Staffing sales has become harder. Market shifts, tight talent pools, and changing buyer expectations are making it tougher to win new business, while AI and other emerging technologies promise to give sales teams an edge. But with margins under pressure, staffing firms need to look beyond the latest shiny tool and ask a more practical question: Which technology investments can actually improve sales performance and deliver a return? And how do you know which tools to invest in and when?
In this episode of Avionté: Digital Edge, host Casey Wagenfeld, Strategic Partnerships at SimpleVMS, a division of Avionté, speaks with Mark Winter, Principal and CEO of The WinSource Group and a staffing industry veteran with more than 20 years of experience. Together, they explore where technology can truly strengthen staffing sales, which tools are worth the investment, and when the timing is right to make a move.
Mark shares practical insights on building stronger pipelines, improving sales execution, and evaluating technology through the lens of what will actually move the business forward.
This is a partial transcript of the full conversation. Listen to the podcast episode for the complete discussion.
Casey Wagonfield:
Always enjoy talking to you, Mark. I want to jump first into why staffing sales is harder right now, and I think this is something we’ve probably been talking about for a couple of years now, but you and I have both been around staffing for a while.
You a lot longer than me, of course. But why do you think so many staffing firms are having a harder time consistently bringing in new business right now?
Mark Winter:
I just want to acknowledge that you very politely called me old just then. That was good. Well played, sir. 27 years I’ve been doing this, and I don’t regret a day of it. It’s been so much fun. Listen, staffing sales always has its challenges, and you said we’ve been talking about this for years; we have. The story changes a little bit, though. It is hard now, and it’s hard for different reasons.
So, I think there are four things that are driving challenges in staffing sales. A couple of them are out of our control. One of them is, as much as we’re looking at technology and efficiency and changes in the business, so are our customers. So, they’re having meetings and podcasts and webinars just like this about how they can change things.
And so, if they’ve been a staffing user for a quarter century, they’re probably thinking about, “Well, should I be doing something new? Should I be trying new technology? Should I try something else out?” So we’re dealing with all that. Their business is in a swirl. Sometimes we forget about that.
Number two is that it’s never been tougher to buy something in an organization. I call it internal complexity. So, if you’ve tried to get an invoice across the line, or you’ve tried to get your company to sign on to something, you know it’s tough. Well, it’s tough for our customers too, and so sometimes they may want staffing services, or they may want to talk to us, but they don’t know how to get it done.
They’re not in a position of power to sign off on the invoice, or they have to go to a CFO, whatever the thing is. So, internal complexity is stalling deals left and right.
One that we contribute to is noise. There’s a lot of noise out there. There’s so much noise, and, at some point, people just turn a blind eye or a deaf ear. They turn it off. They flip the switch, and they’re like, “All right, I’m done with that. I don’t want to hear anymore. Even if it’s valuable, I don’t want to hear anymore, because it’s just so much swirl.” And they’re getting hit from every angle.
So that’s, that’s part three. And I say we contribute to that because if you’re not thoughtful about your technology and you’re using tools at an accelerated rate, you’re probably contributing to that noise. I know you don’t mean to do any harm, but you’re probably contributing to that noise.
And then, last but not least, it’s harder to get ahold of people. We’re distributed now; people are working from home, or they have a Ring doorbell at their front door, or at the business, not just at their home. And they’ve got a security guard out front, or the business is shut down, or whatever the thing is, but it’s just straight up harder to get ahold of people.
So, those are the four things that I think are making staffing sales hard right this second.
Casey Wagonfield:
That’s a great breakdown. Those are all things that I’ve seen in the past, too.
I’d love to hear what you’re hearing from the staffing leaders. So, you were at the Avionté user conference, CONNECT, this past summer, and you talked about turning your ATS into more of a revenue engine.
So, after talking with all of those staffing leaders, what were you hearing that lined up with what you’re seeing in the market?
Mark Winter:
Starting with the technology front, one of the questions that I hear from staffing leaders is, “Am I behind? Am I doing the right things? Am I focused on the right stuff?”
I feel like, and I’m paraphrasing, but a staffing leader says to me, “I feel like I’m so far behind right now, like I should have things hooked up and integrated and tools running, and I don’t even know where to begin.” And that’s got to be a lot of weight to carry for some of those staffing leaders, right?
So, I hear a lot about that. I hear, “How much reliance should I have on my sales team? How should I structure my sales team? What types of salespeople should I have?” I hear, “What used to make us successful is not making us successful anymore.” I hear, “I’m paying a whole boatload of commission to a salesperson who’s been with me a couple of decades or a decade, and I’m getting zero productivity. They haven’t closed anything in a long time, but the commission checks are fat, and they keep rolling out.”
All of these things cause staffing leaders to start to question the entire sales package. Am I structured the right way? Do I have the right tools? Are we doing the right things? And that’s before they even get to messaging and capabilities and all of that other stuff. It’s a lot of weight to carry.
