Scaling sales enablement: a product marketing perspective

I want to start this article off with one of my favorite parts of product marketing, which is storytelling. One of my proudest (and also probably weirdest) moments was the day that somebody thought I was a Slack chatbot.

Yep, a Slack chatbot.

Let me give a little bit of context. See, at Pluralsight we actually use Seismic for our sales enablement. I'm remote from Los Angeles, we have a global sales team, and I'm always sending out a tonne of messages via Slack all the time, so you can see how Sapphire the Seismic Slack chatbot sounds like a really, really good Slack chatbot.

I was kind of weirded out by this whole thing, but at the end of the day, I was actually pretty proud. Because let's think about some of the attributes of a chatbot.

• They're personalized,
• They're relevant,
• They're accessible,
• They're analytical, and
• They're often really human-centered.
  

And so when I approach sales enablement, I'm totally coming from a product marketing background - I have zero sales experience. I'm sure there are a lot of readers who could school me at this but I think of my seller like my customer and I approach them in the same way that I would approach the buyer of the product that we sell at Pluralsight.

So in doing that, these aren't bad brand attributes, right? I was really, really happy to say, “Hey, that's what somebody thinks of me? That's pretty damn great.”


What I really love about product marketing is understanding how people tick and storytelling. So let's have some Reels talk - why are you reading this article? I’d guess there are a lot of product marketers on the other side of the screen, probably some sales enablement pros, but generally, we're chasing around similar challenges. Maybe it’s:

• 'Hey, I'm a product marketer and there is no formal enablement function in my organization, there's a lot of inefficiencies, we need to sand something up,' or
• 'Hey, we're not able to empower ourselves with the right tool, they're not able to win against the competition, they can't communicate value, deal sizes and go up,' or
• 'Hey, our sellers aren't ramping up quickly and we're not able to teach new behaviors to our existing sellers.’
  

What I like to talk about as the holy grail is how to actually measure impact. So I want to share with you a bit about my specific challenges and where I'm coming from.

Rewind back to four years ago, I was at a healthcare IT startup called PatientCo. It was a very product-focused company, there were very few resources for sales and marketing. As a product marketer, I was a team of one in a team of four marketers. It was very, very misunderstood as a function. We had about five sellers and they didn't use anything, we lobbed it over the wall and it lay there flat.

About a year and a half after I started at PatientCo, I joined Pluralsight and I knew that sales enablement was an area I really wanted to make an impact in quickly. When I joined, we had a lot of growth. We had acquired eight companies in eight years, which brought a lot of changes to the organization. We were aggressively expanding into new global markets,  and with that, we had a new B2B enterprise sales motion. We were moving from not just being B2C and B2B, but going all the way to enterprise, and we actually had different sellers - we were selling to different folks in the organization.

So, rather than focusing on selling to HR and L&D, we were actually selling to tech leaders now. Throughout all this, we were trying to introduce a new sales process, because we were moving into this enterprise space, we were moving into more value-based selling, which was new for a lot of folks, and there were a lot of disparate systems, no consistent behaviors, and no consistent messaging.

To top everything off all this was being led by a new team - brand new CMO, brand new product marketing team, brand new sales leader - there's a lot of change in the organization, post two and a half years ago. Here we are two and a half years later, and what have we been able to do?

We've been able to create. I want to talk about some of the intangibles - there are a lot of metrics and things like that I can talk about but for me personally, what matters is we've created a trusted enablement brand.

Our sellers know that they can come to us for what they need and we'll help solve that for them. We've created consistency, which is so critical for what we do as product marketers or sales enablement folks, we are proactive versus reactive, and we are able to anticipate what our sellers are going to need.

We have much better collaboration, and as we collaborate, we're better able to pinpoint and triage pain points. And we're actually able to show you the impact that we have. Our sellers are now communicating value and winning against the competition. They're more productive, and they're ramping faster.

We're also hitting quota and driving higher deal size in our business. And as a company, we went public, we've increased revenue, we've improved efficiency, and we've expanded globally.

So let's talk a little bit about how we got there. We knew going into this B2B motion that we needed structure or we'd drown - everything was new, with a lot of different changes, so this was the perfect time to introduce some of that. And statistics support that if you don't have some sort of framework, structure, and process, you can actually lose revenue. So the first thing I went about doing was creating a framework. I knew I wanted something that wasn't just a moment in time thing - we were going to grow, we were going to change.

