Software Sales Simplified: MOVE to Success

Software Sales Simplified: MOVE to Success

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

Episodes

May 12, 2026 49 mins

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 ...

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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...

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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 ...

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This Week's Episode:

In this episode of Software Sales Simplified: Move to Success, Kevin and Matt catch up with Mark Krebs, a seasoned software sales leader with a diverse background in startups, accounting, and software. They explore the challenges of scaling sales organizations, the importance of process and methodology, authenticity in sales, and the psychological aspects of leadership and startup success.


About our Guest...

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This Week's Episode:

In this episode of Software Sales Simplified: Move to Success, Kevin and Matt sit down with Craig Bloom, an expert in SaaS onboarding and customer success. They explore the importance of customer engagement and alignment between sales and service delivery teams. Craig shares his journey from film and advertising to customer success, highlighting how storytelling strengthens customer interactions. He explains...

This Week's Episode:

In this episode of 'Software Sales Simplified', Matt and Kevin engage with Chris O'Dowd, who shares his unique journey from the Marine Corps and FBI to enterprise software sales. The conversation explores the importance of genuine curiosity in sales, the impact of AI on sales processes, and the evolving expectations of buyers. Chris emphasizes the significance of building trust and relatio...

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This Week's Episode:

In this episode of Software Sales Simplified, Kevin and Matt discuss the complexities and risks associated with AI chatbots, featuring expert Michael Wasielewski. The conversation covers the importance of security, governance, and the potential business risks that come with deploying AI chatbots. Michael shares insights on how organizations can implement effective strategies to mitigate risks while le...

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This Week's Episode:

In this episode of Software Sales Simplified, hosts Kevin and Matt sit down with John Cavanagh, a seasoned sales professional, to explore the intricacies of software sales, the importance of mentorship, and the evolving landscape influenced by AI. John shares his career journey, highlighting the significance of internships (co-op programs), the value of understanding customer needs, and the qualities ...

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This Week's Episode:

In this episode of Software Sales Simplified, hosts Kevin and Matt discuss the current landscape of hiring and recruitment in the software sales industry with expert Robyn Gilmartin. They explore the impact of AI on recruitment processes, the challenges candidates face in a competitive job market, and the importance of networking and building relationships. Robyn shares insights on how candidates can ...

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This Week's Episode:

In this episode of 'Software Sales Simplified', Kevin and Matt engage with podcasting expert Ryan R. Sullivan to explore the significance of podcasting in business, particularly in the realm of software sales. They discuss the benefits of starting a podcast, the importance of identifying a niche, and foundational strategies for success. Ryan shares insights on the complications of corporate po...

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This Week's Episode:

In this episode of Software Sales Simplified, Matt & Kevin engage with Meredith Golden, a seasoned sales enablement leader. They discuss the nuances of sales enablement, the importance of having a sales background for effective training, and the challenges faced in implementing enablement programs. Meredith shares her journey from sales to enablement, emphasizing the need for alignment with business prio...

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This Week's Episode:

In this episode of 'Software Sales Simplified', Matt and Kevin sit down with Kimberly S. Arnold, founder of Somatic Leadership, to explore the intersection of stress management and sales performance. Kimberly shares her journey from corporate consulting to healthcare, emphasizing the importance of resilience and emotional well-being in high-pressure environments. The conversation delves into practical techniques...

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This Week's Episode:

In this episode of 'Software Sales Simplified', Kevin and Matt talk with industry expert Dave Anderson to explore the evolving landscape of software sales. They discuss the importance of authenticity in selling, the alignment of product marketing and sales, and the challenges of navigating product-led growth versus enterprise growth. The conversation delves into the role of AI in enhancing customer e...

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This Week's Episode:

In this episode of 'Software Sales Simplified: MOVE to Success', hosts Kevin and Matt speak with Corey Bruce, a seasoned software sales leader. They explore sales leadership, building team trust, and hiring challenges. Corey shares his career journey, stressing empathy in leadership and the importance of understanding metrics without losing sight of people. They also address the pitfalls of unrealist...

This Week's Episode:

In this episode of Software Sales Simplified, hosts Kevin and Matt engage with enterprise software sales expert and author, Brian Wolff, to discuss the importance of emotional value, discovery, and authentic engagement in closing deals. They explore how understanding buyer psychology and creating a compelling narrative can significantly impact sales success. Brian shares insights from his books, emphasizing ...

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This Week's Episode: In this episode of 'Software Sales Simplified', Kevin and Matt engage with guest James Fox, Head of Business Development at Pina Vida and Co-Founder for the AI-driven productivity tool ScrumBuddy to discuss the critical alignment between sales and marketing in the software industry. They explore common misalignments, the importance of understanding customer insights, and the evolving behavior of buy...

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This Week's Episode:

In this episode of 'Software Sales Simplified', hosts Kevin and Matt talk with with guest Priyanta Dharmasena, to explore the intersection of leadership, technical depth, and personal growth in the software sales industry. They discuss the importance of foundational skills in both diving and sales, the challenges of balancing technical expertise with management responsibilities, and the critical rol...

This Week's Episode:

In this episode Kevin Donville and Matt Long welcome technology growth leader Jessica White. The conversation explores Jessica's unique methodology, the 'Circles of Connection', which emphasizes the importance of building genuine relationships in the digital age. They discuss the epidemic of loneliness, the need for intentionality in fostering connections, and the role of AI in enhancing human...

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This Week's Episode:

In this episode of Software Sales Simplified, hosts Kevin Donville and Matt Long welcome Tamer Osman, a seasoned expert in software partnerships. They discuss the critical role of partnerships in driving sales success, the evolution of Tamer's career, and the innovations shaping the software industry. Tamer shares insights on hyperscalers, the impact of AI and automation, and the importance of education...

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In this special episode of Software Sales Simplified: MOVE to Success, Matt and Kevin unveil a brand-new initiative: the Industry Education Series—a collection of free, short-form YouTube videos designed to demystify and deepen understanding of key concepts in enterprise software sales.

These 5–15 minute episodes break down topics like sales engineering, discovery, objection handling, presentations, QBRs, and more, delivered in focu...

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