Casey Wagonfield:
And at the same time, I guess you can have the value propositions, but if you don’t have the right messaging, you don’t have the right people in place, you don’t have the right technology, or give them the ammunition they need to go out and be successful as salespeople, then, I mean, it all kind of comes together, right?
Yeah. You have to have it all working in sync.
Mark Winter:
Yep. I talked to a staffing leader who had a niche. That niche was administrative roles for construction. And I thought, that’s really niched, right? But that’s really great. Super clear messaging.
Just by hearing that one line, I know exactly where they should network, how their marketing should look like. They also had no salespeople, and they were like, “Well, we don’t have any business coming in. I’m questioning whether or not that’s a viable line for us, if that’s space we should play in.”
And I’m like, “Well, hang on. You got to have both. You got to have somebody knocking the doors out there. You can’t just put up a website and hope for the best.”
Casey Wagonfield:
You know, it’s funny you say that, with the niche too. I mean, there’s so much opportunity out there. I know companies that have hundreds of crossing guards on assignment. Some companies only place paraprofessionals inside schools, and they’ve got hundreds of them. Like, the things that you wouldn’t know or think use staffing that are out there.
So, when we talk about where staffing firms should actually focus first, if revenue is tight and the budget isn’t unlimited, where do you start? Is it the people, the process, the technology?
What usually needs the most attention first?
Mark Winter:
I think the thing that needs the most attention first is that question. Is it people, process, or technology? And the question is, are we people, process, or technology? Meaning the staffing company.
So, I hear staffing companies all the time that say, “We’re in a people business. We’re in this for relationships. How can I get my marketing automation to create a sales funnel without actually having to talk to someone?” Well, those two things don’t work. You can’t be in the people business and then separate yourself from the people.
The thing’s not going to work. So, I would say the first question is: Are you people-centric, process-centric, or technology-centric? That’s the place to start. And then the investments should follow that line.
So, if you came back to me and said, “I’m a technology-first company,” then your tools better work. You can’t be trying things out on your end user. You’ve got to make sure the technology works, invest in that, then invest in a solid website to capture leads and align yourself to a great VMS partner like SimpleVMS so that you can promote that and the technology works when you expect it to.
If you’re a process-driven company where everything’s about how quickly you’re able to get medical, administrative, or IT staff on projects, then invest in that process. Make sure that you don’t have any gaps in the structure that supports that process. Meaning, you can’t have a process-built company around a good recruiting process and have five openings for recruiters on your team.
That’s not going to work. Your process is going to break down. So, invest there. If you’re a people-focused company where relationships are important, and you do a lot of grassroots marketing, then spend your money on networking. I would rather see you put up a booth at a trade show and spend 25 grand on that type of marketing than invest in a new piece of technology, if that’s your focus, the people focus.=
So, I think staffing firms should focus on something that aligns with their aspirations: people, process, or technology.
Casey Wagonfield:
I love that. And when we talk about sales teams, are they actually productive or are they just busy? I think that’s one question a lot of staffing companies struggle with. And I remember going through this when I ran a sales team in staffing, talking with people like, “Yeah, you left 1,500 messages last month, but you talked to one person.”
So, that tells me you’re just throwing things in there to make the CRM happy, to make it look like you’ve done something, because you can make a ton of calls, send a ton of emails, and make it look really busy. But how do you tell the difference between activity that’s actually creating momentum and activity that’s just keeping people busy?
Mark Winter:
Yeah. It’s about connections. Are we making connections? Now, here’s the thing: If left to their own devices, people will gravitate toward work that they like, or that feels good. That’s what I know. If you give little to no direction to your sales team, that’s where they’re going to spend their time.
They’re going to spend their time on what they like and what feels good. So, busting out 1,500 calls might feel good because you’re like, “I made more calls than anybody else.” Well, in that case, we just have to focus on making connections then. So, we’ve got to take that good momentum, we’ve got to take all that activity, and we’ve just got to redirect it.
And frankly, that’s the work of the sales leader. I think right now we are underestimating the potential of our sales leaders out there. Sales managers, sales directors, whatever your company has, or in some cases, it’s the CEO doing some of that work, and that’s fine. But we underestimate how much direction, guidance, and coaching our salespeople need or even want.
Listen, good salespeople want to be successful. They want to make connects. They want to move deals through the pipeline. And I assure you, if someone’s making 1,500 calls and they’re not making a connect, they’re super frustrated. And they know that you know, and they know that they know, and they just want to have a conversation about it.
And man, wouldn’t they love it if somebody could help them get better? So, I would say, if you’re not knee-deep in some sales management philosophy with them, if you’re not regularly having coaching calls, pipeline visits, ride-alongs with your salespeople, then your salespeople probably are just being busy.
They probably are being left to their own devices, and they’re doing things that feel good or that they like to do, and it’s probably not the most productive work. And so, I would suggest that people get in there and see it with their own eyes.
