Vice President, Sales

We are seeking a strategic, results‑driven VP, Sales to lead and align our Sales and Marketing functions under one cohesive revenue strategy. As a member of the executive team, the VP Sales will be responsible for driving consistent revenue growth, expanding market share, and ensuring long‑term customer satisfaction and retention within our existing clients. This player Coach role will provide focused leadership to a select team of professionals.

The ideal candidate brings a proven track record of growing revenue, building high‑performance go‑to‑market teams, and optimizing the full customer lifecycle—from lead generation and acquisition to onboarding, adoption, and retention.

This is a hybrid role, located in Toronto or Waterloo, Ontario.

The salary range is $160,000 to $200,000 annually.

• Own all aspects of revenue generation, including direct and broker sales.
• Develop and execute scalable sales strategies for acquiring new clients and growing existing clients.
• Build and manage a high‑performing sales team; establish clear KPIs, quotas, and incentive plans.
• Oversee pipeline management, sales forecasting, and performance analysis using Salesforce and BI tools.

• Collaborate with marketing teams on strategy, content, events and positioning.
• Align marketing activities with sales priorities and revenue goals.
• Oversee demand generation, lead nurturing, and brand positioning efforts.
• Monitor marketing performance metrics and continually refine campaigns based on data insights.

• Serve as a key member of the executive team, contributing to overall business strategy and planning.
• Foster alignment between Sales and Marketing to ensure a spectacular client experience.
• Identify growth opportunities through market trends, competitive intelligence, and emerging customer needs.
• Collaborate with the Operations and Tech teams to influence roadmap priorities based on customer feedback and market insights.

• 10 to 15 or more years of progressive commercial leadership experience, including direct accountability for Sales, Account Management, and/or Go‑to‑Market execution.
• Demonstrated success leading revenue‑generating teams in a B2B environment, with Insurance or financial services sector experience considered a strong asset.
• Bachelor’s degree in business Administration, Commerce, Marketing or related field. MBA or relevant graduate degree considered an asset.
• Proven track record of building and leading revenue‑generating teams.
• Experience selling into the Canadian property and casualty insurance community is a bonus.
• Strong analytical skills and fluency with CRM/Rev Ops tools (e.g., Salesforce, Linked In etc.)
• Excellent communication, leadership, and change management skills.
• Strategic thinker with the ability to translate market insights into execution plans.
• Passion for leading and developing people.
• Continuing education in sales leadership, commercial strategy, or related technical fields as required.
• Professional certifications (e.g., Sales Leadership, Rev Ops, Market related (Insurance) certifications) considered an asset

Why Crawford?

Because a claim is more than a number — it’s a person, a child, a friend. It’s anyone who looks to Crawford on their worst days. And by helping to restore their lives, we are helping to restore our community – one claim at a time.

At Crawford, employees are empowered to grow, emboldened to act and inspired to innovate. Our industry‑leading team pioneers new solutions for the industries and customers we serve. We’re looking for the next generation of leaders to take this journey with us.

We hail from more than 70 countries and speak dozens of languages, reflecting the global fabric of the audience we serve. Though our reach is vast, we proudly operate as One Crawford: united in purpose, vision and values. Learn more at

Our total compensation plans provide each of our employees with far more than just a great salary

Pay and incentive plans that recognize performance excellence

Benefit programs that empower financial, physical, and mental wellness

Training programs that promote continuous learning and career progression while enhancing job performance

Sustainability programs that give back to the communities in which we live and work

A culture of respect, collaboration, entrepreneurial spirit and inclusion

• Job Identification 3641
• Job Category Administration
• Posting Date 01/16/2026, 09:37 PM
• Job Schedule Full time
• Locations 2300 University Ave.
  
  E., Suite 200, Waterloo, ON, N2K 0A2, CA (Hybrid)