SalesTech Star

SalesTech Star Interview with Jason Holmes, COO at Showpad

Tell us about journey into Marketing and Sales Technology. How did you arrive at Showpad?

Before I came to Showpad, I served as the VP of Global Professional Services at Adobe, followed by a five-year run at Marketo, where I last served as Chief Operating Officer. I came to Showpad in August of 2017, back when the company first established its U.S. headquarters in Chicago. I was actually the first Showpad employee in Chicago.

I saw a ton of potential in Showpad before joining the team. I like working in Sales and Marketing technology. In fact, I’ve worked in these categories my entire career. And I saw a huge market potential for Sales Enablement. The category is moving quickly, growing rapidly from a ‘nice-to-have’ tool for organizations to a ‘need-to-have’ solution. I realized this potential for growth, and that sold me on making a career jump. I’m excited about the Sales Enablement category and work for a great company where the culture is driven by people who are passionate about what they do, including the founders. Given how quickly the industry is growing, I’m motivated by what the future holds for Showpad.

What is Showpad and how do you differentiate it from other Sales Enablement platforms?

Showpad is a Sales Enablement platform that increases sales productivity and maximizes marketing’s impact. Our platform combines smart content, training and coaching recommendations for sales reps so they can both improve performance and deliver the right materials to prospects at the right time. The platform is powered by AI, which not only provides sellers with contextual content that buyers actually care about, but offers scalable training and coaching materials based on seller performance. This saves managers time meeting with every rep and helps sellers improve continuously over time.

Showpad is the first and only integrated Sales Enablement platform to combine content, training and coaching in one solution. Other platforms don’t provide these capabilities in one place, which forces enterprises to work with multiple vendors for the tools they need. We’re the only platform offering a user experience that sales and marketing love to use, with fast deployment time, enterprise capabilities and a global reach. Often, organizations need to choose which functionality is most important – we provide them all so our customers don’t have to choose.

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How different is your role at Showpad compared to the ones you had at Marketo and Adobe?

At Adobe, we were much more focused on B2C marketing, and at Marketo, our priority was B2B. At Showpad, we’re focused on Marketing and Sales Engagement in the B2B space. The audience that I target at Showpad has shifted to now include both B2B marketers and sales teams, which has been an interesting and exciting adjustment as I’ve learned how to best approach these parties and tailor our offerings to meet their unique needs.

My role has also broadened quite a bit. At Adobe and at Marketo, I was focused on customer success, whereas at Showpad, I’m in charge of not only retaining customers, but acquiring the best ones. See more, win more, keep more – those are my priorities as President and COO. I’ve moved from customer success to making sure our entire model at Showpad and the Sales Enablement category as a whole are successful, as well as making sure that our teams are fully aligned to enable this success.

Tell us more about equating the state of the Sales Enablement industry with the traditional Maslow’s Hierarchy of Needs?

Think back to the early days of sales. Salespeople had books of clients they’d call on the phone or visit face-to-face. The image of the traveling salesman sticks out in my mind. This is the bottom level of the pyramid.

Organizations then realized they needed more organized ways of reaching prospects, and CRM solutions came about, which empowered organizations to focus more closely on customer retention. Given these solutions were primarily sales focused, Marketing Automation came on the scene as a means to streamline marketing processes and ensure that prospects were hit with the right engagements before even reaching the sales team.

At the top of the pyramid is Sales Enablement. Once organizations mastered the bottom levels of Sales and Marketing engagement, they realized a need for tools that fully aligned these teams’ efforts. Modern Sales Enablement solutions ensure marketing and sales align to create content that’s successful throughout the buyer’s journey and empowers salespeople to meet quota more frequently. We’ve reached the peak in the sales and marketing technology evolution.

How much have the Sales Enablement practices changed since the time you first started at Showpad?

Since I started at Showpad in 2017, the Sales Enablement category has moved from a ‘nice-to-have’ to a ‘must-have’ functionality for today’s organizations. Businesses are realizing the importance of relevant content, coaching and training in closing more deals, improving seller capabilities and enhancing the overall buyer experience. The category has moved to near essential status – it seems like everyone on the planet is buying Sales Enablement tech, which wasn’t the case when I started. It’s been exciting to play a key role in pushing the category forward and shaping the perception of Sales Enablement.

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Which technologies in Sales and Marketing help to achieve better Sales Enablement?

AI has completely evolved how sales teams approach prospect interactions today. Our platform uses AI to learn which content buyers engage with most frequently, which helps sellers better understand which content will help close deals in the future. With this knowledge, sellers are better equipped to  present relevant content to prospects that demonstrates our differentiated business value.

We’ve also seen Augmented Reality make its way into the Sales Enablement space. In fact, Showpad was the first in the industry to implement AR in the sales process, enabling sellers to present complex products in any space, at any time. This helps sellers in both remote and field sales scenarios better demonstrate to buyers how products can fit in their unique organizational settings.

