SALES LEADER BREAKOUTS
June 9 1:15-1:45pm
From Trucks to Tech: How to Build Role-Aligned Sales Compensation Plans Across Transportation
Transportation & logistics includes dozens of unique selling motions, from truckload capacity and brokerage margins to SaaS subscriptions, marketing services, Freight Forwarding, and multi-year contracts for TM/warehouse operations. As individuals move between organizations, inappropriate cross-pollination of SIP architecture inevitably occurs.
This session breaks down why each sales motion requires distinct incentive design, driven by differences in value drivers, sales cycles, margin structures, customer ownership, and renewal/retention dynamics.
You'll learn the core principles for tailoring plans to:
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Asset/trucking sales (yield maximization, revenue-based)
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Brokerage (high-velocity, margin-based)
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3PL/FF (multimodal complexity, global reach)
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Marketing & services (deliverables, retainer models)
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Software/SaaS (recurring revenue, expansion, renewals)
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Long-term TM/warehouse contracts (consultative, RFP-driven, multi-year)
You’ll leave with a clear framework for evaluating any sales role in the T&L ecosystem and designing sales compensation that motivates the right behavior, drives profitability, and supports long-term customer relationships.
Beth Carroll
CEO, Prosperio Group
Beth is the CEO of Prosperio Group, a compensation development firm that focuses on the strategic management of compensation for global transportation & logistics companies. Beth has over 25 years’ experience developing incentive compensation plans for companies across the globe in a variety of industries. Beth has completed projects with more than 400 Transportation & Logistics companies, in a variety of sectors (asset, non-asset, asset light, etc).
June 9 2:00-2:45pm
Stop Managing Activity: Building a Sales Team That Actually Moves Deals
Most sales leaders aren’t struggling with effort. They’re struggling with consistency.
Some reps are closing. Others are busy but not progressing deals. The pipeline looks full, but it’s hard to know what’s real, what’s stuck, and where to step in.
This session focuses on how to create clarity across your sales team: what good looks like, how deals should move, and how to coach reps without micromanaging. We’ll explore how to use your existing tools and data more effectively, not just to track activity, but to improve performance and decision-making.
Expect practical conversation, real scenarios, and a working session that helps you get more from the team you already have.
Jason Reynolds
Chief Training Officer, Sandler by The Ruby Group
Jason Reynolds is the Chief Training Officer and Senior Partner at Sandler by The Ruby Group, where he works with leaders and sales teams to improve performance through practical, results-focused training and coaching. With a background in both sales and operations leadership, he brings a real-world perspective to how teams execute, manage pipelines, and drive revenue.
Meet the speaker
Beth Carroll
CEO, Prosperio Group
Beth is the CEO of Prosperio Group, a compensation development firm that focuses on the strategic management of compensation for global transportation & logistics companies. Beth has over 25 years’ experience developing incentive compensation plans for companies across the globe in a variety of industries. Beth has completed projects with more than 400 Transportation & Logistics companies, in a variety of sectors (asset, non-asset, asset light, etc).
Beth holds a BA from Bucknell University, an MA from The University of Chicago, an MBA from Northwestern University, and is a World at Work Certified Sales Compensation Professional.
Beth is the author of Taming the Compensation Monster: Using Freight Broker Compensation to Drive Urgency, Performance, and Profits which is available on Amazon in soft cover, audio and kindle editions.