According to the State of Sales Enablement Report, an estimated 90% of organizations now have enablement functions, representing a 20% year-over-year increase. So with this growth in mind, how can organizations successfully implement an enablement platform that ensures long-term success?
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 Shara Simms, the Director of Global Revenue Enablement at Cloudinary. Thank you for joining us Shara. I’d love for you to tell us a little bit about yourself, your background, and your role.
Shara Simms: Thanks for having me. My name’s Shara. I am from the San Francisco Bay area originally moved down to San Diego and never left, married. Two beautiful little girls. I’m the director of Global Revenue Enablement at Cloudinary. The scope of my role is not just the sales teams, but also our customer support teams as well as our partners.
So the revenue enablement kind of umbrella hits all of those different teams. And I think something probably really important to call out around the role is when people hear the term enablement, a lot of times they hear or focus on just the training aspect of it. But I think it’s, it’s so much more than that.
It’s strategic partnership, it’s sales process, efficiency. It’s the connector between everything going on in the product world and the go-to-market motion and how that information gets filtered down to sales or again, partners or customer support. So that’s a little bit about me and my role.
Shawnna Sumaoang: Thank you Shara! We’re glad that you’re here with us. And I couldn’t agree more. I’ve seen the evolution of the enablement profession just absolutely change from kind of being focused on content or focused on training to really taking a strategic seat at the table to help lead the strategy for the organization and how we bring kind of all the go to market motions together.
So I love to hear that you’re kind of overseeing that for Cloudinary today, and you have a ton of experience in both sales enablement and leadership roles. I would love for you to talk to us a little bit more about that journey into enablement and how has your approach to sales enablement evolved over the years?
Shara Simms: So I actually started out in the finance world working really closely with financial advisors in a customer support manager role. Just supporting day-to-day operations internal systems processes. I was in my, my young twenties, still trying to figure out, you know, what direction I really wanted to take my career.
And there was a part of me that had considered going into teaching. I had realized this, this passion that I had for just taking complex situations or overwhelming scenarios and breaking them down into digestible information. And so with that in mind, and while I was working in this support role, an opportunity came up at the same financial company to do some internal training, onboarding for financial advisors, industry best practices, that type of thing.
And I think that that was really the first turning point in my career where I realized I can take my business degree and this learned, you know, financial and business literacy and combine it with adult learning. Yeah. So adult learning quickly became not just a job, but really a passion and spent a good amount of my career at this.
Finance company going beyond operations and into more marketing and sales type training. From there, I eventually made a jump into tech. I was with ServiceNow for a couple of years, doing a variety of roles from strategy to learning design, and then leading a team of instructional designers and trainers.
And then I eventually made the move to Cloudinary and I would say after what has been my career so far that the background of adult learning mixed with the operational and business fluency is really what has served me well. And I think even though I don’t have a background as a seller per se, that’s really the background.
The adult learning background and operational and business is what I’ve been able to effectively apply into the world of tech sales and enablement.
Shawnna Sumaoang: I love that. I love that operational background that you have. I think it will apply to a lot of what I’d like to talk to you about today.
As I mentioned in the introduction,sales enablement is becoming more and more mainstream for a lot of organizations, and those same organizations are trying to figure out, you know, what are the right people, processes, and tools that I need to have in place. Place in order to really do enablement.
Right. You know, to your point at that sort of strategic level, and I know that you guys at Cloudinary had been on a previous enablement platform, and moved over to Highspot. I’d love to understand what motivated you to reevaluate and change your enablement tech stack.
Shara Simms: So yes, we did move to Highspot a few months ago.
I would say there were two really big motivators there for us. The first one, one of the largest ones would be the G Suite interability. There are a lot of platforms out there that have G Suite integration, but Highspot was able to support more of an advanced use case that we had, and the specific example, the previous platform we were on, so they did integrate with Google Drive in the sense that you could make updates to your master Google documents and then those updates would flow through to the version that the sales reps accessed on the platform. I think most platforms can do that, but beyond that basic integration, we had to jump through some hoops to achieve kind of what we really wanted, which was ultimately to take our internal customer data, have that flow through the platform, and then automatically transpose onto our templated customer facing slides for things like account reviews, which saves our CSMs and our account managers just hours of time Highspot can support this, which was really important for us. Whereas the previous platform, we would’ve needed to get virtual machines like parallels, for example, which came at an incremental cost.
But more than that, our security team just they weren’t thrilled with that, and it was just extra workaround. So that G Suite Interability was huge in being able to apply our internal data to the slides. And then the, the second big motivator was the administration piece of it. We are a very small team, but a mighty team.
But we spent a lot of hours trying to maintain and effectively administrate our previous platform. So the ease of use on Highspot, specifically ease of use with Salesforce integration, that and G Suite was the two big motivators.
