Strategic Sales Optimization - SSO

Software Sales Simplified: MOVE to Success

Business EN ↓ 43 episodes

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

Author

Strategic Sales Optimization - SSO

Category

Business

Latest episode

May 12, 2026

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Episodes

Ep. 43: AI and the Human Touch for Sales Success - with Guest, Sacha Kupaj 12.05.2026

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 t...

Ep. 42: - Mastering AI Success in Sales for 2026 with Guest, JD Miller Ph.D. 22.04.2026

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 ex...

Ep 41: Fractional Experts - Sales Success in 2026 with Guest, Andrew Devlin 24.03.2026

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 buildi...

Ep 40: Secrets to Scaling Sales Teams with Guest, Mark Krebs 02.03.2026

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 an...

Ep 39: The Secrets to Customer Success in 2026 with Guest, Craig Bloom 10.02.2026

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 strengthe...

Ep 38: Curiosity and Sales Success in 2026 with Guest, Chris O'Dowd 23.01.2026

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...

Ep 37. Gen AI Bots: The Hidden Risks with Guest Michael Wasielewski 30.12.2025

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 strateg...

Ep 36. Empathy & Trust: Unlocking Sales Success. With Guest, John Cavanaugh 02.10.2025

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 cust...

Ep. 35: Recruiting & AI: The Human Factor. Guest - Robyn Gilmartin 25.09.2025

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 i...

Ep. 34: Guest Ryan R. Sullivan. Getting it Right: Strategies for Podcast Success 17.09.2025

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...

Ep. 33: Guest - Meredith Golden. Enablement: Unlocking Sales Success 10.09.2025

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...

Ep. 32: Guest - Kimberly S. Arnold. Turn Stress Into Sales 27.08.2025

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 conversat...

Ep. 31: Guest - Dave Anderson. Cut Out the Noise: Marketing, AI, and Strategic Focus in Sales 21.08.2025

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...

Ep. 30: Guest Corey Bruce - Must-Haves for Sales Leaders in 2025 13.08.2025

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 al...

Ep. 29: Guest Brian Wolff - Storytelling & Building Buyer Trust. 06.08.2025

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 i...

Ep. 28: Guest - James Fox. Sales Success: Content, Alignment & More 31.07.2025

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 insight...

Ep. 27: Guest - Priyanta Dharmasena. Leadership Lessons; Diving & Demos 23.07.2025

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 res...

Ep. 26: Guest - Jessica White. Circles of Connection 18.06.2025

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 connection...

Ep. 25: Guest - Tamer Osman. Partner Groups: Powering Sales Success 04.06.2025

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 automat...

Ep. 24: Introducing our Industry Education Series - Free videos to help you sell better! 28.05.2025

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, presentati...

Ep. 23. Guest Janet Jaiswal - The Fragile Currency: Building Trust In Sales & Marketing 21.05.2025

This Week's Episode: In this week's episode, Kevin and Matt sit down with industry leader, Janet Jaiswal, CMO and Global VP of Marketing at Blueshift , to explore the evolving landscape of software sales and marketing. They discuss the importance of storytelling, empathy, and understanding customer pain points to differentiate in a crowded market. Janet emphasizes the need for collaboratio...

Ep. 22: Guest Dustin Chamberlain - Making it Work: Essential Skills for Presales and Sales 14.05.2025

This Week's Episode: In this episode of Software Sales Simplified, hosts Kevin Donville and Matt Long engage with Dustin Chamberlain , who shares his unique journey from being a practitioner in software solutions to a pre-sales leader. The conversation explores the essential skills required for success in pre-sales, the importance of collaboration between account executives and sales engineers, an...

Ep. 21: Guest Lynn Powers - Unlocking Success in Software Sales 07.05.2025

This Week's Episode: In this episode of Software Sales Simplified, hosts Kevin Donville and Matt Long welcome Lynn Powers , a successful sales professional at Clari. Lynn shares her journey in software sales, her experiences at Clari, and her insights on building successful customer relationships. The conversation covers the importance of understanding customer needs, investigating their sales...

Ep. 20: Guest Derek Francis - Create a Winning Sales Culture 30.04.2025

This Week's Episode: In this episode of Software Sales Simplified, Matt Long and Kevin Donville engage with Derek Francis, a seasoned sales executive with over 25 years of experience. They discuss Derek's journey from engineering to sales, the importance of culture in building effective sales teams, and the challenges of scaling in the creator economy. Derek shares insights on hiring for p...

Ep. 19: Guest Peter Kuhn - Mastering Software Sales Leadership 23.04.2025

This Week's Episode: In this episode of 'Software Sales Simplified', hosts Kevin Donville and Matt Long engage with Peter Kuhn , co-founder and CEO of Baku , to discuss the intricacies of software sales, the importance of understanding customer needs, and the challenges faced by companies in scaling their sales efforts. Peter shares insights from his extensive experience in the industr...

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