If you’re a CEO that’s asking this question: “Are my sales teams busy or productive,” go ride with them for two days. Not for one day, not for two hours, for two days, bell to bell, all day long, because nobody can hide anything for two days. Not that salespeople are hiding anything, but you’ll see the true essence of sales come out if you spend a couple of days in a field with a salesperson.
And I know that seems like a lot of time, but you’ll get the answer to your question, and then you’ll know exactly where to help them.
Casey Wagonfield:
That’s great.
Mark, when you talked about a connect, what to you is a connect? To me, that’s somebody who responded to my email, somebody who answered the phone and talked to me, or somebody who talked to me in their lobby. Maybe I connected with somebody at a networking event.
I feel like that’s the end goal we should be looking at: How many connects does it take to make a meeting? Is that what you would consider a connect? Any of those?
Mark Winter:
Yes. It is not at all important what the salesperson did. It is important what the prospect does. That’s how you know you have a connect.
If the prospect answered the phone, if the prospect met with you, if the prospect showed up in the lobby, if the prospect was at a networking event, that’s a connect. That’s what’s important. If you really want to measure something, that’s the thing to measure.
Now, there are people out there that hear me say that and they’re like, “Well, okay, we won’t measure calls and emails anymore.” Nope. That’s not what I’m saying. You got to have both. Calls and emails are like your speedometer in a car, and connects are like your mile markers on the highway.
So, we want to make it a certain distance. We still need to know what our speedometer says. We still need to know what our instrument panel says. So, you need both, but the connect is about what the prospect does.
Casey Wagonfield:
And each individual rep should know, whether it’s making phone calls, doing drops, or emails, how many calls does it take me to make one connect, and how many connects does it take to get a meeting? Now I have a real understanding of how many calls I should make.
Mark Winter:
Yeah, that’s right. You should have some sense of that. I mean, if you’ve been doing it long enough, it doesn’t take long to bust out 1,000 calls a week or so. And you should have some data.
And sometimes we don’t want to look at that number because it sucks.
But if that’s what it is, that’s what it is, right? Yeah. Now we know. And so, then the question becomes, well, okay, either A, let’s get some technology that helps us get better quality lists, or let’s try a different phone tree in the organization, or let’s try a different approach.
Maybe we show up in person if that’s something that our business can do.
Casey Wagonfield:
So, what’s the biggest mistake you think salespeople or sales leaders make when they look at their pipeline or their people’s pipeline and think that things are healthier than they really are?
Mark Winter:
Yeah. I’m going to give you a short list of things on this. The biggest mistake is they don’t know where the thing is supposed to be. They know where it is. They can look in there, and they can see a bunch of deals, but they don’t know things like, well, a deal of that size and shape should only take six weeks to close, but that deal’s been in there for 24 weeks.
That’s a problem. So, they look at a pipeline, and they look at the value of the pipeline, and they think because of the value of it or because there’s a bunch of stuff in there, and they see the last activities done, they feel like it’s probably okay. But the real health of a pipeline is: Is stuff moving?
Is it progressing from one stage to the next? So that’s the biggest mistake leaders are making, and frankly, salespeople too. You know that we have such great salespeople out there in the field that are just diehards. They go back over, and over, and over to the same door, and they think to themselves, “Eventually, it’s going to close.”
I’ve asked salespeople, “When are you going to pull that out of your pipeline?” And they say, “Never. It’s going to break.”
And listen, I’m all for that stick-to-itiveness, but listen, man, there’s timing to this.
There are questions you can ask that will tell you when this thing’s going to close, or if it’s going to close, and there are things you can do to push this thing along. And so not knowing what those things are, or just using pure tenacity to try to close deals, that’s a huge mistake on a salesperson’s part.
Casey Wagonfield:
Yeah. I was always in the mind of, you don’t want it to sit in your pipeline, because then it just looks bad, right? You’ve got this huge pipeline that’s not closing, and just because you remove something from your pipeline because it’s stalling or not moving doesn’t mean it’s not an opportunity for the future. It’s just not an opportunity right now, right?
Mark Winter:
Right.
Casey Wagonfield:
It’s still a lead. But I also think when you have that pipeline, and you have different stages within that pipeline, it’s a good way to also train your salespeople to know, okay, well, if a lot of your deals are getting stuck in negotiation stages or in what we’ve offered them stages or whatever it might be, maybe that’s what we need to work on: your negotiation or your messaging, whatever it might be.
But it helps you identify where different sales reps might be struggling within different pipeline stages.
Mark Winter:
Yeah. And since you brought up pipeline stages, let’s put a plug in here for Avionté. One of the things that is so easy to do in Avionté is change the pipeline stages. So, you can make that reflect your business, and that’s a mistake that I see people do is they don’t.
Now I’m not saying you’ve got to go crazy and put 15 stages in there, but it should reflect the way your people sell, so that you know what’s expected at every stage. And your people should know what they’re expected to do and what the exit criteria is for each of those stages.
