Our show discusses challenges Enterprise and Technical Sales teams encounter every day and creative ways to overcome them. Kevin and Matt have over 50 years experience selling Enterprise Software solutions, running sales teams, leading implementations, and driving consulting practices with some of the biggest companies in the world.
Kevin and Matt, authors of "Winning Faster: The MOVE Methodology", share their experiences with listeners and guests; exploring how technology is changing selling, consulting, and business.
Visit us at https://www.strategicsalesoptimization.com
Ep. 43: AI and the Human Touch for Sales Success - with Guest, Sacha Kupaj
This Week's Episode:This episode features insights from sales expert Sacha Kupaj on mastering enterprise sales, leveraging AI, and building effective team strategies. Discover practical tips on discovery calls, stakeholder management, and adapting to the evolving sales landscape.
About our Guest - Sacha Kupaj
Sacha Kupaj is a France-born enterprise sales leader based in Austin, who moved to the U.S. in 2018, began his career as an SDR, and has grown into a senior enterprise sales role at Conversica, where he focuses on conversational AI and complex customer engagement.
His career reflects a progression from frontline prospecting to enterprise-level selling and hospitality solution leadership, combining hands-on sales discipline, mentorship, competitive research, and a strong belief that AI can improve seller preparation, but trust, curiosity, and human execution still win complex deals.
Learn more about Sacha:LinkedIn - LinkedIn Profile (https://www.linkedin.com/in/sacha-kupaj-%F0%9F%87%AB%F0%9F%87%B7%F0%9F%87%BA%F0%9F%87%B8-71026b156/)
Conversica - LinkedIn Page (https://www.linkedin.com/company/conversica)
00:00 Introduction to Software Sales Simplified
01:02 The Role of SDRs in Sales
03:01 Transitioning from SDR to Enterprise Sales
08:59 The Importance of Mentorship in Sales
11:52 AI's Role in Enterprise Selling
16:01 Human Element in Sales
19:46 Collaboration and Team Dynamics in Sales
24:53 Leveraging Team Synergy for Sales Success
27:28 Building Trust and Emotional Connections in Sales
29:18 Effective Communication and Collaboration Strategies
32:19 The Importance of Preparation and Dry Runs
35:01 The Role of Humility and Continuous Learning in Sales
35:35 Navigating Transitions in Sales Roles and Industries
38:41 Understanding the Competitive Landscape in AI Sales
40:36 Leveraging AI for Sales Efficiency and Research
45:43 Advice for Aspiring and Established Sales Professionals
49:04 Like, Follow, and Subscribe!
About Software Sales Simplified:Visit us at: (https://www.strategicsalesoptimization.com/)https://www.strategicsalesoptimization.com/ (https://www.strategicsalesoptimization.com/%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0)
Follow us on Linkedin: (https://tinyurl.com/2tcx7mjx)https://tinyurl.com/2tcx7mjx (https://tinyurl.com/2tcx7mjx%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0)
Send us your questions at - Sales@stratsalesllc.com (mailto:Sales@stratsalesllc.com)
"What is a Sales Engineer?" - SSO’s Education Series on YouTube: https://www.youtube.com/playlist?list=PLxuHbkRfIWtVj_Hg1GYBIg-o5M-icJLn0 (https://www.youtube.com/playlist?list=PLxuHbkRfIWtVj_Hg1GYBIg-o5M-icJLn0)
Get Your Copy of "Winning Faster"!
Available Here: (https://www.strategicsalesoptimization.com/move-book) (https://www.strategicsalesoptimization.com/move-book%E2%81%A0%E2%81%A0%E2%81%A0)https://www.strategicsalesoptimization.com/move-book (https://www.strategicsalesoptimization.com/move-book%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0)
Why Listen to Software Sales Simplified?
Make Software Sales Simplified: MOVE to Success, your go-to podcast for mastering enterprise software sales through authentic customer engagement and actionable consulting insights. Join us for each episode as we break down proven strategies and real-world experiences to help you build trust, close deals, and drive long-term success along your Enterprise Software Sales or Consulting journey.
Copyrighted Broadcast:
Thank you for tuning in to Software Sales Simplified: MOVE to Success. This podcast is produced by and is the sole property of Strategic Sales Optimization LLC, copyright 2025 and 2026. Reproduction or use of this broadcast in whole or in part without express written permission from Strategic Sales Optimization LLC is strictly prohibited. All rights reserved.
