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 empathy in sales, the role of training and role-playing, and the challenges posed by AI in the sales process. John emphasizes the importance of building trust and nurturing relationships in achieving long-term success in sales; success which John stresses requires a seller to remain curious to be effective.
About our Guest - John Cavanaugh:
John Cavanaugh 20 year software sales veteran, primarily in the online learning and HR Tech space. He works with customers to understand business challenges and form a collaborative approach to solve them. A multiple time President’s Club member, he started his career in pre-sales and sales operations before moving to enterprise sales 20 years ago. He currently serves as a Sr. Enterprise Account Executive at Attensi. Attensi is a bleeding edge provider of bespoke situational gaming simulations designed to be immersive, fun, and engaging. The outcomes are enabling behavior change at scale, increasing employee confidence, and measurable business impact.
Where to Learn More About John:
You can find John’s profile on LinkedIn: https://www.linkedin.com/in/johncavanaugh/
Chapters
00:00 Introduction to Software Sales Simplified
01:13 Inspirational Sales Leaders
02:39 John Kavanagh's Career Journey Begins
03:09 The Value of Co-op Programs
04:31 Understanding Their Benefits
05:04 First Co-op: Learning the Sales Landscape
07:08 Navigating Challenges in Early Roles
10:53 Transitioning to Sales
11:53 Culture Shock at Centra Software
14:19 Experiencing Virtual Learning
17:12 Learning from Different Personalities
19:15 Finding Your Unique Style
19:38 The Essence of Effective Selling
21:17 The Role of Leadership
24:05 Building Trust in Sales Relationships
27:33 Navigating the AI Landscape
32:18 The Importance of Customer Advocacy
33:10 Innovative Sales Training Techniques
38:40 Learning from Failures
39:45 Advice for Aspiring Sales Professionals
45:01 Bye for Now!
About Software Sales Simplified:
Visit us at: https://www.strategicsalesoptimization.com/
Follow us on Linkedin: https://tinyurl.com/2tcx7mjx
Send us your questions at - Sales@stratsalesllc.com
"What is a Sales Engineer?" - Education Series on YouTube:
https://www.youtube.com/playlist?list=PLxuHbkRfIWtVj_Hg1GYBIg-o5M-icJLn0
Get Your Copy of "Winning Faster"!
Available Here:
https://www.strategicsalesoptimization.com/move-book
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. 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.
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 to streamline their recruitment processes. The conversation also touches on shifting priorities in recruitment and the need for companies to retain top performers.
About our Guest - Robyn Gilmartin:
Robyn Gilmartin is a seasoned recruiter with nearly 30 years of experience building high-performing teams in the software / SaaS industry. She works directly with executives in growth mode to attract and retain elite GTM talent who consistently outperform. Robyn’s placements don’t just fill roles, they consistently accelerate business outcomes. Her candidates regularly stack rank at the top of their teams, earn Rookie of the Year and President’s Club honors, and advance quickly into leadership.
Where to Learn More About Robyn:
You can find Robyn’s profile on LinkedIn: https://www.linkedin.com/in/robyngilmartin/
You can find ForefrontSearch here: https://www.linkedin.com/company/forefront-executive-search-llc/
Chapters
00:00 Introduction to Software Sales Insights
03:59 Current Trends in Hiring and Recruiting
08:07 The Shift from Candidate-Driven to Client-Driven Markets
12:06 The Role of AI in Recruitment
20:47 Standing Out in a Competitive Job Market
24:38 Networking and Building Relationships for Success
30:38 The Importance of Storytelling in Interviews
32:39 Navigating the Recruitment Landscape
35:21 The Reality of Internal Hiring Practices
38:10 Age and Experience in the Job Market
40:08 Bad Practices in Hiring and Retention
43:02 The Evolution of Sales Compensation
46:33 Streamlining the Recruitment Process
52:35 Like Follow and Subscribe
About Software Sales Simplified:
Visit us at: https://www.strategicsalesoptimization.com/
Follow us on Linkedin: https://tinyurl.com/2tcx7mjx
Send us your questions at - Sales@stratsalesllc.com
"What is a Sales Engineer?" - Education Series on YouTube:
https://www.youtube.com/playlist?list=PLxuHbkRfIWtVj_Hg1GYBIg-o5M-icJLn0
Get Your Copy of "Winning Faster"!
Available Here:
https://www.strategicsalesoptimization.com/move-book
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. 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.
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. The conversation emphasizes the need for consistency in podcasting and how to leverage content across various platforms. Ryan also introduces a program for businesses to test podcasting before fully committing, highlighting the potential impact of podcasts on personal and professional growth.
About our Guest - Ryan R. Sullivan:
Ryan makes music, podcasts, and creative strategies. He’s the owner of Podcast Principles, a boutique content strategy and production company for B2B businesses. After his own podcast and music career took off in 2019, he began helping other business owners launch their own.
Since then, he’s helped hundreds of founders, entrepreneurs, and multi-platinum artists around the world launch and grow their podcasts and media brands. His mission is to help thousands of business owners expand their reach and revenue through the power of creative podcasting and media.
