Highlights[01:09] - His long journey to becoming a sales leader.[04:14] - How to know if it’s time to move to a new role.[06:26] - Navigating the ups and downs of being a new sales leader.[11:20] - The Wild West of managing managers.[14:04] - Striking a balance between managing and leading in any management position.[18:58] - Yesware - helping high-performing sales teams do meaningful email outreach at scale.[25:01] - Why you should allow your salespeople to think outside the box and do things on their own.[27:00] - Mentoring, coaching, and leading your salespeople: What sales leadership should look like.[28:39] - One of the most challenging situations he has faced as CEO.In this episode of the Transformed Sales Podcast, I had a chat with Joel Stevenson, the CEO of Yesware, a leader in sales productivity software. Prior to Yesware, Joel was the GM and Founder of Wayfair's B2B division which he grew to several hundred million in revenue. He began his Wayfair career by leading the company's home improvement products division, followed by his role as Managing Director of Wayfair UK, where he drove the growth of the company's international presence. Joel then served as Vice President of FP&A while Wayfair was making the transition to a public company. Before joining Wayfair, Joel held a variety of sales and marketing roles at Ariba, Innovus, and Verizon and was a consultant at ZS Associates. Joel earned an M. B. A. from the Yale School of Management, a B. S. in Business Administration from the University of Illinois, and studied Chinese at Harvard-Beijing Academy.Join us as we look back at Joel’s early career in sales and tech and the common ideas that have run through all of his work. We also talk about employing software and technology to optimize sales processes, how sales managers can boost productivity and create great work environments, what sales leadership should really look like, and so much more. I hope you gain as much value as I did from all the wisdom that Joel had to share.Quotes“You’re gonna typically get better results if you tailor your management style to the individual person and how that person operates and what they’re motivated by and what they need to do to get better” - Joel Stevenson“The best thing you can do is understand the way that somebody makes decisions and how they reach a certain judgment, and then try to help that person get better at that process” - Joel Stevenson“You really want your sales rep to be the person that’s gonna take what your company offers and match it up with what another company needs” - Joel StevensonLearn More About Joel Stevenson in the Links Below:LinkedIn - https://www.linkedin.com/in/joelstevensongm/Website - https://www.yesware.com/Email - jstevenson@yesware.comConnect with Wesleyne Greer:Wesleyne’s Website - https://transformedsales.com/Wesleyne on LinkedIn - https://www.linkedin.com/in/wesleynegreer/Wesleyne on Facebook - https://web.facebook.com/wesleynegreerWesleyne on Twitter - https://twitter.com/wesleynegreerEmail Her at wesleyne@transformedsales.com