Today is a special day—we’re celebrating our 100th episode! For this milestone episode, we’re diving into a theme at the heart of enablement: making the impossible, possible. In today’s business landscape, only 28% of sellers expect to hit their quota. So how can you enable your teams to overcome the challenges of the current market to achieve consistent go-to-market 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.
In this episode, we’ll hear from nine leaders who transformed challenges into business outcomes, delivering impact against their go-to-market initiatives through enablement. From earning leadership buy-in to aligning go-to-market teams and boosting productivity, these leaders enable the impossible for their businesses. We hope their stories will inspire you to push boundaries and redefine what’s possible in your organization.
Driving consistent revenue growth can feel impossible when silos divide sales, marketing, enablement, and revenue operations. A unified enablement approach can break down these barriers and drive measurable impact. But how do you demonstrate the value of enablement to stakeholders and secure their long-term support? In this part, we’ll hear Pam Dake, senior director of GTM enablement at Menlo Security, share her success story for gaining leadership buy-in.
Pam Dake: My name is Pam Dake and I work for Menlo Security, a cybersecurity company that actually has just surpassed a hundred million ARR. One of the bigger challenges that I’ve had recently has been in aligning the executive teams in order to really, truly understand how to be impactful, leveraging the go to market motion in a way that not only lands the big deal, but also allows us to have a very productive and valuable customer relationship long term.
And so for me, it’s been gaining the opportunity to have that meeting with all of these critical stakeholders, have them see value. Each and every time that you meet with them, so that they feel like they’re getting something out of that meeting where it’s actually really driving the business forward in ways that they may not have seen initially.
And so for me, it’s been setting up a recurring meeting with those folks who are the most senior and executive in the company to be able to drive forward what sales needs, which actually is driven primarily from what sales needs. Really, our customers are looking for from us as a company. Be tenacious about how you’re able to make a difference with aligning their internal stakeholders and really driving forward the programs that will make a difference, not only in the short term and the long term.
So as you consider the strategy that you’re building. Ensure that you have your other internal stakeholders aligned and do that in ways that create value for them so that they can see the impact. One of the things that we talked about earlier was data. Leverage the data that you have on hand. Leverage tools that provide you with that really impactful data that provide you with insight into the leading indicators that will actually drive the business longer term with the lagging ones. So the bottom line is really taking an outside in approach with what you’re doing from an enablement lens. How does this impact my customers? Therefore, how am I able to build the best programs that I can that will enable My internal stakeholders, my internal teams, in order to be successful and provide value to our customers, not only in the short term with what wins they’re able to achieve, but how they’re able to grow and develop the relationships over time.
SS: You need stakeholder buy-in to break down silos and align your go-to-market teams – but why is that alignment so critical? Without it, you can’t coordinate, plan, and execute the initiatives needed to drive the business outcomes that matter most. And when 90% of organizations fail to execute their strategies successfully, it clearly takes more than guesswork to achieve those outcomes. So how can you define, execute, and optimize your go-to-market initiatives to deliver unprecedented impact? In this part, we’ll hear stories from enablement leaders who brought key go-to-market initiatives to life through enablement.
First, let’s start with a common initiative that impacts teams across the go-to-market organization: product launch. Effectively bringing a new product to market can make or break your revenue targets. We’ll hear from Chris Wronski, senior program manager at Keysight, on how he helped deliver a product launch that contributed to the first revenue growth in seven years despite a tough market.
Chris Wronski: My name is Chris Wronski. I’m a Senior Program Manager at Keysight Technologies, and I am the architect behind our Highspot implementation.
The last couple years have been very difficult in the, across the entire industry, right? Every, many companies are talking about it, us included. If you go pull our quarterly info, you can see the last seven quarters have been very difficult for us. So what I talked about earlier, the focus on new product introductions.
That’s an opportunity for us to make some hay. That’s an opportunity for a, we’ve got a brand new product, we’ve got a brand new reason to go talk to customers. Even if they have no opportunities, at least go explain to them what we’ve got, right? There might be something in there.
We’ve done a lot of work around building sales plays in a way that the seller can consume it and trying to crush it down. Really, um, aggressive simplicity is what I would call it. But by building that in and giving them just a little bit of info to start the discussion in a way that we knew you could start that discussion with nearly any customer, that’s enough to get the ball rolling and let them go do their sales job.
We’ve done a ton of pushing training to them. I can see that in the numbers. I can see when we do our training. I can see the following week there’s a huge spike in people going to those sales plays and looking at them and using them. And so, Last quarter we, we turned the curve, right? Turned the knee of the curve and brought back at least a little bit of growth. We were positive for the first time in seven quarters.
SS: Next, let’s dig into an initiative that is likely on the minds of many GTM leaders with the new year around the corner: sales kickoffs and events. Starting off a year on the right foot can provide a business with momentum that carries through the rest of the year. Brooke Cole, manager of global field readiness at Workato, shares with us how her team drove an impressive boost in NPS with their first in-person SKO events.