Where to Learn More About Ryan:
You can find Ryan’s profile on LinkedIn: https://www.linkedin.com/in/sullybop/
You can check out his podcast here:
https://www.linkedin.com/company/podcast-principles/
Chapters
00:00 Introduction to Software Sales Simplified
01:21 The Importance of Podcasting in Business
02:24 Ryan Sullivan: Podcasting Expert
04:03 Benefits of Starting a Podcast
05:58 Identifying Your Niche for Podcasting
08:21 Foundational Strategies for Podcast Success
10:12 Getting Started with Podcasting
12:34 The Evolution of Podcasting Skills
13:56 The Market's Role in Podcast Success
17:43 Podcasting for Sales Professionals
20:28 Navigating Complications in Corporate Podcasting
23:30 The Power of Authentic Storytelling
26:38 Podcasting vs. Podcast-Style Content
29:50 Shifting Focus from Software to Stories
32:58 Leveraging Podcast Content Across Platforms
38:08 Testing the Waters with Podcasting
39:54 Finding Your Voice in Podcasting
45:34 See You Next Week!
About Software Sales Simplified:
Visit us at: https://www.strategicsalesoptimization.com/
Follow us on Linkedin: https://tinyurl.com/2tcx7mjx
Send us your questions at - Sales@stratsalesllc.com
"What is a Sales Engineer?" - Education Series on YouTube:
https://www.youtube.com/playlist?list=PLxuHbkRfIWtVj_Hg1GYBIg-o5M-icJLn0
Get Your Copy of "Winning Faster"!
Available Here:
https://www.strategicsalesoptimization.com/move-book
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. 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.
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 human element in sales training. The conversation highlights the critical skills needed for aspiring enablement professionals and the importance of understanding the sales process to create impactful training programs.
About our Guest - Meredith Golden:
Meredith Golden is the Senior Manager of GTM Enablement & Acceleration at Aircall. Drawing on a career built in enterprise, mid-market, and transactional sales, she brings a front-line understanding of what it takes to win in the market. She has a proven track record of sales excellence and applies her expertise to leading Go-to-Market strategy and execution, orchestrating key programs that drive sustainable business growth.
Where to Learn More About Meredith:
You can find Meredith's profile on LinkedIn: https://www.linkedin.com/in/goldenmeredith/
Chapters
00:00 Introduction to Software Sales Simplified
01:41 Meet Meredith Golden: Sales Enablement Expert
04:03 The Transition from Sales to Enablement
07:33 The Importance of Sales Experience in Enablement
11:11 Understanding Different Sales Roles
15:11 Building Effective Enablement Programs
18:02 Aligning Leadership and Field Expectations
21:20 Understanding Team Dynamics in Enablement
24:24 The Role of Product Enablement
25:25 Aligning Sales and Product Marketing
28:10 The Importance of Early Involvement in Training Development
29:15 Leveraging AI in Sales Enablement
32:17 Balancing AI and Human Expertise
38:57 Transitioning into Sales Enablement
42:15 Key Takeaways for Aspiring Enablement Professionals
45:33 See You Next Week!
About Software Sales Simplified:
Visit us at: https://www.strategicsalesoptimization.com/
Follow us on Linkedin: https://tinyurl.com/2tcx7mjx
Send us your questions at - Sales@stratsalesllc.com
"What is a Sales Engineer?" - Education Series on YouTube:
https://www.youtube.com/playlist?list=PLxuHbkRfIWtVj_Hg1GYBIg-o5M-icJLn0
Get Your Copy of "Winning Faster"!
Available Here:
https://www.strategicsalesoptimization.com/move-book
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. 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.
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 fostering a supportive culture in sales teams. Listeners gain insights into how to turn stress into strength and the significance of mindfulness in achieving success in sales.
About our Guest - Kimberly S. Arnold:
Kimberly S. Arnold is a seasoned leader in organizational strategy, change management, and customer success, with a career spanning Fortune 500s, fast-growth tech firms, and global consultancies. She built her expertise through senior roles at Price Waterhouse, PwC, Vignette, Blue Shield of California, and nearly a decade at Salesforce—where she guided enterprise transformation and payer strategy on a global scale.
Today, Kimberly channels that experience into Somatic Leadership LLC, the firm she founded to help executives and teams build resilience, clarity, and authentic presence in the face of complexity. As CEO and “Chief Resilience Alchemist,” she blends decades of corporate know-how with a focus on human-centered leadership, guiding organizations to thrive through change.
How to Find out More About Kimberly:
You can find Kimberly’s profile on LinkedIn: https://www.linkedin.com/in/kimberlysarnold/
How to Find out More About Somatic Leadership LLC:
You can find Somatic Leadership’s page on LinkedIn: https://www.linkedin.com/company/somatic-leadership-llc/
Chapters
00:08 Introduction to Software Sales Simplified
02:36 The Importance of Stress Management in Sales
04:19 Kimberly's Journey: From PwC to Introspect
10:38 Transitioning to Blue Shield and Healthcare
17:03 Navigating Stress at Salesforce
22:35 The Birth of Somatic Leadership
26:38 Understanding Stress Responses and Their Impact
29:32 Navigating Stress and Personal Challenges
31:05 Real-Life Stress Scenarios in Professional Settings
44:01 Practical Techniques for Managing Stress
46:01 Implementing Stress Management in Teams
50:25 Outro
About Software Sales Simplified:
Visit us at: https://www.strategicsalesoptimization.com/
Follow us on Linkedin: https://tinyurl.com/2tcx7mjx
Send us your questions at - Sales@stratsalesllc.com
"What is a Sales Engineer?" - Education Series on YouTube:
https://www.youtube.com/playlist?list=PLxuHbkRfIWtVj_Hg1GYBIg-o5M-icJLn0
Get Your Copy of "Winning Faster"!
