Fractional Chief Revenue Officer

A North American freight brokerage and transportation company, founded in 2019, is seeking a fractional Chief Revenue Officer to strengthen its commercial function and support a significant growth phase. The successful candidate will work directly with ownership and the sales team to assess current processes, introduce structure, improve execution, and build a culture of accountability. The role combines strategic oversight with hands-on involvement across sales, coaching, marketing, and organisational design.

A key priority is supporting the commercial launch of a proprietary Transportation Management System and client portal, which will allow customers to quote, book, and track shipments through a centralised platform. The CRO will help position the business as a technology-enabled logistics provider rather than a traditional freight broker, and will align go-to-market strategy, messaging, and sales capability accordingly.

• Assess and redesign the current sales organisation, processes, pipeline, and performance frameworks
• Develop and implement a structured, repeatable sales methodology covering the full sales cycle
• Coach sales representatives on prospecting, objection handling, negotiation, and closing
• Lead the go-to-market strategy for a new proprietary TMS and client portal
• Align B2B marketing and lead-generation efforts with sales priorities and target accounts
• Define sales roles, compensation structures, and performance-management frameworks to support growth

• Significant senior B2B sales leadership experience as a CRO, VP Sales, or Head of Sales
• Proven track record building or scaling sales organisations in growth-stage companies
• Strong CRM, forecasting, pipeline management, and sales reporting expertise
• Demonstrated ability to coach individual contributors and improve team-level performance
• Experience designing sales compensation, incentive structures, and organisational hierarchies
• Background in freight brokerage, 3PL, transportation technology, or B2B SaaS is a significant asset

3 Step Recruitment Inc. is a Canadian recruitment firm operating in the logistics and transportation sector. Based in the Kitchener-Waterloo region of Ontario, it supports companies in sourcing commercial and operational talent and connects the current mandate with a growing North American freight brokerage and logistics business.