Road Warrior Radio by Lola

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Testing for Coachability



For the first time, Road Warrior Radio will feature not one, but two people here in person at Lola Studios.

David Donlan is the CRO over at Crayon, and Mary Rogul is his VP of Sales Strategy and Engagement. Mary and Ryan used to sit next to each other in the trenches in their days as sales reps. David was one of Ryan’s first managers and certainly one of the most influential in his career.

Now you may hear the gang reminisce a little bit about the early days at Hubspot and some of the learnings that they have tried to apply to future roles. Some of those learnings worked and a lot didn’t.

The group dives into the importance of attention to detail in your sales process and what to research and prepare for when holding a meeting.

Finally, how do these seasoned sales leaders test coachability and curiosity during the interview process? Why those answers such important harbingers for success?


About our guests:

Mary Rogul, VP Sales Strategy - Crayon

As VP of Sales Strategy & Engagement, Mary Rogul is responsible for driving the mid-market and enterprise sales teams for Crayon, with a focus on sales hiring, training and developing a world-class team of account executives. Mary brings to the position a successful track record of more than 20 years that includes high-profile sales leadership expertise and recognized sales achievements in the B2B high-tech, healthcare, and financial services industries. A frequent speaker and panelist for Women in Sales Leadership and Women in Tech, Mary specializes in formal development and execution of strategic alliances and programs that add significant value to the customer relationship.

Prior to joining Crayon, Mary advised most recently to global enterprises to dive deeply into platform alignment, implementing strategic software and service initiatives with Cerner Healthcare and PricewaterhouseCoopers, LLP. The major contributions within these assignments are nurturing key relationships and engendered strategic partnerships that led to a much deeper understanding and support of their overall business initiatives.

Mary joins the Crayon executive team as a HubSpot alumna (2009-2015) and was part of the Enterprise Sales Scale-Up from 2011 through the public offering in 2014.

David Donlan, CRO - Crayon

David Donlan serves as the CRO for Crayon in Boston, MA. As a sales leader, he is responsible for developing market intelligence strategies that cater to the Mid- Market, and Enterprise looking to increase their sales and top-line revenue growth.

In his first 2 years, Donlan grew Crayon from 5 beta customers to more than 3,000 paid users, $5 Million in revenue, and helped raised $18 million in venture capital. Donlan is also a TEDx speaker and frequent guest lecturer at many Colleges and Universities.

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