Available Here:
https://www.strategicsalesoptimization.com/move-book
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. 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.
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 engagement and the complexities of marketing in a crowded marketplace. Dave shares insights from his extensive experience in the software industry, emphasizing the need for marketers to understand their customers deeply and to be actively involved in the sales process. The episode concludes with practical advice for new marketers and product teams on how to effectively go to market in today's competitive environment.
About our Guest - Dave Anderson:
Originally hailing from Melbourne, Australia, Dave Anderson is a marketing executive, keynote speaker, and podcaster who explores the intersection of technology, human culture, and storytelling. He’s the voice behind popular shows such as Tech Seeking Human and Robbo Live, where he dives into insights on DX, cloud, AI, and the human side of tech.
Dave's career has focused on building stories that scale: from rebranding and repositioning Dynatrace ahead of its IPO (where Dave led the S-1 narrative, investor deck, and roadshow story), to defining AI and agent strategy at Contentsquare today. Dave has helped companies move from multi-product to platform, from features to outcomes, and from SaaS to AI-first.
How to Find out More About Dave:
You can find Dave's profile on LinkedIn:
https://www.linkedin.com/in/daveando/
Chapters
00:00 Introduction to Software Sales Simplified
01:03 The Importance of Authenticity in Selling
02:21 Dave Anderson's Background and Experience
04:18 Aligning Product Marketing and Sales
06:37 Navigating Product-Led Growth vs. Enterprise Growth
10:16 Understanding Customer Engagement and Retention
14:10 The Role of AI in Enhancing Customer Experience
15:40 AI Buzzword Reality vs. Perception
21:36 Strategies for Reaching Customers in a Noisy Market
23:40 The Impact of AI on Marketing and Positioning
30:17 Understanding Customer Needs and Sales Collaboration
41:17 Advice for New Marketers and Go-to-Market Strategies
47:36 Like, Follow, Subscribe & Comment
About Software Sales Simplified:
Visit us at: https://www.strategicsalesoptimization.com/
Follow us on Linkedin: https://tinyurl.com/2tcx7mjx
Send us your questions at - Sales@stratsalesllc.com
"What is a Sales Engineer?" - Education Series on YouTube:
https://www.youtube.com/playlist?list=PLxuHbkRfIWtVj_Hg1GYBIg-o5M-icJLn0
Get Your Copy of "Winning Faster"!
Available Here:
https://www.strategicsalesoptimization.com/move-book
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. 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.
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 Guest - Corey Bruce:
Corey Bruce, MBA, is a transformational executive and private equity growth partner with over two decades of leadership in scaling revenue operations for high-growth, private equity–backed companies in the EHS, SaaS, and Compliance as a Service (CaaS) sectors. He led the U.S. market entry for Donesafe, an Australian safety tech startup, driving its growth through acquisition by HSI/Waud Capital Partners, and has held senior roles at StarTex Software (EHS Insight) and HSI/Donesafe. As Founder of Sozo Advisors, LLC, Corey advises private equity investors and portfolio companies on due diligence, acquisition strategy, board advisory, and revenue acceleration across compliance and regulatory tech.
Presently the Chief Executive Office (CEO) for SafetyIQ, Corey is renowned for aligning sales execution with investment strategy, Corey has built global sales organizations delivering 30%+ year-over-year growth and securing enterprise partnerships with Lowe’s, Apple, Tesla, Walmart, and Uber. He has partnered with leading private equity firms including Broadview Group Holdings, Blackstone, Providence Equity Partners, and Susquehanna Growth Equity, consistently driving scalability, operational rigor, and long-term enterprise value creation.
How to Find out More About Corey:
You can find Corey's profile on LinkedIn:
https://www.linkedin.com/in/coreybruce/
Chapters
00:00 Introduction
02:54 Corey Bruce's Journey
05:08 The Importance of Trust and Risk in Leadership
08:18 Navigating Leadership Challenges
11:15 Building a Culture of Accountability
14:06 Hiring Challenges in Software Sales
17:06 The Complexity of the Interview Process
19:48 The Role of Fractional Consulting in Hiring
24:42 The Challenges of Hiring Fractional Leadership
28:06 The Risks of Rapid Hiring Decisions
30:47 Hiring for Attitude Over Skills
34:58 Navigating Pressure from Leadership
39:08 The Importance of Metrics in Business
42:19 Humanizing Business Interactions
46:11 Advice for New C-Level Executives
51:43 See you next week!
About Software Sales Simplified:
Visit us at: https://www.strategicsalesoptimization.com/
Follow us on Linkedin: https://tinyurl.com/2tcx7mjx
Send us your questions at - Sales@stratsalesllc.com
"What is a Sales Engineer?" - Education Series on YouTube:
https://www.youtube.com/playlist?list=PLxuHbkRfIWtVj_Hg1GYBIg-o5M-icJLn0
Get Your Copy of "Winning Faster"!
Available Here:
https://www.strategicsalesoptimization.com/move-book
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. 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.
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 with their clients, and to focus on the personal wins for buyers. The conversation also touches on the significance of tools like virtual sales rooms and the potential for effective discovery techniques in the sales process.
