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. Their conversation highlights the evolving landscape of buyer behavior, the importance of aligning executive messaging with customer value, and building business cases collaboratively to connect value to executive priorities.

About Ryan Anderson:For over two decades, Ryan has been at the forefront of driving innovation at McAfee, Google, Accenture Song, and Wipro Digital. With deep expertise spanning Marketing, Enterprise Sales, and Customer Experience, he brings a cross-functional perspective on what truly drives deal success—or failure. In this conversation, Ryan unpacks how a buyer’s definition of value ultimately dictates the outcome of every deal and why sellers often miss the mark. Tune in for insights that could transform the way you approach sales, reframing opportunities, and customer relationships.

https://www.linkedin.com/in/ryananderson515/

About Software Sales Simplified:

Visit us at:⁠⁠⁠⁠⁠⁠⁠⁠ ⁠https://www.strategicsalesoptimization.com/⁠⁠⁠⁠⁠⁠⁠⁠⁠

Follow us on Linkedin:⁠⁠⁠⁠⁠⁠⁠⁠ ⁠https://tinyurl.com/2tcx7mjx⁠⁠⁠⁠⁠⁠⁠⁠⁠

Send us your questions at ⁠- ⁠⁠[email protected]⁠⁠⁠

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.

Book 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.

Chapters:

00:00 Introduction to Software Sales Simplified

02:07 Understanding Value in Sales

05:36 The Importance of Buyer Alignment

09:02 The Role of Communication in Sales

13:03 Shifting Buyer Perspectives on Value

16:26 Consultative Selling and Value Discovery

19:06 Transforming Value Propositions for Executives

19:56 Aligning Executive Messaging with Customer Value

22:23 Challenging Buyer Assumptions

25:07 Mapping Value to Customer Needs

27:50 Quantifying Value and Building Business Cases

32:39 Using Customer Data for Value Creation

36:14 Connecting Value to Executive Focus

40:14 Actionable Steps for Value-Based Selling

44:20 Outro

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 and sales success, emphasizing the significance of authenticity and relationship-building in today's market.

About Tony Marshall:

Tony Marshall is a seasoned sales professional who transitioned from enterprise software sales to become an innovator in the property insurance sector. Leveraging his expertise in customer engagement, consultative selling, and mentorship, he drives success by aligning measurable sales criteria with actionable customer insights. Tony is an accomplished ultra-distance runner who has an impressive racing history. Tony feels there's many touch points between running and successful enterprise selling and attributes the discipline he learned from running as part of his winning philosophy.

https://www.linkedin.com/in/tony-marshall-1234643/

About Software Sales Simplified:

Visit us at:⁠⁠⁠⁠⁠⁠⁠ ⁠https://www.strategicsalesoptimization.com/⁠⁠⁠⁠⁠⁠⁠⁠

Follow us on Linkedin:⁠⁠⁠⁠⁠⁠⁠ ⁠https://tinyurl.com/2tcx7mjx⁠⁠⁠⁠⁠⁠⁠⁠

Send us your questions at ⁠- ⁠⁠[email protected]⁠⁠⁠

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.

Book 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.

Chapters

00:00 Introduction to Software Sales Simplified

01:03 Meet Tony Marshall: Innovator in Property Insurance

03:02 Transitioning from Enterprise Sales to Insurance

05:42 Skills for Success in Sales

07:28 The Evolution of Communication in Sales

09:38 Changing Dynamics in Enterprise Sales

12:56 Understanding the Modern Buyer

15:36 Tony's Journey into Sales

19:33 Mentorship and Growth in Sales Careers

21:36 Qualifying Deals and High Win Rates

24:49 The Importance of Demos in Sales

26:59 Discipline in Sales and Ultra Running

32:41 The Journey of Ultra Running

35:06 Building Authentic Relationships in Sales

40:02 Outro

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 the importance of authenticity, emotional connections, and continuous learning in sales.

About Sara Levinson:

Sara has sold and launched transformational technology initiatives with the world’s largest & most influential brands, including Gap Inc, Disney, Farmers Insurance, Petco, Symantec, Tiffany and Co., Ashley Furniture, O’Reilly Auto Parts and many more. 

Sara has been named a Linkedin Top 100 Sales Star, a top female sales practitioner by Sales Hacker, and is a frequent presenter, moderator, and podcast guest in the tech sales community. On the OMG Sales Assessment taken by over 2 million sellers globally, she scored in the top 6%. 

As Head of Strategic Accounts at Claravine, The Data Standards Company, she helps Fortune 500 brands make sense of their marketing data, leading to faster insights and smarter business decisions. Sara held previous roles at Prometric, LivePerson, Clicktale (acquired by ContentSquare) and IBM.

