I'm going to try to reach and I have an email address for them, I switch a little button in my CRM and an automated email goes to them that just says, "Hey, I'm Ashley. I love huge metal rooftops. I don't love cold emails, but I wanted to introduce Seamless. You've heard the name. Nothing else to do here. Have a great day." But that is what works.

In any type of cold email, nothing drives me crazy more than this long, detailed dissertation of everything that we can do, possibly do, how we could possibly help you, and then "is it worth a 15-minute chat to learn more?" You haven't earned the damn right to ask for 15 minutes of my time, right? All we want to do is make an introduction and get any type of response, even if that response is no. Some type of response.

But I love how low pressure you're making it. I want to pivot that real quick into coaching reps to build trust, right? Because it is low pressure and you've built training programs for sales teams. How do you make sure that your coaching process mimics what you're saying? That empowers the reps instead of teaching them to drive the pressure, which in turn, in my opinion, makes them feel the pressure.

Correct. Yep. So, a lot of what my coaching revolves around is mindset. And to me, I actually really believe that mindset is a big deal. It is really important.

To go into any kind of phone call—whether you're cold calling somebody you don't know or having a discovery call with a CEO, it doesn't matter. Your mindset is incredibly important when you go into that call.

Yeah. And one of the things that I teach everyone is the person sitting across from you or on the other end of that phone is a human being. They are a human being. They fed their dog this morning. They spilled coffee all over themselves when they were taking their kid to school. They just got to their desk and sat down and they've got sweat dripping down and they're like, whatever, ready for it.

So we're all the same. Nobody's cooler than anybody else. So don't fan-girl. Don't freak out. Just be there, be in the moment, be present. And I think that changes people's mindset. I also tell them that no is an okay answer and probably the second best answer that any rep wanted to hear. And so go for that if that's what you're going for. That kind of lowers the pressure for the outcome, right? So completely detach from the outcome.

Abundance, detachment, and intention are my three pillars that I stand by, right? So have an abundant mindset. Know that there's enough for everybody to go around. If that guy says no, hang up. Call the next one. Totally fine. Not a big deal. Have high intent. I also always say a no is not a no forever. Never is a no a no forever.

And you're closer to the next yes.

Exactly. Exactly. The goal of the no is to figure out why. Why is it a no? Maybe they're not a right fit now. To your point, maybe they're not a right fit ever, but you find out that answer and you move on.

Absolutely. It's just being able to move the needle a little bit to the next one. Make that one along.

I told Dale no probably 10 times before I agreed to work with him.

He ran as fast as he could because he didn't know what the hell he was doing. I'm just kidding.

Well, I mean, truly though, no is one of the things that baby sales reps don't want to hear ever. Yeah, it is so good to hear once you learn that it's the thing that keeps the motion going, that keeps things moving.

And Ashley, do you think that comes from just experience? Like, have you always been like that or is that something you've learned over time? Because I think the older Adam gets, he's starting to understand it. But earlier in his career, he just did not get it. So I'm curious whether this is something I failed you all.

I think it's something that is there. There is some of it that was already there. I came into my sales career with a lot of confidence in myself already. But not confidence in sales or the sales process necessarily or what it felt like when somebody was maybe going to say yes and I should keep them around a little bit longer. That type of thing. That stuff I got more confident in as I went. But I definitely walked into the room for the first time saying I'm going to sit across from this man who's interviewing me and I know that he likes to watch football on Sundays.

# Transcript

And so that's fine.

That type of thing. And I think that that's important in reps. I also think that it's important to want the win for yourself, right? We talk about, like, for super high achievers, we want to win. But it's also super important to want to win for your team. Like, I'm a big believer in team values and team players and, you know, people that are on a team together playing with each other instead of against each other. And I think sometimes in sales that's hard to find. You know, you find these people that are like, "I'm going off with a kill for myself. That's all there is to it." And, you know, there can be a lot of fighting and territories and, like, rep land and things like that. But if we all are just in it together, then there would be so much more for everybody to go around. The abundance just continues to grow if everybody helps each other out instead of fighting against it.

I love that. Yeah, it's huge. In fact, I always tell Adam everything he puts in has to be a positive, not a negative. But he has this different mindset. But we'll get there. It's a hard nut to crack.

It's a hard nut to crack.

It's interesting because also sales reps are typically very high adjustment people.

Yeah.

You know, say no, move along. Say no, move along. But some of the best sales reps that I've ever met are not actually that high adjustment. They really do care, and they really do want that deal to move because they believe. They genuinely believe they can help that person. And so letting some of that attachment level can definitely be higher.

So this leads into the next really interesting part of what I'd like to talk about, which is the mindful sales leader. So the non-Dale sales leader, he's just jealous. He's jealous I can find my zen very quickly. But I mean, that is very true. So how do you set that tone for the sales team to cultivate both performance and well-being? Like, is there something that you guys do as a team? Is there something you recommend individually? Like, what are the things to kind of balance that, especially like either at the end of a quarter or the end of the year where that real pressure turns the dial?

Well, it's a different ecosystem, so where I am now is much different from where I was in automotive advertising or in tech. You know, like a one big roofing job can make your year in, like, large commercial roofing situations like this. Sometimes.

