Why AI Alone Won’t Save Your Sales Team—And What the Best CROs Know About Leading With EQ and Execution

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Implementors

Guidewise

61 episodes

3 days ago

We get it. Ideas are easy, but implementation is hard. Presented by Guidewise, the Implementors podcast connects you to the insights, stories, and lessons learned of individuals who have mastered implementation. Through intimate interviews with entrepreneurs, business leaders, changemakers, and other Implementors, Guidewise CEO and Implementors' host, Ted Wolf, guides the audience through engaging, entertaining analyses of how implementation can make or break your company. Join us as we uncover the secrets of successful implementation, so you can conquer your implementation struggles.

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Why AI Alone Won’t Save Your Sales Team—And What the Best CROs Know About Leading With EQ and Execution

Implementors

49 minutes 25 seconds

3 months ago

Why AI Alone Won’t Save Your Sales Team—And What the Best CROs Know About Leading With EQ and Execution

Ideas are easy. AI implementation is hard. We make it smarter, faster, and more human. Subscribe now to lead AI change.

Join host Ted Wolf, Co-Founder & CEO of Guidewise, for a high-energy, no-fluff conversation with Tim Wilson—Chief Revenue Officer at ProductWind and seasoned sales leader—on the latest episode of Implementors. With decades of experience scaling high-growth tech companies and helping enterprise brands navigate the digital commerce landscape, Tim offers a grounded perspective on the real challenges facing modern sales teams. In this episode, Tim shares why AI alone won’t fix your sales problems—and what great CROs are doing differently. From rethinking the role of BDRs to building emotionally intelligent sales cultures, Tim unpacks the evolving relationship between people, process, and tech in the revenue engine. He talks candidly about what AI can do well, where it still falls short, and how leaders can blend human empathy with digital tools to unlock real performance. Whether you’re leading a sales team, driving GTM strategy, or just trying to make sense of how AI is reshaping the buyer journey, this episode is full of practical wisdom, hard-won lessons, and a refreshing dose of humor and humility.

ABOUT TIM WILSON: Tim Wilson is a growth-driven revenue strategist and seasoned sales leader with deep expertise in digital commerce, AI in sales, and enterprise go-to-market execution. As Chief Revenue Officer at ProductWind, Tim leads all revenue-generating functions—driving strategy, sales, customer success, and operations to help enterprise brands win in a rapidly evolving e-commerce landscape. With a proven track record scaling high-growth tech companies—including CommerceIQ, Pattern, and 1010data—Tim has helped take startups from zero to unicorn by building and leading high-impact sales teams. He brings a rare blend of technical fluency, emotional intelligence, and GTM precision to the CRO role—advocating for sales cultures rooted in communication, curiosity, and continuous learning. At ProductWind, Tim is helping redefine how brands engage with retailer algorithms using AI-driven tools to enhance visibility, improve media efficiency, and scale growth. Follow Tim on LinkedIn: https://www.linkedin.com/in/timothywilson/. Learn more about ProductWind: https://www.productwind.com.

ABOUT GUIDEWISE: At Guidewise, we blend operational expertise with AI-driven workforce analytics to guide enterprise organizations through impactful, enterprise AI implementation, digital transformation, and change adoption. Let's talk about your organization's AI strategy and change adoption needs today: https://www.guidewise.ai/contact/.

OUTLINE:

00:00 Building the Future of Sales

01:18 The Role of a Chief Revenue Officer

05:29 The Evolution of BDRs in Sales

11:50 Navigating Sales in the AI Era

23:59 The Future of Sales and AI

27:53 Unlocking Team Potential

29:18 Understanding Sales Challenges

32:10 Gaining Insights from Clients

33:45 The Role of AI in Sales

35:50 Transforming Sales Mindset

38:28 Revolutionizing Recruitment in Sales

40:56 The Importance of Communication

43:05 Guiding Growth in Small Businesses

PODCAST LINKS:

- Subscribe on YouTube: https://www.youtube.com/@implementorspod

- Podcast Homepage: https://www.guidewise.ai/podcast

- Spotify: https://open.spotify.com/show/6uliK2fpHOOgjLDgUv1pNF?si=6520239306224710&nd=1

- Apple Podcasts: https://podcasts.apple.com/us/podcast/guidewise-presents-implementors/id1678368738

- Amazon Music: https://music.amazon.com/podcasts/8fcf7ddd-bf82-47cf-9339-efc29a75500d/guidewise-presents-implementors

SOCIAL:

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- LinkedIn: https://www.linkedin.com/company/implementorspod/

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