About our Guest - Brian Wolff:
Brian Wolff is the Founder of The Wolff Den, a revenue consultancy and community dedicated to sharing best practices among fellow professionals in closing roles. A 15-year sales veteran and multiple President's Club award winner, he is focused on understanding the foundations of how/why buyers think and act, delving deep into concepts ever newcomers can understand.
He currently serves as an Enterprise Account Executive at Glassbox, working with Fortune 100 companies to reduce customer struggle and fraud events in their digital experiences.
How to Find out More About Brian:
You can find Brian's profile on LinkedIn:
https://www.linkedin.com/in/wolff-brian
Chapters:
00:00 Introduction to Software Sales Simplified
01:16 Understanding Emotional Value in Sales
04:13 The Misconception of Value in Enterprise Sales
06:11 Contextual and Experienced Value Perceptions
08:52 Identifying Personal Wins in Sales Conversations
11:30 Tactics for Effective Discovery
14:02 The Virtual Sales Room Concept
16:08 Building Trust and Urgency in Sales
18:50 Emotional vs. Material Value in Sales
21:56 The Importance of Discovery in Sales
30:23 Effective Storytelling in Sales
34:53 Understanding Buyer Frustrations
42:19 Building Trust and Relationships in Sales
48:37 Like, Follow, Subscribe, and Comment!
About Software Sales Simplified:
Visit us at: https://www.strategicsalesoptimization.com/
Follow us on Linkedin: https://tinyurl.com/2tcx7mjx
Send us your questions at - Sales@stratsalesllc.com
"What is a Sales Engineer?" - Education Series on YouTube:
https://www.youtube.com/playlist?list=PLxuHbkRfIWtVj_Hg1GYBIg-o5M-icJLn0
Get Your Copy of "Winning Faster"!
Available Here:
https://www.strategicsalesoptimization.com/move-book
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. 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.
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 content, the impact of AI on sales processes, and the necessity of human connection in a remote work environment. James shares valuable insights on effective content strategies and the significance of partnerships in driving business success, concluding with advice for newcomers in the industry.
About our Guest - James Fox:
James is a results-driven sales leader with 12+ years of experience growing software businesses. He’s currently Head of Business Development at Pina Vida and Co-Founder of the AI productivity tool ScrumBuddy.
Known for uncovering clients’ unspoken needs, James has built strong relationships and delivered high-impact solutions. At Pina Vida, he built the sales engine from the ground up, converting cold leads into lasting enterprise clients.
Now focused on AI, James is bringing ScrumBuddy to market while exploring how technology can help teams better understand and deliver on what clients and projects truly need.
How to Find out More About James:
Chapters
0:00 Introduction to Software Sales Simplified
00:46 Aligning Sales and Marketing for Success
02:51 Common Misalignments Between Sales and Marketing
04:19 The Importance of Collaboration
07:56 Understanding Buyer Behavior in the Digital Age
10:56 The Role of Video Content in Marketing
13:36 AI's Impact on Sales and Marketing
17:54 Overcoming Buyer Resistance in Sales
20:41 The Shift to Remote Work and Human Connection
24:04 The Importance of Personal Interaction in Sales
27:14 Valuable Content Types in Modern Marketing
30:28 Simplifying Messaging for Better Communication
33:21 The Role of Partnerships in Business Success
36:11 Advice for Newcomers in Sales and Marketing
41:41 Like, Follow, and Subscribe!
About Software Sales Simplified:Visit us at: https://www.strategicsalesoptimization.com/
Follow us on Linkedin: https://tinyurl.com/2tcx7mjx
Send us your questions at - Sales@stratsalesllc.com
"What is a Sales Engineer?" - Education Series on YouTube:
https://www.youtube.com/playlist?list=PLxuHbkRfIWtVj_Hg1GYBIg-o5M-icJLn0
Get Your Copy of "Winning Faster"!
Available Here:
https://www.strategicsalesoptimization.com/move-book
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. 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.
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 emphasizes the need for continuous learning and adaptability in a rapidly evolving field, offering valuable insights for aspiring professionals.
About our Guest - Priyanta Dharmasena:
Priyanta Dharmasena has spent nearly two decades translating cutting‑edge cloud technology into measurable business value for customers at companies like Oracle, Seibel, Salesforce and beyond. Credited with spearheading complex wins as a lead Solution Engineer, Pri helped lay the groundwork for several record‑setting deals that still shape customer successes and trajectories today. Priyanta pairs deep technical fluency with commercial savvy, sharing practical perspectives on emerging topics such as AI security—most recently highlighting Skyflow’s new agentic privacy layer for the presales community. Guided by his personal motto “go beyond the impossible,” he is known for customer‑first storytelling, cross‑functional mentorship, and a relentless focus on delivering outcomes that matter.
Priyanta is also an exemplary professional diver who teaches at the Master Instructor level. His diligence and discipline in his diving endeavors is well known and carries over to his selling activities.