Sara holds an M.A. in Professional Writing from Carnegie Mellon University and a B.A. in English from Gettysburg College, where she serves on the Alumni Board of Directors. Her writing has appeared in Thrive Global, the Pittsburgh Post-Gazette, The Gettysburg Times, and the American Scholar.

https://www.linkedin.com/in/levinsonsara/

About Software Sales Simplified:

Visit us at:⁠⁠⁠⁠⁠⁠ ⁠https://www.strategicsalesoptimization.com/⁠⁠⁠⁠⁠⁠⁠

Follow us on Linkedin:⁠⁠⁠⁠⁠⁠ ⁠https://tinyurl.com/2tcx7mjx⁠⁠⁠⁠⁠⁠⁠

Send us your questions at ⁠- ⁠⁠[email protected]⁠⁠⁠

Get 25% off with Coupon Code “SELLFASTER2025”!

Order a digital/PDF copy of the #1 Best Selling book on Amazon, "Winning Faster: The MOVE Framework for Enterprise Software Sales" on our website and get 25% off until February 28th.

Book 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.

🎙️ EP 10: Proving the Value in Enterprise Sales – The Key to Closing Deals 💡

🔹 Why do so many software deals stall before the finish line? Because sellers don't engage with prospects effectively and do not prove value in a way that resonates with decision-makers.

In this episode of Software Sales Simplified: MOVE to Success, hosts Matt Long & Kevin Donville break down the final pillar of the MOVE Framework—Engagement—and discuss what goes into proving value, securing stakeholder buy-in, building trust, and driving long-term success. 🚀

🎯 Lessons Learned:✅ The importance of proving value and the benefits that delivers✅ Techniques for proving and communicating value throughout the sales cycle✅ How to align demos, POCs, and Case Studies with real business value that impress✅ Common mistakes made when developing ROI analysis and business cases✅ Why delivering value effectively is your best competitive advantage✅ How proper discovery builds the blueprint for proper engagement and long-term success💡 Who Should Listen?
👉 Enterprise software sellers looking to accelerate deal cycles
👉 Pre-sales & solution consultants wanting to deliver impactful demos
👉 Sales leaders who need to improve proof-of-value execution

🔗 Listen now and start proving value the right way!

About Software Sales Simplified:

Visit us at:⁠⁠⁠⁠⁠ ⁠https://www.strategicsalesoptimization.com/⁠⁠⁠⁠⁠⁠

Follow us on Linkedin:⁠⁠⁠⁠⁠ ⁠https://tinyurl.com/2tcx7mjx⁠⁠⁠⁠⁠⁠

Send us your questions at ⁠- ⁠⁠[email protected]⁠⁠⁠

Get 25% off with Code "SELLFASTER2025" at Checkout

Order the digital/PDF version of our #1 Best Selling book, "Winning Faster: The MOVE Framework for Enterprise Software Sales" on our website and get 25% off at checkout with code "SELLFASTER2025" until Feb 28th. 

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.

🚀Are your software demos losing deals instead of closing them? Too many sales teams fall into the same traps—feature overload, lack of customization, and failing to connect with what truly matters to the buyer. In this episode ofSoftware Sales Simplified, hostsMatt Long and Kevin Donville break down why so many demos fail and, more importantly, how to fix them.

🔹What You'll Learn:

✅ The real purpose of a software demo (hint: it's NOT to show every feature)

✅ The biggest mistakes sales teams make in their demos—and how to avoid them

✅ Why "less is more" when presenting your product

✅ How to craft demos that resonate with your buyers and accelerate the sales cycle

✅ The role ofcustomer success and services teams in improving demo effectiveness

💡 Whether you're an AE, SE, or sales leader, this episode is packed with actionable insights to transform your demos intopowerful deal-closing machines.

🎧Listen now and start winning more deals with better demos!

About Software Sales Simplified:

Visit us at:⁠⁠⁠ ⁠https://www.strategicsalesoptimization.com/⁠⁠⁠⁠

Follow us on Linkedin:⁠⁠⁠ ⁠https://tinyurl.com/2tcx7mjx⁠⁠⁠⁠

Send us your questions at ⁠- ⁠⁠[email protected]⁠⁠⁠

Get 25% off with Code "SELLFASTER2025" at Checkout

Order the digital/PDF version of our #1 Best Selling book, "Winning Faster: The MOVE Framework for Enterprise Software Sales" on our website and get 25% off at checkout with code "SELLFASTER2025" until Feb 28th. 

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 toSoftware Sales Simplified: MOVE to Success. This podcast is produced by and is the sole property ofStrategic Sales Optimization LLC, copyright 2025. Reproduction or use of this broadcast in whole or in part without express written permission fromStrategic Sales Optimization LLC is strictly prohibited. All rights reserved.

This Week's Guest - Geoff Galat

In this episode of Software Sales Simplified, hosts Kevin Donville and Matt Long speak with CMO Geoff Galat about the evolving landscape of software sales and marketing. They explore shifts in the customer buying processes, the impact of AI on selling, the effect of easily downloaded solutions, the role of trust, and the need for continuous engagement in SaaS. They also cover challenges of remote communication on selling, changing buyer behavior, and potential AI market consolidation.

