Team Spotlight: RollWorks New Business Sales


As the newest platform in NextRoll’s robust product offerings, the RollWorks team is quickly making itself known as a leading account-based platform for growing B2B businesses. This in part is thanks to the amazing work of the RollWorks Sales team. 

Shawn Cook, RollWorks’ VP of Sales, is leading the team with an impressive 37-year Sales career behind him. While he initially planned to be a radio personality, Sales became his true love (outside of his wife Nikki who he married around the same time!). 

“I’ve been fortunate to lead professional salespeople at some great and fast-growing companies including Vocus, Eloqua, Triblio, and TrackMaven,” he said. “Fast forward to today with the advancement of technology and buyer access to information, so much has changed including me.”

So what drew him to NextRoll and the RollWorks Sales team in 2022?

“I was actually interviewing and close to moving forward with another company when I heard from Darragh Fitzpatrick, the RollWorks Chief Revenue Officer, about the role of VP of Sales over the New Business Sales team,” he said. “Making the decision to join RollWorks was an easy one for several reasons: 

  1. I love MarTech - The industry was valued at $749 million in 2020 and is projected to reach 1.6 Billion by 2027. I’ve often described myself as a marketer in a salesman’s body. So I get to be a part of both worlds, which are incidentally colliding and it’s also what I love about account-based marketing. 

  2. The NextRoll/RollWorks culture - I met with multiple people during my interview process and without me actually inquiring, each person I met authentically shared with me how our culture was not just a statement on our website; they actually embodied the things the qualities that I wanted. Diversity, Equity, and Inclusion were just the tip of the iceberg. Each team has a Vision/Mission Statement that revolves around employees having the best experience of their careers. Culture eats strategy for breakfast, lunch, and dinner every day of the week, and the culture I experienced made it easy for me to want to add my supply to this organization.

We wanted to hear more from Shawn about how the RollWorks Sales team finds success with a newer brand in a crowded market. Here’s what he had to say! 

Tell us a little bit about your team.

The RollWorks sales organization consists of six teams. Two each in Commercial/Small Business, Growth/Mid-Market, and Strategic/Enterprise areas with 8-10 Account Executives on each team. Drew Madison and Daniel Nelson oversee the commercial team, Pleasant Middelhof and Elise Schafer lead our growth teams, and Asa Hochhauser and Randy Yabes oversee our strategic teams. 

They are each remarkable leaders, and I’m fortunate to support them as they serve their teammates. We have a bold vision of growing that from six to 25 teams by January 2028, which means adding a record number of RollWorks customers and helping more B2B companies boost their business. We believe we can grow our commercial segment to 12 teams, our growth team to eight, and our strategic segment to five teams with three VPs, six Directors, 25 Sales Managers, and 200-250 Account Executives. Our goal is to be a high-performance team of leaders who know the way, go the way, and show the way. Much like the other departments within RollWorks, our mission is to ensure our Sales AEs have the best sales experience of their careers. 

What are some exciting future projects in store for your team?

There's a bunch of research from Gartner, Sirius Decisions, and others that point to changes in buyer behavior that we must align with to reach our goal and realize our vision by 2028. This starts by moving away from “selling” to a focus on “facilitating buying process” – or helping prospective buyers to determine whether they should be in a buying process. While sales success is the ultimate goal demonstrated by our ability to consistently exceed our sales quotas, we must first establish a Five-Star Standard (think Ritz Carlton) for our prospect engagement that serves to “eliminate our chance of failure” while ensuring a differentiated experience for buyers who are self-educating at a high-rate and are generally distrustful of salespeople. 

Most recently, we’ve embarked on a “team selling approach” that we affectionately call “choose your own adventure.” We’ve created 14 value-based discussions that prospective buyers can choose from to support their evaluation and help them best determine whether or not we are fit based on their goals, challenges, and success measures. This includes meetings with our solutions consultants, product team, technology and agency partnerships, marketing, sales, and our customer success and onboarding team to ensure they are aligned on how we will ensure their success as a customer with RollWorks. We even have an orchestrated business case/proposal meeting where we summarize the findings of their evaluation and deliver a comprehensive and compelling business case to help them gain consensus and approval for our solutions. 

