Episode 96: Tyler Zeman on the Intersection Between Sales Enablement and Marketing

Shawnna Sumaoang: Hi, and welcome to the Sales Enablement PRO podcast. I am Shawnna Sumaoang. Sales enablement is a constantly evolving space and we’re here to help professionals stay up to date on the latest trends and best practices so that they can be more effective in their jobs. Today, I’m excited to have Tyler join us from Pluralsight. Tyler, I would love for you to introduce yourself, your role, and your organization to our audience.

Tyler Zeman: I’m excited to be here with you guys. So yeah, how my role works at Pluralsight– great question. Product marketing is just so different at different companies, so many different ways to organize. So for us, we have three product marketing leaders.

Each is focused on three different domains: product, market, and sales, and I lead the sales focus team. I’ve been with Pluralsight for a little over three and a half years, and I was brought on to revamp the function from scratch and build the team. I was the second person of a new team and we started leadership first and have grown to be over a dozen strong now.

We started from scratch with new messaging, positioning, demo script, sales assets, you name it, all in an effort to help our enterprise sales motion, which was the big focus at the time. Along the way, I’ve helped create a strategy for our annual conference, Pluralsight live, and created our customer advisory board. I organized and ran our customer reference and testimonial program, and launched and administered our sales enablement platform. Through all that we re-accelerated B2B sales, which was the goal of me joining the team, so pat myself on the back there. We got that one done and successfully took the company public. We listed two years ago on NASDAQ and got to be involved in the roadshow and IPO efforts there. Certainly a thrill, and a proud moment of my career. It’s been a fun run.

SS: Well, Tyler, I’m really excited to have you here. Obviously it sounds like you’ve accomplished some amazing things at Pluralsight and given your extensive background in product marketing, I think for our audience in particular– which is made up of those that either have sales enablement directly in their title or do it as a part of their function, and oftentimes I think that does fall to product marketing within some organizations– I’d love to hear from your perspective, what does that intersection look like between sales enablement and product marketing and how do they complement each other?

TZ: Yeah, fantastic question. It’s a blurry line to a minimum, and I’ve been quoted as saying that sales enablement is actually the outcome of a healthy product marketing and sales training team.

For us at Pluralsight, we have a team that is actually called the sales enablement team, but in other companies they’d just be called the sales training team. Semantics aside, together we focus on delivering the intelligence and assets that reduce ramp time for new reps, increase deal size, and accelerate pipeline.

We’re just focused on what our global revenue org needs to know, say, and show to both prospects and customers. Sometimes that’s competitor battle cards that are internal only, or slides that are external facing, or a sales play that has a little bit of everything. Both teams stay super connected to sales leadership, and individual reps to keep that finger on the pulse of our revenue org.

It’s really important that we stay focused on the right work and that we’re plugged in in the right ways to know what that right work is. We’re careful not to be order takers or slide monkeys along the way. We have to strike that balance of ensuring that we’re actually listening and responding to their needs while not just creating whatever they ask for.

We really need to apply some of our logic and prioritization and focus on business objectives, not just crank out each order. It is a delicate balance and it really relies heavily on relationships. Leaders and reps just need to actually trust me, trust that I’m listening, trust that I have their backs and trust that when I deliver something it’ll actually work for them.

SS: I love that slide monkeys. I haven’t heard that term before.

TZ: But everybody knows what it means.

SS: Exactly. Now as the marketer what are some of the challenges that you experienced though, when trying to roll out new content or messaging to sales reps?

TZ: Yeah, absolutely. We sometimes look at our comms plans and feel like we’re just beating a dead horse. We’re like, ‘Really, do we need to say it so many times, so many places?’, but without fail, every time there are going to be reps who say they didn’t get the message or they were unaware of an update or something new that occurred.

Right now, we’re very intentionally focused on cleaning up our comms to help alleviate that problem, but it’s sort of just the reality of the situation. The business needs to communicate a lot of updates to reps, they’re getting hit from all directions. We try to focus our comms to help them digest the most important items that they, and we, need to be understood. We use one Slack channel where reps can ask questions and get help nearly 24/7 from product marketing. We’ve partnered with our training team to create standards for our communication calendar and process.

Additionally, we leverage our executives and sales leaders to share and enforce certain topics, and we do that very selectively. We created really healthy agreements with them to make that work. Again, this comes as an outcome of healthy relationships and building a reputation for sharing content and messages that matter.

We didn’t focus on this part. At first, we focused on creating the best materials, building the relationships, and then it’s sort of like we had that foundation and that clout to support a process and ask for favors, like leaders being an additional mouthpiece or reinforcing. If they didn’t trust that what we were doing is something they could stand behind. They wouldn’t be doing that for us. I would say to kind of depends on where someone’s at, where they should put that focus, but for us, that’s what we’ve created to help with rolling out new content and messages.

SS: That’s fantastic, and I think you guys built that very organically, with your sales reps. Now pivoting a little bit away from the rep side of things and looking at the buyer’s side, what are some of your best practices for ensuring that content is being used effectively and that the messaging that you’re creating and trying to land through your sales reps is actually resonating with your buyers?

TZ: Yeah, you definitely need to pay attention to that. My answer is always just to get in the trenches. For us, that means accountability to actually join sales calls or listen to recordings for the times that we can’t participate live. We need to see both how the rep is using the intel or asset, plus see or hear the actual real reaction. Also, it’s really great practice for us to practice what we preach. I remember being pretty crushed a few years ago, after my peer delivered a pitch principles training at our sales kickoff, I thought he did an amazing job, really hit on all of the intent and hit the right points of our really honed-in demo.