How to Find out More About Priyanta:
You can find Priyanta's profile on LinkedIn:
https://www.linkedin.com/in/priyanta-dharmasena/
Chapter List:
00:00 Introduction to Software Sales Simplified
02:05 Exploring Leadership and Growth in Sales
04:53 Priyanta's Journey: From Oracle to Cybersecurity
07:55 Diving into the Basics: Lessons from Scuba Diving
11:39 Balancing Technical Skills and Management
16:55 The Mindset of Continuous Learning
19:55 Career Paths: Management vs. Individual Contributor
22:03 Personal Growth and Career Decisions
24:08 The Evolving Landscape of Cybersecurity
27:54 Data Protection and Security Strategies
30:35 Understanding Business Pain in Technology Sales
34:20 AI's Role in Cybersecurity
37:48 Advice for Aspiring Professionals in Cybersecurity
40:24 Like, Follow, Subscribe and See You Next Week
About Software Sales Simplified:Visit us at: https://www.strategicsalesoptimization.com/
Follow us on Linkedin: https://tinyurl.com/2tcx7mjx
Send us your questions at - Sales@stratsalesllc.com
"What is a Sales Engineer?" - Education Series on YouTube:
https://www.youtube.com/playlist?list=PLxuHbkRfIWtVj_Hg1GYBIg-o5M-icJLn0
Get Your Copy of "Winning Faster"!
Available Here:
https://www.strategicsalesoptimization.com/move-book
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. 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.
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 trust within organizations, strategies for gaining executive buy-in, and the significance of finding purpose beyond employment. The episode concludes with advice for navigating career transitions and the importance of community engagement.
About Our Guest - Jessica White:
Jessica White is a Growth Executive passionate about helping companies grow through international expansion, new channels, and new capabilities. With over 25 years of experience at IBM, Accenture, and now Honeywell, she has a proven track record of developing people-first software and services practices on the world’s leading technology platforms such as IBM, Google and Microsoft. Jessica’s expertise spans corporate strategy, M&A, consulting, software sales, and building industry-leading strategic alliances with companies such as SFDC and NASCAR. Jessica is also the author of a methodology for connection in the digital age called #circlesofconnection.
How to Find out More About Jessica:You can find Jessica's profile on LinkedIn:
https://www.linkedin.com/in/jessicaswhite4701/
How to Find out More About Circles of Connection: Check out the LinkedIn Group for more info: https://www.linkedin.com/groups/9558277/
Chapter List:
00:00 Introduction to Software Sales Simplified
01:44 Meet Jessica White: A Technology Growth Leader
03:28 The Role of a Growth Leader
06:13 Circles of Connection: A Methodology for Empathy
13:15 Addressing the Loneliness Epidemic
17:41 Fostering Physical Connections in Remote Teams
21:27 Building Community in the Workplace
25:03 Strategies for Client Connection
25:31 Building Trust Through Peer Connections
28:35 The Impact of Connection on Sales Success
29:31 Navigating AI in Human Connections
33:31 Optimizing Human Talent with AI
36:12 Overcoming Challenges in Team Dynamics
38:08 Creating Executive Buy-In
38:28 Finding Purpose Beyond Employment
42:10 Resources for Circles of Connection and Jessica
48:53 See You Next Week!
About Software Sales Simplified:Visit us at: https://www.strategicsalesoptimization.com/
Follow us on Linkedin: https://tinyurl.com/2tcx7mjx
Send us your questions at - Sales@stratsalesllc.com
"What is a Sales Engineer?" - Education Series on YouTube:
https://www.youtube.com/playlist?list=PLxuHbkRfIWtVj_Hg1GYBIg-o5M-icJLn0
Get Your Copy of "Winning Faster"!Available Here:
https://www.strategicsalesoptimization.com/move-book
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. 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.
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 commitment and collaboration within organizations to build effective partner programs.
About Our Guest - Tamer Osman:
Tamer Osman is a respected leader in the tech partnerships space with over 25 years of experience driving growth and innovation across enterprise software, cloud services, system integrators, and startups. He has built and scaled partner programs at major organizations including AWS, IBM, Salesforce, KPMG, and Infosys, contributing to five successful company exits. Known for his results-driven approach and ability to build trust with stakeholders, Tamer has managed strategic alliances generating over $1B in partner-influenced business and founded RGlobe, a collaborative selling SaaS platform adopted by Oracle. His career began during the dot-com boom, where he helped launch KPMG’s e-business division and held impactful roles with Cisco, Microsoft, and others.
Beyond tech, Tamer is passionate about social impact. He co-founded the Diablo Valley Tech Initiative (DVTI), partnering with local colleges and civic leaders to create tech career opportunities for underserved communities while promoting sustainability and economic inclusion in the San Francisco East Bay. A keynote speaker and global traveler, Tamer holds a B.S. and M.A. in Industrial Technology from Cal Poly and completed postgraduate studies in Innovation and Entrepreneurship at Stanford. He believes in staying curious and giving back—because the more you give, the more you get.
How to Find out More About Tamer:
You can find Tamer's profile on LinkedIn:
https://www.linkedin.com/in/tamerosman/
Chapters:00:00 Introduction
01:49 Tamer's Background
04:55 The Importance of Partnerships in Software Sales
06:45 Innovations and Disruptions
09:59 Building Successful Partner Programs
13:22 Fostering Collaboration Between Sales and Partners
16:04 Different Types of Partnerships
18:44 Driving Success
21:18 The Importance of Partnerships
23:22 Disruptions
24:21 AI and Automation
28:24 The Rise of Marketplaces
35:00 Building Successful Partner Programs
39:03 Common Pitfalls
40:57 Advice for Partner Managers
45:13 Goodbye
46:21 Subscribe!