Shawnna Sumaoang: m. Well I’m glad that you are now a Highspot customer and I think when you make an investment in the right tools for your teams, you wanna make sure that it’s getting adopted and, and they’re able to take full advantage of it.
And I know there can be challenges sometimes when rolling out a new enablement platform in driving that adoption, along with maybe, you know, a few other challenges that come along with kind of that change management, what are some of the biggest challenges that you think enablement practitioners might face when they’re rolling out a new enablement platform, and how have you overcome some of those challenges as you prepare to launch?
Shara Simms: Yeah. I think first and foremost, the challenge of having a really good and realistic strategy for the rollout and the adoption. I’ll circle back to that thought in just a moment, and the other would be, again, the hurdle of maintenance and administration. It really is time consuming and if you’re a small team without a dedicated resource, it can be challenging. So with that in mind, circling back to my original thought, which was that realistic strategy for rollout and adoption, what we did was recognize, okay, we don’t have a lot of resources here. What is going to be the most impactful thing to our teams and drive, I wouldn’t say drive adoption right out the gate, but drive that initial buy-in and the excitement from our sales teams.
We all love our salespeople, but we also know that behavior change and new system adoption can definitely be a challenge. So what’s going to get them excited to where they want to use this platform? For us, we determined it was seeing that Salesforce integration before even getting into building out landing pages and navigation and fancy training curriculums.
Just having that Salesforce or whatever, CRM, you may use integration with Highspot so that. The sales individuals can see the recommended content to use right there within their opportunity page. Rolling that out. Got them really excited and bought in and, and it got them asking me on a weekly basis, when are we getting this whole platform?
So we took a phased approach, realistic expectations of what we could do within our given resources. Phase one, Salesforce and Highspot integration Phase two, which is where we are right now, Digital Sales Rooms customizing content and sales facing landing pages. We purposely did not want to rush this portion of it because having a really well thought out organization of content on the various landing pages or HighSpot calls ’em spots, we use the term landing page internally.
I think that’s probably a really important piece. So that went into our phase two. Then lastly, phase three will be the second half of the year, all of our learning and training curriculums.
Shawnna Sumaoang: I love that. I know building strong professional relationships is another key focus of yours. As you implement a new enablement platform, how do you plan to drive adoption and build excitement? As you mentioned, how critical that is just a moment ago for your programs amongst the sales teams that you support.
Shara Simms: Yeah, retouching on, you know, the strategy of our phased approach, but beyond that, I think maintaining really close relationships with our sales leaders is very important. It’s something that I do, you know, ensuring that they’re bought in and that we have a measurement of success that the teams will be held to as well is critical.
So for example, we’re currently tracking our sales collateral usage. Are the teams using it effectively at the right stages, what’s working, what’s not? And as part of this tracking, we have an agreement with our sales leaders going into phase two of our Highspot rollout. And the agreement is we will be tracking that the teams are using certain pieces of collateral that have been deemed.
Essentially a required piece of content to share for all deals. And we’re tracking that. They share it via Highspot. So if they have their own version or own copy of the material that they send directly, we aren’t tracking that. If they didn’t send it through to Highspot, it didn’t happen. And again, the sales leaders are partnering with us to hold their teams accountable.
So that kind of strategic relationship at the sales leadership level I think is really important and it’s what’s helped driving our success with adoption of the platform.
Shawnna Sumaoang: I love that. As you mentioned in your introduction, shara, you have a lot of experience in training. What are some of your best practices for designing and implementing effective training, and how do you see a new enablement platform optimizing these efforts?
Shara Simms: Yeah, so first and foremost, always having clearly defined and stated objectives. This is your North Star. It’s gonna help you define if the. Expectation is a behavior change if it’s truly just knowledge retention, if it’s more so a communication versus training. So without a doubt, I want to call that out as probably the most important thing, and not only stating the objective, but also having really clear alignment and agreement of those objectives with your stakeholders.
Beyond that, which was maybe stating the obvious. I think a blended learning approach is always the best tactic to use as well, which is one thing I’m really excited about to build enablement on Highspot with this kind of mixed learning. We’re gonna have the ability to pull in my live webinar schedules combined with any on-demand training courses, then technical product documentation that I need the team to read as part of the overarching curriculum.
And it’s all going to be on one platform and one curriculum. We also use a tool called Second Nature, which is like an AI simulation tool for sales. It’s pretty cool. And we can also integrate those AI role plays into the same high spot curriculums. So just the ease of pulling in all of those different types of learning elements into one place.
It’s gonna be a really exciting second half of the year for us. I’m also really excited to build out curriculums that are role-based or skill-based. So tying in not only the learning component, but then any collateral or resources from the platform into one place based on the specific role or the specific skill gap that I am ultimately trying to solve for.
