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Jenn gave this presentation in September 2019, when she was Senior Director, Global Sales Enablement, at Monotype.

During my career in sales enablement I’ve come to the realization that in order to be the ultimate sales enabler, we need to be the ultimate sales psychologist too.

In this article, I’ll explain how I got to this point in my role at Monotype, how I navigated joining a new team with a rich history but one I didn’t fully understand, how I built up all-important credibility, the importance of enablement and empathy, organizational behavior, emotional intelligence, and ultimately how to motivate a sales team by employing psychological techniques alongside sales enablement skills.

Sales enablement & part psychologist

I have this 84-year-old uncle from Boston. He's a former Boston Fire Department captain, completely enamored by the fact that he has a niece that's in this corporate field, he's always asking me questions about it.

I just recently made a transition from Brainshark to the Monotype team, and we were at my daughter's sixth birthday party and he's like, "So what the hell are you doing now? What's this sales enablement stuff all about?"

I start giving him the textbook definition and he's just looking at me, he has no idea what I'm talking about. Finally, I go, "Listen, I'm like a teacher for sales reps. I teach them how to be successful". Then I joked and I said, "And I'm also part psychologist".

At the time, I was joking about that. But as I made the transition from Brainshark to Monotype, I realized there was a lot of truth to that statement. We hear and read a lot of great presentations and articles about sales coaching, scaling programs, strategy for sales enablement, and I actually intentionally want to take a very different point of view.

I figure you'll either love it, hate it, or you'd completely relate to it. I want to talk about the fact that sales enablement is a little bit of a sales psychology.

Background and current role

I'm only going to focus on my past three roles - I'm actually coming up on my 20th year of having a career.


I worked at a company called Jabra, which is a headsets company. They had no training program at all and this is circa 2011 before sales enablement was a thing. By the time I left, five years later, my role had evolved into sales enablement.

It was all about making this program, certification, quantifiable metrics, so I used this software in order to do this and that software was Brainshark. Because I was a one-person show, I needed to be able to create content, I needed to house that content. I needed to have video-based coaching, and Brain Shark allowed me to do that.

When it was time to make a move, it made sense to go to that company. How cool is it to say, I'm in sales enablement, and I get to work for a sales enablement company? I had a rep at Brainshark come to me about 2017 and he said, "Listen, I have a really difficult sales enablement manager that I'm trying to sell into. She's a champion, but I don't think she's a champion, I can't get in her head, please help me get in her head".

So I did, I helped him get in her head and even I was like, "Ooh, that's a completely different sales enabler than me. But we're going to get this deal closed". And we did. Well, fast forward to this past March, that individual left the company and I was like, "What the heck, I'm gonna join Monotype" and that's how I ended up at Monotype.

That was the company that we sold into. I liked going to Monotype, let me tell you a little bit about it because it definitely ties into why I'm so passionate about sales psychology right now.


Monotype is a brand company. Chances are you've already interacted with our IP today and you didn't even know it. Monotype is really known for two things.

One side of the company is this business called Olapic -it's this concept of user-generated content. I wear my Swarovski necklace that my husband got me for Christmas. I take a selfie and I post it. Monotype's technology pulls that, gives it to Swarovski, now it's part of their campaign - that's about as dumbed down as I can give you.

The other one is fonts - who knew that fonts were a business? Selling fonts, fonts as an IP, is literally a $60 million a quarter business and I had no idea. I thought I knew about this company and then I joined the company and I was blown away.

You're gonna see us if you're working out and you're wearing Nike, guess where that font came from? You're washing your hair in the shower after you worked out. You're using your credit card to get your Starbucks in the morning. You get in your car and you see the GPS.

That's all Monotype.

I was joining this company that has this really rich history. Also, a company that is global. We have offices in Germany, the UK, APAC, Argentina, throughout the United States. Over 100 years of history and a lot of acquisitions, a lot of mergers, and in recent years, a lot of change.

Change is easy, right?

No. Here I am joining this sales enablement team that no longer exists, the foundation is there, but I had no idea the logic that was used to create it, because it's not my logic, and there was no one there to transfer that logic to me. Plus, I'm trying to learn this really unique business, where they've had mergers and acquisitions and a lot of change very quickly.