I knew I wanted something that would allow me to focus on the full program or specific enablement activity, and I didn't want to align to any one tool. I didn't want to say, “Hey, I have to go use this thing in order to do this.” So that was the first thing I did.

The second thing I did (and as I mentioned, I'm not coming from a seller background, I'm not coming from a sales enablement job) was build it on the competencies that I already had, which were go-to-market strategy skills. As a product marketer, I understood how to build a strong business case, message, and position something out, deeply understand my buyer, and their journey, and how to build a product that works for them. By building it on the competencies that I already had, I could get started quicker.

Let me talk a little bit about my framework.

For this, I'm going to go deep, I'm going to be covering a lot on the first two stages, which are discovery and development, and then I'll mention a little bit about launch and iteration.

Discovery

As far as discovery goes, I knew this was a really critical moment for us. There's a lot of things that we already knew, but I knew we needed to dig deeper. I needed to uncover the core problems so that I could make meaningful connections with my sellers and build a product that they actually wanted to buy.

Where did I start? I looked at business context and data and asked the following questions:

• What's our mission?
• What's our vision?
• What are our objectives?
• What targets do we have as a company?
• What was the past performance?
• What was future performance supposed to be?
  

I also looked at the sales context:

• What's their process?
• What are some of the best practices there?
• What are their specific targets?
• What is the quota?
  

All those different elements, and then some non-traditional sources. We ran some surveys, we actually surveyed our wholesales organization off the bat to understand what was and what wasn't working for them. We looked at win-loss data to understand how our customers were experiencing the buying process. We also looked at product NPS data to understand once customers were actually sold, and how they were experiencing the product, and then we also moved in and interviewed.

Profiles & personas

As a product marketer, I'm used to spending a tonne of my time in front of customers to really understand how they tick, so I did the same thing with sellers. I used that sales performance data and I talked to high, average, and low performers. I wanted a profile of all of them, and I interviewed them through the lens of what they do.

“Hey, take me through a deal. How did the lead come to you? How did you follow up? What did you do to prepare for the meeting? What did you wish you had? How did you actually track the deal?”

What I was really trying to understand was, were they spending most of their time on core selling activities like meetings, actual research, and work for the customer? Or non-core things like where to go for communications?

The very last thing that we did was shadow sales calls. This was something we were already doing as product marketers because it’s how we get a lot of the data on our customers that fuels our go-to-market strategy. This was where we actually gained the most trust with our sellers because we were able to see exactly what they were experiencing.

As I already mentioned, we were a high growth, new B2B motion, with lots of new teams, and lots of disparate systems, but I wanted to understand things a little bit deeper, so we looked at what we uncovered from a macro and micro perspective.

I created personas for my sellers and as a product marketer, this is something I understand how to do - create profiles and take data. If you're in sales enablement, this is where you can really partner with your product marketing team.

Identify nuances

A really obvious nuance was that our global enterprise sellers were used to a value-based selling process idea. Our commercial and small sellers were not used to that. Across all these different personas, one of the things that we saw was they didn't really have high trust in marketing. They assumed that marketing did not respond to what they needed and they didn't have the tools available to them.

One of the biggest things they mentioned to us which no one else had was:

“We have no way to go out and propose our full platform. I don't know how to talk about the mission and the vision, the capabilities of our platform, pricing, and packaging - I need the one thing, a proposal, that does that for us.”

We also talked to influencer personas. In our case, we categorize sales leaders as influencers because we hired a lot of really experienced sales leaders, we felt like from what we understood about the business, we didn't need to spend a lot of time there. But we also talked to sales supporting roles to understand their motivations.

A really good example of that is our sales ops team. They experience the brunt of bad sales behaviors, and so they were super motivated to help us with this program and drive adoption so they could drive the right behaviors. An example regarding our cross-functional teams is that our sales team was working directly with our creative team to get marketing materials created. Our creative team is really motivated to have accurate brand representation but they're not able to prioritize what sales needs - they can't filter through those requests - so there were tonnes of bottlenecks there.

Core themes

So we created these personas. And then from there, as a product marketer, I message and I position and I come up with those core themes. I really wanted people to know exactly what this program was before I ever started even creating anything. For me,  the core themes were accessibility and ease of use. They felt like they didn't have anything available to them, they didn't know what to find across these systems, so that was one of my core tenants.

Consistency and standardization - We're moving into this new market, we need a consistent message, this really needs to be critical and also on the sales behavior side.

Relevancy and personalization - We had a lot of different personas in their sales org, so they needed to be able to find something that was super relevant to them. And also how to personalize materials regarding content.