About Software Sales Simplified:
Visit us at: https://www.strategicsalesoptimization.com/
Follow us on Linkedin: https://tinyurl.com/2tcx7mjx
Send us your questions at - Sales@stratsalesllc.com
"What is a Sales Engineer?" - Education Series on YouTube:
https://www.youtube.com/playlist?list=PLxuHbkRfIWtVj_Hg1GYBIg-o5M-icJLn0
Get Your Copy of "Winning Faster"!
Available Here:
https://www.strategicsalesoptimization.com/move-book
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. 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.
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 a seasoned pro looking to refresh your approach, this series is crafted to help you level up your selling skills.
This initiative complements our Software Sales Simplified podcast, best-selling book Winning Faster: The MOVE Framework for Enterprise Sales Success, and the upcoming MOVE certification program, starting with a Discovery module.
🎥 First episode: What Do Sales Engineers ACTUALLY Do? https://youtu.be/PxJ521eB6RQ
🎯 Let us know what you want to see next! Drop us a comment or connect with us on LinkedIn.
Chapters:
00:00 Introduction to Software Sales Simplified
01:07 Launching the Educational Series
02:51 Overview of Upcoming Content
03:59 Tools and Techniques for Sales Success
06:27 Feedback and Community Engagement
06:36 Plans for the Holiday
07:29 Closing Remarks - Remember to Like, Subscribe, and Follow
08:03 See You Next Week!
About Software Sales Simplified:
Visit us at: https://www.strategicsalesoptimization.com/
Follow us on Linkedin: https://tinyurl.com/2tcx7mjx
Send us your questions at - Sales@stratsalesllc.com
Get Your Copy of "Winning Faster"!
Order your own copy of, "Winning Faster: The MOVE Framework for Enterprise Software Sales" on our website or on Amazon.
Available Here:
https://www.strategicsalesoptimization.com/move-book
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. 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.
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 customers. The conversation also touches on the challenges faced by newcomers in the industry and the importance of mentorship and continuous learning.
About Our Guest - Janet Jaiswal:
Janet Jaiswal Janet Jaiswal has spent 20+ years in senior marketing roles at private and public companies such as eBay, Paypal, and IBM Tealeaf. She is currently the CMO / Global VP of Marketing at Blueshift, a San Francisco-based company that helps brands automate and personalize engagement across every marketing channel.
Janet is an advisor with Peakspan Capital and has been recognized as a Top 101 B2B Marketing Influencer by CMO Huddles, a FINITE Top 30 SaaS marketer, and one of the Top 14 Marketers to Watch by Drift. Janet earned a bachelor's degree from UC Berkeley and an MBA at the Tepper School of Business at Carnegie Mellon University.
How to Find out More About Janet Jaiswal:
You can find Janet's profile on LinkedIn:
https://www.linkedin.com/in/janetjaiswal/
Chapters
00:00 Introduction to Software Sales Simplified
01:16 Meet Janet Jaiswal: Insights from a Marketing Leader
02:50 Standing Out in a Crowded Market
05:21 The Evolution of Marketing Messaging
07:39 The Role of Marketing in Sales Enablement
08:47 Testing and Adapting Sales Strategies
11:29 The Art of Storytelling in Sales
13:39 Building Trust and Empathy with Customers
16:27 Rethinking Demo Strategies
18:45 Addressing Customer Skepticism
20:33 Balancing Aspirations with Reality
22:10 Navigating Early-Stage Development Challenges
23:53 The Importance of Post-Mortem Analysis
25:26 Learning from Losses
28:16 Validating Value Propositions
31:15 Advice for Aspiring Marketers
38:08 Farewell - Like, Follow, Subscribe and Comment!
About Software Sales Simplified:
Visit us at: https://www.strategicsalesoptimization.com/
Follow us on Linkedin: https://tinyurl.com/2tcx7mjx
Send us your questions at - Sales@stratsalesllc.com
Get Your Copy of "Winning Faster"!
Order your own copy of, "Winning Faster: The MOVE Framework for Enterprise Software Sales" on our website or on Amazon.
Available Here:
https://www.strategicsalesoptimization.com/move-book
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. 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.
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 emotional intelligence, adaptability, and the ability to build relationships in the sales process as critical to success. In this conversation, Dustin Chamberlain discusses the evolving landscape of enterprise software sales, emphasizing the importance of diverse interview panels, the critical role of pre-sales professionals, and the impact of AI on sales execution. He shares insights on building trust in sales relationships, the necessity of adaptability in sales roles, and offers advice for those considering a career in pre-sales. The discussion highlights the irreplaceable value of human interaction in the sales process, despite the growing influence of technology.
About Our Guest - Dustin Chamberlain:
Dustin Chamberlain is the Director of Solutions Consulting at Contentsquare, where he leads teams that help enterprise clients unlock value through digital experience analytics. With over a decade of experience in solution consulting, sales engineering, and technical enablement, Dustin has built a career around bridging product capabilities with customer outcomes. He's passionate about mentoring future pre-sales leaders, building scalable processes, and aligning cross-functional teams to win and retain enterprise customers.
