Jobs to Be Done: The Pricing Strategy That Pays Off Big with Bill Wilson

Ian Clark runs Crescendo Consulting, helping companies monetize AI features. He's advised leadership teams on packaging, pricing metrics, and outcome-based models. And of course, he performed his obligatory stint at Simon Kutcher Partners. In this episode, Ian challenges common misconceptions about AI pricing, explaining why cost-plus pricing is still wrong even with variable AI costs, how to choose the right pricing metrics beyond tokens, and why outcome-based pricing isn't the silver bullet many believe it to be.   Why you have to check out today's podcast:  Understand why AI costs shouldn't drive your pricing strategy, even when margins drop below traditional SaaS levels.  Learn how to identify pricing metrics that correlate with willingness to pay rather than falling into the token-based pricing trap. Discover why outcome-based pricing for AI faces fundamental attribution problems that make it less viable than expected.   "The best way to get willingness-to-pay data and to understand where the value of your product comes from is by doing customer interviews, not the testing, not the data, customer interviews."  – Ian Clark   Topics Covered: 02:59 - Monetizing AI vs. SaaS. The surprising similarities between AI and SaaS pricing, and why cost-plus pricing remains a bad idea even with AI's variable costs. 05:17 - Pricing Strategy in AI.The gross margin threshold where revenue-optimizing and margin-optimizing prices diverge (50-60%), plus the potato chip pricing thought experiment. 09:35 - AI Pricing Strategies.Why token-based pricing is problematic and how to find the right pricing metric that correlates with willingness to pay. 12:24 - Pricing Strategies for AI Tools.Real-world case study of sales enablement AI: choosing between user-based vs. usage-based pricing based on wallet size indicators. 16:27 - Outcomes-based Pricing Skepticism.The attribution problem with outcomes-based pricing and why it's harder to implement than it appears, using grocery shrinkage AI as an example. 20:11 - Outcome-based Pricing for AI. Sierra's "resolved conversations" model critique and the ethics of incentivizing AI agents vs. human labor. 24:03 - Pricing and Value Creation.The three-layer value framework: actual economic value → perceived value → willingness to pay, accounting for risk, timing, and budget constraints. 26:39 - 10% Rule in Pricing Strategy.Debunking the "charge 10% of value created" rule with Y Combinator math showing how small variations (9X vs 11X) can dramatically impact company survival. 30:31 - Customer Interviews for Pricing Insights.Why customer interviews beat data analysis and A/B testing for understanding willingness to pay and pain points.   Key Takeaways: "We have known for a very long time that cost-plus pricing is a really bad idea. And it's not the case that now suddenly that we have AI, now suddenly it's a good idea." - Ian Clark "So the 10x rule, it's great, but it's just woefully insufficient. Why not 11x? Why not 9x? You actually don't know." - Ian Clark "One thing that we like to say about pricing and monetization is that people think it's like architecture, but it really should be like gardening." - Ian Clark   People / Resources Mentioned: Simon Kutcher Partners: https://www.simon-kucher.com/en Alpine Investors: https://alpineinvestors.com/ James Wilton: https://www.linkedin.com/in/jamesdwilton/ Sierra: https://sierra.ai/ Fin AI: https://fin.ai/ Y Combinator: https://www.ycombinator.com/ McKinsey: https://www.mckinsey.com/   Connect with Ian Clark: Website: https://crescendo.consulting LinkedIn: https://www.linkedin.com/in/ian-harrison-clark/ Email: ian@crescendo.consulting   Connect with Mark Stiving: LinkedIn: https://www.linkedin.com/in/stiving/ Email: mark@impactpricing.com

22 Sep 32min

This is an Impact Pricing Blog published on July 21, 2025, turned into an audio podcast so you can listen on the go. Read Full Article Here: https://impactpricing.com/blog/why-empathy-is-your-most-underrated-pricing-tool/ If you have any feedback, definitely send it. You can reach us at mark@impactpricing.com.  Now, go make an impact.   Connect with Mark Stiving: Email: mark@impactpricing.com LinkedIn: https://www.linkedin.com/in/stiving/