Building credibility

The below image shows the different things that us sales enablement people do in order to achieve what we're looking to achieve with our organizations.

Create stakeholders

Creating stakeholders, who are the stakeholders? Maybe the executive team, the senior leaders, the sales managers, do any of you look at your stakeholders as your actual sales reps? You should. They are your stakeholders.

I knew that to build credibility, I needed to create these stakeholders and I kid you not for the first month of my career at Monotype, I was in a call, one hour, back to back, nine hours a day for one month straight.

After each call, I said to them, "Please forgive me in advance. I'm going to have the same conversation with you three months from now so I can look at it from a different point of view once I understand the business better".

The most important piece of creating those stakeholders for me was taking everything that I knew about sales enablement, putting it on the back burner, and pretending I didn't know anything. That is how you're successful as a sales enabler when you're able to say just because I did something somewhere else and it was successful, doesn't mean I can come right in and do it here and expect the same results.


The other thing was communicating. I'm not going to beat a dead horse, we also do a newsletter. It's awesome. It's a great way to help your sales team and to communicate with them on a regular basis.

Present a strategy

A lot of people have talked about that. I just needed to make sure that not only did I present that strategy to my senior leadership team, but I actually shared it with my sales team as well.

I wanted them to know that everything we were doing was to help them so that as a company, we could achieve the things we needed to achieve.

Create a sales enablement movement

I needed to create this sales enablement movement because I got this vibe right away that sales enablement didn't understand them.

I've heard it said that sales reps don't give a shit. No, they do. They do give a shit about being successful. What they don't give a shit about is when you give them stuff that's not going to help them be successful.

Do yourself a favor, make them your stakeholders, and create this sales enablement movement around them helping you help them achieve what they want to achieve.

Implement quick hits

Let me tell you a story. The type business is really interesting. I walked on the sales floor the first week and finally, I took a manager in the room and I said, "What the hell's going on here? I don't hear anyone speaking. I hear no phone calls. What's happening?"

The response, "Oh, well, you can't sell fonts over the phone. It's all done through email. Nobody will take calls". I also learned that the company had just gone to this open office environment so now they felt like they were on blast being judged by their sales reps.

The first things I asked myself were:

  • How do I earn some trust?
  • How do I get some quick hits?

I decided to use a pilot group. I looked at that BDR inside sales team and I thought if I can throw some quick hits in with this team, then I can share their success and their results with the rest of the organization. It's going to create this buzz. Here's what we did.

I said I don't ever want to hear again that you can't call a customer. I don't care what business you're in, you can call a customer. If you don't feel comfortable doing that, I'm gonna give you exactly what you need to do that.

It started with a lunch and learn, a power hour session - how do you research and prospect? Another one - how do you do business communication? These were junior-level sales reps, some of them were right out of college. They really needed a little extra hand-holding when it came to how to communicate with customers.

Then it started with Thursdays - they did a call block from four to five and usually, they weren't making calls but I would literally sit on a file cabinet and they'd look at me and they're like, "So you're going to give me feedback?" I looked at them and said, "No, do you want feedback? I'm listening. I'm trying to learn the business. I'm onboarding here, you're helping me. If you want feedback, I'll give you feedback. But I'm not just going to force my feedback on you".

It was amazing, the reverse psychology of that, they wanted the feedback. We brought in John Barrows. I figured I don't want to just dictate to them let me bring in someone in the business that's known for doing this. Let's bring them in so they have a different point of view. Let's see what they get out of that.

Sure enough, here we are today. They didn't realize it, but at the time, I was building a program for them. We started to implement virtual roleplays, we started to do video-based coaching assessments through the Brainshark platform. After about three months, their LinkedIn connections increased to over 400%.

Okay, good, they're now using the tools, right? They were starting to show that they had mastered certain content, that we had gone through certain exercises by doing the video-based coaching assessment. They were making more connections, and their call rate went up 84%.

They were not comfortable with being uncomfortable, and they just needed to know that they could try it, they could learn from each other, there was a benefit to being in this open office. In doing that, not only were they successful, but all of a sudden, I was able to start sharing that success throughout the organization.

