MarTech360 Interview With Jon Perera, CMO at Highspot

Jon, can you tell us about your professional background and your current role at Highspot.

 Across more than 25 years in the software industry, I’ve held a variety of marketing, technical, and field positions. I’ve spent the latter half of my career growing two businesses from $10MM ARR to well over $100MM, but like many marketing leaders, I got my start doing demos. During my tenure at Microsoft, I had the opportunity to present keynote demos to executives, and I would often copy them onto CD-ROMs – a common practice back in the 1990s – and distribute them to solution engineers to help them showcase the product and win deals. It was challenging to determine who viewed the demos and whether they were effective in advancing deals, but it was the only option for sales enablement back then. Following my time at Microsoft, I took on the role of Vice President of Marketing for Adobe, where I helped to lead the business model transition to Creative Cloud, and drove strategic partnerships and product roadmap for Adobe Sign and Acrobat.

Throughout my career as a marketer, I have worked tirelessly to address the sales enablement issue that is now being solved. This is one of the many reasons why I was drawn to Highspot. Now every day I get to be part of a company that is revolutionizing sales enablement and solving old problems with innovative solutions that revenue leaders like me have dealt with for years.

Highspot has been in the sales enablement space for several years now. Can you talk about how the company has evolved since its inception and the changes you’ve seen in the sales enablement space during that time?

 Highspot has been working to make sales teams more productive since its beginning. While our technology has continuously evolved to anticipate customers’ needs through changing market conditions, our core mission has remained the same. More than a decade ago we set out to empower millions of people to do their best work – and we continue to do just that.

Over the years, Highspot has evolved to become the industry’s only natively-built, unified platform that increases the productivity and performance of sales teams – complete with sales content management, buyer engagement, training, coaching, and analytics. Using Highspot, revenue leaders companies including Aetna, Siemens, and Staples operationalize how they drive strategic growth initiatives and foundational sales programs.

Sales enablement has become a universal need for B2B organizations in every industry, across geographies. According to Verified Market Research, the global sales enablement platform market size was valued at $1.7 billion in 2020 and is expected to reach $7.3 billion by 2028. We saw a major shift in sales enablement happen in 2020 when the pandemic hit. The ability of teams to respond rapidly to changes in their internal and external environments was critical to navigating the unknown – and enablement made this possible. Now amidst challenging economic conditions where companies must do more with less, we’re seeing that the businesses driving efficient growth are those that eschew patchwork enablement strategies in favor of operational rigor. They’re focusing their enablement efforts on driving seller behavior change, ensuring that their people are equipped, trained, and coached to turn new initiative strategies into execution on the frontline. As a result, enablement investments are increasing because of the value it delivers when done well – Gartner estimates that enablement budgets will increase on average by 50% in the next five years.

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What strategies and practices does Highspot employ to maintain its leadership position and drive ongoing innovation in the sales enablement industry?

Innovation is at Highspot’s core. As the world evolves, so too must our product to ensure we’re meeting the constantly changing needs of our customers. To create a culture of continuous innovation, we do four things consistently:

First, we listen to our customers. We’ve set up customer advisory boards in Europe and North America where customers have open lines of communication to bring forth their ideas. This helps us partner with our customers from the start and ensure their ideas are heard and acted upon.

Second, we stay on the leading-edge. Since the early days, Highspot’s advanced team of AI and machine learning experts have worked on foundational AI and ML projects that have positioned us to now leverage recent AI advancements to build the best experiences for our customers.

Third, Highspot hosts a “Hack Week” twice a year, which brings together bright minds across our

design, engineering, sales, and product marketing teams to think about sales enablement challenges together. This collaboration fosters an environment where we think outside of the box and experiment with new ideas.

Lastly, many of our great innovations are joint innovations. Our rich partner ecosystem has been pivotal for building deep integrations – magic can happen when partners work together toward a shared enablement goal. We’re doing very deep level of co-innovation with companies like Salesforce, Gong, Salesloft, Clari, and others.

How can CMOs and CROs work together to drive business growth, and why is their alignment crucial for success?

