Embarking on a career pivot from insurance to the intricate world of legal tech, Jason Grimes, VP of Sales at 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.

Quotes:

"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."

Links:

Jason’s LinkedIn - https://www.linkedin.com/in/jasondgrimes/

Stretto - https://www.stretto.com

Get this episode and all other episodes of Sales Lead Dog at https://empellorcrm.com/salesleaddog/

Join us on Sales Lead Dog where we're joined by Larry Gordon, Managing Director of Emtec Inc., for an enlightening conversation on what it takes to be successful in the world of sales and leadership. Listen in as Larry breaks down his three essential drivers for success: capitalizing on technology inflection points, collaborating with exceptional CEOs, and prioritizing leadership actions over titles. His unique insights on fostering relationships with top-tier CEOs, alongside reflections on his own journey through sales and business development, offer a wealth of knowledge for anyone looking to thrive in the tech industry.

In our chat with Larry, we unpack the transition into sales leadership and the invaluable lessons that come with it. Discover the traits Larry values in potential leaders, including integrity and a deep understanding of the intricacies of relationship-driven business. He shares his strategies for assembling a balanced team, with a mix of personalities to lead effectively. This episode is brimming with Larry's advice on keeping the focus on customer engagement and sales results, offering listeners a blueprint for fostering strong, accountable leadership within their own teams.

We also tackle the sometimes challenging world of customer relationship management (CRM) systems. Larry and I explore the delicate balance between the advantages of centralized customer information and the potential drawbacks of CRMs becoming overly complex or disconnected from sales team needs. Learn about the philosophy of "walking the Gemba" to truly understand front-line requirements, and the pursuit of a streamlined CRM that empowers rather than encumbers sales professionals. If you've ever felt weighed down by your CRM, this episode will guide you towards reassessing and reinvigorating your approach to drive your business forward.

Larry Gordon is Managing Director at Emtec and has been co-founder and Chief Revenue Officer and CEO of several successful start-ups in the IT services and digital engineering and AI spaces. Larry has held senior leadership positions at Cognizant and Capgemini. He has had successful exits and built enduring customer relationships in the AI, security, devops and digital transformation segments. He has also been a successful angel investor in the energy and cloud spaces.

Quotes:

"I love identifying good opportunities at an inflection point in the technology industry. It makes things a lot easier to market, easier to recruit salespeople, and it's exciting."

"Leadership comes down to doing leadership things as opposed to being a leader. That's one of my themes."

"Offering [CEOs] things that are really useful, in my case, it's about driving revenue... I say I can do this and be accountable for it and spend the money the right way."

Links:

Larry Gordon’s LinkedIn - https://www.linkedin.com/in/laurencemgordon/

Emtec, Inc. - https://www.emtecinc.com

Get this episode and all other episodes of Sales Lead Dog at https://empellorcrm.com/salesleaddog/

Discover the keys to becoming a sales and leadership powerhouse as Jeff Fallis of GoFormz joins us for a riveting journey through his career, from humble beginnings to the pinnacle of sales success. Learn how mentorship, a strong work ethic, and the wisdom to carve your unique career path can accelerate your ascent in any industry. Jeff's remarkable story starts with selling hockey tickets in Arizona and evolves into spearheading the digital transformation for companies across construction and field service sectors, embodying the universal applicability of sales skills.

Step into the arena where sports and business strategies converge, offering a masterclass in leadership. In this episode, Jeff and I unpack the nuances of guiding a team through the highs and lows, setting the stage for a winning mentality. We tackle the tough aspects of leadership, from the personal growth that comes with transitioning from individual contributor to a leader, to handling the complexities of delivering difficult news during a crisis like the COVID-19 pandemic. Drawing inspiration from sports legends, we delve into the importance of resilience, role definition, and learning from failure to create a successful business playbook.

Cementing customer relationships and achieving lasting success hinges on the synergy between sales and customer success – a theme we explore with depth and insight. Jeff shares his philosophy that the sales relationship doesn't end at closing; it's only the beginning of an ongoing partnership that can make or break client retention. We reveal the strategies for setting clear expectations, the crucial first three months post-sale, and the benefit of a cohesive team-selling approach. New team members have embraced this philosophy, which keeps salespeople actively involved and supportive, solidifying the foundations of customer relations long after the initial handshake.

Jeff Fallis is the currently the Sr. Director, Head of Sales and Customer Success at GoFormz, a San Diego based company focused on enterprise software for digital forms and data capture. His career spans over 17 years in sales and technology, having held positions as an individual contributor all the way to Executive leadership. As the Vice President of Sales at Blast Motion for 5 years, another San Diego based startup, he helped lead the company's transition from early-stage sales to multi-millions in business. As the VP of Digital Media Sales at Pointstreak Sports Technologies, he was a member of the Executive team which successfully executed the sale of the company in early 2016. Prior to joining Pointstreak, he held the position of Director, Digital Media Sales at The Active Network, which filed an IPO in May of 2011 and was a 4x Presidents Club award winner. Throughout his career, Fallis has consistently built strong sales teams and effective strategic GTM plans in the technology sector. Fallis holds a degree from the University of Dayton (Dayton, Ohio), where he was an NCAA Student Athlete, Honorable Mention All-American and 3 year starter on the Football team. He also holds a Master’s degree in Sports Business Management from The University of Tennessee, where he was a graduate assistant in the Athletic Department for 2 years before moving on to start his career in business. Mr. Fallis was born in Akron, Ohio and resides in Carlsbad, California with his wife Breana and their two children, Stella 3, and Clay 2.

Quotes:

"In sales, the game never pauses. The ability to stay focused and disciplined underpins success in any competitive field."

"Mentorship has played a critical role in my journey. I've been fortunate to have strong mentors who have helped shape my career and leadership style."

"Sales is not just about closing a deal; it's about initiating a relationship that you continually nurture for long-term success."

"Adaptability and learning that you don't know everything are key lessons that I've carried from my early career roles to today."

Links:

Jeff’s Linkedin - https://www.linkedin.com/in/jeffrey-fallis-a8441512/ GoFormz Website - https://www.goformz.com

Get this episode and all other episodes of Sales Lead Dog at https://empellorcrm.com/salesleaddog/