Vice President, Sales
Top Benefits
About the role
Job Description 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.
Responsibilities Sales Leadership
- 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.
Marketing
- 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.
Strategic Leadership & Leadership Team
- 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.
Qualifications
- 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/RevOps tools (e.g., Salesforce, LinkedIn 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, RevOps, Market related (Insurance) certifications) considered an asset
About Us 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 www.crawco.com
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
About Crawford & Company (Canada) Inc.
Crawford Canada boasts an extensive team exceeding 1,000 professionals, including field adjusters, technical adjusters, contents specialists, repair estimate experts, lawyers, engineers and more. Operating from nearly 40 offices nationwide, our diverse and skilled workforce embodies depth and expertise. We work closely with our clients by partnering with them to develop solutions that are tailored to their business needs and focused on their success. Our comprehensive approach allows us to deliver unparalleled claims management solutions for any type of claim.
Crawford Canada s'enorgueillit d'une vaste équipe de plus de 1 000 professionnels, dont des experts en sinistres, des experts techniques, des spécialistes du contenu, des experts en devis de réparation, des avocats, des comptables, des ingénieurs et bien d'autres. Opérant à partir de près de 40 bureaux à l'échelle nationale, notre main-d'œuvre diversifiée et qualifiée incarne la profondeur et l'expertise. Nous travaillons en étroite collaboration avec nos clients en nous associant à eux pour développer des solutions adaptées à leurs besoins commerciaux et axées sur leur réussite. Notre approche globale nous permet d'offrir des solutions de gestion des sinistres inégalées, quel que soit le type de sinistre.
Vice President, Sales
Top Benefits
About the role
Job Description 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.
Responsibilities Sales Leadership
- 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.
Marketing
- 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.
Strategic Leadership & Leadership Team
- 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.
Qualifications
- 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/RevOps tools (e.g., Salesforce, LinkedIn 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, RevOps, Market related (Insurance) certifications) considered an asset
About Us 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 www.crawco.com
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
About Crawford & Company (Canada) Inc.
Crawford Canada boasts an extensive team exceeding 1,000 professionals, including field adjusters, technical adjusters, contents specialists, repair estimate experts, lawyers, engineers and more. Operating from nearly 40 offices nationwide, our diverse and skilled workforce embodies depth and expertise. We work closely with our clients by partnering with them to develop solutions that are tailored to their business needs and focused on their success. Our comprehensive approach allows us to deliver unparalleled claims management solutions for any type of claim.
Crawford Canada s'enorgueillit d'une vaste équipe de plus de 1 000 professionnels, dont des experts en sinistres, des experts techniques, des spécialistes du contenu, des experts en devis de réparation, des avocats, des comptables, des ingénieurs et bien d'autres. Opérant à partir de près de 40 bureaux à l'échelle nationale, notre main-d'œuvre diversifiée et qualifiée incarne la profondeur et l'expertise. Nous travaillons en étroite collaboration avec nos clients en nous associant à eux pour développer des solutions adaptées à leurs besoins commerciaux et axées sur leur réussite. Notre approche globale nous permet d'offrir des solutions de gestion des sinistres inégalées, quel que soit le type de sinistre.