120: Unlocking Inside Sales: Recruiting, Training, and Motivating

Inside sales is evolving, and we’ve been given keys to the kingdom.

Greg Ryan, Senior Vice President of Sales at ThriveHive, joins us to discuss how he helped build a powerful inside sales team from recruitment all the way to the President’s Club.

He’s got a wealth of strategies to help you build a highly effective sales team – from recruiting the right people, training them properly, motivating them successfully, and retaining them in the long-run.

If you’re looking for ways to manage your sales team, you’ve come to the right place. Listen now!


It is the latest edition of the “Conquer Local” podcast, coming to you from Boston. And my good friend Greg Ryan is joining me. He’s the senior vice president of sales for ThriveHive. I’m gonna wind the clock back about four and a half years. I’m in Canton, Ohio. I’m on a speaking tour across about nine states working for Gatehouse Media and Propel at the time and I run into Greg Ryan. He is one of the top salespeople in the space. He’s running a high performance sales organization out of Massachusetts in the Boston area. They’ve got a number of different locations, Gatehouse is one of the biggest newspaper publishers in the world and ThriveHive is their digital arm.

So Greg and I had a chance to sit down and dig into everything when it comes to delivering sales over the phone. Because he is running a high performance sales organization that’s dealing with customers all over the U.S. and they’re primarily doing it with telesales. They do have some sales people that go face to face, but he’s got this telesales team and we’re gonna dig into it. So we’re gonna talk about some of the challenges, we’re gonna talk about some of the ways that you can win on a regular basis, and I find out how they pull off their President’s Club. For sales managers and VPs of sales that are looking to do a President’s Club, Greg will give you some insight into that coming up. All that and much, much more, the latest edition of the “Conquer Local” podcast with Greg Ryan from ThriveHive next.

What’s changed in four years

George: Greg, really good to be here in Quincy, Massachusetts with you. And let’s start with what really has changed in the last four years and if you could just boil it down into one sentence.

Greg: I would say over the past four years, what’s really changed when meeting with customers is that it’s no longer a one solution sale. There’s two, three, or four things that you really need to get on the plate, for that, you know, digital plan to work for that business. It’s not just a search campaign, it’s just not an SEO campaign, it’s not a display campaign. It’s a combination of many, many things that get to the expectations that you and the customer are getting to.

George: And when it comes to proving that result for the client, where, you know, we’re always talking about proof of performance, there’s always new tools to show proof of performance, you know, is it more important today?

Greg: It is much more important today because, you know, there’s a lot of competition out there and everyone will say they’re the best at it. But you need to really be transparent in what you do. If you need to say, you know, the X, Y, and Z, this was from us and whether that’s from Google Analytics, whether that’s from dashboard access, but you really have to be 100% transparent.

George: Let’s talk about your inside sales organization. Can you give us the keys to the kingdom and take us out of the hood? And tell us about it.

Greg: So what I do on a daily basis is I look over the direct sales team. So anything that is direct is considered you know, it’s our direct inside sales team. It’s located up in Manchester, New Hampshire and it’s also our field sales consultants out there all over the country. We’re tripling the size of our inside sales office this year, currently, right now we have a training going on, we have five or six individuals in there, it’s very much harder to find that inside sales person because of, you have to look for that motivation. We can train on digital, we can train you how to speak to, how the results page works on Google or other search engines, we can show you how the social works.

What I need is someone that can pick up the phone, they can dial, they can not, you know, feel bad if someone hangs up or says, “I’m all set,” or something like that. But I need someone that comes into the office, has a plan, we train every single morning. That’s something that’s key up there is our sales reps, if you’re working for us in the inside sales, you are made to train every single morning for 15 to 20 minutes. And we break that down to three different sessions. Because we firmly believe on that, you know, a lot of people when I said this a year ago, didn’t agree with me, but we proved it out in 2017 that there’s no difference in contract sales of what you should see from an inside sales team to a field sales team.

George: That’s a powerful statement. You’re saying that we send a rep out in a car to call on a client or we put them on the phone to call on a client and they’re gonna bring back the same size order?

Greg: Yep. Just about…we see, maybe a $1500 difference in contract sales from a field sales to an inside sales person.

George: So it doesn’t surprise me because I work inside a sales organization where we extract very large contract values over the phone. But I think that what it points to is that the clients, they’re actually used to this type of sales approach.