Finally, the role of video in the sales process has evolved the industry tremendously. While it of course enables sellers to conduct more calls in remote settings, it gives managers the ability to coach employees from any location. Traditionally, sales reps received feedback in face-to-face, formal settings, meaning that managers often had to travel. To eliminate costs and resources associated with this lift, video was brought into the sales coaching process so managers can provide feedback in real time. This helps reps scale improvement over time.

What role does Customer Success play in retaining customer groups and consolidating revenue opportunities?

The role of the customer success team is to make value visible to decision makers. This can be a challenging undertaking, as decision makers are always really engaged in the solutions that they own. If you start here and show decision-makers how your solution can help them achieve success, they’ll become advocates who can spread the word and create more advocates, which feeds growth.

At Showpad, we approach customer success with this mindset. As a high-growth business, we’re constantly maturing processes, but making value visible to decision makers is our unifying mission.

How do you achieve a culture-balance at Showpad? What percentage of this is driven by the application of technology, reporting tools and coaching?

We achieve a culture balance at Showpad by prioritizing our people, processes and technology. For me, the people are most important. In order for sales organizations to be successful, you have to hire the best people – both sales reps and sales leadership. We want our leaders within Showpad to be focused on hiring the best talent and continuously mentoring their teams. Personally, I focus 60% of my efforts on hiring the right people, 20% on our sales methodology and processes and 20% on technology enhancements.

Tell us how you achieve marketing-sales alignment at Showpad. How does it impact your targets?

Our sales and marketing leaders operate as essentially one team at Showpad – in fact, they sit next to each other, share a wall and probably spend more time with each other than their own teams individually. Achieving sales and marketing alignment is all about the relationship between the two teams’ leaders. My responsibility as COO is to make sure that they’re both arguing and agreeing but at the end of the day, aligning with each other. The problem that most organizations face is that there isn’t a single individual managing the coordination of these teams, which don’t get along naturally. If organizations can have someone at the top managing alignment and get sales and marketing back on track when the dissonance starts, then the relationship works wonderfully.

How do you leverage AI and automation for sales performance at Showpad?

We use every bit of automation and AI that’s available on the market today within Showpad, whether that’s AI-powered content recommendations to help salespeople more effectively deliver the right message to customers at the right time or training and coaching materials based on recent prospect interactions. At Showpad, we are completely bought into the idea of the modern seller, and that seller is powered by AI and automation. The traditional, manual methods of sales are a thing of the past.

How do you prepare for an AI-centric world as a Sales Technology leader?

At Showpad, we conduct internal R&D to determine the different and practical types of AI that will bring value to our customers over the next few years. A lot of this research is conducted through the constant stream of technology and tech-enhanced services that sell to us. We learn a lot from these companies on the bleeding edge about where we can go next with AI.

In some cases, we’re watching what the biggest tech players are doing and saying about AI. These companies are able to move markets, whether it’s through dialogue or what they’re actually doing with the tech. We’re keeping our eyes on the larger SaaS players, as their predictions often dictate the future and give us a roadmap of solutions we should be exploring to improve our individual customers’ experiences.

Which events and webinars do you most occasionally attend and why?

I get all of my industry information by reading.

Your advice to other CMOs and Sales professionals in the sales tech industry?

Focus on your salespeople. User experience is incredibly important, and investing in your sales team ensures that you provide the next-level, differentiated interactions buyers demand. The sales tech industry isn’t a winner-take-all situation. There’s room for more than one winner. What’s important is organizations prioritize making value visible to decision makers. This is the long-term win.

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Thank You, Jason, for answering all our questions. We hope to see you again, soon.

showpad logo


Showpad, the global leader in sales enablement, empowers sales and marketing teams to deliver better buyer experiences. The Showpad Sales Enablement Platform unifies sales content management, training, and coaching into a single user experience.

The most comprehensive data on successful sales interactions powers Artificial Intelligence to recommend the right content and training for every opportunity. With the industry’s only Sales Manager Hub, Showpad empowers sales leaders to turn middle performers into top sellers. Showpad services more than 1,200 customers across the globe including Johnson & Johnson, BASF, GE Healthcare, Fujifilm, Bridgestone, Dow and Honeywell. Founded in 2011, the company has headquarters in Ghent and Chicago with offices in Brussels, London, Munich, Wroclaw, San Francisco, and Portland.

Jason is responsible for leading and integrating Showpad’s global sales, marketing, customer success, and business development teams. As the leader of Showpad’s go-to-market teams, Jason takes pride in delivering solutions that help our customers’ marketing and sales teams grow revenue faster. As the father of an aspiring software engineer, he also has a personal passion for growing the tech community in his hometown of Chicago.

Prior to joining Showpad, Jason served as Chief Operating Officer at Marketo (pre-IPO through take-private), where he was charged with driving the company’s broad growth initiatives while unifying management of strategy, execution, and accountability across the entire organization. He also played a crucial role in the $1.8 billion take private acquisition of Marketo by Vista Equity Partners in August 2016. Before Marketo, Jason served in global executive roles at leading technology companies including Adobe, Omniture, and Oracle. He holds an MBA from Northern Illinois University.