Episode 17: Driving Productivity Through the Highspot and Salesforce Integration


Shawnna Sumaoang
Shawnna Sumaoang
Vice President, Marketing -Community, Highspot
Jesse Potter
Jesse Potter
Director - Field Enablement, DocuSign
Podcast Transcript

Research from LinkedIn found that 47% of sales professionals claim that they use technology in sales at least once a day. So how can enablement teams ensure they are giving their reps the right tools to optimize productivity?

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 Jesse Potter, the Director of Field Enablement at Docusign. Thanks for joining, Jesse! I’d love for you to tell us about yourself, your background, and your role. 

Jesse Potter: Thanks for having me. I started out my career in sales, both in hardware and SaaS sales. I spent a number of years at Apple and then after that, I did a brief stint at a really small startup, sort of seed-level startup, and then came to DocuSign about seven years ago. I started out in sales here at DocuSign and then quickly moved into enablement. During my time here I have worn just about every hat within the enablement function. Now, I currently manage the team that is focused on any of the global programs that we do here at DocuSign that really affect everyone in the field. It could be everything from product enablement to process and technology, new hire onboarding, and everything in between. We also have an in-house instructional design team within my organization and we handle enablement platform administration, such as Highspot. 

SS: Thank you so much for giving us a little bit of that insight on your background, Jesse. I’d love to start with just understanding how Highspot has helped your reps with their productivity, especially in the current economic climate where teams are really needed to do more with less.

JP: Well, you’re spot on about efficiency. That’s really the name of the game, especially right now. It’s been a huge focus for us for a while, especially during Covid. Really, everything that we do as enablement should be trying to help the field spend more time with their customers and less time on non-revenue generating activity. 

I think from the perspective of how we can try to solve that, it’s critical to have that single source of truth where people go to find information, training, content, and everything that they need, and try to surface it for them in the places that they’re doing their work. How do we get our reps to find that content more efficiently without them having to search for it, navigate to it, bookmark it, download it, etcetera. 

We’re really focused on things like targeting the right content in Salesforce so that I can give a rep the exact competitive battle card that they need for their opportunity based on the product they’re selling, the industry that they are selling into, the competitor they’re up against and they can surface the exact right content for them, as long as the rep keeps Salesforce updated. With that, we’ve been able to shave over two hours per week off of the average amount of time that a rep has had to spend searching for content or information, which is a huge win and obviously that is a big focus for us right now. In the current climate, the focus is on making sure that we’re making our reps as productive and efficient as possible.

SS: Before highspot, what were some common obstacles your reps were experiencing when it came to finding and sharing the right content and how has Highspot helped to solve this to improve your sales team’s productivity?

JP: I think we had the same challenges that most companies have. The content was in so many different places, and reps were never sure what was really up to date or if it was the official version. This leads to the reps having to figure it out themselves, and sometimes that means they make their own content or use stuff that they’ve saved to their desktop. They had no idea of the version or how up-to-date it is. More importantly, they had no engagement or understanding of how the customers are viewing or using that content. Really it’s just sort of a black box.

Marketing is working hard to create really compelling materials and enablement is working really hard to build the training and the information that they need, but without a tool like Highspot, or the ability to measure that, it’s limiting. That’s really been the big thing for us, is trying to standardize that single source of truth.

I’d say the other thing that is really beyond just being that repository and that central source is then adding in the pitching and being able to track the engagement and actually making it a sales engagement platform. A great example is we have a lot of SMB sellers. They obviously don’t have the resources of our enterprise team to have the proposal writers build out custom proposal decks for each deal. One of the big wins with Highspot has been standardizing our proposal template, making it easy for reps to clone that, add in the details for their customer, and then pitch it out and get real-time data on how a customer is interacting with their proposal. 

We had a great testimonial from a rep who closed the deal right at the end of the year, a real-time crunch scenario. He sent over the customer a proposal with a few options, option A, option B, and option C. He was able to see that the customer spent just a few seconds really looking at option A and option C, but over an hour looking at option B over multiple sessions of viewing. That enabled the rep to know exactly which way the customer was leaning and accelerate the deal cycle by actually having the quotes approved, the order form generated, and ready to go for option B before they even got on the call with the customers. That sort of acceleration and efficiency has been a huge win for us.