Greg: They are and, you know, it just, it never changes. Time is money so they can do it on their schedule. We also taken, you know, I don’t want to give all the keys to the castle out. But we take video into this a lot. We utilize video in almost every single call because we can see that person on the other side that they’re paying attention to us. They’re not just doing anything. They know that they’re looking in the camera, they’re looking at the demo that’s on the screen, and they like the back and forth. They know there’s a real person that’s here speaking to them. And that they really enjoy that we see our close rate, you know, is really 7 to 10 business days is really our close rate the same as outside sales.

George: Yeah, I really liked the video conference. I remember when we first launched in our organization the reps were a little bit reluctant. But, you know, what it gets you away from is the presenting to the Polycom or in a headset is like presenting to a Sphinx. You can’t really get any feedback or read on the prospect on the other end. You don’t know if what you’re saying is resonating. So video definitely has been a game changer. The other thing that you mentioned was the training cadence. And is it training? Or at the same time is it motivation? Keeping them motivated if they’ve had a bad couple of days?

Greg: Yeah. It’s a little bit of both. We have a morning huddle-up in our inside sales office every day where we’ll go wins and things like that, which is great. Everyone talks about wins, but we actually talk about non-wins also of, “Hey, what really brought you down yesterday? What did you say? What could have happened? How can you change it?” You know, we look at every single problem as actually as an opportunity. And a lot of sales organizations don’t do that. They problem is a problem, but we actually like problems. We have problems just for us, equal opportunity.

George: Yeah, I think that, you know, when I remember going on the road with reps and where you did the one-on-one where you’re in the car, and you finish the call and you got back in the car and you beat them up over the things that they did wrong. It’s the same thing, you’re just doing it in the phone room. Let’s talk about spiffs. I was with an organization a couple weeks ago in Austin, Texas that said, “You know, we spend a ridiculous amount of money on spiffs to get to our targets.” How about you folks?

Greg: We probably don’t do as many spiffs as you’re talking about. We do them here and there, depending upon if we have a certain objective that we want to hit maybe for a specific product or something like that. But we’ll do spiffs more around activity, you know, especially if we’re still talking about the inside. We’ll do more of it around activity and not just simple activity where most places will talk about, you know, outbound calls or talk time. No, we look more for connected calls, we consider connected calls anything over two minutes. We’ll do more kind of things like that for spiffs, where we’re spiffing the right things and not specifically just doing for phone calls or talk time.

George: You know, again, you don’t have to give me all the keys to the kingdom but I’m just thinking around technology that you’re utilizing. When it comes to call recordings, are you doing any sort of an algorithm against a script? Where you say, you know, the rep was… We’ve ran across some organizations where they’ve got a full-on algorithm against a script. What sort of technology are you utilizing in that group?

Greg: Yeah. So we do have that. We do have call recordings and things like that where we can take tones and things like that over the phone of what’s going on. We do…going back to scripting we do have multiple different, you know, combat cards if you wanna call them. Different for each kind of vertical you’re speaking to and who that person is. Is that person an owner, is it the marketing person, you know, there’s different scripts you need to have.

So we do record, we do those for our one-on-ones. We’ll go through, “Okay, let’s listen to what you said,” and they really like it. You know, a lot of people will think that, you know, “I don’t wanna hear myself on the phone.” Actually our group is a lot different I think than other sales teams where they wanna go through their phone calls and learn of, you know, “I just heard myself say that. I said ‘uhmm’ 10 times.” There you go right there. So it really, you know, they really take advantage of it and really learn from listening to their selves on the phone but then having their sales manager with them and say, “Oh, at this point you should have said this.” So they really like it.

George: The other thing I wanted to dig into, one thing I’ve been learning in talking to sales leaders is how much R&D are you doing in your leadership team to find those levers that you can turn or find those best practices other people are using, to improve the performance of that group? Are you doing a lot of that?

Greg: Yeah. It’s a constant thing. You know, we firmly believe that if you don’t train every single day that you’re falling behind, especially we all work in a digital world here that is changing constantly. Also, sales is evolved, it’s changed. So if you’re not changing the way that you train, you’re using the same people that you used to train, you know, 10, 15 years ago that you’re consulting out again, these people will need to look at too is, “Is this the way that things are actually sold these days?” A lot of times, you know, in old school selling, they’ll say everything is objection when it’s not. It’s just a response to something. So you have to train and you constantly have to keep looking for, “Okay, how are we gonna keep ourselves competitive? Or that top dog in the place?”