 Today, CMOs are responsible for driving revenue just as much as CROs are. But the reality is most companies don’t have the basics in place for CMOs and CROs to operate as a unified team. In the current economy, where the importance of achieving efficient growth and customer retention is at an all-time high, failure to capitalize on this opportunity is a significant setback. With this in mind, it’s crucial to align the goals of your CMO and CRO to drive growth for the entire organization.

To work together effectively, you should create a single source of truth to determine whether your organization is winning or losing. This serves to create both visibility and alignment on goals and progress. Equally important is uniting on a shared narrative, ensuring the company’s messaging maintains its core meaning across teams and channels. In the digital era, customers have become more informed and have access to a wealth of information before making a purchasing decision. Thus, the messaging must be consistent across all touchpoints and provide buyers with the information they need at each stage of their journey. These are just a few of the ways CMOs and CROs can ensure they are singing from the same songbook – driving the business forward in the same direction.

What are the most common challenges sales and marketing teams face when trying to align their efforts, and how can they overcome them?

When we talk about sales and marketing alignment, it’s helpful to understand this partnership as the shared system of strategy, communication, execution, and goals that enable sales and marketing to operate as a unified team. Forrester reports that companies that align sales and marketing teams achieve 24% faster growth rates and 27% faster profit growth.

While the results are immense, getting there can be challenging. In my experience, I’ve seen three common issues at the root of most misalignment: companies don’t deeply align on goals; they have poor systems of communication; and they don’t have a system to scale winning rep behaviors. At a high level, to begin addressing these challenges, sales, and marketing leaders first need to get on the same page with their goals. I’ve seen two best practices from winning teams: 1) Create a shared scorecard; 2) Achieve a common understanding of seller confidence through a seller confidence survey. Second, sales and marketing teams need to establish trust. Without the ability to have open and real conversations about the state of the business, there is no foundation to build on. And finally, they need to act on a shared data set that provides insights into what works, and what doesn’t. A data set like this enables sales and marketing to scale best practices across the team and help all reps to master the winning behavior of the top performers – increasing quota attainment and unlocking revenue growth.

How can AI be used to automate and streamline the sales enablement process, from lead generation to closing a deal?

AI is already impacting the buying process for both buyers and sellers. Today’s buying process can be challenging – Gartner research revealed that 77% of buyers reported that their latest purchase was complex or difficult. This is where AI comes in – AI can further automate the buying process, with the ability to do things like instantly surface the information buyers seek, minimizing manual research. For revenue teams, AI is starting to play a big role in making salespeople more efficient. From surfacing content recommendations to analyzing sales calls for coaching opportunities, AI provides revenue teams with instant access to insights on content, behaviors, and strategies that help them close more deals, faster. What’s most exciting is that this is only the beginning.

How do you see the role of AI evolving in the sales and marketing landscape in the next few years?

We are at a massive inflection point for AI. While AI won’t replace the human element in the selling and buying relationship, it will be able to automate, amplify, and augment your work for the better, leaving teams with more insight to improve sales interactions and more time for selling. AI has the potential to catalyze sales productivity, which is a top-of-mind imperative for companies looking to do more with less amid a swath of external challenges such as budgeting changes, economic headwinds, and boardroom demands. Generative AI will mitigate time spent on tedious tasks, enabling leaders to focus efforts on ruggedizing their people to succeed in increasingly competitive environments. Beyond automating tasks, AI will also be able to produce on your behalf, following detailed instructions you give it. This will unlock new levels of productivity and efficiency and pave the way for the next generation of digitally powered sales experiences.

Is there anything that you’re currently reading, or any favorite books, that you’d recommend?

My colleagues and I are currently reading Blaze Your Own Trail by Rebekah Bastian. It underscores that there is no single right path to take and that change is a good thing. There’s an activity within the book that allows you to chart your aspirations, and it’s a refreshing reminder that there isn’t one way to get to where you want to go. This philosophy resonates with me as I believe it’s so important to keep learning, always. Nurturing curiosity and embracing change are a must for growth.

 Thanks, Jon!