It was very much don't take sales enablement's word for it, talk to their managers, see what their managers say, because now they're a champion of sales enablement in this new movement.

My saving grace

The only thing I'm going to tell you is that this was my saving grace. Everything's on my phone. Everything's in my calendar, there was so much chaos when I was onboarding, that I actually had to go to the color-coded calendar for the rest of the year so that every single one of my stakeholders could see what sales enablement was doing and when we were doing it, and it was an absolute lifesaver.

It's obnoxious, I know, but if you have it, and it's a Google Drive document, and you can share this with all your stakeholders, you don't get those last-minute requests, 'We need training tomorrow'. It's like, 'Okay. Let's look at what's going on. Let's talk about if we need to reprioritize' and then they start to realize it could probably wait till November.

It also keeps me on track.

A tale of two E’s

It was the best of times, it was the worst of times. It was the age of wisdom, a tale of two E's - enablement and empathy.


We know what enablement is. I'm not going to give you the definition. We wear a lot of different hats, we have a responsibility to our sales organization. We're getting pulled in a ton of different directions.

The best of times

It was the best of times - I wonder how many of you have come out of a program or a training session and just felt amazing, as though you nailed it. It's awesome. Enablement is a complete roller coaster because three days later, it's the worst of times.

The worst of times

Nobody likes what you're doing. “Your newsletter looks like it's from 1992”. That's a real quote, by the way. You think you can't win.

For us, it's always about the wisdom, whether we're providing that wisdom or whether we're gaining that wisdom from the team. I always say to my team, 'I can learn just as much from you as you can learn from me' - that's a great way to gain that credibility.

But I don't think you would be a successful sales enablement professional if you did not know how to practice empathy.


Empathy is being able to recognize your own feelings. It's being able to recognize someone else's feelings. We need to be able to put ourselves in our rep’s shoes. When we can't do that’s when they're like 'You don't know me. You don't get me. Why are you scheduling something at the end of the month when I'm trying to close deals? Why are you scheduling a certification at the end of the year?'

Empathy is one of the best things that we can practice. I always say my job is to be able to demonstrate things that I would expect my sales reps to demonstrate with our customers and empathy is one of those things.

It's very different than sympathy. Sympathy is very appropriate at a funeral. Don't be sympathetic to your sales reps. That's counterproductive. But certainly, think about the programs you're making with an empathetic point of view.

Organizational behavior

What do you guys know about organizational behavior?

When you create programs today, do you even think of organizational behavior in the process of designing those programs?

By definition, it's the study of both group and individual performance and activity within an organization. It is the area of study that examines human behavior in the work environment. It determines its impact on the job structure, on the performance, the communication, the motivation, the leadership, etc.

What's most important is there are actually five versions of this.


Not good. I don't think any of us would do very well in a sales enablement role with an autocratic model. Real old school - loyalties to the bos, why loyalties to the boss? Because it's toxic, there's fear. You're lucky to have a job.


All about the money. I think about the 80s, think about the movie Wolf of Wall Street - that's literally what it is. How can we give you flashy benefit packages? Does anyone still do company cars anymore?

It's funny when you look at the definition for this, they talk about company cars.

The last three are my favorite and the last three are the ones that we need to focus on as enablers.


I'm a former college basketball player, the collegial model reminds me of my years playing sports, it's all about teamwork. It's all about working towards one simple goal together. It's all about inspiration.

Your sales managers take their role as being the ones that can inspire very seriously.


Then the supportive model is all about recognizing your rising talent. We've now got the talent, how do we keep them? How do we grow them? Who are our future leaders?

In enablement a huge focus for us is the foundational learning, we have to have the onboarding, we are focused on-ramp. But we also need to recognize those stars and we need to have those programs, not just for continual learning, but to really get those people to the next level.

Don’t forget the individual piece

I'm starting to see a shift even in my own career, where I'm able to dedicate a little more time to creating some really detailed and specific plans for individuals. Once your foundation is there, once your continual learning is happening, once you have a plan for that reactive piece (things happen, mergers, acquisitions, you've got to act on it), once you can do all of that, don't forget that individual piece.

I'm doing a ton of work with sales managers on basically two areas, reps that might be struggling - I always look at their engagement. I always want to understand what their onboarding looked like, especially if it wasn't my version, and I want to come up with a plan to try to get them out of that.