George: So on-boarding a new crop of reps…and I think you used the word cluster. So let’s say a new cluster of inside sales reps. You mentioned that you had six of them that were starting right away. Of those six how many will make it through the training and will, you know, will perform?

Greg: You know, so each person is…we’ve gotten a lot better with our hiring of, again, finding that specific profile of the person. So it’s gotten better of, you know, we’re looking at hopefully 60 or 70 people, 60% or 70% of those people are with us, you know, a year from now. We also changed the way we bring them aboard of, you know, these new people again, especially on the inside sales, you know, they’re not digital savvy, they haven’t been selling digital for 4 or 5, 10 years, like the more of the field sales team is. Is that these people, you need to really train them and not give them the stress of carrying a goal right out of training.

So we actually created almost like a consultant or strategist in training for the first two months where they’re calling, they’re setting appointments for their team lead, that person that’s on their team. And they’ll go with those appointments, they’ll get spiffed on those setting those appointments that hold not just setting appointments but ones that hold and also the ones that close by their team lead. Now after 60 days, it’ll be looked at, they’ll start testing themselves on closing their own business so then they graduate at that point. So we know we really have changed our method from, you know, a year ago when a new person was brought in. Right at training they were given a goal, a sales goal and a revenue goal where it really stressed them out. We noticed much, much better over the past six months of doing this, has really put them in the position to succeed.

George: And what about when somebody hits a slump? You throw him back into training? Do they work with the…you know, what is the approach that you’re using? Because as we all know, in sales, it’s not just always up to the right. There’s always going to be some challenges.

Greg: Yeah, and, you know, everything’s a law of averages. And it’s again going back to what they’re doing on a day-to-day basis. Our leadership will get with that person whether it’s a field sales, they’re gonna go out actually out there and they’re gonna go for a three-day ride along up of them getting back going. We also look the marketing team of what can we do to get this person out of the slump? So we’ll do anything it takes with inside, you know, we’ll jump on their calls with them. We’ll get them specific leads, you know, that might be grading higher than others, so we know that we can get them out of the slump sooner than later.

George: I’ve been talking to sales leaders about the end of the month. And I’m wondering if we can find some bloody way to get closes earlier in the, you know, is that a challenge for you? I wanna understand that. Is there that end of the month rush that you have to get business in before the books close?

Greg: Yeah. And, you know, we see it, you know, anywhere of, you know, whether it be the end of the month, or end of the quarter. They do, we do see, you know, 50% to 60% of our business come through, you know, that last 5 or 6 days. The key is creating that sense of urgency with your sales reps, again. But also you have to be careful about it though because, you know, a lot of times sales reps will come to you at the end of the month, or at the end of the quarter.

And they really look for you to discount and things like that, where you really have to take a stand and not do that. Because you’re just devaluing the products and services that you’re offered. So, you know, our end of the month really, it ends at the end of the second week of the month. That’s where we’re really saying, “We’re closing.” You know, we hold them accountable of, you know, “This is halfway to your goal for the month. Here it is.” So that hopefully by the end of the month, we’re not in that full out rush and end up discounting products and things like that.

George: I think that there is that natural cadence of monthly pushes. And what I’m reading into this…and correct me if I’m wrong by having that accountability session on Thursdays, you’re looking for a weekly cadence.

Greg: No, that’s exactly right. So they have their weekly, monthly goals. We’re also, you know, our commission, our comp plan is not just wrapped around sales, but it’s also then wrapped around revenue as well. So just because you sell something that’s great, well, the majority of their compensation plan is revenue of getting things in and getting as live as possible. So they don’t wanna wait to the end of the month because then they won’t have a chance to get it live during that same billing period. But we also will do incentives getting to goal halfway through the month that we’ll put an incentive in place of, you know, “Mr. Salesperson, if you can get to goal by the end of that second week you get X or Y.” So that really pushes them and then also we’ll put in a plan for them from there if they double goal for that that period as well.

George: Well, I wanna get into, you know, I don’t know if you’ve been tanning, but you’re getting ready to go to Aruba because it’s President’s Club. I’m really intrigued by President’s Club. I know that one of the sales organizations that subscribe to our group is the For Rent sales organization under the leadership of Paige and Terry Slattery and, you know, a great group there and they just got back from their President’s Club. I was lamenting because I was watching all the pictures online. They were having a great time. You guys been doing this for a while now? Is it a really important part of the culture of your organization, the President’s Club?

