Episode 39: What a Good Sales Play Strategy Looks Like


Shawnna Sumaoang
Shawnna Sumaoang
Vice President, Marketing -Community, Highspot
Jillian Maiorino
Jillian Maiorino
Manager, Sales Enablement, Vendr
Podcast Transcript

A study conducted by Highspot and a B2B research partner found that sales playbooks enable reps to be more efficient and effective, making them a crucial component of any sales enablement strategy. In fact, 42% of best-in-class companies use sales playbooks, resulting in better quota attainment, customer retention, and lead conversion rates. So how can you build effective sales plays?

Shawnna Sumaoang: Hi and welcome to the Win Win Podcast. I’m your host, Shawnna Sumaoang. Join us as we dive into changing trends in the workplace and how to navigate them successfully. Here to discuss this topic is Jillian Maiorino, the manager of sales revenue training and enablement at Vendr. Thanks for joining Jillian! I’d love for you to tell us about yourself, your background, and your role. 

Jillian Maiorino: Thank you so much for having me, Shawnna. I’m really excited to be here. A little bit about me, I was born and raised in Maine, and I’m actually now back in Maine with my family. I have a husband of eight years and two little ones. After having my kiddos, I was trying to think about what I wanted to do when I went back to work. Prior to that, I graduated and went right into the world of sales. I did everything from BDR to full-cycle AE to post sales, customer success, and account management and then went on to become a mother, the greatest job of all.

When I thought about what I wanted to do when I went back into the workforce, and if I was going to leave my babies, what would fulfill me enough to do that? Enablement at the time was still relatively new. When I think about it at my core, I am an enabler. Through words, content, tools, and processes, I am somebody who really strives to support others. I love the art of selling everything that goes into selling and being able to enable sellers to find everything that they need at their fingertips, be their best version of themselves, and coach them through that has been really fulfilling over the last few years.

SS: Well, thank you so much for joining us, Jillian. Now to start, you actually leveraged Highspot at a previous company and now at Vendr. Given this experience, how have you seen an enablement platform play a really key role in the revenue tech stack? 

JM: I think an enablement platform provides the tools and resources to enable sales teams to be more effective and efficient in their roles, bottom line. It helps reps stay informed and prepared throughout the entire sales process and it’s meeting them where they’re at and really looking to not disrupt their day-to-day workflow. By equipping sales teams with the right information and tools at the right time, in the right way, the enablement platform is really improving their productivity and enables them to ultimately close more deals effectively, leading to increased revenue. 

I think an enablement platform also facilitates the training and onboarding process for new sales hires. It provides a centralized repository for training materials, product knowledge, and best practices really playing a key role in not only getting new hires up to speed but then that ongoing reinforcement and support throughout their entire time.

SS: I love that it is absolutely essential to the revenue tech stack. At Vendr, what are some of the key business initiatives that Highspot helps to support? 

JM: That’s a great question. I joined Vendr and one of the first questions that I had was, “Do you have Highspot?” That just goes to show how crucial it was to me at my previous company. At the time, we were making a lot of process improvements and changes to the business as we became more of a platform product company. The core purpose of Highspot is really here to enable sales teams, again, to be more effective and efficient and ensure that they get the right information at the right time, and so we use Highspot for everything from onboarding all the way through ongoing and reinforcement. 

We have competitive plays. We have persona-based plays. We outline our sales process broken down by the stage and really so they understand everything that goes into each stage and out of each stage. We meet them where they’re at in Salesforce so that they don’t have to leave their workflow. One of the biggest things we did when we launched Highspot here, we lined it up with our sales kickoff earlier this year when we launched our SLG, or sales-led growth playbook. We built that with Highspot. 

Another thing that we do that has really been a big initiative here to make sure that sales reps are getting the right information at the right time is we launched a weekly sales digest, and that is sent via Highspot as well. It is built in Highspot and sent via Highspot, which really allows them to get that highlighted book-ended information of all the things that are getting thrown at them via Slack or in meetings or in trainings and have that end cap at the end of every week surfacing up what they need to know and make sure that they can take action on heading into the following week.

SS: You touched on this, but one area where your company has seen a lot of success in Highspot is through sales plays. In fact, you’ve achieved, I believe, a 91% play adoption rate, which is absolutely incredible. Jillian, can you tell our audience about your sales play strategy and how they support your key business initiatives?

JM: Absolutely. When we think about a sales play, I want to think about it really at the most granular level. We could have a discovery sales play, but within that discovery sales play, I want to have a discovery sales place specifically for our CFO persona. Getting as granular as we can means that reps can pull up the right scenario, sales scenario, and the right play and execute. We break down our sales play with the guidance and the best practices from Highspot into the what to know, what to say, what to show, and what to do framework. 