That was one of the things that I put in my deck at Avionté CONNECT: every stage of the pipeline should have exit criteria. So, you create a set of stages; let’s say you got five or six, right? And when I’ve had a discovery conversation, and the customer says, This is something we could use,” it doesn’t mean that they’re committing to an order, but they’re like, “Yeah, this is something we could use. We could have another conversation.”
Great! Now I can move out of that discovery stage into my advocating stage, or whatever you call that stage, the closing stage. So, you’ve got to make sure that it aligns. I get so frustrated when I show up to a client, and they’re managing a spreadsheet because the Avionté pipeline doesn’t match what they want.
Just build it that way. Just spend a minute and build it. It doesn’t even cost anything, for crying out loud. Then make sure that the stages go in order. One of the things that I see in the field all the time is when we start doing a pipeline review, we’ll see a person that shows up to a job site, let’s call it, three or four times.
So, they show up to a job site three or four times, and then all of a sudden there’s a submittal for a quote; an unsigned quote is sent out. And I’m like, “Okay, well, well, where’s the in-between?” Cause there are probably two or three steps in between, like developing new contacts in the business or doing some sort of discovery.
And what’s happened is they’ve compressed the process. The salesperson has deviated from the process. So, they went from marketing and engagement to, boom, I’m actually going to propose a close. That’s what sending a quote over is doing: proposing a close. And then they’re going to hope for the best.
So, the rest of the sales process is bunk now because we’ve already done step six in place of step two. I think that’s a huge mistake people are doing in their pipeline.
Casey Wagonfield:
I’ve always thought that once you have the meeting, if it’s a prospect you’re calling, “Hey, we have a need, and I’m willing to meet with you,” at that point it’s now an opportunity, or it should go into your sales pipeline, and to your point, follow those.
I had very similar ones. You know, it’s the introduction: they’re willing to meet with me. We’re putting them in the pipeline. Then we develop some type of solution or proposal, contracts, and then fulfillment. And I know a lot of people listening have been in the case where they thought they had the business. They get the contract signed, and it’s sitting in fulfillment, and they either never get a job, never fill the job, or it just never turns into business.
But being able to track that by stages is huge.
Mark Winter:
Huge. To your point earlier, it tells you where things fall off or where things get stuck. That’s another mistake is that leaders look at a pipeline, and they don’t know where things get stuck, and typically it’s in the same area for that salesperson each time, or a lot of times, but not all the time.
Casey Wagonfield:
When you were speaking at CONNECT, you had talked about effort, engagement, and advancement. And I thought that was a really useful way to look at it.
Maybe you could walk us through what those three things mean, and what should a sales leader really be looking for at each stage?
Mark Winter:
So, when I was putting the deck together for CONNECT, I was thinking about the real phases of a salesperson.
So, there’s a whole lot of effort that goes into gathering leads, making contacts. So, in Avionté, what we would do is we’d manage a contact, and we’d put a bunch of activities against that contact. Well, that’s all the effort, right? We’re trying to get engagement, but it’s a bunch of effort.
So, we’re trying to figure out who those contacts are. Maybe you’re using Apollo, maybe you’re using Zoom or RocketReach, or any of those tools out there. But you’re putting a lot of effort in gathering information so that you can then engage with those folks.
When we switch from effort to engagement, the difference is we have something for them, or we believe that they need something from us.
Either way is fine. But at the engagement stage, we’re now trying to unpack the question: yes, no, or not right now. So, every deal, every contact, every company that you talk to, I think in my head, there’s a flag: yes, no, not right now. And so, when I’m engaging them, I’m mining for that.
So, I might send them, I don’t know, wage articles, or I might just be persistent and make calls, and I might tell them about our process. I might say, “Hey, we’re a people-focused company.” Whatever it is that I’m trying to get them to engage. I’m trying to figure out: Do they have a need for us? And if the answer is yes, great.
If the answer is no, they come off the list. If the answer is not right now, they go further downstream. And then that helps me with advancement, because one of the things that salespeople tend to do is they confuse engagement and advancement, and they don’t know when to push the buttons. There are some companies that, if you just ask them, they will tell you, “We will use you, but we’re not going to use you till the start of the year.”
Okay, cool. Now I know why that thing’s not advancing, because I had proper engagement with them. I had that yes, no, not right now conversation. I can either pull it out of my opportunity pipeline, or I can just kick the can down the road with a new date, which is fine, so I can put a new close date on it for the start of the year.
And I still have to touch them during that period of time, but I know how that thing’s going to advance because of the type of engagement. So, I just wanted to have a simple framework for salespeople to say, yes, there’s an effort period where you’re doing all this gathering. There’s an engagement period where you’re sparking interest, and you’re doing that rudimentary filter of yes, no, not right now.
And then look at how your deals are moving. And if your deals aren’t moving, then go back to engagement. And if you’re not getting engagement, then go back to your effort.
Casey Wagonfield:
And everybody should know, for each company, where they sit in there, right?