Management accountability

But I can't own that wholeheartedly, I have to be a part of that but the manager has a lot have accountability there as well. What do we tell sales reps when they're so committed to a sales deal but you're like, "It's not going to close, you need to walk away". What do we tell them? "Cut the tie, walk away".

I don't like to do this with employees that are struggling, but if I truly have somebody that doesn't have the right competencies, and I feel like we've done everything we could, I need to find a better balance. Because chances are I have a rising star that's not getting the attention they deserve.

Nurture talent

The supportive model is finding that talent, nurturing it, having programs, I will sit with sales reps and say, "Where do you want to be two years from now, three years from now?" I know they're having these conversations with their managers, but I can help them with that. I know I can build programs around that.


The system is when you look at a company like LinkedIn, everyone loves working at LinkedIn, why? They're just a great place to work for if you ask a lot of their employees.

They've got the incentives, they've got the development programs. What I really want to say here is for those last three; collegial, supportive, system - this is where we need to focus on.

This is where we need to be advocates as well, to the rest of our organization.

Millennial workforce

We have this millennial workforce, they get a bad rap but I love them. They're fantastic to enable and guess what? There's a stat that I read a couple of months ago, they are going to be our CEOs in the next 10 years.

They're going to be running some of the major companies in the world. Those last three are what they relate to most.

Understanding emotional intelligence

Emotional intelligence is really being able to understand your own emotions and those are the people around you.

Gosh, how are we going to coach people if we don't understand emotional intelligence? On the flip side of this, some people have a natural ability and a high EI, and some people don't.

This is a skill that sales reps need, they need to be able to pick up on cues, they need to be able to read clients.


I'm going to share with you what I do as a sales enablement professional. I'm very self-aware and sometimes I have to force myself to be self-aware.

But being self-aware is my version of understanding myself in and out, side to side. What motivates me, what drives me, what are my strengths, what are my weaknesses.

Tidbits for self-awareness

Does anyone journal? Journaling is such a good thing for self-awareness and you don't have to write paragraphs, you might just do a bullet here and there of what happened during the day.

We're getting beat up every day, we love our sales teams, right? We love our sales team but we're an unsung hero, we get beat up every day. That self-awareness can keep that rollercoaster ride of enablement in check.


I did not practice this the other day, the irony.

It was Sunday, I live on a dead-end street, I have a six and five-year-old and seven of their little friends riding bikes down the street. Someone from New Hampshire came flying down our street, and I yelled at him for going too fast.

Later I was giving my article a look over and I thought "Oh, I didn't practice self-regulation there". Self-regulation is keeping ourselves in check, not taking things personally.

For sales reps, self-regulation is to get them to the point where just because they fail, they don't shut down.


We've talked about it, I'm going to tell you something, sales reps look to us as trusted advisors, but usually, we're the cheerleaders. We're the ones trying to build them up.

We're the ones that when we're offering learning and development because they're struggling, it's less, 'here's what you got to do to succeed' and it's more 'I want to help you, let me know what you need'.

They can also pick up on our emotions, they expect a lot from us, and when we walk around mopey, when we walk around and we're not communicating with them, we're not engaged with them, they pick up on it quickly and wonder if there's something else going on.

Social skills

This is that interpersonal and it ties right back to emotional intelligence. There's a lot of people that need a lot of work when it comes to those social skills, and we can coach on that, we can provide examples of what good looks like or we can create development plans to help them.

Then there's always hope and optimism. It would be very tough to do what I do today and not be optimistic 90% of the time.


There was this quote, that companies that focused on employee motivation and engagement realize 27% higher profits, 50% higher sales, 50% higher customer loyalty levels, and 38% above average productivity. Motivating a sales team does matter.

It does actually impact not just your ability to retain your talent, but also your customer and buyer journey.

Motivating a sales team

There are actually three types of salespeople. We have our:

  • Underperformers
  • Core performers, and
  • Rock stars.

Who's really the unsung hero in this group? It's the core, and we forget about him.

Think about kickoff, we go to kickoff who gets all the credit? The rockstars and they deserve it but the core performers work their asses off and the rock stars get all the kickoff credit.