Insights and action - We need to be able to act on whatever program or activity we're creating, we need to be able to act on it for our sellers.

Development

And then moving into development. For a lot of you, this is nothing revolutionary, but I thought about this from a content, tools and process, a training, comms, and a metric perspective.

Starting with content, I went back to that discovery and actually audited all the content. So, thinking about those core themes, making sure there's consistent messaging, and making sure that the different content aligns to the different personas and the sales process. We knew that our enterprise sellers were having a lot of trouble selling to this new department, this new organization, so we made sure we had persona PDF. They were also facing a lot of competition, which we learned through win-loss data, so we made sure that we had those competitor battle cards.

For the commercial sellers, we knew that they didn't really understand the value-based selling process so we had a lot of tools for the sales process and sales documentation. Really making sure not only to tailor our content to our product customer but our sales customer as well. We did all this audit of the content, and then we closed the gaps on that.

One of the biggest things that we created at this point was a proposal generator. And this was kind of a two for one special for us because it gave us the ability to communicate with sales:

“Hey, this is exactly how you should be talking about our platform…”

...but it also gave them the ability to tailor that to their specific customers and their deals. And at the same time, it was internal - yes it’s for customers, but it's also a teaching tool. So as they went through it, as they read it, as they worked with it, they understood this is how we should talk about it, this is what the pricing and packaging are. So it worked really well for us.

Delivery

From there, I thought a lot about delivery. As somebody who is in product marketing, I just didn't even know or think about how much time I would spend on 'how does this content actually need to be delivered?'. So when I first loaded it into our tool, I was like:

• top funnel
• middle funnel
• bottom-funnel
  

...and our sellers were like, 'No, that doesn't work for me'. So I tried a lot of different things and based on how I understood that our sellers were searching for information I organized it by sales stage, I organized it by role, and I organized it by customer goal problem needs.

What do your sellers need?

A really easy way to get to know what our sellers need is to do a card sorting exercise. So we’d give them a bunch of things such as a pitch deck, one sheet cards, and ask them how they would organize it. From there, we went into tools and processes, and so the first thing we knew we had to choose was a delivery tool because we had disparate systems.

We wanted to align it to our core themes, and after evaluating platforms we ended up going with Seismic because it aligned to those core themes:

• It was accessible
• It was a one-stop-shop
• It was relevant
• It had insights
  

...again always anchoring back to those core themes that we had created.

Tools & process

From there, we had to do a lot of work around tools and processes. I didn't understand exactly how much time I would spend on creating the process, I know a lot of times when people think of processes they think that is the antithesis of moving fast and iterating, but it was really critical for us to do this, and not just small things like how we license the new sellers on this tool and get them access. The biggest thing for me was actually creating a process for those stakeholders that were working with us to build this program.

So where I first focused a lot of my time was on the content pipeline: how would I work with the creative team to get all the content we need, get it loaded into the system for people to request new content? All that good stuff. I also looked a lot at communication governance. There was a tonne of noise going out to our sellers. I took the time to really evaluate all the information that was coming to them. We prioritized it by urgency and relevance. And then we created different distribution channels, so it would get routed to the right seller.

The final area that I created a lot of processes around was the feedback system. Our sellers felt like we weren't responding. So we had content analytics to understand who was using what. We did surveys, interviews, and shadowing, and then we also created a request form. And then we implemented everything.

Document everything

From that, document the process again. This was really critical for us to get those stakeholders to drive the right behaviours.

Think about it, if I come to you in sales ops and say, “Hey, you need to participate in this programme to help drive those right behaviours for sales,” and you say, “Well, what do I need to do?”, and I say, “I didn't think about that part.”

So I documented everything for them.

Think about launch plans

Because I am on the product marketing side, I often think about launch plans. And so I tailored our existing launch plan to sales enablement, I figured out what the nuances are of launching a product versus launching a new activity or tool or program for sales enablement.

I built out something so that when a product marketing manager comes on, they know exactly what it looks like to communicate a small product update, versus promoting a really relevant new piece of analyst content. It is important they understand what those nuances are.

Create a charter

The next thing we did was create a charter. This is something that we really felt the pain of in our organization. There were a lot of people dancing around sales enhancement. So we sat down - we had a sales training and productivity team at the time - and documented exactly what each team was doing.

This gave us a lot of efficiencies and it also helped us pinpoint and be clear on who was doing what so we could move faster.