Mark Winter:
Yeah, absolutely. And these get blended all the time. We have sales leaders that accidentally blend this. So, they’ll say to their salespeople, “Hey, what do you have that’s going to close in the next 30 days?” But that salesperson is squarely in the effort stage.
And so even if something closed, chances are it wasn’t a result of that salesperson selling. It might’ve been luck and timing, which is fine. I’ll take that kind of win all day long. But it’s not a result of that salesperson’s skill and knowledge.
Casey Wagonfield:
Right. So, I wanted to touch on whether companies are getting enough out of their current ATS or CRM that they already have. So, before somebody goes out and buys another tool, how much could most staffing firms probably get out of the ATS and CRM they already have?
Mark Winter:
So, the short answer is no, they’re not getting enough out of the ATS and CRM that they already have. But there are a couple of reasons.
One is knowledge. So, I can’t tell you how many times I’ve had a conversation with someone who says, “Uh, yeah, we’re kind of using the Avionté CRM. I don’t know how great it is.” And so, then my radar goes up. “Well, you don’t know how great it is. Okay, cool. Well, what do you know about it? Like, how do you use it?”
“Well, you know, there was a training class two years ago, but I didn’t go.” “Okay. So, let’s just start there.” And 80% of the time, the things that they thought the CRM was incapable of actually exist in there, or there’s a way to get it done. They just didn’t know.
So much of it is a training issue. They just don’t know, and they don’t bake the time into their schedule to learn. So, you’ve got to learn, and you can’t just pass that off to your salesperson. If you’re a sales leader, you’ve got to be the knowledgeable one to pass that information and coaching on to your salesperson.
You can’t expect your salesperson to call in for a help ticket or whatever. So, you got to be training that stuff from jump street.
The second thing is they don’t know what they truly want their ATS or CRM to support. So, they’ll say things like, “Hey, I think we ought to move to HubSpot.”
“Okay. tell me more. ” What are you doing right now that your current CRM doesn’t support that you think you would get in HubSpot?” And they’re like, “Uh, I don’t know, but HubSpot looks cool. It’s very user-friendly.”
“Okay. Sure. So, before you go writing off what your CRM can or can’t do, you’ve got to know what your process is. Your system should be supporting your process. And if you’re a company that’s really focused on marketing automation, let’s say, I’ll use that because I know HubSpot’s really good at marketing automation.
Listen, Avionté can send emails right out of the CRM. You know how many people don’t know that? A lot. Okay, so if your salespeople are the ones sending the emails and you don’t have centralized marketing automation, then the Avionté CRM’s probably fine. If you’re going to do 1,000 emails a day through some tool, and you need HubSpot to manage it and lead score, okay, well that’s a different animal.
But tell me that. Don’t just tell me that you want to go to HubSpot because it’s more user-friendly. Know what the deficiencies are, know what you’re shopping for, and that’ll help you decide what CRM you need or even if the capabilities exist in the CRM that you have today.
And most of the time, the system’s good enough. We’re just getting enamored with flashy lights and the latest and greatest technology. For 80% of staffing sales, basic CRM, CRM 101, is good enough. So, before you go laying out six figures on a new technology tool, be careful. Know what you actually need to get supported.
Casey Wagonfield:
I remember years ago, talking to the Salesforces and HubSpots and the Microsoft Dynamics, and none of them at that time really played well with VMSes. So, you had to purchase them and the integration to link them together.
Then you have two systems. So, which one do I put the data in? Which one is the system of truth? And to your point, after doing all that, we just simply asked the ATS we were using at the time, how can we best utilize this for our salespeople and sales processes? And I think that’s the question that listeners should take away: go to your ATS and ask them, how can my salespeople be the most productive using your tool as a CRM
Mark Winter:
Totally.
There have been a number of times where I’ve leaned on the Avionté team. I’m like, “Hey, my customer’s doing this thing. How do we get it done?” And they’re like, “Oh yeah, that’s easy.” Click, click, click, and boom, it spits it out. And I’m like, “Oh, well, okay, so we just had a knowledge issue.”
One other thing that I want to touch on here, Casey, about this: Are they getting enough out of their ATS and CRM? You cannot under-invest in this stuff. And I think people underestimate the cost. So, they hear things like they’re going to try a new CRM or something, or they’re trying to get a new tool like an Apollo or whatever, and they hear the seat license cost and they kind of waffle.
They’re like, “Yeah, all right. I guess we can swing 1,500 a month,” or whatever the cost is. Listen, whatever you’re told by a technology company, I would double it. I would double the cost. And that’s just Mark’s rule of thumb. There’s no science behind that. But I do that because then it gives me a little bit of a buffer for things like integrations, add-ons, bells and whistles. B
Because what happens is, let’s say, I’ve got a client that’s got Avionté, and they’re using HubSpot. Well, they bought the base model HubSpot. And so now they’ve paid for a CRM outside of Avionté, and it still doesn’t do what they want it to do because that’s in the Cadillac package.
