Mat Singer is the Head of Sales Enablement at Upland Software.  He joined The Collaborator to discuss the role of change management in the Enablement process.

Mat took the time to guide us through the key steps required to consistently achieve adoption and deliver on the expected changes.

1️⃣Start with a defined need, sales execs agree on the priority/ urgency and it supports a top strategic goal for the year

2️⃣Build executive alignment on the solution, timeline for implementation, their role in supporting the initiative

3️⃣Build alignment with second level sales leader. If you need to design/ configure, get leaders and SMEs involved so they’re bought in.

4️⃣Craft a communication plan

5️⃣Implementation.  Key points are to have champions, stay with it to deliver full adoption, and train and remind of why this matters.

6️⃣ Reporting.  Baseline current state, track, and report horizontally and vertically.

7️⃣Depending on size, commit resources long-term as many changes require long-term process and people support to become adopted and create the desired changes.

So much goodness.  Give a listen and remain curious.

Audio Transcript

Mat Singer
for inviting me, I really enjoy conversations like this. So I’m excited to join.

The Collaborator
And I’m super excited to have you on. I know, for our listeners benefit, I’ll say that you told me you’re up in the mountains of Colorado, with average Wi Fi. So please, if things get a little disconnected, bear with us, I know it’s going to be worth listening to all the Matt has to say, regardless Now, now, Matt, give us a little bit of a background about who you are, where you you know, what kind of work you do and all of that.

Mat Singer
Yeah. So I’m about, you know, eight, nine years into being a sales enablement professional. I carried a bag before direct sales and also worked in operations as well in various capacities. But sales is my passion. I ran a large sales effectiveness team at CenturyLink for about seven and a half years, and then joined up on software in January. And I report to our president and chief Commercial Officer, Rod fab Ron. And my scope is pretty broad. As a relatively small company, I get involved in m&a, sales strategy, territory, planning and design. Really, tactical programs, solve specific problems for our different sales teams, even down to building reports and dashboards when necessary. So some days I can be doing sales strategy with our sales leaders, and some days building a dashboard on so productivity. So

The Collaborator
I’ll just say for me, that would be a blast, you’re never doing the same thing twice, or certainly not two days in a row, which is, which is amazing. I got to imagine and I got to ask you, it’s gotta be nice to there’s probably pros and cons, to reporting into the president of the company. You know, for people wondering about that anything you can share?

Mat Singer
I absolutely. I’m blessed in that at my last job at CenturyLink. I reported to Lisa Miller, who was the president of one of the sales organizations. And I tell you, his sponsorship is so critical when you want to get initiatives approved, if you want to buy software tools, services, sponsorship is absolutely such a key ingredient. So I’ve been at lower levels trying to fight my way out at the table. So I can be influential and help guide a sales organization. And so I think I’m at the right spot, because with the right amount of executive support, I can actually implement change. I don’t I don’t like running on a treadmill, I like really, you know, driving meaningful change.

The Collaborator
I like having a phrase that way running on a treadmill. And that’s what a lot of enablement teams are doing. We’re just running in place being busy all day long, and not necessarily moving the needle. So it’s nice to be able to have that person that per view at that right level in the organization. That is the team. I forget, though, is that a team of one? Are you a team of one today? Or do you have multiple people working with you?

Mat Singer
Yeah, the biggest change in this particular stop in my career, I went from having 100 person to my last job to being an army of one right now. I, I am kind of matrix and I partner with our fairly large business systems and sales operations team. So there’s numerous leaders over there, and there’s probably 50 people in that department. But for the strategic contribution that I have, and what I do, yeah, army of one right now.

The Collaborator
I gotta go off off topic for two seconds. What was the like running a team of 100? Was it all enablement? Was it enablement operations and multiple roles?