I think lastly, of course, the measurement component is also key. Being able to get insights that I can actively move against and identify, you know, where do I need to spend more of my time? By rep, by individual rep scorecards. So really, really excited for all of those kind of components and pulling in the best practices of learning.
Shawnna Sumaoang: On the topic of insights, as you move forward with the implementation, how do you plan to use data and insights to continue to refine your strategy and really ensure a successful launch?
Shara Simms: So I mentioned before that we are tracking collateral usage. Obviously we want to know what reps are using, not using how that correlates back to one or lost deals, but also from a behavioral change perspective.
We want to also use that data to help us see how well our reps are following the sales process and where we might need to double down on either reviewing the content because it’s not working or reviewing our actual process because there’s some hurdle in the way for them that we need to solve.
There’s also the customer engagement cracking that we’re hoping will help move the needle. So for example, as our reps start using the digital sales rooms, if they share a proposal there and the customer views it, great, there’s an indicator for the rep to follow up, see what questions they may have if the customer doesn’t view a case study that was shared.
Okay, follow up with an email, highlight the key points from that case study to ensure the customer sees it. The customer engagement tracking is going to be a really big one that we’re going to to build off of. And then the last thing I’ll say in regards to data is. Specifically sales leaders or the manager’s insights, it’s going to be really important that my team actively works with the sales managers so that they understand, you know, how to read their teams.
Data and their team’s insights. Again, I keep talking about behavior change, but really putting a focus on helping the manager turn into an effective coach for their team versus just a manager, right? Manager versus coaching, and really being able to use that data to help their teams get better. So I think those are the three big points.
Shawnna Sumaoang: I love that. And, and while we’re on the topic of data, and as you mentioned earlier, you’ve been working on making sure that you have the integration set up between Salesforce. And Highspot, what value do you see in this integration and what outcomes are you hoping to achieve?
Shara Simms: Yeah, the Salesforce integration is wonderful.
I absolutely love it. We are definitely trying to drive better use of our internal collateral. Not only just using the content, but using the right content at the right stage, and being able to easily track that. Right now it’s very manual for us. Another big piece of this is. Time efficiency. You know, no more searching around to find the piece of collateral that, that a salesperson might need.
It’s gonna appear right there in the opportunity for them. And then lastly, selfishly, from an administrative perspective, gaining a lot of time back in maintaining the Salesforce integration already. The integration works seamlessly. I’ve not had. Any trouble versus our, our last platform, we really just never got it to work correctly.
Anytime we would update a field name on Salesforce, we would need to manually update the field, you know, in the platform. And that’s just not the case with Highspot. It’s just all in automatic flow. It’s saved us a ton of time.
Shawnna Sumaoang: I’m glad to hear that. And as we look ahead, as you look to post-launch, what are some of the key go-to-market initiatives that you’ll be focused on driving? And how will your enablement programs help support these?
Shara Simms: Yeah. Our biggest initiative right now that I think is we’re gonna support is the sales process. Adherence the right collateral. Right messaging, right process, all at the right, you know, time and the right stage. This is a mix of the SFDC integration and the landing pages we’re creating in Highspot, which are going to follow more of a sales process versus product-led theme.
And what I mean by that is basically being guided by the opportunity situation versus having a seller go in and say, Hey, I just need information on this product. Well, do you really? Or are you jumping straight to solutioning? Where are you right now? Are you in discovery? And you need to pull in this material and have this type of conversation?
So it’s really the entire go to market. Sales process that we’re trying to refine and ensure that our sales team is again, following the actions that should be taken versus jumping straight to product or solution material.
Shawnna Sumaoang: I love that. This has been fantastic. Shara, last question for you, for our audience, for folks that are looking to roll out a new enablement platform, what’s maybe one piece of advice that you would give them to set them up for success as they get started?
Shara Simms: Before you start organizing your content, have a solidified agreement behind the scenes on the methodology for how you want that content to be served up to reps and what content you want to be served up for your reps. It can be really easy to fall into a bottomless pit of content. On a platform, all of the internal resources, all of the FAQs, everything that product or product marketing has ever created, and it contend to get out of hand for reps really quickly.
I think it’s fine if you want all of that internal material available, but just have a really smart way that you’re organizing and serving up the content. And I’ll give you our example. So I’m sure there’s, you know, a hundred different ways to do this as a best practice and the way that I do it might not be the best way for you, but again, that’s why we did the SFDC integration first, so that just the key content.
Was rolling into the opportunity while we gave ourselves extra time to really think about content organization on our backend and align with product marketing on how we were gonna organize it to be fed out to the teams.
Shawnna Sumaoang: I love that. I do think that’s a fantastic tip for our audience. So Shara, thank you again so much for joining us today. I really appreciate it. To our audience, 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.