For our customers, this differentiated experience in our “no selling zone” ensures they are coached to success rather than rushed to signature.

For our sellers, this means they have more confidence and control of their sales process and can more effectively lock down the next steps with a prospective buyer while focusing their attention on understanding the buyer while maintaining momentum. Better than 60% of our lost/deals are lost to “no decision,” stalled, or “gone dark.” The “choose your own adventure” meetings empower each AE to recommend and prescribe prospect interactions that empower sales executives to lock in a series of next steps and avoid “chasing” prospects. 

What makes RollWorks’ Sales team different from others?

In my 30-plus years of leading sales teams, I’ve had the privilege of working with some extremely talented and successful AEs that many would describe as “A-players.”

What makes the RollWorks team different is our process (when fully implemented) will reflect the behaviors of an A-player. This means if you’re a C-player with ambition, a B-Player struggling to make your way, or if you’re already an A-player, following the movements of this process will cause you to take on the physique of an A-player while also having the best sales experience of your career. 

Our goal is that our AEs would enter into conversations with prospective customers at the level of a “strategic contributor” who has done their homework and is prepared to engage with them and that by the time they have gone through a cycle with us have moved us up to the level of a trusted advisor. 

What is the biggest problem your team is solving?

Predictability. I believe ALL sales should begin and end with insight. Today, we’re seeking to utilize our amazing Sales and Revenue Operations team to provide insights that help ensure our predictability. Our vision of growing to 25 teams from six in this short period of time is certainly not automatic but it will be easier with insight. 

As I reach the end of my first 90 days on the RollWorks team, I’m pleased to say we’ve identified many of the “Cooperative Components” that are necessary for us to ensure predictability. For example, we’ve learned that when a prospect completes four meetings with us, our win rate is 16%. When a prospect completes five meetings with us, our win rate is 31.6%. If a prospect completes seven meetings with us, our win rate is 57%. This further substantiates the value of our “choose your own adventure” meetings. Having 14 possible meetings and needing to complete just five of them to ensure a third of our deals move to closed/won will help as we seek to solve the challenge of predictability. We’re uncovering as many insights/cooperative components as possible that assist with this. 

How would you describe your management style?

I believe in leading from the front. My desire is to be a leader who inspires and who my team trusts instead of a leader who commands and controls. My desire is to unleash the greatness in others to perform to their fullest potential, which would be far above our expectations.

I’m big on commitment over compliance, transformational over transactional, effectiveness over efficiency, and inspirational over motivational. I believe in managing things and leading people over managing people and leading things. I would much rather release and unleash than control and contain. Although I will freely admit that while I’ve been leading teams for a very long time, I don't claim to have “arrived,” and I’m constantly reading and listening to books while gathering feedback from my team in the areas where I can improve. In my opinion, being a good leader requires that I be “humblofident” (a combination of both humble and confident). Humble FIRST and confident always, which comes from being prepared.

How do you set your team up for success?

The ability to DEFINE = the ability to achieve. I approach success for my teams with the understanding that we all want to be successful in our prospective roles. However, in sales, we know consistent success for everyone is sometimes elusive. 

I believe in going slow to go fast. As a team with a vision as lofty as ours, success starts with a defined standard. Who do we want to be as sales professionals and why? Once we have a common standard in place, we apply a bill of rights to ourselves and our team members that ensure the following:

  1. Context - A roadmap to success and knowledge of where you are.

  2. Consistency - Have your voice heard and responded to across all communication channels.

  3. Clarity - Know what you can expect from us and how we will help to make you successful.

  4. Continuity - Know the RollWorks long-term vision and understand how being a part of our team will benefit you personally and professionally, which includes access to a community of internal or external experts and peers to assist in your development.

Are you ready to grow with RollWorks? Check out open roles on our Sales team!