They got themselves a Toyota Camry, and they should have paid for the Cadillac package. So don’t under-invest in these systems. Make sure you’re really clear about what you want it to do, so that whatever system you buy actually does it, and budget appropriately. This idea of, “Oh, we’re going to grow into it,” is bunk.
You’ll do brand damage before you actually get it off the ground.
Casey Wagonfield:
So, I want to also talk about when another tool actually makes sense. Because you’ve made the point that the first question shouldn’t be: what technology do we need? It should be: what are we actually trying to do?
Mark Winter:
Yeah. New technology makes sense when you’re going to create process efficiency. So, if you know what your process is, and you’ve got that process measured, and you see a way to make that process faster, better, or more productive, then explore technology to get that done. That makes total sense.
That’s when you should do it. So, if you have a team of 25 salespeople out there on the street, and those 25 salespeople are spending X amount of time putting data in a system, let’s say they put four hours a week of measured time putting data in a system, and you feel like, man, those four hours a week could be used for productivity, and there’s a technology tool that could save me two of those hours, great.
Then start exploring, do a proof of concept, and start looking at that technology. That’s a perfect use case. So, efficiency is the first place, process improvement for sure. The other thing is whether it can help you engage with your customers better in the way you choose to engage.
So, if technology will allow you to get more in-person meetings if you’re a people company, or if technology will allow you to push better branding out there to build better relationships for your technology, then great. Then do that.
Casey Wagonfield:
When we talk about does technology actually makes salespeople better, most people know the answer to this if you have some common sense. But if I give a salesperson ZoomInfo or Apollo, like you mentioned, or LinkedIn Sales Navigator, AI, and a sequencing tool tomorrow, does that actually make them better at sales, or does it just make them faster at doing bad sales?
Mark Winter:
It can do both. You know what makes them better is training, and I know I’m a training guy, so I’m going to say training. But what makes them better is actual training, because training is, tell me, show me, let me, coach me. That’s the training path. So, I always say, you can’t learn how to make a grilled cheese without flipping a grilled cheese in the pan.
You can watch a video on it. You can see someone else do it. You can look up what’s the best cheese to use, and should I use mayo on the bread instead of butter? You can know all of that, but until you flip a burner on and put a grilled cheese in a pan yourself and get a feel for how it goes, it’s never going to click.
And I feel like the same thing with these technology tools; we stop partway. So, we do the tell me, show me part. We don’t follow through with the let me, coach me, and that’s where people get better. So, they get smarter with the tell me, show me, but it’s the let me, coach me that’s the flipping of the grilled cheese.
You know what I’m saying? So if you’re going to use these tools, and you’re going to make your people better, you have to follow through. You have to be with them on the follow-through. You’ve got to say, “Okay, here’s the tool. Here’s your list. Curate your list. Now make 100 dials. You used to get one appointment for every 100 dials. Let’s see if you get two or three. If you do, then we’ll know the technology’s working, right? Then we’ll see it.” But you’ve got to take it all the way through the process.
Casey Wagonfield:
100%. You know how many grilled cheeses I’ve burnt until my wife coached me?
Mark Winter:
Yep. So, I think the short answer is technology alone is not going to make people better.
In fact, you run the risk of just confusing people or causing brand damage yourself because your folks are going to get list after list after list of people that they can just blindly send emails to, or they can just dial for dollars, and that could actually have a negative impact on your prospect list.
So, be careful with that. Make sure that you’re getting the results that you want with the tools that you put in play. Follow through all the way from initiating that tool to using the tool to seeing the results of that tool.
Casey Wagonfield:
There’s so much competition in those types of services nowadays. You’ve got to shop around. They all have similar data.
Now, I did want to talk about using technology to find a real person to call, and this is probably the part I care about more than just getting somebody’s contact info.
Anybody can get a name, an email, or phone number now. How do you use technology to figure out who’s actually worth calling, and what the reason is to call them?
Mark Winter:
Let’s say I’ve got ZoomInfo. I’m going to use the technology of ZoomInfo to curate a list around my ideal customer profile.
So, I’m going to take my ideal customer profile, and I’m going to find companies that look like that. Then I’m going to find buying roles in that organization that match how I sell. That’s going to get me my list.
Then I’m going to look at, okay, based on what I know about this company and the fact that they’re an ideal customer profile, what’s the highest likelihood they would need us for? So that’s my reason to call. That’s where I’m starting to develop the reason to call, based on my prior experience in that industry or prior experience in that niche or whatever.
And then what I want to do at that moment is get an agreement with leadership or a sales manager to say, “Okay, this is what I think is a curated list.
This is what I think it looks like. Here’s what I’m thinking about using for a script. This is my step one, step two, step three.” And by the way, you’ve got to get past step one. You’ve got to have your first few steps mapped out because we already know it’s going to take more than one call to get people.
So, I want to get it mapped out, but I want to get it agreed upon with my sales manager. And you might be asking me, “Well, that seems clunky. Why would we involve the sales manager here?”