But that's heroic sales.

Yeah, absolutely, absolutely. Well, and the culture is so self-led here and so team-oriented that you can't help but know that you're carrying the weight of this, you know.

How did that happen though? Like, how did you get such a self-led culture? Because that is one of the hardest, if not the hardest, things to do without people needing to be told what to do every minute of every day.

It's true. I mean, we're still a small team, so that's part of it, right? So it's still a small team, but from the small team, we have business development, we have operations people, and we even have our service, like our service trucks that are on the road. Those guys make their own schedule. They know what's in the CRM. They know what needs to be taken care of and what the priorities are. And we don't tell them, "Go here, go here, go here, go here." We let them look at the calendar and decide what makes sense and work as a team to decide where to go. And also, because we do that, they are more motivated to continue to increase that service business and help the company make more revenue. So when I come in and I'm like, "Hey, have we been communicating with our service customers post-service at all?"

No.

Cool. If I started doing that, would you guys enjoy that? And would that help increase revenue and help increase touch points with our customers?

They're like, yeah, that would be great.

Yes, please.

And they are into that. And so that team mentality, like we're all growing this together, has been what has. And I know that can be kind of contrived. And so that whole, like, we're all a big team, haha, one big happy family.

As long as we don't use the word family. I don't think the word family has a place in corporate.

Correct. And we don't either. But a team is important to us. Like, we are cultivating an office space and an office environment. We have mandatory fun once a quarter where it's during their workday and we all get together.

So I'm the only woman that works here.

I like that.

I like that though. Mandatory fun. Dale, stop working me so damn hard.

Dale, you can handle it. I promise.

And there's usually work that still happens. I mean, it's like play 18 holes of golf together or watch.

I would love to see Adam out on a golf course.

What does that mean? Tell me what that means, Dale. You don't think?

No, no.

I don't think you could handle it. I don't think he could handle the heat.

Interesting.

Interesting.

I got pulled into golf because all of these guys golf and mandatory fun was golf and I was like, well, I'll be damned if I'm going to miss out on mandatory fun.

Yeah.

So I'm going.

I love it.

Listen, I don't love golf. I can golf. The reason I don't love golf is there are not many people, Dale included, that I want to spend four hours with in the hot sun on a golf course where I have to drink to get through the day.

Fair.

You don't have to drink to get through the day. That's a different problem with you. I take my kid to Drive Shack all the time actually.

Well, and my daughter appreciates it because my daughter and my husband golf. And so then when I started here and the guys got me to golf, and I went and golfed with my husband and my daughter, my daughter was like, "Someone's coming golfing. This is awesome."

I love it. I love it.

Yeah. So, I mean, we do stuff like that and everybody's invited to, you know, drink what's in the refrigerator, you know, eat whatever is on the shelves, and we stock things from, you know, just a small group. But it's also everything's for everybody. We all share.

Yeah, yeah. That's awesome, yeah.

So you're scaling and you're growing. You're building this company. The goal, and I love the everyone sharing, but the goal is to, you know, I'd imagine get bigger and better and continue to grow. As you do that, often times culture dissipates, right? Like I saw this happen a lot at Toast. We had this phenomenal culture that everyone wanted to work here. And the bigger we got, the more we lost ourselves. How do you make sure that that human-first, consultative approach, we're all in it together, mandatory fun, like how do you make sure that doesn't get diluted as you grow?

You completely self-fund your business for the rest of forever and don't ever have. That would be the only.

Shout out to all our VC and PE friends here on the Bridge the Gap podcast. No, I mean, it is absolutely, it absolutely comes down to making sure, and I hate the word. I don't enjoy both of these words, but synergy and alignment are incredibly important when it comes to the human beings that you are doing business with. And so if you do not feel like your values and what you want to do day-to-day aligns with all the other people that you are with day-to-day, then it's not going to work.

I just want to interrupt for one second because I don't think it's just investment. I think investment creates undue pressure of expectations. But everything is an expectation thing. The reason why VC and PE firms don't work is because the expectations aren't aligned with what you're trying to accomplish. And the same thing if you're not, if you're family-owned or you know, single-person-owned, you can only hire so many A-players. And if you have all A-personalities on the team and all of a sudden you're growing from ten million to forty million, absolutely, that growth trajectory, you're going to end up with C and B players. That's just what's going to happen. So you have to, like, almost reset your expectations as you're growing to figure out how that's going to work. Like today it works very well and you can build that culture from a foundational perspective to make sure when you hire. Which was a question I was going to have for you. Like, if you had to restart the hiring process, say, what are the three values or the three things that you would look for in your hires? Like, what would that be?

Oh, good question.

Very interesting question. That's a great question. Well, I want to. So, one of the things this kind of goes back to the question that you asked prior, and I just wanted to, like, kind of re-answer it because it does. When you're the coaching part and, like, keeping culture, part of that is about not.

Having a team of 20 people and saying everybody's goal is to make 100 calls today is about sitting down with those people and saying, "Let's talk about your goals and what makes sense for you and what's manageable for you." And you guys, I am from like the YM and 17 magazine. Give me a quiz and tell me what Disney princess I am days. And so I love a personality.