As enablers, this is a group that we sometimes try to tap into too much. Why are they rock stars? They work really hard. They travel a lot. They work ungodly hours. When we ask things of them all the time, we're going to train them out. We're going to prevent them from being rock stars.

Core performers

Unsung heroes, the core performers, what better way to encourage them and to motivate them, then to give them an opportunity to come in and speak to a team. I'll call a core performer any day and say, "Hey, do you mind throwing two slides together to deliver during the next Power Hour, you're really good at research and prospecting", or "I think you could really provide some good insight to our BDR's inside sales teams".

These are individuals where the talent is there and we have to prioritize our ability to bring them to the next level because they actually want to be challenged. I really love this group.


The underperformers, one of two things, either the core competencies weren't there to begin with, and that's going to require a lot of hand-holding. But I have seen a lot of success stories don't give up on them. I've seen a lot of success stories where they were able to become a core performer or a rock star. They're worth it, they're worth the effort.

But just like I would tell my sales team, sometimes you don't see the level of engagement from them, and you can't help someone that doesn't want to help themselves. It's all a balancing act.

Motivational techniques

These are just some of the motivational techniques that I practice every day.

Know what the team considers important

I will sit with my reps and just say, "Hey, how's it going? What's going on? What can I help you with?" I want to know what they consider important.

Consistent and open communication

I'm always consistent and very transparent in my communication and I give them opportunities so that they can communicate to the rest of the organization too.

Recognizing success

Whether it's shoutouts in our newsletter, whether it's spotlighting their sales deal, I'll say, "You bring me a deal you won. We're going to write up a sales spotlight, we're going to give you a little credit, I'm going to throw you $100 gift card. How's that sound?"

They all want to do it because now it's a competition, now it's a game, and who the heck doesn't like to be on a stage getting a little bit of attention? Then I'll actually say "If you lost a deal, so what, we lose deals all the time. You give me a spotlight out of your loss, I'll give you $200".

Serving as an advocate
We're their advocates guys, remember this. We advocate what they need to our sales managers and leaders, we advocate for what they need to our product marketing team. That is how you achieve ultimate trusted advisor status.
Understanding their personal goals

I truly believe that if you don't understand what every single one of your reps is driven by, what they want to achieve, where they want to go in their career, if you can't have that open line of communication with them, you're probably cranking out some good programs, but you could be cranking out better programs.

Honestly, I tell my reps, if you leave, I take that personally, whether I had anything to do with it or not, I'm sad that you left.

Focus on behaviors vs. results

Know what “good” sales rep behaviors are

Make sure that your version of what good sales rep behaviors are matches what your sales managers and your sales leaders think.

Start with KPIs and work backwards

If it's a vendor I’m bringing in, if it's a manager that asks for something, I don't do anything without saying, "Okay, cool. We can do this. But how are we going to measure it? What's the measurements of success? What's the KPIs that this is directly going to impact?".

Emphasize learning by doing

If I don't actively listen to my sales team, how is my sales team going to actively listen to others? If I don't pick up on social cues, how is my sales team going to pick up on others?

I constantly ask them, when we're going through role-plays or exercises or they say something, I always look at them and I say why? I'm like my five-year-old son, but why? But why? Eventually, they'll look at me in the go, "Oh, you're doing that thing again. You're treating me like I should be treating the customer. Right?" Yeah, absolutely.

I hold my managers accountable for this too. If they're not demonstrating the right behaviors, I'll call them out on it.

Change. New behaviors have to stick

It's not a one and done. I'm gonna leave it at that, you get it. You can't just do this once and expect it to stick. It requires consistent reinforcement.

Sales behaviors drive sales activities

Sales behaviors drive sales activities, and that in turn is going to give you the results that you're looking for. So focus on the behaviors versus the results.

Always measure

I always measure and it's not easy. I do surveys around the board. I didn't like to hear that my newsletter looked like it was from 1990 and then a week later, it looked like it was from 2002. I thought maybe we're making progress.

I ask my sales manager all the time, can you go to Ben (my CRO, that's who I report to) and ask him how enablement is doing? Do the 365. It's not easy, but it's important.

Thank you.

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