Are you struggling with misaligned pricing strategies that leave money on the table? Many sales leaders find themselves caught between traditional seat-based models and what customers value. There's a better approach that can increase contract values by over 200% while simplifying your sales conversations.

In this episode, Keith Bossier, VP of Sales at SDOCS, shares how his team transformed their entire pricing strategy from user-based to consumption-based models. His insights reveal practical steps for aligning pricing with genuine business outcomes that customers care about most.

Keith breaks down the critical misalignments between marketing, sales, and customer success teams that drain revenue potential. He explains how removing traditional barriers—like eliminating SDRs entirely—can create more direct pathways to qualified prospects and accelerate deal cycles. Revenue Operations Framework for Growth

Keith discusses implementing a comprehensive revenue operations program that aligns teams around shared goals. He shares how they restructured customer success roles to function more like account managers with implementation responsibilities, creating new revenue streams from existing accounts.

The conversation explores building effective partner ecosystems without massive hiring sprees. Keith reveals how SDOCS signed over 50 new partners in 12 months by focusing on system integrators and technology partnerships that amplify reach efficiently.

Learning from Sales Failures

Keith opens up about a six-figure deal he lost early in his career—not because of product gaps, but because he failed to connect with the customer's real pain points. This experience shaped his entire approach to coaching sales teams, emphasizing empathy over feature presentations.

He shares practical techniques for handling rejection and building team resilience. His approach focuses on understanding why deals don't close rather than simply pushing through objections, creating stronger connections with prospects.

What You'll Learn:

● How to transition from seat-based to consumption-based pricing models ● Strategies for aligning marketing, sales, and customer success around revenue goals ● Methods for building partner ecosystems that expand reach without adding headcount ● Techniques for coaching teams to handle rejection and build resilience ● Why slowing down in discovery can actually accelerate your sales cycles

Keith's approach demonstrates that successful sales isn't about perfecting your pitch—it's about genuinely understanding what keeps your customers awake at night and positioning your solution as the bridge to their desired outcomes.

Key Moments of This Episode

00:01:46 - Introduction to Keith Bossier and SDOCSKeith Bossier, VP of Sales at SDOCS, introduces himself and explains how his company provides document automation and e-signature solutions that help businesses accelerate contract processes and revenue collection.

00:03:44 - Personal Journey: Overcoming Heart Surgery ChallengesKeith shares his inspiring personal story of surviving two open-heart surgeries and how he's thrived despite health challenges, even competing in triathlons and half-marathons.

00:06:28 - Pricing Strategies in Volatile Market ConditionsDiscussion of current economic uncertainty and how companies must adapt to pricing models. Keith explains the shift from user-based to consumption-based pricing at SDOCS, resulting in significant contract value increases.

00:13:43 - Aligning Marketing, Sales, and Customer Success TeamsKeith addresses common misalignments between departments and shares three key strategies: aligning revenue responsibilities, creating cross-functional accountability, and focusing on lead quality over quantity.

00:17:56 - Customer Success as Account Management with ImplementationExploration of how customer success teams can function more like account managers with revenue responsibilities, requiring sales-minded professionals rather than traditional support staff.

00:29:45 - Building Effective Partner Ecosystems for GrowthKeith discusses partner-led growth strategies, including working with system integrators and technology partners to expand reach efficiently without hiring additional full-time employees.

00:37:02 Learning from Sales Failures: The Power of EmpathyKeith shares a pivotal early career loss that taught him the importance of understanding customer pain points rather than just showcasing product features, shaping his coaching philosophy.

00:41:57 - Building Resilience: Handling Rejection in SalesStrategies for helping sales teams manage rejection, including debriefing losses, celebrating progress milestones, and maintaining emotional equilibrium through the ups and downs of sales cycles.

About Keith Bossier

Keith Bossier has 20 years of experience in driving revenue growth and optimizing sales operations with a proven track record in diverse industries, Keith has delivered exceptional results and provided unrivaled solutions to customers worldwide. His expertise spans from go-to-market strategy to revenue optimization and practical strategies for sales success. He has significant experience in SaaS sales, having held key roles at Salesforce, NetSuite, and FIS, and holds a B.A. from DePaul University as well as an M.B.A. from the Quinlan School of Business, Loyola University Chicago.

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