SS: I love that. You and your team at DocuSign really engage your executives, which I think is something that our audience would love to get some best practices around. How have you gone about ensuring that the enablement team remains a must-have in the eyes of the executives at DocuSign?

JP: That’s a good question. It’s a constant process and I wouldn’t say that we’re even masters of it ourselves at all times. I think that’s the real risk that enablement teams can face. You can start and establish really great relationships and partnerships with your executives and especially your sales leaders, but like any relationship, you need to keep investing in it and you need to keep checking in regularly to see how things are going. We can’t just assume that because we aligned with the head of sales at the beginning of the year that we’re still on the same page in Q2 and Q3. 

Sometimes, I think for enablement, we are hesitant or a little afraid to check in with those executives and see if we’re still on the same page, maybe because we’re afraid of the answer or maybe because we just don’t think about it. That constant realignment is really important. On top of that, I think especially in these crazy times, there’s always a lot of turnover and change from new leaders coming in or changing their role, remit, or strategy. It’s really all about trying to establish that trust and partnership early on. That’s number one, getting your foot in the door with a new executive as early as possible and helping them understand that they can rely on you, then backing that up with proven success, even if it’s not flashy metrics on how much revenue you help bring in, can you even just show that you’re able to deliver for them when they come to you with a need? That’s a good trust builder and a great way to establish that relationship and partnership. 

Finally, especially when it comes to executives, consistency is key. Delivering quality programs consistently, communicating consistently, checking in consistently, and even just asking them the same questions to make sure that they know what to expect from you and what you’re expecting from them to make sure that you’re always aligned. 

SS: Those are some fantastic pieces of advice, Jesse. Now, one way that teams can improve productivity is by leveraging integrations in the tech stack and one that your team has found a lot of value in is the integration between Salesforce, your CRM, and Highspot. I’d love to understand from you, what are some key ways that you use the salesforce integration in your day-to-day role. 

JP: From my perspective, the Salesforce integration is huge because it allows me to really tie some of the activities that the reps are completing within Highspot with results. I can actually look and see the hundreds or thousands of opportunities that were positively influenced by some of the content or training that we surface to them through the Highspot and Salesforce integration. That data component is really huge and being able to tie back pitch activity or training completion or content utilization to closed revenue or activity in Salesforce and things like that. 

Salesforce is that single source of truth. We always say, if it doesn’t happen in Salesforce, it didn’t happen. Anything that we’re doing on a platform like Highspot or any other tool is put into Salesforce so that integration is number one to us. What is most critical for me is that level of data and then, again, being able to surface the right materials to the reps at the right time is really powerful and means that my team can be more efficient and effective and not have to build everything at all times. It means the menu of options can be a bit more tailored because we know exactly what reps need based on what’s coming to us from Salesforce. 

SS: To drill in a little bit more, what value does the salesforce integration bring to you and your reps, especially as it relates to productivity? What specific results have you seen? 

JP: I think for the reps one big thing is just being able to stay in Salesforce and being able to access all that content and training that Highspot provides within Salesforce is huge. That means there’s one less tab open that they have to have and there’s one less window that they need to go to. Another huge thing through the Salesforce integration is that now when they send out a pitch, it’s going to automatically relate that pitch to the right account and the right opportunity.

For us, we have a fairly large account team and obviously when we have territories and inherit new accounts, being able to go back and see the activity and content that has been shared with that customer previously is huge and allows a rep to quickly get up to speed on that account. 

I think in terms of results, it does come down to that efficiency and speed of being able to get to know a new customer which we’ve seen just dramatically reduces the time that it takes for a rep to inherit a new account and then be able to quickly see what’s happened previously, and even go and find the content in Highspot that they’ve seen and see if it needs to be updated or anything like that. 