About Geoff Galat:

Geoff Galat has over 30 years of marketing leadership experience, having played key roles in shaping emerging markets such as digital customer experience, IoT analytics, and marketing technology. With leadership positions at Mercury Interactive, Tealeaf, Silverpop, AGT International, and Clicktale, he has extensive experience driving strategic growth, category creation, and enterprise software marketing innovation.

https://www.linkedin.com/in/geoff-galat-a8569/

About Software Sales Simplified:

Visit us at:⁠⁠⁠ ⁠https://www.strategicsalesoptimization.com/⁠⁠⁠⁠

Follow us on Linkedin:⁠⁠⁠ ⁠https://tinyurl.com/2tcx7mjx⁠⁠⁠⁠

Get 25% off with Coupon Code “SELLFASTER2025”!

Order a digital/PDF copy of the #1 Best Selling book on Amazon, "Winning Faster: The MOVE Framework for Enterprise Software Sales" on our website and get 25% off until February 28th.

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.

This Week's Guest - Anna Hockett

https://www.linkedin.com/in/annahockett1/

Visit us at:⁠⁠ ⁠https://www.strategicsalesoptimization.com/⁠⁠⁠

Follow us on Linkedin:⁠⁠ ⁠https://tinyurl.com/2tcx7mjx⁠⁠⁠

Send us your questions at ⁠- ⁠[email protected]⁠⁠

Order your own copy of the #1 Best Selling book on Amazon, "Winning Faster: The MOVE Framework for Enterprise Software Sales".  Available in paperback, PDF/eReader, and Kindle formats.  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.

Today we're joined by Richard Harris, seasoned sales consultant of Harris Consulting Group, author of the popular book, "The Seller's Journey - Your Guidebook to Close More Deals with N.E.A.T. Selling", co-host of the popular "Surf and Sales" podcast, and it's associated ground-breaking conference for sellers.

In this episode, hosts Kevin Donville and Matt Long engage with Richard Harris, as they explore challenging themes in the sales industry, including the importance of active listening, the challenges of unrealistic expectations, and the evolving nature of sales strategies.

Richard shares insights from his experiences, emphasizing the need for sales professionals to understand customer pain points and the significance of data in making informed decisions. The conversation also touches on the role of technology in enhancing sales processes and the value of internal communication within sales teams.

How to Contact Richard Harris:

You can connect with Richard Harris on Linkedin at https://www.linkedin.com/in/rharris415/ or at his website https://theharrisconsultinggroup.com/

The Surf & Sales Podcast:

Visit us at:⁠ ⁠https://www.strategicsalesoptimization.com/⁠⁠

Follow us on Linkedin:⁠ ⁠https://tinyurl.com/2tcx7mjx⁠⁠

Send us your questions at ⁠- [email protected]⁠

Order your own copy of the #1 Best Selling book on Amazon, "Winning Faster: The MOVE Framework for Enterprise Software Sales".  Available in paperback, PDF/eReader, and Kindle formats. 

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.

Today on Software Sales Simplified: MOVE to Success, join us as Matt and Kevin and special guest Brandon Lopez, co-founder of Persimmon Marketing, a full-service marketing agency based in California, discuss challenges with Sales and Marketing alignment, the growing importance of AI in present-day marketing strategies, the importance of messaging alignment, and best practices for creating a successful Sales Kickoff. About Our Guest:Brandon Lopez is an entrepreneur, & Silicon Valley tech marketing executive with deep GTM expertise across startups, SMBs, and enterprises. Brandon has been a marketing leader at LinkedIn & Salesforce, where his team launched LinkedIn Sales Navigator and scaled it up from $0 to $100M in less than 3 years. He’s also the CMO & Co-Founder of MySideCar AI, a marketing strategy & execution platform.

Connect with Brandon on LinkedIn or visit www.persimmonmarketing.com to learn more.
About Software Sales Simplified: MOVE to Success

Visit us at: ⁠https://www.strategicsalesoptimization.com/⁠

Follow us on Linkedin: ⁠https://tinyurl.com/2tcx7mjx⁠

Send us your questions at ⁠[email protected]⁠

Get our Bestselling Sales Skills Book on Amazon!Order your own copy of the #1 Best Selling book on Amazon, "Winning Faster: The MOVE Framework for Enterprise Software Sales".  Available in paperback, PDF/eReader, and Kindle formats.  Get Yours Here:  https://www.strategicsalesoptimization.com/move-book

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.

Today on Software Sales Simplified: MOVE to Success join us as Matt and Kevin explore the MOTIVE step in their methodology and discuss practical tips sellers can use right now to better prepare for and plan a discovery meeting.  Using the Business Case as a blueprint, your hosts share their tactics for good information gathering, why the information is critical, and how it’s relevant for every step of the sales campaign going forward.

Visit us at: ⁠https://www.strategicsalesoptimization.com/⁠

Follow us on Linkedin: ⁠https://tinyurl.com/2tcx7mjx⁠

Send us your questions at ⁠[email protected]⁠

FYI - Order your own copy of the #1 Best Selling book on Amazon, "Winning Faster: The MOVE Framework for Enterprise Software Sales".  Available in paperback, PDF/eReader, and Kindle formats.  Note: The Kindle release does not require a Kindle device - just the free-to-download Kindle Reader app!Order on Amazon or from us:  https://www.strategicsalesoptimization.com/move-book

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 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.

Key Takeaways from Today's Episode: