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 - Mark Krebs: Mark Krebs is a seasoned sales and revenue leader with ...
Mar 02, 2026•48 min•Season 1Ep. 40
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 how effective onboarding, proactive engagement, and early alignmen...
Feb 10, 2026•50 min•Season 1Ep. 39
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 relationships in sales, continuous learning, and the value of mentorship for new sales profes...
Jan 23, 2026•43 min•Season 1Ep. 38
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 leveraging the benefits of generative AI. The discussion emphasizes the need...
Dec 30, 2025•55 min•Season 1Ep. 37
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 of effective sales leaders. The conversation delves into the necessity of ...
Oct 02, 2025•45 min•Season 1Ep. 36
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 stand out, the role of experience in hiring, and strategies for companies ...
Sep 25, 2025•53 min•Season 1Ep. 35
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 podcasting, the value of client interviews, and the role of storytelling in sales. Th...
Sep 17, 2025•46 min•Season 1Ep. 34
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 priorities and the role of AI in enhancing, rather than replacing, the ...
Sep 10, 2025•46 min•Season 1Ep. 33
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 for managing stress, understanding physiological responses, and...
Aug 27, 2025•51 min•Season 1Ep. 32
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 t he role of AI in enhancing customer engagement and the complexities of marketing in a crowded marketplace. Dav...
Aug 21, 2025•48 min•Season 1Ep. 30
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 unrealistic expectations and the value of a supportive company culture. About our Gue...
Aug 13, 2025•52 min•Season 1Ep. 30
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 the need for sales professionals to build trust and relationships wi...
Aug 06, 2025•49 min•Season 1Ep. 29
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 buyers in the digital age. The conversation also delves into the role of video c...
Jul 31, 2025•42 min•Season 1Ep. 28
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 role of cybersecurity in today's technology landscape. The conversation emphasiz...
Jul 23, 2025•42 min•Season 1Ep. 27
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 interactions. Jessica shares insights on creating a culture of growth and t...
Jun 18, 2025•49 min•Season 1Ep. 26
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 in partnership strategies. The conversation emphasizes the need for com...
Jun 04, 2025•47 min•Season 1Ep. 25
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 focused, digestible lessons. Whether you're new to the industry or...
May 28, 2025•10 min•Season 1Ep. 24
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 collaboration between marketing and sales, the significance of win-loss analysis, and the value of building trust with c...
May 21, 2025•39 min•Season 1Ep. 23
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, and the common pitfalls in recruiting for pre-sales roles. Dustin emphasizes the significance of emoti...
May 14, 2025•41 min•Season 1Ep. 22
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 cadence, leveraging technology, and developing the role of a trusted advisor in the sales process. Lynn...
May 07, 2025•41 min•Season 1Ep. 21
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 potential, navigating over-hiring, and applying enterprise sales principles to new industries. The conversati...
Apr 30, 2025•44 min•Season 1Ep. 20
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 industry, emphasizing the need for deep customer understanding, effective messaging, and the tactical application of AI...
Apr 23, 2025•43 min•Season 1Ep. 19
This Week's Episode: In this episode hosts Matt Long and Kevin Donville delve into the MOVE framework , focusing on the ' Opportunity ' aspect. They discuss the importance of understanding budget , time , and power dynamics in the sales cycle, and how external factors like economic uncertainty can impact sales opportunities. The conversation emphasizes the need for sales professionals to identify red flags and mitigate challenges to ensure successful deal closures. Matt & Kevin explore how, ...
Apr 16, 2025•38 min•Season 1Ep. 18
This Week's Episode: In this episode of "Software Sales Simplified: MOVE to Success", hosts Matt Long and Kevin Donville talk with guest Marty Funk about the intricacies of enterprise software sales The three discuss Marty's extensive career journey with industry powerhouses such as Iron Mountain, Domo and Oracle , as well as the evolution of big data, and the importance of curiosity and negotiation skills in sales. They explore how to build effective sales teams, navigate AI in sales conversati...
Apr 09, 2025•43 min•Season 1Ep. 17
This Week's Episode: Kevin and Matt engage with Josh Gillespie , Head of Growth at Aomni , discussing his journey from philosophy major to sales leader in the AI space. They explore the importance of research in sales, the challenges of discovery calls, and the growth strategies for startups. Josh shares insights on leveraging technology for sales success and the evolving landscape of AI in the industry. In this conversation, Josh Gillespie shares insights on the realities of startup life , the ...
Apr 02, 2025•44 min•Season 1Ep. 16
This Week's Guest: JD Miller, PhD Hosts Matt Long and Kevin Donville engage with JD Miller PhD, Operations Advisor to Five Arrows Capital Partners, with a rich background in software sales. They explore JD's journey from Sales Engineer to Sales Leader, discussing the importance of mentorship, the evolution of sales technology, and the role of private equity in shaping sales strategies. Additionally, they discuss the intricacies of sales forecasting, the importance of transparency in board commun...
Mar 26, 2025•46 min•Season 1Ep. 15
This Week's Guest: Gary Williams In this episode of Software Sales Simplified, hosts Matt and Kevin sit down with Gary Williams, VP of Sales at Monetate, to explore his journey in sales leadership and the evolving landscape of the Personalization and Testing markets in software sales. They discuss the importance of process, the challenges of validation fatigue, and the role AI plays in enhancing Personalization and Testing offerings. The conversation also touches on privacy concerns in the new A...
Mar 19, 2025•43 min•Season 1Ep. 14
This Week's Guest: Ryan Anderson In this episode of Software Sales Simplified, hosts Matt and Kevin talk with sales guru, Ryan Anderson, to explore the concept of value in sales. They discuss the importance of understanding buyer alignment, the role of effective communication, and the necessity of consultative selling. Ryan shares insights from his extensive experience, emphasizing the need for sales professionals to adapt their value propositions to meet the unique perspectives of their buyers....
Mar 12, 2025•45 min•Season 1Ep. 13
This week's Guest: Tony Marshall In this episode of Software Sales Simplified , hosts Kevin Donville and Matt Long engage with Tony Marshall, sales leader and innovator in the property insurance sector. Tony discusses his transition from enterprise software sales to insurance, the evolution of sales techniques, changing buyer expectations, and the importance of discovery in the sales process. Tony shares his journey into sales, the role of mentorship, and draws parallels between ultra running an...
Mar 05, 2025•40 min•Season 1Ep. 12
This Week's Guest - Sara Levinson In this episode of Software Sales Simplified: MOVE to Success, hosts Matt Long and Kevin Donville sit down with their guest, Sara Levinson, who shares her journey from sales reluctance to sales mastery; highlighting how her structured, authentic, value-based, approach drives winning outcomes. They explore Sara's unexpected journey into sales, her early challenges, and the evolution of her confidence as a seller. Over the course of the episode, Sara emphasizes th...
Feb 26, 2025•46 min•Season 1Ep. 11