Mat Singer
Yeah, it was a combination of a bunch of sales systems support people, IT support the development of Salesforce and aptus. And in homegrown CQ, Doc, you know, we had Adobe sign at the time, but yeah, electronic signature. So really ongoing support for development day to day support, I had a quote team. So like, I’m sure you find in other companies, the definition of sales enablement, sales operations is so fluid. And in that in that iteration, it was a big team and, and that was fun. It was great fun managing that scope. And at this iteration, it’s just a smaller, newer function at upwind. And you know, I’m doing my best to demonstrate the value and to get more resources invested in our sales organization in this capacity.

The Collaborator
And the reality is most of most enablement. Organizations, I believe are teams of one or two people. There’s rare exceptions. When you start to get Big and bigger than that. And I think that’s when you, you’re working in a large enterprise, and you’ve been able to demonstrate the power of what you’re doing. So I’m sure you’ll get there. Talk Talk to us about change management, though, Matt, you know, one of the things that you and I talked about was, how important it is for enablement. In general, how do you do change management? or What does it look like? It’s probably a better way of asking it at upland.

Mat Singer
Yeah, I’ll reflect back on where this became so important to me, at my last stop and have brought over those lessons learned is implementing changes is relative, depending on the size of organization that you’re impacting and affecting, at CenturyLink. We had 2000 global sales people. So any programmatic change that was intended to benefit that many people was a huge deal, like you to to effect change at scale is a whole nother ballgame. And so I really learned many different, you know, lessons learned along the way, at upland here, we, let’s say we have about 100 125 people with selling responsibility, direct account sales or customer success with a quota. And some people say, Well, that’s a lot of people, you know, and I say, Well, you know, it’s relative, it’s really not a lot of people. Challenges are the same, how you go about impacting change, which I can go into, people are still people, whether they listen to how you’re communicating, whether they want to change or not, you know, many of those things that you have to overcome,

The Collaborator
was gonna say, are you using? Or have you used more formal processes like, or approaches like add car? Or, you know, from Pro psi or other kinds of methods? Or is it mostly just Well, I understand how humans work, and trying to drive them through a more formal and rigorous process, how have you typically done it?

Mat Singer
So I, I have certainly been through training classes on formal change management approaches. And I think, what I’ll what I’ll share with you is just more of my personal approach of what’s worked and not worked. And if you want me to dive in, I’d love

The Collaborator
to have him back. Yeah, let’s go as deep as you want to, because I think that’s where people really get a lot of value from it. So please feel free.

Mat Singer
Yeah, so the first thing is having a very clearly defined need. But the interesting experience that I’ve had is, I am solicited by people want to sell me something constantly. And earlier in my career, I would entertain far too many solicitations. Oh, that’s interesting. That’s interesting. I love technology, that’s cool. But finding a technology or finding a need to match a technology is really, really hard. It’s like 1000 times harder. When you have a defined need that you’re starting with, that your sales executives agree I agree with you on. Okay, great. Now we’re somewhere executives have bought in Yes, we need a we need a solution. It’s a priority, if it can align with a corporate strategic priority, or an initiative. Wonderful, that’s exactly what you need. And then of course, you need funding to be able to whether it’s staff, software, services, consulting, whatever it may be. So the executive established, establishing a defined need, having the executives completely bought into that need is the starting point. Because really any meaningful long term changes, I kind of refer to it as if you’re changing the operating system of sales, you are going to expect a multi year effort. Here at upland, we have an account management tool, I’m implementing that account management tool account planning tool within our own team, we happen to sell the software, we also are implementing it, this is going to take a year or two to get truly ingrained in how people operate. And so with sustainable long term change, you need executives, executives to be bought in to that change. So can I so that’s kind of bad because

The Collaborator
I agree with you completely. I think if you don’t have an executive sponsor right at the beginning, you’re doomed. You may be doomed. It may take a long time or a short amount of time, but you’re doomed. Do you ever think it makes sense for and just from an enablement perspective? Does it ever make sense for enablement to say, I’ve got this cool idea if it’s not tied to something that the executive team is worried about,

Mat Singer
Oh, I definitely think that proposing ideas, there’s no question about it. I think that that’s, that’s helpful. I guess what I, what I found is that when you’re going to look for a big investment, then it needs to be at a high enough strategic priority for, for them to prioritize the funding. Now, if I say, hey, I’ve got some new productivity dashboards that I’d like to roll out, they’re like, Yeah, I love that idea. Yeah, I don’t have to pay a zillion dollars for it. So. So that’s, I think that’s maybe the difference is, they’ll still take? Yeah, yeah.