But I overheard a rep in the crowd say, “I’m so tired of marketing telling sales how to sell. If you’ve never carried a quota, don’t waste your time telling me how to sell”, and I was like, ‘Damn, ouch’. We had to get in the trenches with the reps and earn a few battle scars with them. We started small, offering to give an overview of upcoming product launch or a demo of a new feature that a rep was less comfortable with, and we could offer that because we were closer to it. Once reps saw that we could do the dance and we actually brought value to the conversation, it fostered a really genuine trust that we’ve built on over time. You said the word ‘organic’, and I think that really applies here.

We’re in the fight with our reps, and they feel that, and that creates a different dynamic. We’re in team meetings, we participate in deal reviews. We’re as omnipresent as we can be in Slack channels. We go onsite, like I’ve traveled with our sellers and gone onsite with a bunch of our customers.

When you walk through those doors as a partner, and you go through the experience together and then you recap afterwards, you take that intel into building your next asset or messaging, or everything that you create, it gets steeped in that knowledge that you earned with them.

Then you don’t have to worry as much about ensuring your contents being used efficiently or it’s resonating, cause you’re there with them, you know firsthand. We just try and see as much as we can firsthand and then supplement that with data from our sales enablement platform and then the feedback we also get from leaders and reps for the rest.

SS: Oh, that’s fantastic. Now, you touched on this a little bit at the end about how to take that intel and kind of weave that back into everything else that you guys are doing, but how do you work with sales enablement to really optimize content, and ensure that it continues to land with the field?

TZ: Yeah, it’s not very different. It’s really the same process for ensuring content’s being used efficiently and making sure it resonates with the buyers, but it really is just trust and communication and getting in the trenches. We have a regular cadence where product marketing and sales enablement get together and share observations and talk about what’s occurring, what we’ve seen, what we’re hearing.

They’re the business partner I communicate the most with, because together our perspective is much wider and more likely to capture the reality that we need to know about. Additionally, if we’re having an asset or a message issue, we have those conversations about if it’s really about the reps getting more practice or training with how to use the assets or if it’s actually a problem with the message.

One of my buddies on the enablement team uses, in my opinion, a great analogy that anchors on the fact that everyone knows how difficult golf is. Nobody’s an overnight success at learning how to golf. People spend their whole lives, trying to master the game. Giving a new golfer the best clubs won’t actually help them, it doesn’t create a good golfer just to give them the best materials, the best tools.

Similarly, becoming a great sales rep takes a lot of practice in years of honing that craft as well as access to equipment. We can’t just hand reps some battle cards, PDFs, and slides, and expect them to just go crush it. Even if they’re excellent assets and intel, they need help knowing how and when to use them, they need practice. So together product marketing and sales enablement look at our world through that lens– is this an asset or a training need or both? And then we move forward.

SS: I love that, and I love that at your organization, product marketing and sales enablement come to the table on a very regular basis.

Now I’ve loved this conversation, Tyler. I have a closing question for you, and normally I don’t like to land on kind of a negative, but let’s see how this works. What are some of the challenges though that you’ve experienced in building or maintaining that cross-functional alignment with your partners in sales enablement, and how have you worked to overcome those challenges?

TZ: Challenges? No, it’s been sunshine and rainbows since day one. That is a great question. You know, I talk about where we are today, but I’d be remiss if I didn’t talk about what got us there. It’s absolutely been a challenge at times. Pluralsight invested in building our product marketing team long before our sales enablement team. That created an environment where we were doing some of the work that now gets done by the sales enablement team. We had to, we were doing our best to fill that gap until the team was built, and then as the sales enablement team’s been growing product marketing’s been peeling back. I talk about it as like it’s scaffolding, we were temporary support. Now with the permanent process in place, there’s certainly been some conflict about specific topics or the speed of that transition at times.

There are still areas we discuss regularly, but we’ve moved from contentious to constructive debate. I had to really keep my attitude in check and approach the relationship with a desire to build and help versus complain about the ‘coulda-woulda-shouldas’. Additionally, I put a lot of effort into building a relationship with the leader of our global sales enablement team.

Both teams, both her team and my team, look at us to model how our teams work together. By spending more time– one on one with her and getting to know her, and what topics are okay to discuss as a group or maybe what’s a little more sensitive and something that we should talk about just ourselves and then share with the group– we’ve built a much more harmonious environment for our teams together. So much so that now we have shared documents with transparency about what teams are working on. Like I said, shared comms, plans, calendars, and we include each other in quarterly planning cycles, but you’re right, it didn’t start that way and it’s taken a lot of effort to create that.

SS: Well, I think that you guys have landed in a really solid place. I’m glad to hear that you guys have been able to build a fantastic partnership between product marketing and sales enablement at Pluralsight. Tyler, thank you so much for taking the time to chat with us today. I really enjoyed the conversation.

TZ: Yeah, it’s been a pleasure. Thanks so much for having me.

SS: To our audience, thanks for listening. For more insights, tips, and expertise from sales enablement leaders, visit salesenablement.pro. If there’s something you’d like to share or a topic you’d like to learn more about, please let us know. We’d love to hear from you.

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