Sr. Director, Commercial Learning & Enablement

ABOUT THE JOB:

Lead WillScot’s commercial learning and seller enablement strategy to increase seller productivity, accelerate ramp time, and drive consistent adoption of sales standards and tools. This role sets the vision and roadmap for enablement, builds and leads high‑performing teams, and partners cross‑functionally to embed coaching, process, and go‑to‑market excellence across the sales organization.

WHAT YOU'LL BE DOING:

Key Responsibilities

1. Set the enterprise sales enablement strategy and roadmap aligned to WillScot’s growth priorities and go‑to‑market model.


2. Design and oversee role‑based learning programs that build selling, coaching, and account growth capabilities at scale.


3. Establish and embed sales coaching and operating standards across forecasting, pipeline management, account planning, and deal reviews.


4. Partner with Sales Leadership to improve seller productivity, ensuring enablement directly supports performance and execution.


5. Champion adoption of tools, playbooks, and processes that drive consistent selling behaviors and commercial discipline.


6. Define and measure  success through certification, adoption, ramp‑time, and productivity metrics, and refine programs based on data insights.


7. Lead change management for new GTM strategies and initiatives, ensuring readiness and sustained behavior change.


8. Lead and develop the commercial learning team, including trainers, instructional designers, and sales development coaches.


9. Align cross‑functionally with Sales, HR, Marketing, Product, and Enterprise teams to prioritize and scale enablement efforts.

Success Measures

• Improved seller productivity and revenue outcomes driven by consistent enablement and coaching.


• Reduced ramp time for new hires (time‑to‑productivity).


• High certification and adoption rates across sales roles for core competencies, tools, and playbooks.


• Strong, sustained engagement and satisfaction scores from sales teams and leadership.


• Demonstrated linkage between enablement initiatives and measurable business outcomes.

EDUCATION AND QUALIFICATIONS:

• 10+ years in leading Sales Enablement, Commercial Excellence, or Revenue Operations, including enterprise or multi‑branch sales environments.


• Proven experience building and leading enablement teams at scale.


• Strong foundation in coaching systems, sales process design, and change management.


• Ability to translate business strategy into practical, adoptable learning and execution standards.


• Executive presence with the ability to influence senior sales and enterprise leaders.