The Collaborator
And and it’s a lot of ways to me it’s a similar to if I’m going to go sell a solution to you, I bet are tied to a sufficiently expensive pain point for which you are going to want to spend money to solve it. Otherwise, go away.

Unknown Speaker
Very well said.

The Collaborator
Yeah. So that makes a lot of sense. What else? So executive sponsorship, understanding their pain? What else? What else does the process look like to really drive this long term change path?

Mat Singer
So then, then you go with the, you get the next layer of leadership aligned with, okay, here’s the program, here’s, here’s our approach, here’s the value of what we’re intending to accomplish. And here’s a timeline and how it will affect your sales team. And so that second tier, buying in sponsorship is also important. So if you want something indoctrinated into a weekly, daily, monthly behavior, the sales leaders are those who are going to have that reinforce. And so that second tier sponsorship along with here’s the plan, here’s what to expect, here’s the time I need from you, and from your sales team members. That’s, that’s the, like the essential next ingredient.

The Collaborator
How do you do that? Well, in your opinion, map, you know, whatever, whatever the change is, but you’ve executive team is excited. They’re like, yeah, Matt, we need to solve that. How do you bring that to the leadership team, or the next year as the the sales manager here and say, guys, here’s, here’s what we want to do.

Mat Singer
Um, you know, I think sales enablement, people have to be non stop evangelists, when it comes to any meaningful change. Yeah. And so, I’ve, I’ve said many times, I sell, like a software tool 100 times more often than the sales rep sells it to me, because I’m selling it over and over again. So when I meet with people, I don’t it again, it’s something meaningful, not just like, Hey, I’m gonna roll out some dashboards, then I have to explain to them, why do I need your time commitment? Why do I think this is valuable? And I have to be passionate, I have to know what I’m talking about. Why?

The Collaborator
Yeah, exactly. Exactly.

Mat Singer
Yeah. And so yeah, so that evangelism is such an important part of it, and, and knowing what you’re attempting to accomplish. And so I think the next next ingredient is having a good communication plan. Now, that goes out to the field. So next thing is, people consume information in different ways. So my learning through over time is, we can email and we’ll get a certain percentage of the audience, we can have an all hands call where their sales leader says, hey, we’ve got this new great program, a new methodology, a new planning tool, or whatever it may be. Okay, all hands, some percentage, listen, we’re gonna post it on the internet in an article. So now we have multiple channels at which we communicate. And then we have to repeat ourselves because even those who like to read the email or watch the replay, or watch the live all hands, still not everybody was there that day or whatever, they couldn’t make it that a customer call. So you got to repeat multiple channels, repeat your communication. So it connects with people who prefer to learn and listen in different ways.

The Collaborator
I think that’s so important, Matt, whether it’s a team of 10, or a team of 1000 that you’re trying to reach, because even if they heard you three times, they may not have actually understood or absorbed it or bought into it three times. So I love that message. Just keep putting it out consistently across multiple channels. What else? I love this.

Mat Singer
So the other part of the next ingredient is having champions. So for I’ll just use the account planning example. If you have a template. I can propose a best practice template, but if I get a bunch of champions involved in designing the template, not I’ve just recruited other evangelists. So I’m bringing in people who can kind of make sure it’s in the language and does According to the what these experts, you know how they think it’ll work best. Yeah. And then I’ll make them cheerleaders as they go along, because I’m like, Listen, you guys are the ones who helped design this. And and you need those cheerleaders and evangelists within the ranks. So when, when I’m not on stage or you know, proverbial stage, doing my song and dance, when they’re actually in a team meeting going through, well, who the hell out of this a comp plan? Well, we, we worked on together.