Training and comms

Then I moved into training and comms, I didn't just think about how to train my sellers, I also thought about how to train the influencers. It wasn't enough just to build documentation, I actually had to get them on board with it.

One of the things we did for sales leaders is tied engagement with our program to performance. So, we would expose a low performer on the team and say “They're not using anything that we've made available to them.” We put the onus on the sales leaders to actually do that coaching, we don't even have to do it.

And then regarding sales support and cross-functional, we didn’t just ask  “can you help us? Can you do this process?”, we actually trained them on it.

Driving behavior change

Because we were moving everything to one tool, Seismic, we were super focused on driving a behavior change. It was a one-stop shop. Everyone in the organization learned that when a seller asked for something they replied, "Well, have you checked Seismic yet?" And it actually worked.

On the sales side, some of the things I did include creating a watering hole; we had a Slack channel, and anytime a seller asks a question we promise a really quick response. The other day somebody asked something and it was like three seconds before they had 10 different people on my team answer. So we always make sure we're quick to respond.

And then I tried the model of going everywhere that they were. I created self-service training videos for somebody who's like, 'Hey, I'm hopping on this flight, I'm in the car, I'm just trying to learn what I'm doing here,' so we did that.

I had office hours where I said, 'Hey, I'm hanging out on Zoom for the next hour, come find me', and then I went into their different meetings, and worked with the sales leaders to create specific training for their teams. And then sales onboarding courses, something that I didn't really account for when I first rolled this out, and maybe something to work with as a product marketer or work with your product marketing team.

What’s in it for you?

One of the things I didn't understand was the nuances of their daily workflow and their role and so when I rolled out this training, I started from a role perspective. I said, 'hey, you're an account executive, that looks a lot different than your role as a customer success manager' and I always framed it in a 'what's in it for you?' way.

That was a huge missing thing for me; as a seller why should you use this content or this program? Because it's going to help you close more deals. And then I would actually demo Seismic and I'd say, imagine you get a new lead and you don't know anything about this persona, come into Seismic, see the PDF, 'Oh, you got a call with them? Here are some discovery questions. By the way, once you get to that proposal stage, we got you covered and then 'anytime you get hung up on the Salesforce process, just log in to Seismic and you have all your documentation there'.

That looks really different than what we would talk about with CSMs where we would say, 'Hey, drive engagement, here's all the stuff on the product'. So just really those nuances, that's something I didn't think about at first.

Metrics

And metrics for us, just kind of rounding out, we focus on deal size - are we getting set B2B enterprise motion, we focus on attribution - is product marketing moving the needle? And then we also focus on sales MPS, sales with our customer, are they happy? Are they satisfied?

Test & validate

At this point we tested and validated everything, we didn't think about a launch until we actually knew that this was going to work and so I went back to those folks I interviewed and I said, “Hey, you're our beta customers, get access first.” I was testing:

• Are the communications working?
• Is the content working?
• Am I targeting them with the right message?
• Is it relevant?
  

So we really validated that the program was working before we even launched it. And then we moved into launch.

Launch

This is something like go-to-market in product marketing, I do this launch motion all the time. I think some of the nuances for me around this were:

1. Made sure I understood what launching to sales was versus launching to a global market
2. Making sure that I ran everything by sales leaders before I tried to launch stuff to get them on board, and
3. Making sure I was actually tracking metrics at that time and launching to all those different folks that we talked about.

So what were we able to do?

Within just a few months of launching, we got 90% adoption of our sales enablers to Seismic, we had 60% of sellers being daily active users and we had a really high NPS. So there's a lot of engagement there. Let me show you some Slack messages for that proposal tool that we had created, it's consistently the number one use tool.

And it's also helped us land one of the biggest deals in our company history. I've had a seller send me a note saying, 'hey, I work in the government space, I have to create these on the daily, you've saved me so much time', another seller moved into a new role, and he was immediately able to land an increase on a deal.

I'm not sharing this to humblebrag about myself. It took a lot of work to build this trust and get to this point, so it can be thankless but you can get there. And then the last thing, they always felt like we were there, that was the number one thing, they said, 'you are always there, Sapphire', and I thought, 'Wow, that feels good.'

And as a result, our deal size went up and we were able to hit our numbers.

Iteration

So then moving into iteration - how do I actually analyze data and make recommendations? The first thing I was focused on was how do I make quick pivots? And this is actually something I learned from my friends at Seismic and through this coaching process, this idea of enablement readiness versus sales-readiness.