19 Sep 5min

Ton Dobbe is the founder of Value Inspiration, helping SaaS companies transform from commoditized to remarkable. He's the author of The Remarkable Effect, where he explores what makes products stand out and command premium prices. And he's a keynote speaker and podcast host himself. In this episode, Ton shares his insights on how SaaS companies can escape the commodity trap and command premium pricing by focusing on their unique approach to solving customer problems, rather than just features and functions.   Why you have to check out today's podcast: Learn how to identify and articulate the real problems your customers face that keep them awake at night. Discover why competing on your approach rather than features is the key to premium pricing. Understand how guarantees and risk reduction can justify higher prices and improve your entire business operation.   "Start thinking about what you do and why customers would pay a premium for that. And if you cannot answer that, there's work to do. It's a very simple question. What would it take for people to start paying a premium for it?" – Ton Dobbe   Topics Covered: 02:37 – Startup failure and value proposition: Why 75% of software scalers fail despite achieving product-market fit and how the inability to market at appropriate value becomes their downfall  04:07 – Value is a story: Ton's definition of value as "a story in the head of a customer" versus Mark's "result of solving problems" and how perception drives pricing acceptance  09:28 – Value pricing and guarantees: How adding guarantees reduces customer fear of making mistakes and enables premium pricing, plus the psychology behind buyer decision-making 12:33 – Guaranteeing results for customers: The insurance model approach to guarantees and how implementation success creates win-win scenarios for both vendor and customer 15:28 – Competing on approach, not features: Why software companies must differentiate based on their unique approach to solving problems rather than feature comparisons with competitors  19:09 – Secret sauce for ideal customers: Ton's 12-step "pressure cooker" process for identifying your value foundation and connecting company knowledge to customer segments  22:11 – Ideal customer segmentation benefits: How focusing on perfect-fit customers accelerates sales cycles, increases win rates, stops discounting, and improves every business function  27:59 – The value of AI solutions: Why companies fail when they position themselves as "AI-powered" instead of focusing on the specific problems their AI capabilities solve 30:39 – Premium pricing strategies: The fundamental question every company must answer - why would customers pay a premium for what you do, and what would it take to achieve that?   Key Takeaways: "Value is a story in the head of a customer. When I say to you, for example, this is 30,000 US dollars. Some people will say, that's expensive. And other people will say, that's a bargain. And the difference is how well you communicate the value in a way that clicks with them." – Ton Dobbe "The moment you can add something like a guarantee or like a reliable promise to that, you can even charge more on pricing because it takes a lot of objections away around the fear of messing up." – Ton Dobbe "If you compete on a feature function level, everybody will lose. So you have to make a choice, are we going to compete on the feature function level or are we going to compete on something else?" – Ton Dobbe "The moment you get that idea in their head, this is the choice and they're gonna solve my problem better than anyone else. They're gonna give me more value than anyone else. Well, why should I even start talking about discounts?" – Ton Dobbe   People / Resources Mentioned: The Jolt Effect (book on buyer indecision) Christian Owens, CEO of Paddle   Connect with Ton Dobbe: Website: https://valueinspiration.com Book: https://theremarkableeffect.com LinkedIn: https://www.linkedin.com/in/tondobbe/    Connect with Mark Stiving: LinkedIn: https://www.linkedin.com/in/stiving/ Email: mark@impactpricing.com

15 Sep 33min

This is an Impact Pricing Blog published on July 14, 2025, turned into an audio podcast so you can listen on the go. Read Full Article Here: https://impactpricing.com/blog/two-buyers-talked-and-nothing-bad-happened/ If you have any feedback, definitely send it. You can reach us at mark@impactpricing.com.  Now, go make an impact.   Connect with Mark Stiving: Email: mark@impactpricing.com LinkedIn: https://www.linkedin.com/in/stiving/

12 Sep 4min

Scott Kelly is the founder and CEO of Blackdog Venture Partners, and he has been for 25 years. He's the host of VC Fast Pitch and he has about a dozen companies with the name Blackdog in them. Scott has taken 3 companies public and raised $5 billion throughout his career. In this episode, Scott explains how important it is for entrepreneurs to listen to their customers when setting prices, as he shares his knowledge on maximizing profits through effective pricing strategies that investors love.   Why you have to check out today's podcast: Learn how crucial recurring revenue models are to attracting investors and why subscription-based pricing provides the consistency they seek.  Find out why selling on price alone is bad for both sides of the transaction and how to focus on value instead.  Understand the power of letting your customers help you determine pricing through relationship-building rather than transactions.   "Let your customers help you price." – Scott Kelly   Topics Covered: 02:00 – How Scott accidentally discovered pricing through helping hundreds of entrepreneurs raise capital and maximize profits  03:00 – Why competing on lowest price destroys value for both buyer and seller - and what to do instead  05:00 – AI's double impact on pricing: Using it for better decisions vs. pricing AI-enabled products  06:00 – The carpenter analogy: Why AI is just a tool and the real value comes from expertise in wielding it  07:00 – How AI will democratize business like the internet did - and what that means for pricing 09:00 – The art of determining "what the market will bear" through customer relationships and feedback  12:00 – Why Scott brings up pricing "almost immediately" with entrepreneurs (and why you should too)  14:00 – Finding the pricing "strike zone" - where customers won't jump for joy but won't run out the door  15:00 – The relationship vs. transaction mindset: How to get customers to help set your prices  17:00 – Scott's final wisdom: Let your customers help you price - the ultimate customer-centric approach   Key Takeaways: "At the end of the day, you want to provide enough value so they stick around at a price that can keep you sticking around." – Scott Kelly "AI is a tool. You need to make sure you have the right carpenter or the right instrument and the right professional playing that instrument. So I think how you price that is the value add that you bring to this tool that's AI." – Scott Kelly "You have to spend time getting to know them. I think it's a process of establishing a relationship versus a transaction." – Scott Kelly   People / Resources Mentioned: VC Fast Pitch: https://vcfastpitch.com/    Connect with Scott Kelly: Website: https://blackdogventurepartners.com/   LinkedIn: https://www.linkedin.com/in/blackdogceo/    Connect with Mark Stiving:  LinkedIn: https://www.linkedin.com/in/stiving/  Email: mailto:mark@impactpricing.com