22 Apr 2026
Ep. 42: - Mastering AI Success in Sales for 2026 with Guest, JD Miller Ph.D.
This Week's Episode:
In this episode, JD Miller, author of 'The AI Handbook for Sales Professionals,' joins Kevin Donville and Matt Long to explore how AI is transforming sales. They discuss practical applications, ethical considerations, and strategies for leveraging AI to enhance human skills in enterprise sales.
About our Guest - JD Miller, Ph.D.:
JD Miller Ph.D., is a seasoned executive leader specializing in sales transformations for PE-backed and pre-IPO firms. With six exits and decades of experience in multinational tech companies, he excels in building high-performing teams and implementing rapid growth strategies. As an Operating Advisor for Five Arrows Capital Partners, JD leverages his expertise at the intersection of business, technology, and humanity to strengthen the companies he works with. A frequently-requested conference speaker, JD also shares his roadmap to success in the bestselling book “The CRO’s Guide to Winning in Private Equity.”
Learn more about JD Miller PhD at: https://www.jdmillerphd.com/ (https://www.jdmillerphd.com/)
JD's Latest Book: The AI Handbook for Sales Professionals: (https://www.example.com/ai-handbook-sales)https://www.example.com/ai-handbook-sales (https://www.example.com/ai-handbook-sales%E2%81%A0)
Additional Resource: AI-Sales-Fail.com: (https://ai-sales-fail.com)https://ai-sales-fail.com (about:blank)
Chapters
00:00 Introduction to Ep 42: Talking About AI
01:57 The AI Handbook for Sales Professionals
04:55 Understanding AI in Sales
08:27 Transforming Sales with AI
11:21 The Future of Sales Jobs
13:34 The Risks of Over-Reliance on AI
16:37 Adapting to AI in Sales Careers
20:33 Organizational AI Integration
22:44 Establishing Governance for AI Tools
24:23 Navigating Expertise and Trust in AI
25:52 AI's Role in Enhancing Sales Engineering
27:58 Leveraging AI for Effective Communication
30:15 AI as a Writing Companion
32:40 Synthesizing Data and Ethical Considerations
36:35 Embracing AI: Strategies for Organizations
39:15 The Human Element in AI Integration
47:22 See You Next Episode!
About Software Sales Simplified:Visit us at: (https://www.strategicsalesoptimization.com/)https://www.strategicsalesoptimization.com/ (https://www.strategicsalesoptimization.com/%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0)
Follow us on Linkedin: (https://tinyurl.com/2tcx7mjx)https://tinyurl.com/2tcx7mjx (https://tinyurl.com/2tcx7mjx%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0)
Send us your questions at - Sales@stratsalesllc.com (mailto:Sales@stratsalesllc.com)
"What is a Sales Engineer?" - SSO’s Education Series on YouTube: https://www.youtube.com/playlist?list=PLxuHbkRfIWtVj_Hg1GYBIg-o5M-icJLn0 (https://www.youtube.com/playlist?list=PLxuHbkRfIWtVj_Hg1GYBIg-o5M-icJLn0)
Get Your Copy of "Winning Faster"!
Available Here: (https://www.strategicsalesoptimization.com/move-book) (https://www.strategicsalesoptimization.com/move-book%E2%81%A0%E2%81%A0%E2%81%A0)https://www.strategicsalesoptimization.com/move-book (https://www.strategicsalesoptimization.com/move-book%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0)
Why Listen to Software Sales Simplified?
Make Software Sales Simplified: MOVE to Success, your go-to podcast for mastering enterprise software sales through authentic customer engagement and actionable consulting insights. Join us for each episode as we break down proven strategies and real-world experiences to help you build trust, close deals, and drive long-term success along your Enterprise Software Sales or Consulting journey.
Copyrighted Broadcast:
Thank you for tuning in to Software Sales Simplified: MOVE to Success. This podcast is produced by and is the sole property of Strategic Sales Optimization LLC, copyright 2025 and 2026. Reproduction or use of this broadcast in whole or in part without express written permission from Strategic Sales Optimization LLC is strictly prohibited. All rights reserved.
