Multi-Year Deals and the Illusion of Better Pricing | Russell Lester

In this episode of Mostly Growth, Kyle and CJ are joined by Russell Lester, President and CFO of Tropic, for a deep dive into what real procurement data reveals about SaaS pricing. They break down multiyear discounts, why volume matters more than contract length, how AI is reshaping pricing models, and when longer commitments actually hurt buyers. Plus, lessons on negotiation leverage, price increases, and navigating today’s increasingly complex SaaS market.

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SPONSORS:

HockeyStack is an AI platform for modern go-to-market teams that unifies sales, marketing, and customer data into a single system of action. With AI agents that prospect accounts, support reps, improve forecasting, and automate what’s already working, HockeyStack helps teams move faster without guessing. Trusted by companies like RingCentral, Outreach, ActiveCampaign, and Fortune 100 teams—learn more at https://www.hockeystack.com

RightRev is an automated revenue recognition platform built for modern pricing models like
usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale
monetization without slowing down close or compliance. For RevRec that keeps growth moving,
visit https://www.rightrev.com

Tropic is an intelligent spend management solution that consolidates your spend data and processes into one unified offering, enabling insights and decisive action. From spotting hidden optimization opportunities to automating painful procurement workflows and giving you the best market data to turn vendor negotiations in your favor, Tropic combines smart insights with real human expertise to keep you ahead of the curve. Visit https://www.tropicapp.io/mostlymetrics to learn how.

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LINKS:

Tropic: https://www.tropicapp.io/
Russell on LinkedIn:   / russell-lester-aa98463  

Mostly Metrics: https://www.mostlymetrics.com
CJ on LinkedIn:   / cj-gustafson-13140948  

Growth Unhinged: https://www.growthunhinged.com/
Kyle on LinkedIn:   / kyle-poyar  

Slacker Stuff: https://www.slackerstuff.com/
Ben on LinkedIn:   / slackerstuff  

https://www.mostlymetrics.com/p/your-...

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RELATED EPISODES:

Where Did All the Middle Managers Go?
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TIMESTAMPS:
00:00:00 Preview and Intro
00:01:12 Sponsors — HockeyStack | RightRev | Tropic
00:05:11 Welcome Russell Lester, Pricing and Discounting
00:06:41 Meeting Punctuality, Culture, and Waiting Rules
00:08:19 Transition to Multi-Year Discounts and Pricing Strategy
00:09:12 Procurement Data Insights: Volume Beats Term
00:10:00 AI Products, Risk, and Multi-Year Contract Tradeoffs
00:11:05 Multi-Year Discounting vs Negotiation Leverage
00:13:18 Lock-In Value and Avoiding Annual Price Uplifts
00:14:43 The “AI Tax” and Emerging AI Pricing Models
00:17:19 Why SaaS Pricing Data Is Messy and Context-Dependent
00:18:42 How Companies Actually Save Money on SaaS
00:20:40 Tropic as a Case Study in Pricing Model Evolution
00:22:28 Measuring ROI, Value Pricing, and Bundled AI Services
00:23:16 Cost Avoidance Pricing and Proving Real Savings
00:26:34 Buyer-First Marketplaces and Negotiating Objectivity
00:27:31 AI Pricing Complexity and Too Many Choices
00:29:47 Everyday Low Pricing vs Discount Theater
00:31:20 Pricing in the Real World: Credits and Audible
00:33:12 Expansion Revenue Through Gamified Consumption
00:34:15 Gartner’s “OaaS” Term and AI Category Confusion
00:35:07 CES Worst-in-Show and Gimmicky AI Products
00:36:23 LinkedIn Experts, AI Noise, and the Illusion of Insight
00:37:50 AI, Real Expertise, and Extracting Signal from People
00:38:48 Credits

#mostlygrowthpodcast #pricingstrategy #SaaSEconomics #AIPricing #gotomarket