The Collaborator
Exactly. Yeah. See, that’s Ukraine advice, too, because you’re right, you’re not gonna push it through all by yourself. You need to get people to join the, to evangelize, as you’ve said multiple times on that journey with you. So that’s awesome.

Mat Singer
Yeah. And then I would say, Pro, the next thing is, again, I mentioned operating system. So if you’re really doing something that’s meaningful over over time, you’ve got to have a plan to stay with it. So that it is adopted. So it’s incorporated into how people operate. And there’s a lot of different ways to do that. One of the ideas and things that’s been successful for me is to have coaches. So you can have a coach that has and let’s, let’s differentiate between a coach and a trainer. So a trainer is going to teach you the methodology or teach you the new, you know, territory planning tool or the new, you know, a comp plan tool or whatever. But when you start using it, then you have the questions and you really start to apply. Okay, how do I use this? What’s the really the best way to do it, that’s when one on one or small group coaching sessions really help people rationalize and get it clear why this is beneficial. It’s a great reinforcement tool. And then it helps them sort of move past that early. I think I kind of remember what it was in training. But now i’d really, I get it now. This is the coaching session really helped move that, analyze it

The Collaborator
to yourself to your situation, it starts to you start to connect with the information better. Yeah, that by that? Yep.

Mat Singer
And so the long term plan also incorporates data. And when you justify your solution, you you start with, like, business, big business case, things like improve win rate by X percent or shorten sales cycle time. But I, my belief is you start with adoption, or usage. Are people using it? How are they using it? How frequently? What’s the scope and scale of how people are using it? jumping to win rate to quickly when you’ve got like half of the group actually adopting it or last is sort of false positive on whether it’s a successful program.

The Collaborator
I agree, if you’re trying to drive some meaningful change, and only a quarter that people are using it? Well, that may be okay for some situations, but it’s probably not for the vast majority. So driving adoption of prime is so important. So I love that as well, Matt. Yeah.

Mat Singer
And then that reporting can be both communicated to the frontline sales leaders. But also, you’ve got to have executive readouts, you can keep your exact spot in and sponsoring. So I have a recent example, I sent out an internal email, I said, Hey, here’s how we’re doing on on this rollout. And here’s some things I need from you sales leaders, here’s some reminders on training content that you should share with your team. right afterwards, my boss, again, President replied all and said, I fully support this initiative. This is a priority. I want everybody to stay behind this. And this is six months in. So I mean, that’s, that is the perfect response from an executive sponsor.

The Collaborator
Oh, it’s awesome, too. And let’s be honest, people may or may not pay attention to you or me as our in our enablement roles, many will. But there’s certainly more people are going to pay attention to the boss. When they say this is important, do it so that that’s absolutely powerful. What have

Unknown Speaker
you ever been? I’m

The Collaborator
sure you have I know I have we all have. Have you been in this situation? We rolled out a project, it seems to be going well, but adoption sort of sticks. You know, it’s the six or like 40 50% and you’re like crap, I just can’t seem to get over that hump. And I know there’s a million reasons why but I’m curious if you have any thoughts on how to approach that, in general.

Mat Singer
Yeah. Yeah, I can absolutely relate to that, again at CenturyLink with that scale of organization It’s, you know, it’s not the military, you don’t have a absolute command and control, you know, chain of command all the way all the way down to the

The Collaborator
gunnery sergeants to run around and go, Hey, do this. Yeah, it’d be awesome. Yeah.

Mat Singer
My suggestion is, you go back in and within reason what’s practical go back in and sort of re optimize, find out? Is it just because your first version of what you designed for that, let’s territory planning tool or complaining to whatever, maybe it just wasn’t working over complicated. It’s not uncommon where those group of subject matter experts, they overcomplicated it? And you’re like, Listen, I’d rather have less features and more adoption. And so go towards simplifying. And and then see, all right, everybody, does this work better for you? Now we cut out some of the complication and some of the extra work, right? There’s some optimal point there of effort where people don’t feel like they’ve gone over that limit of actually wanting to do it.