SS: Fantastic. From your perspective, how have Highspot and Salesforce integrated also helped with a better understanding of which deals to go after and delivering the right content to reps at the right time?

JP: For us, that’s something that we’re just starting to scratch the surface of. Determining now, based on the data that we’re getting back, what content is most effective and what content is the most valuable to target to a rep. I think when we started out, probably like a lot of customers do, we tried to throw a lot of stuff at a rep within the context of an opportunity and it was like, here’s everything that you might need for this opportunity based on all the data we have available. We found that wasn’t the most effective way to go about it, which was actually about trying to find the most specific piece of content that’s going to be the most important for them and delivering that to them at the right time and the right stage of their deal cycle and things like that. We’re just starting to make strides there with our targeting in Salesforce. 

In terms of what deals to go after, being able to see like, hey, you know, X number of opportunities are more likely to close when we share this demo video as opposed to this white paper really has been a huge boom for our marketing team to understand like, okay, this is the type of content that’s resonating and whether it’s a video versus a white paper or more about the message that it’s trying to convey, we can say, all right, this video here talks a lot about mitigating risk for customers that seems to be resonating, so let’s lean more into that. Then we know, when we have customers coming to us with that sort of problem that they’re trying to solve, we know that that’s something we have great material for and we can probably win more effectively.

SS: Thank you for sharing your story on how you leverage Highspot and Salesforce together. Another key way that your team leverages Highspot to drive productivity is through sales plays. Since implementing sales plays that DocuSign, what direct results have you seen in terms of confidence and productivity for reps when they’re talking to customers? 

JP: I think one of the big wins for us as we launched sales plays at the peak of Covid and we had a lot of new and emerging use cases that were coming out for DocuSign products as a result of Covid. These were things that we just would never have been able to anticipate were going to be priorities, including things like vaccine testing and testing site management. These were not things that we thought of as obvious DocuSign use cases until they became the most important thing. We were able to launch sales plays specifically targeted for those use cases that are allowed and equipped reps to speak with confidence with the right content to back it up on something that they wouldn’t have received a lot of training on and probably don’t have a lot of previous experience selling to these different industries or personas that they’re talking to now. 

That was really huge for us because we were virtual and working from home, so it’s not like we could pull everybody together necessarily and do a bunch of training. Highspot allowed us to move very quickly and instill that confidence because we could build a play, build some content, get it out there, and get people speaking more comfortably about these new scenarios. We’ve tried to continue to replicate that with our sales plays and use it as a way to both enable the field and get more confidence, but then also be able to track and see like, okay, these plays are being effective and these aren’t so we can target more of that material. 

SS: I love that. DocuSign is also currently piloting Highspot’s training and coaching. What benefits have you seen from having a single platform for reps to work and learn from and how has that also impacted the way that you track productivity? 

JP: This has been huge for us. Like a lot of companies right now, we’re trying to consolidate and make sure that we’re making the best use of the tech that we have, rather than trying to have different apps for every different thing. If we can have a single platform that allows us to do everything that the enablement team would need and provide everything that a rep would need, that’s going to be a huge win. 

What we had previously was a lot of the content in Highspot and that being the source of truth, and then, from there, if you needed to complete a training module or a course, you would click on a link and it would take you out to another app. Maybe you’d come back, maybe you wouldn’t, but even just that simple piece of not having to click out and go to a different experience in a different place is huge for us. It means that we’re more likely to get engagement with that material. The other piece that we’re really excited about with training coaching is being able to do more microlearning. Traditionally we’ve done a lot of our learning courses and things like that in sort of fairly large, monolithic events, such as a 30, 60, 90-minute course that you need to take. For reps, it feels like this big endeavor to complete and that they need to carve some time out. Whereas instead, the training and coaching will allow us to create bite-sized micro-learning within the context of where they may already be going to find out about a new product. 

For example, if we have the product demo video and the pitch deck, and some of the messaging guidelines all right there on the page in Highspot, we can also have a little learning experience right there within that same environment. It’s a lot more intuitive and we can break things up more easily. We’re excited about that and being able to make more of that bite-sized, digestible learning happen within the platform that we’re already using.