Because it’s the sales manager’s job to make sure that I, as a salesperson, don’t spin my wheels, that I’m not going after something that we’ve already chased or that we know is going to be a dead end. I think about my early days in staffing.
One of the things that I did accidentally during my first month in staffing is that I closed a 100-person order at a call center. We were not equipped to service a call center. And, had I known that, had I had that kind of coaching and guidance, I would’ve saved a ton of time and embarrassment and frustration on the customer’s part.
It was an abysmal failure. It was good learning, and I never forgot it, but it could have been nipped in the bud at the moment we were building our list. So, as far as finding a reason to call, now there are all kinds of tools out there that show buyer intent. So, stuff like Apollo will show you buyer intent.
It’ll show you companies that are making Google searches about staffing, contingent help, workforce management, all of those things. You can use all of that to your advantage. But we all know the first call that you make has to be something that’s providing some kind of help or offering something or giving something.
Otherwise, you’re just going to sound like every other salesperson. So, to boil down that question, use the technology to help build the list. Use the technology to help define who the buyers are within the organization. Use the technology to ensure that it matches your ideal customer profile.
Get alignment with whoever your internal hierarchy is to ensure that that’s the right list to chase. And then, start to look at multiple calls around buyer intent and try to find reasons that they’re sourcing staffing.
Casey Wagonfield:
I love that. And it leads into the next question, because you can’t talk about tech without talking about AI. And I think AI could certainly help with some of those things that we just talked about there too.
There are a lot of AI tools being pushed at sales teams right now. What are you seeing salespeople using AI for today that you think is legitimately making them better? And on the other side, what are they using it for that could actually make them worse?
Mark Winter:
So, there are a number of tools out there that record conversations, like sales calls, and they provide outstanding coaching. I mean, they really pick up on some great stuff. So, I think that helps make salespeople better. I’m a fan of using tools to develop a transcript for meetings. Obviously, you’ve got to let your prospect know that you’re doing that, that you’re transcribing, but I use it for my own coaching all the time. I’m seeing nuggets of things I can do better, or word fillers, or it monitors things like, do you talk too much? Are you asking enough questions? I think all of those things are great, and AI is awesome for that.
AI is helping us build lists at a rapid clip, so it’s helping us figure out who’s where and who’s doing what and who’s using staffing. And so all of that is great on some level. It’s making our job a whole lot easier.
It’s given us insight into companies. Nothing’s sacred anymore. We can find out anything about anybody. So, that’s great. Don’t be a stalker, but that’s still cool. Use that to your advantage. As for what salespeople should be cautious about, AI runs the risk of making us dumber.
I feel like some salespeople are disconnected from their own messaging. There’s something about sitting down to an email and crafting that email for a specific person. Like, I’m getting ready to write a couple lines to Casey. Put a little joke in there, or I might put something that was unique between the two of us; there’s something about that that connects me to that moment, and AI strips us of that.
So, if you’re the type that just has AI do your emails and then you’re just sending them as written, that could actually make us worse, because you’ve got no skin in the game, and I think a salesperson needs to have that palpable feeling like, ” Man, I hope I get this. I really want this thing. I want them to respond.”
Well, you get that because it’s so personal to you. If you’re letting AI do all that work for you, it’s no longer personal to you, and you’re like, “Oh, I’ll check my email box later. Hopefully something shows up.”
Casey Wagonfield:
Yeah. But I think there are also ways that have AI in those scenarios.
If you have a call with somebody and you run that transcript through AI and say, “Make sure I’m not forgetting anything on my follow-up here. Bullet out what I need to follow up with this person to help you at least generate a better email on your own.” I think those could be huge for people who need that type of help.
And you already touched on that, but AI for research and prospecting; I think that’s really from a sales perspective, where people can really have an advantage by using AI. So, using AI to look at a company: what’s going on there, their hiring trends, any new locations they have, leadership changes, potential problems they have, labor demand indicators, or active staffing signals.
How much do you think that changes the way a good salesperson should prepare before they reach out?
Mark Winter:
Yeah, I think AI helps us get really smart about what’s happening behind a closed door. So that’s cool, that’s awesome.
But isn’t the magic of sales getting the door open? That’s the magic. So, get educated, use it to tip the scales in your favor. I always use The Hunger Games; you’ve got to tip the odds in your favor as a salesperson. You need all the advantages you can get.
But you’re still looking at a closed door. You’re still sending emails into the void. You’re still sending texts to who knows what. You’ve never met the person. There’s no substitute in my mind for showing up at a networking event. Any town, USA, any staffing company, any type of staffing, the first question I’m going to ask as a new salesperson is, “What type of networking are we involved in?” Because you want to go where people are hanging out, and networking gives you at least a peek through the keyhole. You at least get to see what’s inside the door, because you’re talking to people. You’re getting a real conversation.
Even if they’re people that aren’t going to buy from you, they’re giving you insight. They’re being a little bit of an informant. It helps you get a better visual of what’s on the other side of the door, and you couple that with AI, and that’s unstoppable.
