#LivePricingCoachingWithMarkStiving: From 35% to 70% Win Rates, Mark Richman's Pricing Transformation

What happens when a former client returns for a live pricing coaching session?

Mark Richman, CEO of Skeleton Key, shares how applying Mark Stiving's value-selling principles helped increase his close rate from 35% to 70% by focusing on customer outcomes instead of pitching solutions.

Now, he returns to the hot seat to workshop his toughest pricing challenges in real time—from buyers who can't quantify value to outcome-based pricing and pricing for emotional outcomes.

This isn't another pricing interview; it's a front-row seat to a CEO getting his sales strategy challenged, refined, and rebuilt in real time.

Why You Have to Check Out Today's Podcast:

• Steal the framework that helped transform a 35% win rate into 70% — without changing his product.
• Find out why your prospects' "solution" is often the biggest obstacle to closing the deal.
• Watch Mark Stiving challenges Mark Richman's sales strategy and uncover the hidden pricing opportunities he almost missed.

"That willingness to not talk about what we do and that focus on why the client's there in the first place and how you can really help them achieve the outcome they want has transformed the way I sell. I went from about a 35% close rate to a 60 to 70% close rate."

— Mark Richman

Topics Covered:

01:30 – A Live Pricing Coaching Session Begins. Mark Richman returns to the hot seat as Mark Stiving coaches him through real pricing and sales challenges.

03:10 – Why Nobody Cares About Your Product. Mark Stiving explains why buyers purchase outcomes, while Richman shares how this mindset transformed his sales process.

05:15 – From 35% to 70% Win Rates. Mark Richman reveals the conversation shift that doubled his close rate, and Mark explains why it works.

08:45 – When Buyers Ask for the Wrong Solution. Mark Richman shares a real AI sales conversation, and Mark shows how to uncover the real problem instead.

16:20 – Pricing Emotional Outcomes. Can you charge for less stress and more time? Mark and Mark Richman debate when emotional value is enough.

19:15 – The Customers You Should Walk Away From. Mark explains why buyers who can't define success are often impossible to serve well.

27:40 – Finding the Right Pricing Metric. Mark shares alternatives to outcome pricing that let your revenue grow alongside your customers' success.

30:50 – The Pricing Opportunity Richman Almost Missed. A regulatory deadline becomes a lesson from Mark on willingness to pay and pricing confidence.

36:10 – The Biggest Lesson from the Coaching Session. Mark shares one pricing experiment every business should try, while Richman explains the sales lesson that changed everything.

Key Takeaways:

"You're not exploiting the customer by charging for value. The only question is whether the customer believes the price is fair." — Mark Stiving

"What matters isn't your hourly rate. What matters is whether it's a fair exchange for the value you're creating." — Mark Richman

"Raise your prices. Win fewer deals at higher prices and make more money." — Mark Stiving

"Helping clients uncover the value of solving the right problem changed everything about how I sell." — Mark Richman

Connect with Mark Richman:

• Website: https://skeletonkey.com
• Email: mark.richman@skeletonkey.com
• Linkedin: https://www.linkedin.com/in/markrichman/

Connect with Mark Stiving:

• LinkedIn: https://www.linkedin.com/in/stiving/
• Email: mark@impactpricing.com