In terms of tracking productivity, I think that’s going to be huge because we’ve already built the pipes and feeds from Highspot into our data warehouse and have the dashboards already aligned, so now it’s just adding in the training element so that we don’t have to have a content utilization dashboard and a sales performance dashboard and a training completion dashboard. We can try to bring all those things together, which is gonna allow us to save time and resources and build all that, as well as tell tighter narratives around when you complete this training and use this deck that we provide, which results in this result, which is exciting. 

SS: In a similar vein, how do you leverage analytics in Highspot to gather insights on the efficiency and effectiveness of your teams to continue to evolve future enablement programs based on the areas of most need? What are some of the benefits of tracking these metrics in Highspot?

JP: I think, again I’ve been talking a lot about data and measurement here, but it is a big focus for us and I think for most enablement teams, right now, we are trying to do a better job of quantifying the impact and the return from our efforts and the training that we provide. I think doing that in Highspot has a lot of benefits because number one, again, we’ve already got it integrated with our core systems, which is huge, so it’s connected to Salesforce. It’s connected to our SSO platform and all of that, so a lot of automation is happening just by using a single platform again rather than multiple.

One of the nice things about Highspot is it gives us a predefined way to share that data. All of our frontline managers can log in and view the data that they need for their individual teams. We can roll up that data to more of an executive level or if marketing wants to view all of that, they all have that access. We’re not doing as much manual reporting and data dumps out of the system as we had to do previously with other platforms, we are able to pre-build the right reports within the tool. Then we still have some other dashboards that we build, where we’re combining different data sets. The connection there in the integration is so tight and the data is very clean and reliable. We’re able to like work really easily with that data set to build out custom dashboards and tie it up with Salesforce data and things like that.

SS: Thank you, Jesse. Last question for you. How do you expect your organization to continue to evolve with Highspot? 

JP: We’re really excited about the partnership. We’re really excited about the idea of a true enablement platform. Being the enablement team, we love the vision that Highspot set about being the best enablement solution. With the future innovation that you all are working on, it is really exciting for us to be able to feel like we’ve made the right choice. Knowing that we’ve got a partner that we can really work with has been great. 

I think just for our field and for our reps in their day-to-day, the more that we can continue to build that. We’ve done a good job of saying, Highspot is now your source of truth, that’s where you go for everything. It’s like, come for the single repository and the trusted content that you know is up to date, stay for the customer engagement data that you get and the ease of pitching out content via Gmail or outreach or things like that. The ability to create landing pages and microsites for your customers, and the ability to collaborate with your peers on pitches and content, like it keeps opening up more opportunities for our team to accelerate their sales cycle and be more efficient and effective. 

For us, it’s just about continuing to drive that because you see the results grow exponentially the longer you’ve had a solution in place the more that people are adopting it and buying into it. We’re just excited to see it continue to evolve. We’re excited about the future innovation that’s on the roadmap. We’ve also had a great partnership and the team at Highspot has been really great to work with, so we’re excited to see what’s in the future. 

SS: I appreciate you sharing your insights, Jesse. Thank you so much for joining us. 

JP: Thank you. It’s great talking with you 

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. 

Related Resources

Sales Playbook Blueprint to Unleash Sales Productivity
Sales Plays
Sales Playbook Blueprint to Unleash Sales Productivity
Learn how to build an effective sales playbook, measure and drive sales playbook adoption, and optimize sales performance.
Episode 39: What a Good Sales Play Strategy Looks Like
Sales Plays
Episode 39: What a Good Sales Play Strategy Looks Like
Jillian Maiorino, manager of sales enablement at Vendr, shares best practices for creating an effective sales play strategy.
Guide: Unleash the Power of Effective Seller Guidance
Sales Plays
Guide: Unleash the Power of Effective Seller Guidance
Unlock the potential of effective seller guidance and boost sales success. Discover clear sales plays, adoption best practices, and impactful metrics.