Now you can be educated about what’s going on at that company. You can see what’s in the news. You can hear what they’ve done in the past. AI will give you prompts and good discussion topics to have with people of the right level, so you’re ultimately prepared.
You’ve got all the tools in your tool belt, and then you show up at some kind of networking event, and that door cracks open for you a little bit. That’s gold. That’s great.
So, my advice is just keep it in perspective. Keep the AI and research in perspective and know that it’s not going to be a substitute for action.
Casey Wagonfield:
Networking will always be my number one. Nothing like getting in front of somebody face-to-face. And I think, yeah, you want to use AI to do some research, but there’s a line between doing too much research and doing just enough research to sound different. That’s something we came across on the Staffing Made Simple podcast: when talking to buyers, they really appreciated it when somebody called them and had something unique to say about their business that they knew.
They did the research, and they were able to tell them something about their business, which set them apart from the other people that called and were saying the same things.
And when we talk about automating too much, there’s another side to all of this. We can automate emails, LinkedIn, follow-ups, and let AI write the message. At what point do we just automate ourselves into sounding exactly like everybody else?
Mark Winter:
Yeah, it goes back to that first question. We’re kind of coming back to where we started: the people, process, technology. If your whole thing is automating processes, well, that’s great.
I don’t know that you can automate too many processes, so that’s awesome. If you’re on the people side of things and you’re automating to the point where it’s separating you from your customer, then you’ve automated too much.
So, I don’t know that there’s a blanket answer. I think it depends on whether you’re people-, process-, or technology-focused, and align your level of automation to those three swim lanes.
Casey Wagonfield:
And for sales leaders that are listening right now and coaching their people, if I’m sitting down with my team every week, what should we actually be talking about? What should I be coaching instead of just looking at all the calls and the emails and accounts and activity numbers?
Mark Winter:
Okay. First question of every sales leader: this is my dream. They walk into a branch, or they pick up a phone, after you get past all the pleasantries or whatever, the first question is: What can I help you get across the line today? What can I help you close? That’s the question.
That’s the goal, isn’t it? At the end of the day, that’s the whole thing: how can we realize some revenue? So, if sales leaders started every conversation with that, it would really send a message that movement through the process is the important thing, not just activity.
Even though we measure activity, movement of the process is the important thing. So, if I were a sales leader, I would say, “What can I help you close today?” And then I would say, “What’s new? What have you brought into your pipeline that’s new?” Because you’ve got to keep that pipeline full. So that way you’re working both ends.
I would then focus on the sales process. So then if you’ve got time, dig into the sales process. Pull up Avionté, go into the system, pull up all your opportunities, and just do a debrief on each opportunity and figure out where they are and what it’s going to take to move them to the next phase. That’s the best thing you can do as a sales leader.
Casey Wagonfield:
I agree. And as we bring it home here, I want to make this practical. So, if I’m now running a staffing company, sales need to get better. I don’t have a huge budget. I’m not buying six or more tools, and I’m not hiring 10 more salespeople. What are a couple of things that you’d tell me to focus on first?
Mark Winter:
Start with your sales process. Know what things are supposed to take how much time. So, if you start with the leads, make sure you have a lead process, a way for leads to get to you and to your salespeople. If you’re focused on opportunities, then make sure you’re doing pipeline reviews.
Make sure that your opportunity flow matches your actual process. Use the system. Don’t give up on the system, even if you think the system’s broken. Next time you do a pipeline review, jump into the system and let the system help guide you through the pipeline review. Because then you’ll be able to say exactly how the system’s broken or how it doesn’t meet your needs or what it needs to be tuned up or how it needs to be configured.
So, use the system to help guide that conversation. But process is key, so focus on your sales process. Know how long it should take you to close a deal. Make sure that you’re using up-to-date lists and tactics and all that stuff, but really it comes down to process. Focus on the process.
Mark Winter
Principal and CEO at The WinSource Group
Mark is an expert at driving sales performance, keeping focus on customers, and keeping things simple. He is a Six Sigma Black Belt and holds master certifications from some of the top sales training organizations in the world. Whether its strategic planning, sales process development, sales training, customer acquisition & engagement, sales team performance, or system and tool adoption, Mark can help get your team on track.
Casey Wagenfeld
Strategic Partnerships at Simple
Casey Wagenfeld leads Strategic Partnerships at Simple, an industry-leading VMS platform.
Modern technology has revolutionized the way we live, work, and play. It’s also what’s fueling the gig economy which has dramatically changed employment practices. So, what does that mean for staffing and contingent work? In our Avionté Digital Edge podcast series, we will speak directly with industry experts to explore topics and trends related to the digital transformation of staffing and temporary employment in the US workforce.
WorkN is now Avionté Mobile. Building on the power and functionality of WorkN’s talent mobile app, Avionté Mobile is built for the high-volume staffing and recruiting industry.
