The Sales Evangelist: Sales Training|Speaking|Business Marketing|Donald Kelly

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Many women in sales struggle with feeling like they’re not fully qualified for leadership roles, even when they’re already doing the work. That self-doubt can make it harder to pursue promotions and career growth. To help break this down, I invited leadership coach and tech executive Erika Chestnut to share the challenges women face when advancing their careers and how sales leaders can better support them.Meet Erika ChestnutErika Chestnut is a transformational leader with more than 25 years of experience in the tech industry. She is passionate about helping individuals and teams rethink leadership, communication, and workplace culture to create stronger performance and long-term success. Through coaching, leadership development, and strategic guidance, Erika equips professionals with practical tools to build confidence, strengthen relationships, and lead more effectively.The Confidence Gap Holding Women BackErika shares how often women underestimate their readiness for leadership opportunities. She explains

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Should your demo and discovery call happen in the same meeting? If you’re combining the two, it may be the reason your pipeline is not converting the way you want it to.Wesleyne Whittaker, sales professional and author of Sales Reset, joins me to challenge how most teams run demos and discovery and why it might be the reason deals are stalling. She also shares practical frameworks from her book Sales Reset to help you run more effective discovery calls.Meet Wesleyne WhittakerWesleyne Whittaker is a sales strategist, coach, and author of Sales Reset. She’s known for helping sales professionals rethink how they approach conversations so they can stop going through the motions and start actually closing deals.What makes her approach stand out is how she blends mindset with real sales execution. She does not just talk about what to do. She shows you how to do it in a way that feels natural and effective.She works with sales teams across different industries, helping them run stronger discovery calls, ask better q

40% of a seller’s time is spent on prospecting. That’s a big investment, especially when a lot of it does not lead anywhere. So how do you make sure that time actually turns into real opportunities? Let’s break down how to prospect in a way that leads to conversations and closed deals.Leverage Intent and Relevant DataA big part of prospecting comes down to timing. You want to reach out when buyers are already looking for a solution.That is where intent data comes in. Tools like ZoomInfo and 6sense can help you identify prospects who are actively researching solutions like endpoint protection.When you do reach out, make it relevant. Speak directly to their industry and back it up with a recent success story from a similar company. That is what helps build credibility early.Utilize Advanced LinkedIn SearchingInstead of reaching out to everyone, focus on a smaller group of people who are more likely to respond.You can build a list of 30 to 40 individuals by narrowing your search. Look for people who are new in t

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