So as a product marketing team, we were really good at having the market context figured out, having a process, having content, having tools, basically everything until that seller received the content was in tip-top shape. What wasn't there was some of the sales readiness and so they didn't have the context they needed. They didn't have maybe the skills or competencies and they weren't incentivized to use it.

One of the ways that we quickly pivoted was, rather than just having all these continent tools, we built out enablement decks. We had everything that they would need to tackle - it was role-based, and it was topic-based.

So in this instance, we have Pluralsight for cloud computing, why would you use it? And this was how we did it. I went into team meetings and actually trained on it. So it wasn't just a self-service model, I actually went into the team meetings and talked about, specifically for a pitch deck:

• Why did we create it this way?
• What research went into it?
• Have customers already responded to this?
  

And that was something that I really learned around making sure they were ready; having testimonials from customers who had actually received the materials, say "we showed this to customer X, and they said Y, and it ended up in this for sales". So I started launching things with sales success stories, where major pieces of content would be attributed to a deal.

Quick pivots

When I go out and I launch a product, there's always a case study or testimony or reference that comes with that and so I did the same thing when I was launching these different sales assets, and I also taught them how to use the deck, I'm somebody who loves storytelling, I love digging in, I love tailoring what I'm saying. And so I focused on how to do that. So just really quick pivots.

Metrics, content usage & attribution

Another thing was metrics. I know this can be a hairy area, there are so many things that can go wrong in trying to get to metrics. We thought content usage in Seismic was going to directly lead to attribution.

Due to some system and data issues on our side and also just not being able to drive some specific behaviors, we weren't able to get there. And so we had to introduce a new step where we looked at content usage, we said, “Okay, you, seller, are using this content, let's talk to you, look at your NPS scores, let's do some interviews, figure out where you've used it,” and then we get attribution.

So we would start posting deal reviews on Slack saying, 'hey, this person used this thing and this happened'. So it was really a way for us to actually get attribution. We're not getting all of it, but we're getting some of the credit and understanding where we're moving the needle.

Long-term pivots

I want to talk a little bit now about some of the long-term pivots we made. So now we're two and a half years later after building this system and we have a system that works, it always needs tweaks, but in this iterating phase our events team came to us and they said, "Hey, we have a conference, our sellers now have a quota to sell tickets to our conference, and they're not doing it."

So once we dug in, we understood that it was an unclear value to sales, they thought 'why should I sell tickets to a marketing conference, I literally couldn’t care less.' They didn't understand how to sell the conference. There was a gap in tools and there were no best practices. And so I went out and reframed the why, and I created How to Sell playbooks.

We had this whole campaign stating ‘invite your customers to Pluralsight live and you'll get three x deal size.

Here are some examples of top sales performers, they've sold a tonne of tickets. Here's an example of the amount of money that's been closed.’ So we looked at the pipeline. We looked at dollars closed. So really reframing it and positioning it to what they actually care about, which is dollars in their pocket.

Tailor your materials

We also created materials that they could tailor to different personas because they mentioned that that was a gap. And then from there, I put everything into playbooks. We knew from our personas that we had some sellers who would spend 30 minutes going through an entire playbook because they were brand new, and they wanted to ramp up really quickly. And then we had those enterprise sellers who were like, 'Hell, no, I'm not spending 30 minutes on anything'.

So we created a checklist, we were trying to solve for both of those people at the same time. And it wasn't just about, 'hey, here's a tool'. It was, 'hey, here's a tool. Here's how we use it. But if you have a better way, come shout at us.' And then we launched it.

I went out and I evangelized in meetings, I went to a tonne of different sales meetings. We have a field marketing team and sales leaders that we partnered with really closely to make sure that they were actually driving usage and one of the biggest things that I did is actually created self-service videos.

Because we're starting that sales process for our conference, it's a long, long sales cycle. We just had our conference in August, we're already starting to sell more tickets, and so every single month, I would have a video that said, 'This is what's in it for you. Here's a success story from last year. Here are some event updates.'

So they would get those crucial communications that we had created, 'and oh, by the way, here's a reminder of all the tools that we've created and how to use them.' So it's that repeated exposure and just making sure that I was launching it.

The key takeaway

So if I could leave you with one key takeaway, it would definitely be to treat sales like your customer, make sure you know them intimately and are really solving their problems. Use your go-to-market skills - we all have them, whether you're on the product marketing side or sales enablement side. So make sure you use those skills.

And the last thing is to make sure you fail fast to the framework and iterate. We got it wrong more times than we ever got it right. But we moved quickly and that's how we built that trust.