Leading Sales Success Through Culture and Tech Innovation – Jason Grimes, VP of Sales


Embarking on a career pivot from insurance to the intricate world of legal tech, Jason Grimes of Stretto brings a compelling blend of legal expertise and sales acumen to the table. In our latest Sales Lead Dog episode, Jason shares his fascinating journey through the labyrinth of bankruptcy and corporate restructuring, showing how leveraging his legal background has been a game-changer in his sales strategy. As the VP of Software Sales, he reveals how understanding the exacting needs of legal professionals has not only honed Stretto’s offerings but has also reinforced his credibility and effectiveness in a market where precision is paramount. 

Building an authentic and resilient sales team culture is an art, and Jason paints us a vivid picture of how he does it. With a player-coach approach and a strong emphasis on vulnerability, he creates an atmosphere that encourages genuine interaction and confidence. He also throws in a unique meeting tip to help his teams segue into discussions with ease and authenticity. Jason’s insights are a masterclass in nurturing a sales environment that aligns with company values while also fostering individual growth and collaboration. 

Technology isn’t just a buzzword for Jason; it’s the backbone of operational success. Through anecdotes and expertise, he unwraps the importance of a robust CRM system, the art of conducting nuanced job interviews, and the intricate dance of integrating sales and marketing tech. This episode doesn’t just scratch the surface; it’s a deep exploration into creating a synchronized ecosystem where sales and marketing technologies work in concert, offering a glimpse into the future of strategic business growth. Tune in to discover how Jason Grimes orchestrates the symphony of sales, legal tech, and leadership. 

Jason is a seasoned leader with over 20 years of revenue-generating experience in the legal technology industry and a proven track record of success. With a long history of building and leading high-performing teams, he brings practical expertise to his role at Stretto where he leads the organization’s business-development efforts for its Best Case by Stretto business unit. Jason understands the importance of serving as a trusted partner to clients and is passionate about helping law firms achieve their business goals by leveraging technology resources to maximize productivity. As a licensed Attorney, he is a recognized legal-technology expert and has been featured in publications such as The American Lawyer, The National Law Journal, and Law360, and is a frequent speaker at industry events. Prior to joining Stretto, Jason held various senior positions with LeanLaw, AbacusNext (CARET), and Aderant. 


“Unlocking the secrets to a high-performing sales team starts with a culture that embraces vulnerability and authenticity.”  

“The leap from insurance to legal tech sales wasn’t just a career shift; it was an integration of my legal expertise into a winning sales strategy.”

“The internal sale is just as crucial as the external one. Gaining stakeholder buy-in at all levels is key to a thriving sales environment.”  


Jason’s LinkedIn  

Stretto Website  


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