How to Find out More About Dustin Chamberlain:
You can find Dustin profile on LinkedIn:
https://www.linkedin.com/in/dustinmchamberlain/
Chapters:
00:00 Introduction to Software Sales Simplified
01:59 Dustin Chamberlain's Journey from Practitioner to Pre-Sales
08:26 Skills for Success in Pre-Sales
12:09 Insights from the Practitioner Side
15:12 The Role of Pre-Sales in the Sales Cycle
17:38 Effective Collaboration Between AEs and SEs
20:07 Recruitment Mistakes in Pre-Sales
20:52 The Importance of Diverse Interview Panels
21:41 Navigating Changes in Enterprise Software Sales
24:20 Building Trust in Sales Relationships
26:45 The Evolving Role of Pre-Sales Professionals
29:38 Guiding Principles in Sales Management
31:52 Advice for Aspiring Pre-Sales Professionals
32:34 The Role of AI in Sales Execution
35:15 The Irreplaceable Value of Pre-Sales Professionals
40:44 Like, Follow, Subscribe and Comment!
About Software Sales Simplified:
Visit us at: https://www.strategicsalesoptimization.com/
Follow us on Linkedin: https://tinyurl.com/2tcx7mjx
Send us your questions at - Sales@stratsalesllc.com
Get Your Copy of "Winning Faster"!
Order your own copy of, "Winning Faster: The MOVE Framework for Enterprise Software Sales" on our website or on Amazon.
Available Here:
https://www.strategicsalesoptimization.com/move-book
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. 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.
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 emphasizes the significance of collaboration, optimizing sales processes, and the value of mentorship in achieving success in sales.
About Our Guest - Lynn Powers:
Lynn Powers is an award-winning enterprise sales leader and #1 performer at Clari since 2019, most recently closing Q1 at 280% of quota. With a career spanning Oracle, MapR, and Xactly, she’s built a reputation for turning insight into impact—partnering with the world’s most ambitious companies to run revenue with confidence.
Lynn is a keynote speaker, 2x LinkedIn Sales Star, Sales Success Summit alum, and featured guest on the 30 Minutes to President’s Club podcast. She currently serves as Co-President of Clari’s Women’s ERG and was a previous board member at Women in Revenue. Her commitment to elevating others extends beyond tech—she recently partnered with the American Heart Association to prepare the next generation of female scientists, doctors, inventors, and changemakers through STEM-focused volunteer efforts.
Passionate about bringing human ingenuity and AI together to overachieve, Lynn is a fierce advocate for innovation, inclusion, and impact. Her leadership is defined by mentorship, strategic thinking, and an infectious energy known fondly as “Lynnergy.”
A graduate of the University of San Francisco, she holds a degree in Sociology with minors in Legal Studies and Philippine Studies. Lynn is a proud AAPI advocate and lifelong learner—fueling her growth through a steady diet of tech and personal development podcasts.
How to Find out More About Lynn:
You can find Lynn's profile on LinkedIn:
https://www.linkedin.com/in/powerslynn/
Chapters:
00:00 Introduction to Software Sales Simplified
01:56 Lynn Powers: Journey in Software Sales
04:25 Understanding Clari: The Revenue Platform
07:11 Keys to Success in Sales
10:49 Identifying the Right Buyers
13:50 Leveraging Technology in Sales
17:33 The Importance of Collaboration
20:22 Building Trust with Customers
23:05 The Role of a Trusted Advisor
25:49 Optimizing Sales Processes
28:37 Advice for Aspiring Sales Professionals
40:47 Like, Follow, Subscribe, and Comment!
About Software Sales Simplified:
Visit us at: https://www.strategicsalesoptimization.com/
Follow us on Linkedin: https://tinyurl.com/2tcx7mjx
Send us your questions at - Sales@stratsalesllc.com
Get Your Copy of "Winning Faster"!
Order your own copy of, "Winning Faster: The MOVE Framework for Enterprise Software Sales" on our website or on Amazon.
Available Here:
https://www.strategicsalesoptimization.com/move-book
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. 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.
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 conversation emphasizes the need for adaptability, continuous growth, and leveraging networks in sales.
About Our Guest:
Derek Francis, Global Head of Revenue Growth for Merchfarm, is a seasoned go-to-market executive with over 24 years of experience in enterprise software, including 16 years leading high-performing teams ranging in size from 4 to over 100. He played a pivotal role in scaling a $4M startup into a $300M global business—now valued at over $5B—through strategic expansion and disciplined execution. Derek has consistently outperformed sales targets at top-tier companies such as IBM, MicroStrategy, Infor, and Contentsquare, and began his career selling ERP solutions under the mentorship of a former CFO. His expertise spans GTM strategy, operational excellence, and authentic leadership, with a proven ability to build strong cultures and diverse teams. He has led successful engagements with retail giants like Walmart, Amazon, Verizon, and Sephora, and is recognized for pioneering virtual engagement models and developing future leaders.
How to Find out More About Derek:
You can find Derek's profile on LinkedIn:
https://www.linkedin.com/in/derek-francis-176937/
Chapters:
00:00 Introduction to Software Sales Simplified
01:12 Derek Francis: A Journey Through Sales
04:05 Transitioning from Engineering to Sales
09:02 The Impact of Y2K on Careers
13:52 Building a Sales Team at Clicktale
19:07 The Importance of Culture in Sales Teams
21:34 Navigating the Challenges of Scaling Sales Teams
27:21 Transitioning to the Creator Economy
32:24 Applying Enterprise Sales Principles to New Industries
35:50 Building Brands in the Creator Space
43:46 Embracing Change and Continuous Learning
47:44 Like, Follow, Subscribe, and Comment!
