Director, Commercial Success

The role

The Director, Commercial Success will own the Commercial Success function across Mid-Market and SMB. You will set strategy, lead a team of CSMs, and own outcomes for customer retention, net GPV growth, and NPS. You will also develop and implement AI-powered success models.

What you will do

• Set the Commercial Success strategy and 12–18 month plan for Mid-Market and SMB.
• Design the coverage model and capacity plan.
• Run the operating plan including quarterly plans, milestones, and forecasts.
• Own the AI strategy for Commercial Success to automate and augment work.
• Shape company decisions by bringing commercial segment context to leadership.
• Coach and develop the CSM team.
• Drive execution on retention and growth.
• Own executive escalations for key accounts.
• Model AI use by using Claude daily and building agents.
• Build relationships in person at customer offices, on set, and at industry events.

Required qualifications

• 10+ years in customer success, account management, or payroll operations.
• 5+ years leading customer-facing teams.
• Experience owning a customer segment or function end to end.
• Deep knowledge of the commercial production payroll industry.
• Track record of owning and improving retention, expansion, and NPS.
• Experience designing and leading both high-touch and scaled or digital customer success motions.
• Hands-on AI fluency including daily use of Claude or similar tools and building agents or workflow apps.
• Strong analytical skills with dashboards, health scores, and churn analysis.
• Credibility with customers and executives.
• Ability to influence cross-functional leaders without direct authority.

Benefits

• Unlimited Paid Time Off
• Work from anywhere in Canada and USA
• Health and Dental benefits
• Up to $1,500 USD/ $2,025 CAD towards IT set up for your home
• Up to 2% matching RRSP / 401K
• Learning and Development opportunities
• Up to $50 USD/ $67.50 CAD towards Internet/Cell phone service

About the company

Wrapbook is the AI platform for production finance. The team is building a system of action for finance teams to manage payroll, spend, and accounting for feature films, TV, and commercials.