Greg: No. It really is, you know, sales, it’s a competition of everyone wants to be number one. And we give these badges that they’re really able to attach to their signatures and their emails. And it’s something they take pride on when they know that they win, they ask our sales coordinator for that updated version for that thing, that badge to add on to their signature, you know, it’s the best of the best. If they wanna prove to themselves that they’re the best of the best, you know, they basically, promised their significant other that they’re gonna get it. And once you go to President’s Club, you do not wanna miss one.

George: Well, the one thing that I made a mistake a couple years ago, we did a trip. That we were going to award and everybody had a chance to win the trip if they did enough revenue, but we didn’t invite the significant other. And I think that that would be very, very powerful if you had a dinner to launch the thing. Is that the way that you guys do the launch?

Greg: Well, it’s just that you can take, you know, we can give you enough motivation to, you win the contest, you wanna win it. But we also want that person when they go home, they’re also motivated by their significant other, “Are you hitting goal? Are you hitting goal? Are you bringing it in? Are we gonna go to Aruba this year or not?” So it works both ways.

George: It’s brilliant. I love it. I was, you know, I was expecting that you would say that. And, you know, I respect the organization that you built here. Let’s talk about, you know, when we went for dinner a little over a year ago, you said you were having a lot of fun. Are you still having a lot of fun?

Greg: If I didn’t have fun, I wouldn’t be here. You know, a couple years ago, before I was promoted I said in front of the entire sales team of, you know, “Life’s too short.” I learned at an early age that life’s too short. That if, you know, yes everyone gets in a slump, they might not like going to work every day. But if that turns into a thing, well, I’m just not gonna be here. And everyone that I work for knows that. So, you know, I love coming to work every day. I look forward to it. Sometimes I can’t sleep because I’m excited to get to work. I’m constantly thinking about what I can change to make people more money on the sales side of things, and the company, bring it to the next level. But yeah, I like coming to work every single day.

George: Well, there’s no organization in North America and I may be able to say in the world that is growing faster than this news organization in acquisitions. And then on the other side, the ThriveHive organization, yeah, it just keeps growing. I’m here in the Quincy headquarters, I remember when you guys were only half of one floor and now you’re two entire floors. Plus a building in downtown Boston, plus a building upstate where you have your inside sales team, plus all these reps spread all across the country. So congratulations on your success. And thanks for joining us on the “Conquer Local” podcast.

Greg: Thank you very much, George.

George: Before we dig into the key takeaways from this edition, make sure you’re asking your friends and make sure that you are subscribing to the podcast. We really are building this incredible audience and we’re getting some great feedback. I appreciate the feedback we’ve been receiving. The best place to reach out to me is on LinkedIn. It’s George Leith, L-E-I-T-H on LinkedIn, love to add you to my networks, almost 14,000 members in my LinkedIn profile now. And I read every single comment that is sent my way. And actually we’ve booked some great guests in the months to come from that audience. So thanks to everybody that’s been reaching out.

Well, I like to put people on the podcast that are walking the walk and talking the talk. And Greg isn’t some guy sitting in an ivory tower. He’s on the floor, working with the sales people on a day-to-day basis and you can see that. The interesting thing, there was one big takeaway before I get to the President’s Club stuff because I’m obsessed with this thing. I wanna understand it inside and out. But the one big thing that he’s talking about, they are now getting the same transactional sale over the phone with a screen share as they’re getting with a salesperson face-to-face.

And that’s how the industry is changing where buyers are just saying, “Yeah, you know, I’m used to buying things over the phone, I’m used to a screen share, and I will spend the top dollars. I’m not buying in that you have to be face-to-face for all purchases nowadays. It’s because our prospect’s time is valuable.” And they really are appreciating the telesales type model where you have the screen share, because we’re able to articulate the value proposition even over the phone and with the screen share. So that was one of the big takeaways from that. The second one was this President’s Club thing. And Greg really talks about how it is one of the drivers, it’s part of that competitive nature of sales.

How do you pull it off? Where are some of the places to do it? How do you set the budget so you can run it by the CFO and get their buy in on it? And it really is driving top performance for the ThriveHive Organization and other organizations that I’ve run across over the past six months or so. We are looking for your feedback and we’ve got some great additions of the “Conquer Local” podcast planned as we move into Q2 and Q3. Connect with us on LinkedIn and also reach out to us even by email at gleith@vendasta.com. I look forward to your feedback, good, bad, and ugly. We wanna hear it. It’s how we make the editions more and more popular and more and more valuable for sales reps. My name is George Leith. I’ll see you when I see you.

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