“Macro market changes within the healthcare industry are driving our biggest sales challenges. Our targeted buyers are facing a fluid economic situation as they make the arduous shift to a quality-based model.


  1. Our lead generation opportunities are coming in earlier in the sales cycle, requiring more customer education and additional touch to avoid clogging the sales team funnel with early-stage opportunities.
  2. Our currently funneled opportunities are also requiring more education to reduce the investment risk, requiring us to bring in a specialist to facilitate this education. This is resulting in elongated cycles and higher costs.
  3. Our customer education burden requires a well-oiled training machine to ensure consistent messaging across the team and segments while also solving for territory-specific challenges/messaging.”




Executive Vice President

Sales & Business Development

Parata Systems, LLC.



“I was hired by UC4, a private-equity backed company, to participate in a top–down transformation project, which involved a name change and rebranding effort, as well as rebuilding and retooling a global sales organization to manage unprecedented growth. The biggest challenge we have encountered is about managing expectations for change. It has been a bit like taking over a 6-10 NFL football team…We had to swap out the playbook, swap out 40+ percent of the players, swap out 50 percent of the assistant coaches and instill the rigor and discipline of a well-designed program. We were quite successful in the first year. … To complete the analogy, we finished Year One of the transformation at 9 -7, but installed the infrastructure of people and processes for further growth in Year Two. Of course, the board wanted us to win the Super Bowl!! The biggest lesson for me was clearly aligning the program, the expectations and the time needed to define success.”



Chief Sales Officer






“Identifying sales professionals – both individual producers and leaders – who have the character and commitment to fit into our culture is the biggest challenge we face. When you are a growth-minded company with aggressive goals, finding talented people, especially those with exceptional intangibles and the proper mindset, is almost always your biggest limiting factor.”



Chief Sales Officer

Heartland Payment Systems






“We have had a great year in sales in 2014 with record bookings, and our biggest challenge in 2015 will be to repeat this performance and deliver record bookings again. To achieve that success, we are focused on refining and improving our segmentation process and better enabling our channel partners both domestically and internally.”




Executive Vice President

Global Sales








“One constant challenge is not allowing the day- to-day whirlwind to distract focus from the “big rocks” necessary to execute your strategy. In the battle to grow profitable revenue, we must continuously evolve the sales coverage model. This includes connecting the addressable/attainable market opportunity with the most efficient market coverage and resource leverage, evolving and executing territory plans, and maintaining appropriate account assignments.”




Chief Sales Officer

Global Sales Organization





Leading the Sales Team As CEO

This month, our cover story profiles Jack Lynch, the CEO of Renaissance Learning, the educational analytics company that counts Google Inc. among its investors and was acquired last year by private equity firm Hellman & Friedman for $1.1 billion. You’ll get a close-up look at how Lynch has worked to transform Renaissance’s sales operation and improve market penetration.