SBI recently spoke with Kent Cissell, the senior vice president of sales operations at Heartland payment systems. Heartland serves over 300,000 businesses in the US by offering best in class payment, payroll and POS solutions for businesses of all sizes. Kent has a lot of responsibilities at Heartland, including sales enablement, recruiting, and sales strategy. Our topic of conversation focused specifically on sales enablement. How has Kent been able to successfully enable his sales team so that they hit their revenue growth objectives consistently?


Business Outcomes for the Sales Enablement Team

We began our discussion around the business outcomes for the sales enablement team. What does Kent’s team need to deliver?


“When I look at our primary business outcomes we’re looking to achieve, I think there are two big ones,” explained Kent. First, he looks to provide consistent growth of the sales organization by implementing solutions that lead to increased productivity of the sales team. And secondly, he looks to build platforms or solutions that allow them to effectively scale this grown.


Essentially, productivity and scale are two big things his sales enablement team works twoards. And in order to do so, there are strategic focus areas that Kent looks at across 5 different areas:


  1. Sales talent – from hire to retire, he focuses on equipping employees with the knowledge needed to maximize their opportunities while at Heartland.
  2. Architecting distribution approaches – the enablement team must build and manage the multi sales distribution approach as their offerings and channels continue to evolve.
  3. Efficiencies through technology solutions – Heartland embraces several different technology solutions that enable them to scale.
  4. Process improvement – Kent’s team spends a lot of time compiling, organizing and analyzing data and information that allows them to drive the business ahead.
  5. Sales support – at Heartland, they pride themselves on having a strong sales support organization that works in partnership with the sales production team to help reps navigate tricky scenarios and off load support responsibilities.


Sales Enablement Org Chart

What type of team does Kent have that allows him to meet these objectives and goals? He was able to dive in and explain how his team works at Heartland. Ultimately, there are 5 groups to Kent’s enablement team:


  1. Sales training team – they are responsible for orientation, ongoing talent development, learning content management, and leadership development.
  2. Sales analytics team – this is essentially a small business intelligence group focused purely on the sales team’s needs.
  3. Sales technology group – this group builds and maintains their sales enablement platforms and translate the business needs into technology solutions.
  4. Sales communications team – this is a “mini-marketing team” that ensures consistent and strong communications are made to deliver information to the right groups in the right medium at the right time.
  5. Field marketing team – this group works with the product teams to ensure alignment with the appropriate distribution channels.


At the end of the day, Kent’s sales enablement team is a key piece to their overall sales strategy. With every new rep added, there is an expectation to generate revenue growth as quickly as possible. Kent has been able to do just that at Heartland by setting clear objectives for his team. Leverage the How to Make Your Number in 2018 Workbook to access a revenue growth methodology to hit your number quarter after quarter, and year after year.


John Staples

Leads teams of highly qualified experts, all relentless in their pursuit of helping you make your number.

John is the global leader of SBI’s account management business unit. As such, he and his team help clients across 19 verticals drive top line growth and operational efficiency in sales and marketing.


John’s marketing, sales and product expertise span a multichannel strategic approach. He has an unyielding focus on strategic and key account development, which enables strategic alignment between all functional team members in order to reduce acquisition cost and increase lifetime value.


His broad experience in sales, marketing, product and engineering allows him to bring a unique problem solving approach to his team and clients. As he has discovered through decades of experience, clients are often distracted by the symptoms of a larger problem and overlook the root cause of it.


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