Brooke Cole: My name is Brooke Cole, and I’ve been at Workato for almost three years. A business challenge that myself and my team have overcome that we’re really proud of is probably our first in-person SKO events that we executed earlier this year.
Because of COVID and just the nature of the world, we had been unable to get together in person as a collective regional team. Really, ever. We hadn’t. We had one scheduled, and then we had to cancel it, of course. Uh, so, earlier this year, our team, we ended up doing it regionally. So, in North America, in APJ, and in EMEA, our team was tasked with putting on three different SKO events within three to four weeks. And we traveled to each one of them. And the way that we overcame that really was just a sense of teamwork and camaraderie. We built trust with one another. We had really open dialogue and communication. And we really used our skill sets and our collaboration. To put on an event that got an NPS score of 85 globally. We heard the phrase, this is the best SKO we’ve ever had.
And truly, to be fair, it’s the only one we’ve ever had in person. But people left jazzed, and they left inspired, and we leveraged Highspot as a part of that. Going into this next year, this is the second year where Highspot will be our landing page for our global event that we’re having, and so it’s going to be the Know Before You Go, and we did that as a trial period last year, and it worked out really well.
The traffic was great when people had questions, we were able to direct them to Highspot for that, and I think we were proud overall of just the vision that we put together. And how we executed the tools and the apps that we already had at hand in order to bring everybody together in a centralized place to give them the awareness and create excitement around the events.
SS: Now, we’re diving into an initiative that can have a profound impact on productivity: the sales process. Research shows that just 28% of a rep’s time goes to selling, and an optimized sales process can help you streamline workflows and save time. Let’s hear from Jay Livingston, head of enablement at Corporate Visions, on how his team is improving the sales process and delivering time savings as a result.
Jay Livingston: I’m Jay Livingston. I lead Global Sales Enablement at Corporate Visions. I remember when I got involved in enablement, one of the things that I learned is that sellers spend an inordinate amount of time each month preparing their own content. They have a lot of goals.
so we in a headquarters environment have time to sit around and think about how to improve some of these processes. Salespeople don’t, right? They’re running from call to call, always trying to be ready to meet that moment. And so one of the, one of the main challenges I’ve been focused on quite honestly for more than just the last couple of years at CVI is how do we make.
Content and resources and tools and assets more purpose driven more readily available, more easily findable, and then more from a usability perspective, make it easier for, again, for those sales folks to be able to execute in those moments.
And so I remember when we first rolled out Highspot here back a few months ago one of the things that, that a member of my team Eric is a VP on our team, would say, man, he’s I just, I don’t have time to do all the things that I need to do because I’m constantly getting emails or messages or slacks about, hey, where’s this and where’s this and where’s this, Highspot literally I no longer have to field any of those calls.
As a matter of fact, when we were here in August, I had a chance, we were sitting around the table to share a story that just in the month, I think we had been maybe a month in at that point the amount of time that Eric has been able to get back in his day. To not have to field those annoying, it can be very annoying requests, right?
Because how many times do we tell our sellers where things are, how to use them, right? And you almost wonder sometimes, are they listening, right? Are we not communicating it effectively? All of a sudden now we’re seeing literally no request for where is this? How do I use it, right? And so again, what I would say is it’s not bulletproof, right?
There’s always going to be opportunities to improve. But one of the hallmarks of the way that I’ve tried to lead enablement organizations is to really have it boil down to two things. One, what is the seller’s, or what is your colleague’s ability to be able to execute in this moment?
We can lean into the ability to help them get better. And two, what is their willingness? And willingness, oftentimes, is influenced by how easy something is to execute. And so if we can remove the willingness component, then we can just focus squarely on the ability. And so as we continue to move forward those are really the two things that, that we continue to evaluate ourselves by.
Are we making it simple? And how are we helping folks coach or how are we coaching folks to get better and to be more effective and to utilize these amazing tools and opportunities that we all have
SS: And now, let’s talk about an initiative at the heart of enablement: training. When done right, sales training can drive the behavior change reps need to consistently hit their targets–but often, that can be easier said than done. Let’s hear Anthony Doyle, director of sales enablement at Turnitin, explain how he revitalized training and ultimately improved seller engagement.
Anthony Doyle: My name is Anthony Doyle, and I’m the director of sales and development at Turnitin. In terms of overcoming really difficult problems, the biggest problem is engagement—engagement from the sales teams, leaning into the enablement programs, spending time, and investing their time in their own development.
I think that’s what we’ve seen a real uptick on and success on in the past, maybe six to twelve months. We’ve seen a change in attitude. We’re getting success now when launching new training programs. People are leaning into them, they’re completing them, and they’re giving us good feedback too, which is something that I probably never thought I would have said twelve months ago because we started investing a lot of time and building a lot of training, but then that wasn’t really getting consumed.