The Collaborator
Yep. That’s great advice. Any other any other final steps that people should be keeping in mind, Matt, as as you’re going on this journey of rolling out change?

Mat Singer
Yeah, I think if if it is one, one of it’s significantly long term, you’ll find that leaders come and go, and new employees join along the way. So you’re going to have to have an education program for the new employees, typical sales org may have 10 to 20% attrition. And so you got to account for that in your plan. And you got to account for sort of reselling important sales leaders, and then rolling with the changes, because sales, sales teams reorg, and, you know, change direction, probably far too frequently than we would like. But yeah, this has to be nimble and accommodate for those things.

The Collaborator
So true. And you’re right, the turnover rate in the sales team is, is high, compared to some types of organizations. What do you do? I’m curious, your thoughts on this one, because this happens a lot to your champion leaves.

Mat Singer
Yeah, it certainly happened. Um, if you’ve done a good job, getting buy in at the next tier of leadership, and having evangelists and champions within the ranks, you’re not so critically dependent on the one executive sponsor, it does come back at renewal time, where you may have to resell reestablish the value of the investment. But, you know, don’t don’t put all your money on that one single leader, and you won’t be so susceptible to that change.

The Collaborator
That’s really good advice. Do you recommend, you know, I’m thinking, let’s say it’s a software tool you just bought, seems to be helping the business, but the new new person comes in and they’re like, screw that. I’m not interested in that. Digi try to rewind back to the original pain point and take them back on that journey that you went through? Is that a good process? Or do you try other things?

Mat Singer
Yeah, no, I know, it’s a good suggestion, you’ve got to recap where you started and why you are where you are? Yeah, you’ve got to, I think, be effective at beyond the monitoring, usage and adoption, monitoring the return on investment. So if you’ve got that positive, credible set of, you know, evidence of return on investment, it’s not so much of an emotional thing. Like I like that methodology. I don’t want to use that methodology or whatever, is like, Listen, we’ve got a program we’ve invested all this time. You know, here’s where we are, here’s the benefit that we’re getting. So I think I think that data and evidence is what helps you convince a new leader to stay the course.

The Collaborator
Love it. Love what happened. We talked about that along the change management journey here that we’ve gone on. Are there any other things that you’d like? Geez, I want to bring this up before we end the conversation.

Mat Singer
Yeah, I would say back to the point about measurement and data is baseline as best you can document not only just measure what you can but also get anecdotes and get qualitative information about how people are doing their jobs, because return on investment in my book is a combination of the data that you can demonstrate, win rate, sales, cycle time, more opportunities, bigger opportunities, but also namebrand customers that you’ve won, what are the deals and quotes from leaders or reps who say this is how it’s changed how I do my job, in that combination of sort of the anecdotes and the examples of credible people and credible customers, along with the data can really make for a very strong knowing story.

The Collaborator
map that that that’s a huge point. And thank you, thank you for bringing that up. It’s not just about the data in the CRM system. It’s also about how people are feeling out there and saying how it’s impacting them for the better. You have to marry both pieces of data. Sometimes one is more important than the other. But But I think that’s so spot on. Hey, thank you so much for coming on today. Matt. This was amazing. And anybody listening, if you have questions for Matt, is it okay, if they reach out to you on LinkedIn? Not tell not to sell. But if you have questions about change management, I’ll say this, Matt, this was probably the most comprehensive and well articulated walkthrough of how to really drive change. I’ve heard in a long time, so I want to thank you for that. It was just fabulous and fantastic. So thank you. Thanks, john.

Mat Singer
Thanks for having me. This was a lot of fun. I really appreciate it.

The Collaborator
But I hope you enjoyed the snowy cold weather in Colorado. keep enjoying Alright, bye bye.

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