Truckstop.com Promotes Three Leaders to Executive Roles to Accelerate Growth

The company’s new chief revenue officer, chief operating and strategy officer and general counsel bring years of institutional, customer-centric knowledge

BOISE, Idaho — Sept. 11, 2026— Today, Truckstop.com, an all-in-one freight platform connecting carriers and brokers across load matching, compliance and payments, promotes three of its longtime leaders into new executive roles to help sustainably scale the business. The company names Elyse Nagler, formerly vice president of sales, as chief revenue officer. Sean Dehan transitions from vice president of corporate strategy and development to chief operating and strategy officer. Lynsey Pickenpaugh’s role expands from head of legal to vice president and general counsel.

Elyse Nagler steps into chief revenue officer role

Nagler brings five years of sales leadership at Truckstop to the chief revenue officer role. Most recently, as VP of Sales, she led a strategic shift in selling motions that drove 19% YoY growth in customer bookings while delivering more value to new customers and improving retention. She’ll turn that momentum into strong, sustained growth.

Sean Dehan and Lynsey Pickenpaugh move into senior leadership

Both with Truckstop for four years, Dehan and Pickenpaugh have grown into senior leadership roles at the company. During that time, Dehan has led acquisitions, which have resulted in meaningful contribution to Truckstop’s success, including Denim which has produced 50% year-over-year growth while tripling operational efficiency for Truckstop’s fintech division. He’ll bring that same discipline to customer operations and strategy. Pickenpaugh led legal strategy on the Denim and Wize Load acquisitions, structuring and closing both, while building Truckstop’s governance, risk and AI compliance foundation. She’ll continue guiding the Board and executive team through the company’s next phase.

In his new role, Dehan will oversee customer operations and strategic initiatives alongside corporate strategy and development. Pickenpaugh will advise the Board and executive team on corporate governance and risk management and the product, operations and engineering departments on privacy, data protection and AI governance issues.

“Elyse, Sean and Lynsey truly understand Truckstop, our industry and our customers,” said Scott Moscrip, founder and CEO of Truckstop. “Time and again, they’ve used that knowledge to chart sustainable growth and provide a better experience for our customers. I can’t wait to see where they take Truckstop from here.”

A year of milestones and momentum

This announcement follows several milestones demonstrating Truckstop’s momentum and growth. These include completing two acquisitions, transportation-focused financial technology company Denim and heavy-haul rate intelligence provider Wize Load; Truckstop’s factoring platform, Truckstop Financial, crossing $3 billion in processed payments; and the completion of the 30 for 30 series, in which the company unveiled 30 product updates in a single calendar year.