When I think about those sections, the what to know section is really where we’re educating our audience about the scenario with context, information, training materials, and FAQs. The person really responsible for this section is our topic subject matter expert. If we are doing a competitive battle card, our product marketing manager who owns our competitive intel is really owning that what-to-know section. This is where we clearly explain why the play was created, and why its content matters and highlight information like what is it for, who is it for and what outcomes does it drive? Then we incorporate any training courses to solidify the new knowledge around that play if it’s a long tour competitive battle card. 

The next section is what to say. Within this section is where we’re really preparing our audience to have an effective conversation with the prospect or customer through talking points, questions to ask, highlighting Gong calls of what good looks like so that they can see that and replicate that and start to practice, as well as customer stories. Now, the person that we have responsible for this section is the audience subject matter expert. The enablement partner is partnering on all of these sections, but the audience subject matter expert really is who is this play intended for? If it’s intended for a sales rep, I may bring on a rep to help me make sure that this is resonating and this is exactly what they need from a what to say standpoint. 

We may create different sections for more granularity and give them examples of questions that they can ask to help uncover situations, for example, where this new product launch might be a good fit. We may include demo tracks here or competitive daggers that help reps get familiar with how similar competing products might be positioned. The What to Say section is all about giving them the snippets and the talk track that they need to be successful with this sales play. 

In the What to Show section, the goal here is to provide our audience with the most relevant and effective content to engage the prospect or customer either before, during, or after the meeting. This may be white papers, case studies, email templates that might be a follow-up template that’s easy for them to plug and play, or even demo videos. The What to Show is really external-facing content. The individual responsible for this section is again, the topic subject matter expert, along with the enablement SME. Then we’ll have best practices here around the content that can be pitched again before, during, or after. 

The last section is the What to Do section. This is specifically where we detail the steps that our audience needs to take in the given scenario. Depending on the play, this section could include something from updating the account progress in Salesforce to coordinating logistics for a meeting as a follow-up. The most often responsible person here is the audience SME as well. We also add a ‘need help’ section to the play, so they have the contact information for the topic subject matter expert as well as the enablement subject matter expert. 

SS: Thank you for outlining that. I think those are some phenomenal best practices. In your opinion, if you could sum it up, what does a good sales play look like? 

JM: I remember the first time that I was on-boarded with Highspot, and I’m not somebody that likes to reinvent the wheel. I like to follow best practices that Highspot has laid out, and I believe they said, like two and a half scrolls with your mouse. You don’t want to have too much information where the intended audience feels overwhelmed, while also making it super digestible. The what to know, say, show, do framework really allows them to go to the exact section that they’re looking for. 

They may go to a play multiple times and need a different section depending on what their action is that they’re taking, so it’s really important to make it digestible. I think that the best sales plays do really have that baseline information on the what to know section, very clear, actionable what to say, snippets, talk tracks, highlighting what good looks like, and then clear follow-up templates and what to do actions to make sure that they’re completing the best practice cycle through whatever it is that they’re learning or executing on that sales play.

SS: That’s absolutely a fantastic definition of what good looks like. As I mentioned, you guys have an amazing adoption rate. What are some of your best practices for driving the adoption of sales plays among your reps?

JM: I love this question because I answer it pretty much the same anytime anyone asks me how enablement is successful. My opinion is that everything lives and dies at the front-line management level. What I mean by that is without your buy-in from your front-line managers, your reps will not adopt Highspot or sales place. The front-line managers really need to be there to drive that adoption and reinforcement and make sure that it’s ingrained in their workflow and their day-to-day. 

One thing that we’ve done is really leveraged the weekly sales digest that I send via Highspot, and let’s say we’re launching a new sales play. The following Monday in their weekly team meetings, their managers are, for better or for worse, pop quizzing them on what was shared in the digest and then specifically in the sales plays. That really got them in the habit of at least reviewing once over on Friday and then knowing where their resource is. 

The second piece is I think allowing reps to access the sales play in their day-to-day workflow that they’re already in. This gives them no other option because it’s right in front of their face in the opportunity view with the Highspot frame. They know if they’re in a competitive scenario at a certain stage in the sales process, the right sales play is going to meet them right there and they can easily click on it and access it without even leaving Salesforce. 

SS: I couldn’t agree more. It is essential to build it in the workflows that your reps are in on a daily basis. How has your sales play strategy helped you to impact the productivity of your reps?