24 Mar 2026
Ep 41: Fractional Experts - Sales Success in 2026 with Guest, Andrew Devlin
This Week's Episode:
This episode explores the rise of fractional leadership, its benefits, challenges, and how organizations can leverage this model for growth. Featuring insights from Andrew Devlin, a seasoned fractional leader, the discussion covers strategic implementation, infrastructure, and the future of fractional roles.
About our Guest - Andrew Dev:
Andrew Devlin spent 25 years building some of the highest-performing sales organizations in North American technology — leading teams at Cisco, Splunk, Cloudflare, and TELUS that generated over $2 billion in revenue and developed more than 100 sales professionals to President's Club. Recognized as Cisco's Sales Leader of the Year and ranked in the top 1% of global sales leaders, Andrew has a track record of building the kind of sales infrastructure that doesn't just hit quota — it outlasts the people who built it.
Today, as President of ScaleTech CRO and a Sales Xceleration Certified Advisor (President's Circle), Andrew works as a Fractional VP of Sales for B2B companies between $10M and $100M — helping founders and CEOs transition from instinct-driven selling to scalable, repeatable revenue. His current clients span Canada, the US, and Australia, with one achieving 192% of quota following a sales infrastructure overhaul. He also teaches B2B Sales at Okanagan College in Kelowna, BC.
Andrew's core belief: companies don't fail to scale because they lack salespeople — they fail because they never built the foundation those salespeople need to succeed.
Where to Learn More About Andrew:
You can find Andrew's profile on LinkedIn: Andrew Devlin on LinkedIn (https://www.linkedin.com/in/andrew-devlin-a727721/)
Andrew's Website: andrewdevlin.co (https://andrewdevlin.co/)
Chapters
00:00 Introduction to Software Sales Simplified
02:08 Understanding Fractional Leadership
03:53 Andrew Devlin's Journey and Insights
07:50 The Rise of Fractional Leadership
11:38 The Value of Fractional Executives
15:16 Implementing Fractional Leadership Effectively
18:59 Recognizing the Need for Fractional Leadership
22:50 Common Traps for Founders in Scaling
23:51 Building Infrastructure for Success
27:38 Understanding Customer Profiles and Market Dynamics
29:52 The Role of Fractional Leadership
34:35 Navigating Change and Trust in Organizations
43:22 Clarity and Scaling in Business
49:32 See You Next Episode
About Software Sales Simplified:
Visit us at: (https://www.strategicsalesoptimization.com/)https://www.strategicsalesoptimization.com/ (https://www.strategicsalesoptimization.com/%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0)
Follow us on Linkedin: (https://tinyurl.com/2tcx7mjx)https://tinyurl.com/2tcx7mjx (https://tinyurl.com/2tcx7mjx%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0%E2%81%A0)
Send us your questions at - Sales@stratsalesllc.com (mailto:Sales@stratsalesllc.com)
"What is a Sales Engineer?" - Education Series on YouTube:
https://www.youtube.com/playlist?list=PLxuHbkRfIWtVj_Hg1GYBIg-o5M-icJLn0 (https://www.youtube.com/playlist?list=PLxuHbkRfIWtVj_Hg1GYBIg-o5M-icJLn0)
Get Your Copy of "Winning Faster"!
Available Here: (https://www.strategicsalesoptimization.com/move-book) (https://www.strategicsalesoptimization.com/move-book%E2%81%A0%E2%81%A0%E2%81%A0)
https://www.strategicsalesoptimization.com/move-book (https://www.strategicsalesoptimization.com/move-book%E2%81%A0%E2%81%A0%E2%81%A0)
Why Listen to Software Sales Simplified?
Make Software Sales Simplified: MOVE to Success, your go-to podcast for mastering enterprise software sales through authentic customer engagement and actionable consulting insights. Join us for each episode as we break down proven strategies and real-world experiences to help you build trust, close deals, and drive long-term success along your Enterprise Software Sales or Consulting journey.
Copyrighted Broadcast:
Thank you for tuning in to Software Sales Simplified: MOVE to Success. This podcast is produced by and is the sole property of Strategic Sales Optimization LLC, copyright 2025 and 2026. Reproduction or use of this broadcast in whole or in part without express written permission from Strategic Sales Optimization LLC is strictly prohibited. All rights reserved.
Who has been a guest on Software Sales Simplified: MOVE to Success
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Michael Wasielewski
John Cavanaugh
Robyn Gilmartin
Ryan R Sullivan
Meredith Golden
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