LU 374: Change Management and Executive Coaching with Joel Stevenson, CEO of Yesware

Yesware is an all-in-one sales software that provides users with everything necessary to prospect, schedule meetings and follow up, all from the comfort of the inbox! Here to talk about the company and his role as CEO is Joel Stevenson! Yesware has raised $47 million as well as acquiring a host of companies along the way and we wanted to bring you the lowdown on how they have done it all. We hear from Joel about his journey from SVP of Sales to COO of Marketing and finally to CEO of the company! Joel explains his relationship with Matt Bellows, the co-founder and former CEO, and a lot of our conversation is spent unpacking the transitions the company has gone through and how they have grown and evolved. Joel started in sales and tech and he is kind enough to look back at his early career and the common motifs that have run through all of his work. We also talk about leadership techniques, Yesware’s belief in executive mentorship, and how they go about communicating in the company. So, for all of that and a whole lot more, listen in with us today!


[00:21] Before we jump into today’s interview, please rate, review, and subscribe to the Leveling Up Podcast!

[00:48] Joel’s long and winding road to his current position as CEO.

[02:10] Departing from Wayfair and finding a home at Yesware.

[02:50] Yesware’s business model, their offers, and how they charge and make money!

[03:52] The growth of the business over the last six years and their move away from freemiums.

[05:09] Developing leadership and Joel’s own path to his current role.

[08:05] Joel’s attitude to change management and keeping the team on board.

[09:12] Matt Bellow’s current role at Yesware and responsibilities that Joel took over from him.

[10:29] The frequency of communication and meetings at the company.

[10:51] The power of executive coaching; the emphasis that Yesware has placed on this.

[11:47] The sales world at this moment; high volumes, dry pipelines and availability.

[13:39] Trends that Joel and Yesware have noted during and before the pandemic.

[14:22] Joel’s emphasis on video for meetings — making use of current circumstances.

[15:41] Joel’s favorite business tools lately; Microsoft To-Do and Whoop.

[16:18] Why Joel’s loves David Allen’s Getting Things Done.

[16:42] The publications and podcasts that Joel keeps up with.

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About Eric Siu

Eric Siu (@ericosiu) is the CEO at Single Grain, a digital marketing agency that focuses on paid advertising and content marketing. He contributes regularly to Entrepreneur Magazine, Fast Company, Forbes and more.

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