8 Sep 18min

This is an Impact Pricing Blog published on June 30, 2025, turned into an audio podcast so you can listen on the go. Read Full Article Here: https://impactpricing.com/blog/everyones-talking-about-ai-almost-nobodys-using-it/ If you have any feedback, definitely send it. You can reach us at mark@impactpricing.com.  Now, go make an impact.   Connect with Mark Stiving: Email: mark@impactpricing.com LinkedIn: https://www.linkedin.com/in/stiving/

5 Sep 4min

Bryan Phelps is the founder and CEO of Big Leap, a digital marketing agency he's been running for 17 years. He's been working in digital marketing and SEO since college and recently served as a juror in a murder trial (though we don't discuss that). Bryan specializes in helping B2B tech companies and professional services firms navigate the evolving landscape of AI-powered search and discovery. In this episode, Bryan reveals how AI is fundamentally changing SEO and digital marketing, why traditional performance marketing tactics are becoming less effective, and how companies can build "brand-led performance marketing" strategies that work across Google, AI platforms, and future technologies.   Why you have to check out today's podcast:  Learn the key differences between B2B and B2C buyer behavior in the age of AI search.  Discover the three pillars of AI SEO and how they relate to traditional search optimization. Understand why building relationships with the 95% of non-shopping audiences creates pricing power.   "A lot of value is created before you ever start a pricing conversation. So that's how we're trying to help our clients shift a bit is, not just focus on that 5% of people that are in market and then compete on price."  – Bryan Phelps   Topics Covered: 01:40 – B2B vs B2C SEO differences: How buyer journeys vary from research-heavy B2B to purchase-ready B2C audiences  04:08 – AI SEO and discoverability strategies: Understanding where audiences search and optimizing for multiple platforms beyond Google  07:44 – AI recommendations and SEO strategy overlap: How AI's "query fan out" method connects Google rankings to AI search results  12:18 – Brand element and popularity component: Why being recognized as an industry authority matters more than broad household recognition  15:05 – Brand-led performance marketing shift: Moving from link-based to mention-based strategies in the post-tracking world  18:45 – Brand ideology and differentiation process: How to define unique viewpoints and align with genuine audience connections  20:22 – AI's impact on content creation: Why long-tail content is losing value and expertise-based content is gaining importance  25:56 – Pricing advice for businesses: Building value with non-shopping audiences to reduce price sensitivity and competition  27:02 – Staying informed in marketing: Bryan's LinkedIn newsletter for non-marketers navigating industry changes   Key Takeaways: "The exciting thing for us is I think it's kind of going back to almost like pre Google. So it really is more of a brand marketing function in a lot of ways." – Bryan Phelps "Being known to your audience is ultimately what matters. You don't have to be the household name, necessarily, but if your audience is just a little bit more niche and specific, you can be the brand in their world." – Bryan Phelps "Our goal isn't to take any company and just try to cover the broadest of brands... we're trying to ultimately create a brand that aligns with our ideal client." – Bryan Phelps "Our goal is to help brands be remembered, not just discovered." – Bryan Phelps   Resources and People Mentioned: Big Leap Digital Marketing Agency: https://bigleap.com  Kobe Bush: Team member who coined "people notice different" concept  Query Fan Out: AI method of breaking prompts into multiple searches  Brand Ideology Process: Big Leap's framework for unique positioning  Zero Click Marketing: New measurement paradigm for AI-driven discovery   Connect with Bryan Phelps: LinkedIn: https://www.linkedin.com/in/bryanphelps/ Website: https://bigleap.com   Connect with Mark Stiving: LinkedIn: https://www.linkedin.com/in/stiving/  Email: mark@impactpricing.com

1 Sep 27min

This is an Impact Pricing Blog published on June 30, 2025, turned into an audio podcast so you can listen on the go. Read Full Article Here: https://impactpricing.com/blog/product-market-fit-is-overrated-for-pricing/ If you have any feedback, definitely send it. You can reach us at mark@impactpricing.com.  Now, go make an impact.   Connect with Mark Stiving: Email: mark@impactpricing.com LinkedIn: https://www.linkedin.com/in/stiving/

29 Aug 5min