It was very difficult to get managers to even back us up and roll it out with our teams. Whereas now, when I’ve just presented to the go-to-market team on a go-to-market all-hands, strategy for the sales academy, there was just a lot of love in the room. A lot of people saying, ‘This is fantastic. We can’t wait to see it in action and get our hands on it.’ So we had a lot of good feedback from that session. And that’s really pleasing for me because it means that the strategy was the right strategy.
I think the message for teams and enablement teams out there, if you are getting those challenges with engagement, is to keep at it, show value, and really drive those proof points. Get those wins regionally with teams who will engage, then present it in a very easy-to-consume way, and in a way that the teams can feel confident about engaging with. You will see the results, and the tide will turn. So that’s something I’m proud of.
SS: Next, let’s explore an initiative that drives long-term impact—coaching. Effective coaching helps sellers apply newly acquired knowledge to maximize their performance. Let’s hear from Andrea Holzwarth, VP of Sales Enablement and Customer Operations at Project Lead The Way, on how she supports ongoing coaching to help reps sharpen their skills.
Andrea Holzwarth: We see a lot of value in coaching and training. We have our senior directors, our sales managers, really providing that one-to-one support for our reps out in the field. And we want them to be able to have those coaching conversations and the meeting intelligence helps with that. So we can see the calls.
What is that? What’s going well? Maybe what are they struggling with? But I think a lot of times. I say this, that it’s easier to edit than it is to get started, and so having that AI feedback automatically in there it’s helpful, that’s a starting point. And then our senior directors, our sales managers can go in, provide more of that personalized coaching that they may see, but it gives them a starting point.
One of the other benefits that I see with Meeting Intelligence is I just think about as a sales rep being in the field especially virtually now that we’re, all we do is meet virtually. It feels like we’re in the, we actually go to schools and districts too, but I would have loved it when I was a sales rep to just see, I think I know how I show up on camera or how I’m speaking to a customer, but, It is so helpful to go back and record and just see man, I said “um” a lot. So it helps with some of that coaching too.
SS: And to close out, we asked our guests for advice on how they enable the impossible in their organizations. Here are a few tips from Suzanne Heller of Flight Centre Travel Group, Jennifer Shelley of QuidelOrtho Corporation, and Susan Kinser of Net Health Systems to help you take your enablement efforts to the next level.
Suzanne Heller: Just go for it. Because we have the tools that make us successful. We have the tools to be able to measure what we’re trying to achieve. And it is okay at the end of the day to go back to the drawing board if it doesn’t work. But we won’t know that if we don’t try. And if we look at enablement 5, 10, 15 years ago, it wasn’t like what it is today.
But because of the trial and errors that have, come up. Advice to anyone that is in an enablement role is just to go with your gut and deliver. And it is okay to go back and look at the data and pivot and optimize. You won’t know what’s successful unless you try it. I think my second piece of advice is buy-in.
To your business, your brand, you tell a story, you bring immense value, and it’s really critical to create that brand awareness for yourself and for your team, to be able to let them know the purpose, and the deliverables, and the ROI that you bring to the business. So this would be my two.
Jennifer Shelley: Not to get discouraged. Sometimes, we initially we will bring to the table things that sound outside of the box and Highspot tends to be on the cutting edge of technology. But technology can be frightening, and I think that you can get discouraged when people are, not as excited as you are about what you’re trying to accomplish with the technology that you have.
And just take your time, stay focused stay, consistent with your message and understand that it takes time for people to really understand the vision that you might have if they haven’t been exposed to all the great the great information that Highspot is providing them in terms of that cutting edge capabilities in the platform.
Susan Kinser: Whether you have a seat at a table or not is to, try to get your voice heard so that you start having those conversations to understand the business outcomes that your team is looking to change, right?
I think that the moment you’re able to ensure that you’re aligning any of your programs or any of your initiatives to those specific strategic initiatives that your company in a larger way is looking to achieve when you get that kind of information and you’re getting that feedback and you’re having more, and then they have that insight into the change that you’re making it just makes you more of that strategic partner and it gives you that space to continue to make that kind of success progress and success, I would say get a unified platform. Use Highspot and use the resources.
And so I think what’s fun is in this ever growing enablement space, having your voice being heard only. makes the impossible more possible, right? As we start bringing things together and we start, having different ideas or having different needs, and we’re able to do things in these different ways, I would say my advice is to get connected to those business strategies, those business insights, and then get that unified platform and keep scaling.
SS: As you heard from the enablement leaders we featured in this episode, nothing is impossible with the right team, tools, and processes in place. In looking to the year ahead, take stock of the challenges on the horizon and rather than looking at them as obstacles, channel them into opportunities to push the boundaries of what you once thought was impossible.
Thank you for joining us for this special 100th episode of the Win Win Podcast. We’d love to hear how you are enabling the impossible—be sure to connect with us in the Highspot Spark Community to share your advice, and tune in next time for more insights on how you can maximize enablement success with Highspot.