JM: Honestly, I think it really comes down to them knowing how to fish for themselves. They don’t have to take that extra step to Slack me and say, hey, how would I approach this scenario? Or, hey, where can I find this piece of content? They know now that all of those things that they need are at their fingertips with Highspot. They can backslash in Slack Highspot and search for whatever they need and I think that that really has impacted their productivity because they’re not wasting that time searching or asking others. They know exactly where it is. 

SS: Absolutely, and in today’s day and age, I think impacting productivity is absolutely critical for organizations to do more with less. What role do sales plays play in your broader enablement strategy? What are some of the key components of your enablement strategy? 

JM: I think sales plays play a crucial role in our broader enablement strategy in a few different ways. They are targeted and orchestrated approaches that guide our reps on how to engage with prospects and customers effectively throughout the sales process. They really do provide a structured framework that know, say, show, do, that aligns with the organization with Vendr’s sales objectives, customer needs, and desired outcomes. 

Sales play also ensures consistency and alignment, so they help our reps tailor their approach to specific buyer personas, industries, or different sales scenarios. Again, as I said, they provide a proven framework for engaging with prospects. They really do facilitate this continuous improvement and optimization of sales approaches and we’re able to track and analyze the outcomes of the different sales plays, gather the insights on what’s working best and what’s not, and then it allows us to have this feedback loop that enables the refinement and enhancement of sales plays over time. 

While sales plays are the starting point of a lot of the things that we do in our enablement strategy, it’s also providing us that feedback loop that ensures the sales team is equipped with the most effective strategies to drive revenue growth and we’re learning from those analytics and insights constantly. 

SS: I’d love to know how your holistic enablement strategy helps to also drive sales productivity. 

JM: I love this question because I really enjoy taking a step back and looking at enablement from a holistic view because there are so many different components and day-to-day in my role, I can get lost in only one of these pillars, if you will. When you take a step back, you’re really thinking about a few different pillars. The first is training and onboarding. By providing structured training on product knowledge and sales methodologies, objection handling, and effective communication, our reps are equipped with the necessary skills to perform their roles efficiently very early on in their journeys at Vendr.

The second piece is the content management piece. A key aspect of enablement is clearly effective content management, which we achieved through Highspot, and we are able to provide the reps easy access to up-to-date, relevant, personalized content that helps them engage with prospects. more effectively. 

The next piece is our sales process optimization. We’re analyzing and optimizing the sales process, looking to eliminate bottlenecks and really streamline their workflow. By identifying inefficiencies or redundancies, or even areas of improvement in the sales process, we’re able to implement changes that lead to increased productivity. 

The next big pillar is sales technology integration, Highspot being a main piece of that. We integrate the majority of our tech stack into Salesforce with Highspot Salesloft and with Gong. We’re really able to give this sort of seamless integration, giving our reps a unified view of their customer, of the customer data, streamlining their data entry, and then they can spend less time navigating between those different tools and systems, which results in increased efficiency and more time dedicated to selling. We have the continuous learning and development pillar where we’re promoting a culture of ongoing learning by providing ongoing support, coaching, and resources to help sales reps enhance their skills and knowledge.

Lastly, the analytics and insights pillar of our holistic enablement strategy is crucial so that we can gain valuable insights into rep performance, content effectiveness, and then sales trends to understand what’s working and where we might have areas for improvement. 

SS: Amazing results at Vendr. Last question for you, Jillian. What are some of the key business outcomes that you’ve achieved through Highspot? Do you have any data points you can share with us?

JM: I have my sync with our Highspot CSM later today, actually, and so I’m hoping we can get some more fresh data points. I think that truly, the biggest one of all, as I said earlier, is getting reps to fish for themselves and knowing where their resources are. That was a huge pain point for us prior to Highspot. We’re at the point now where more and more cross-functional employees are asking, hey, what’s Highspot? Can we get access? We are thinking of more and more use cases that we can use across the business, that isn’t just the standard sales enablement use cases that you would think of.

I think the other thing that’s been really impactful is the use of microsites. Reps are able to really deliver this world-class experience to their prospects of what it would look like to work with Vendr and being able to give them this one-stop shop for all of the content that they’re reviewing, the recordings from the calls that they’ve attended, making it very easy for them to go to their microsite, see all the things that they need to know about Vendr as they’re making their business case and decision and have it there very easy for them to access. Not only are we making it easy for our reps to access information, but we’re also making it easy for our prospects and customers to access information. All in all, I don’t know what we would do without Highspot. 

SS: Well, I absolutely love hearing that. Jillian, thank you so much for joining us on this podcast. I appreciate the time. 

JM: Thank you for having me. 

SS: Thank you for listening to this episode of the Win Win podcast. Be sure to tune in next time for more insights on how you can maximize enablement success with Highspot. 

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