So is Adam. This is amazing.

We're probably the same Disney princess.

Listen, you never know. I am wearing an off pink today, so I'm okay to be a Disney princess today. Well, I mean, you know what I mean? I love a personality assessment and knowing a little bit more about a person and how they operate and what makes them tick. And so, making sure that I'm not sitting down with somebody who wants that high velocity because maybe some people do. And if that's how they operate best, great. And I love a sales team sharing best practices. I do not think that best practices mean that it's going to work for Dale and Adam if it works for Ashley. You know what I mean? I mean, it likely won't work for Dale, but that's it's so important to understand what people's lane of genius are and what's their why. Back to like the mindfulness thing that you're talking about. Like, if you're trying to force people into a lane of genius that just does not fit them, I don't care what you do, it's not going to work. They can be as motivated as possible for a minute.

Yep.

And then that'll just dissipate.

Yep. Absolutely. And I think that so I love people with ADHD for sales. They usually are like—

Most of them have it.

Correct. Myself included, which is why I'm always grabbing something or messing around with somebody.

Yes. Same.

Undiagnosed, but I've diagnosed myself. There are these parts of it that make for a really great salesperson.

Yeah.

Usually high adjustment in the moment. They can speak on their feet pretty quickly and come up with things relatively quickly. But also people who like to have guardrails but not micromanaged. Like if I have to micromanage, I need you to be an adult, but I do want to be there for you and be a teammate and be a team player and help coach you, but I don't want to have to say it's Tuesday at 5:00, have you done your 50 phone calls today? Because that just doesn't feel good for anybody.

Nope.

You know, and I think that letting teammates talk through their own goals together and base things on whatever—some people like to base things on daily goals. Some people would prefer to say this is my weekly goals and I would prefer to face it this way and that's how my head space and my mental works better. And I think that anytime you can give them a mental boost, give a team member a mental boost to operate their way, you're going to get more production, you're going to get more efficiency, and you're going to have a happier employee just in general.

And working genius is the assessment that we when I the very first meeting that I walked into in this building, they were all going over their working genius assessments. And so I took one. And so I've taken that and a Hogan assessment is the other one that I've done that I did a long time ago that I still lean on today. And I know moments of, you know, like one of the things when I'm frustrated or upset or getting derailed about something, I become very imaginative. Like I create stories in my head. Like I'm like they're not going to say yes and I'm never going to close this deal because they don't like my hair, you know? I mean like they don't like Adam's hair either so they aren't going to—

All right, kids. All right, kids. On that, it's time to move to some rapid fire. So here's the rules, Ashley. You get 10 words or less. If you go over, every word you go over, I get to bop Dale a couple times. So here we go. What's one sales myth you wish would disappear?

One sales myth: 10-31.

Tell me more.

10 calls to set three appointments to get one deal.

Perfect.

Totally agree. Those are good numbers. Back to the question I had before: what are three attributes you look for that are non-negotiable at your hires?

They must be a happy, positive person in general. I can't have source. I'm so I only get 10, right?

Positivity.

Okay.

Positivity is important to me. Integrity is important to me.

Ooh, I like that one because I like it's on my list.

I like you to care if your name is on something. I want you to care. So that's very important to me. And then also I know that hardworking and like we're not about the grind, right? I'm not saying that. But like you have to have passion.

I love that. Passion and want to work hard because you have passion.

You hit two of my three. You hit two of my three. I love that. What's your integrity and hard work?

Coachability.

Yeah.

Oh, yeah. 100%.

Oh, good one. Yes, that's such a good one. I forgot. I mean, positivity. Positivity is a good one because Adam would never make it to your team. But hard work and integrity, he is coachable sometimes.

Okay. So you're well over 10 words, Dale. Shut up. Ashley, what's a leadership trait that you believe is undervalued?

Being friends. Like, I know that everybody says don't be friends with your employees, but—

Oh, no. I disagree. I want to know people personally. I want to know about your wife and your kids and what makes you tick and like—

I want to know you as a human, not just a number.

Absolutely. Absolutely. My best friend to this day is someone who I met when I hired him and used to work for me 20 years ago. And to this day is my best friend.

Right. Because why would you want to hire people that you don't enjoy being around?

Yeah. Shut up, Dale.

I saw the look on his face. Next question, Dale. Let's have a fun one to wrap this up. Ashley, dream vacation destination.

My favorite vacation destination?

No. Dream vacation. And it doesn't have to be your favorite. Somewhere like you dream of.

My dream vacation destination right now on the top of my list is the Canadian Rockies. It's so like because it's not like beachy but the Canadian Rockies.

Nice.

I'll take mountains over beach all day long.

I know. I love the mountains. I'm a big mountains girl. And I've never been there and my parents went two summers ago and they loved it. So that is at the top of my list at the moment.

Cool.

Very cool.

Yeah.

Cool. Ashley, thank you so much for joining the show. Thank you for talking about how to humanize this crazy sales world that we live in. We're grateful that we got to spend some time with you.

Of course. Thank you for having me. It was wonderful.

Thank you.