Pour Over

Mastering the Art of Selling with Humility and a Growth Mindset with Jake Cronin

Episode Summary

This episode of Pour Over spotlights Jake Cronin, Co-CEO and Co-founder of Siro, a company building an AI coach for field sales. Our conversation with Jake unpacks the inspiring journey through his career, beginning with his role in field sales, when, at 18, he joined Cutco selling kitchen knives door to door. Jake describes founding Siro and the vision he has for the company’s future. He discusses how developing fundamental sales skills at Cutco was critical in his ability to launch and scale the company, and how mastering the art of selling is universally relevant for any career progression. We dive deeper into the broader importance of sales and discuss the development of and future vision for Siro. Jake shares with us how the importance of humility, authenticity, and a growth mindset have shaped his leadership journey, as well as his hiring philosophy. He then details the traits that set the foundation for a successful team culture: low ego and high autonomy. The conversation concludes with Jake discussing his role models, as well as the habits and rituals that help him maintain his edge as a leader.

Episode Notes

Jake's Journey: Started in kitchen knife sales at Cutco where he learned to cold call for the first time.

Siro Co-Founder: Co-founded Siro, a platform aiming to provide an AI coach for field sales.

Future Vision: Envisions an AI coach like Siro inspiring salespeople, pushing them to set ambitious goals and providing targeted information for success.

Universal Sales Skills: Asserts the universal relevance of sales skills in any career, emphasizing that those who embrace the sales aspect tend to thrive in their careers.

Hiring Philosophy: Looks for low ego and autonomy, believing these traits contribute to a strong team culture.

Team Culture: Values individuals who can aim themselves, execute great work, and exhibit passion.

Leadership Lessons: Stresses the importance of humility, authenticity, and a growth mindset in leadership.

Role Models: Admires Elon Musk for his bold decision-making and his girlfriend, who is recognized for fostering a culture of bringing one's full self to the team.

Habits and Rituals: Maintaining stability outside of work, investing in executive coaches, and keeping a healthy network of other founders.

 

QUOTES

"Everyone, if they reach the peak of their career, becomes a salesperson”

"Low ego is one of the strongest threads through our culture right now, connecting all our Siro employees”

“A great salesperson is providing a service and building trust”

“I was constantly humbled in my sales career with just how tough the job is”

“Anyone can be successful in sales and have a life-changing outcome if they’re willing to put in the work”

 

LINKS MENTIONED IN THIS EPISODE

Siro

Jake Cronin on LinkedIn

Joe Jordan on LinkedIn

John Chen on LinkedIn

Fika Ventures

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