Revenue Rehab EP 106 [Crafting the Click: Mastering Email for Meeting Success with Jeff Winters]

This week our host Brandi Starr is joined by Jeff Winters, CRO of Abstrakt Marketing Group.

While at a previous sales position, Sapper founder Jeff Winters implemented a unique email strategy that consistently landed him in Fortune 100 boardrooms. But every time he finished his pitch, these companies would grill him on his strategy: “Great product, but how the heck did you get this meeting?" In 2013, after hearing this a dozen-too-many times, he started Sapper Consulting. Since then, Jeff has led the business to become one of the fastest growing companies in St. Louis and was most recently featured in St. Louis Business Journal’s list of 40 under 40. He is a candid, thoughtful, and dynamic leader. Once Sapper was acquired by Abstrakt Marketing Group in 2021, Jeff took over as Chief Revenue Officer, leading the sales and sales enablement teams tasked with getting the company to reach their $70M yearly sales goal.

In this episode of Revenue Rehab, Brandi and Jeff address the challenge of ineffective BDR/SDR emails that often get overlooked and demonstrate how a refined email strategy can significantly increase meeting acquisition rates.  

Bullet Points of Key Topics + Chapter Markers:

Topic #1 Evolving Email Strategy in Sales [09:28] “There's no such thing as a good list, you have to verify everything," Jeff states, underscoring the necessity of due diligence in sales prospecting. "A lot of people skip these steps and then wonder why their email campaigns aren't effective. It’s about the discipline in verification, and then actually getting out there and confirming email addresses.” Jeff continues, emphasizing, "This is what separates the successful outreach from the noise in your inbox."

Topic #2 The Art of Writing Sales Emails [17:45] Jeff explains the nuanced craft of engaging potential clients via email. “Avoid traditional greetings and close with something unexpected. Use an ampersand, keep it short, and stay away from jargon that makes your email cringey,” he advises. Brandi adds, “It’s about connecting with the person on the other end, understanding their problem, and presenting your email as a conversation starter, not just a pitch.”

Topic #3 Integrating Technology and Email Sequences [31:09] “Technology now plays a bigger role in making sure our emails get noticed,” Jeff remarks, discussing the evolution of email tools. “We’ve moved from just crafting content to focusing on how to get our emails into the eyes of decision-makers.” He shares, “A successful email sequence involves multiple touchpoints over weeks, combining emailing with calling, respecting the cool-off periods, and constantly testing our strategies to optimize for response rates.” This approach, he notes, is crucial for maintaining domain health and avoiding being blacklisted.

So, What's the One Thing You Can Do Today?

Jeff advises revenue leaders to base their sales planning and budgeting on the number of meetings rather than traditional sales quotas. He suggests assessing how many meetings are held, which channels are used, and the closure rates of each channel. By focusing on these metrics, leaders can create more accurate and reliable forecasts, transitioning from quota-based forecasting to a model that emphasizes the effectiveness of meetings in generating sales.

Buzzword Banishment:

Jeff Winters’ Buzzword to Banish is the term "value add." He expresses his disdain for the phrase by explaining, “It’s just so overused and nebulous. Everyone throws it around without really understanding what actual value they’re adding.” Jeff wants to rid the business world of this term to encourage clearer, more meaningful communications. 


Get in touch with Jeff Winters:       

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About the Author

Brandi Starr

Brandi Starr is a true Modern Marketing Maven; she believes marketing magic happens at the intersection of strategy, creativity, and technology. As Chief Operating Officer at Tegrita Brandi helps companies of varying sizes to attract, convert, close, and retain customers using technology. Brandi is the Co-Author of CMO to CRO, The Revenue Takeover by The Next Generation Executive and the host of the Revenue Rehab podcast.

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