About Software Sales Simplified:
Visit us at: https://www.strategicsalesoptimization.com/
Follow us on Linkedin: https://tinyurl.com/2tcx7mjx
Send us your questions at - Sales@stratsalesllc.com
Get Your Copy of "Winning Faster"!
Order your own copy of, "Winning Faster: The MOVE Framework for Enterprise Software Sales" on our website or on Amazon.
Available Here:
https://www.strategicsalesoptimization.com/move-book
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. 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.
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 to enhance sales processes. The conversation also touches on the trend of utilizing fractional resources to optimize operations and the critical role of leadership in navigating growth challenges.
About Our Guest:Peter Kuhn is a seasoned professional with a strong background in sales and business development, currently serving as the Co-Founder of Baku, a B2B SaaS Go-to-Market growth agency based in Brooklyn, New York. He specializes in helping companies develop scalable and repeatable sales strategies, focusing on founder-led teams and scaling go-to-market teams with significant ARR. Peter has a rich career history, including leadership roles at Moat, which was acquired by Oracle, and advisory roles at Primary Venture Partners. He holds a degree in Philosophy from Temple University, showcasing his diverse interests and leadership skills. Peter is passionate about enabling businesses to overcome obstacles and achieve growth, and he is highly regarded by his clients for his actionable guidance and strategic insights.
How to Find out More About Peter:
You can find Peter's profile on LinkedIn:
https://linkedin.com/in/thepeterkuhn
Chapters:
00:00 Introduction to Software Sales Simplified
01:19 Meet Peter Kuhn: Background and Insights
02:58 Building Sales Systems for Startups
03:56 The Role of AI in Sales
06:08 Understanding Customer Needs
07:07 Getting Up to Speed as a New Leader
10:35 Common Challenges in Sales Messaging
13:30 The Power of Storytelling in Sales
15:20 Customer Centricity in Sales
17:41 Challenges in Scaling Sales Teams
21:54 The Impact of Capital on Business Behavior
24:49 The Role of Founders in Company Success
27:48 Cautionary Tales in Hiring Practices
31:00 The Shift Towards Fractional Resources
35:44 The Importance of Tactical Agility
39:30 Building a Consultancy for the AI Era
45:08 Please Subscribe, Follow, Like, & Comment!!
About Software Sales Simplified:
Visit us at: https://www.strategicsalesoptimization.com/
Follow us on Linkedin: https://tinyurl.com/2tcx7mjx
Send us your questions at - Sales@stratsalesllc.com
Get Your Copy of "Winning Faster"!
Order your own copy of, "Winning Faster: The MOVE Framework for Enterprise Software Sales" on our website or on Amazon.
Available Here:
https://www.strategicsalesoptimization.com/move-book
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. 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.
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, in many circumstances, the buyer isn't even aware of the barriers to their purchase and need good solution advocates to help them navigate those threats.
Chapters:
00:00 Introduction to Software Sales Simplified
01:03 Exploring the MOVE Framework
03:08 Understanding Opportunity in Sales
06:56 The Importance of Budget in Sales
09:47 Navigating Economic Uncertainty and Budgeting
12:21 Long-term Budget Considerations for SaaS Sales
14:02 The Importance of Time in Opportunity
19:38 Understanding Power Dynamics in Sales
25:12 Identifying Red Flags in Sales Opportunities
30:25 Strategies for Mitigating Challenges in Sales
37:27 Comment, Like, Follow, and Subscribe!
About Software Sales Simplified:
Visit us at: https://www.strategicsalesoptimization.com/
Follow us on Linkedin: https://tinyurl.com/2tcx7mjx
Send us your questions at - Sales@stratsalesllc.com
Get Your Copy of "Winning Faster"!
Order your own copy of, "Winning Faster: The MOVE Framework for Enterprise Software Sales" on our website or on Amazon.
Available Here:
https://www.strategicsalesoptimization.com/move-book
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. 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.
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 conversations, and the significance of understanding customer needs. The conversation emphasizes the need for sales professionals to develop their skills and adapt to the changing landscape of sales.
About Our Guest: Marty Funk got his start as a receptionist at Oracle in 1990—just a foot in the door that launched a 30-year career in sales and sales leadership. From CRO at a small company to frontline leader at a global enterprise, Marty has navigated success and setbacks through every market cycle.
What’s stayed consistent is his belief that staying close to the team and the customer drives the most growth. That mindset led him to launch The Marty Funk Group, where he now helps sales teams level up through skills-based training in curiosity, negotiation, urgency, and sales mindset.
Marty’s passion for developing talent and helping others succeed is front and center—and we’re thrilled to have him on the podcast.
How to Find out More About Marty:
You can find Marty's profile on LinkedIn:
https://www.linkedin.com/in/mfunk/
Chapters:
00:00 Introduction to Software Sales Simplified
02:55 Marty Funk's Sales Journey
05:40 Transitioning to Sales Leadership
08:29 Building Effective Sales Teams
11:01 Understanding Team Dynamics
13:50 The Evolution of Big Data
16:23 Navigating the AI Landscape
17:59 Sales Strategies in the Age of AI
22:41 Understanding Customer Needs
25:25 The Role of Data in Sales Conversations
28:35 Curiosity as a Sales Skill
32:33 Negotiation Strategies in Sales
39:25 The Importance of Knowing When to Walk Away
43:16 See You Next Week! Like, Follow, and Subscribe!
About Software Sales Simplified:
Visit us at: https://www.strategicsalesoptimization.com/
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