Director, Commercial Success

The Opportunity - Director, Commercial Success (Remote - Los Angeles, CA)

Our commercial customers are some of the most loyal in the business. We're hiring a Director, Commercial Success to keep it that way and grow the book of business.

We are looking for a Director, Commercial Success to own the Commercial Success function across Mid-Market and SMB. Reporting to the VP of Customer Success, you will set the strategy and own the outcomes that matter most for the commercial segment: customer retention, net gross payroll volume (GPV) growth, and customer satisfaction measured through NPS.

This is a hands-on Director role. You’ll own the function’s strategy, operating model, and plan, and you’ll lead the team directly: your CSMs report to you, and you’ll help a team with deep commercial payroll expertise become best-in-class customer success practitioners. Expect to split your time between setting direction for the function and coaching the team that delivers it. You’ll also own how we use AI across the segment: building a digital, AI-powered success model, and using AI to drive operational efficiency for the entire commercial team. The result is a more proactive team and a better experience for every customer, whatever their size.

This role is remote but must be based in the Los Angeles area. You’ll spend real time with customers in person, at their offices, on set, and at industry events, building relationships with the producers, executives, and decision makers who run commercial production.

What You’ll Do:

Own the Commercial Success function

• Set the strategy and define success. Own the Commercial Success vision and 12–18 month plan for Mid-Market and SMB, with clear targets for logo and revenue retention, net GPV growth (expansion and adoption), and NPS. Define success clearly enough that the team can execute without you in the room.

• Design the coverage model. Decide where high-touch engagement ends and a scaled, signal-driven model begins, where outreach, onboarding, and at-risk recovery are triggered by customer behavior, not inbound tickets, with people focused on the moments that need them. Own the capacity plan behind it.

• Run the operating plan. Turn Customer Success goals into quarterly plans with owners, milestones, and forecasts for renewals, retention, and GPV. Report performance to senior leadership through trends and risk signals, with a point of view on what to do next.

• Own the AI strategy for Commercial Success. Decide what to automate, what to augment, and how to resource it. Lead the AI-powered model for SMB and bring the same approach to Mid-Market so CSMs spend less time on manual work and more time with customers. Measure success by sustained usage and business impact, not by the number of tools launched.

• Shape company decisions for the commercial customer. Bring the commercial segment’s context into company and Client Ops planning. Build relationships with leaders across Sales, Product, Operations, AI Ops, and Finance so commercial customer needs shape decisions before they’re made. Co-own the motion with Sales leadership that turns growth signals in the SMB base into Mid-Market opportunities.

Lead the team

• Coach and develop the team directly. Your CSMs report to you. Set clear expectations, give regular feedback, and hold people accountable. Build on the team's commercial payroll expertise with the skills that make great advisors: strategic account planning, value conversations, renewal and expansion management, and executive engagement.

• Drive execution on retention and growth. Run the weekly operating rhythm across renewals, at-risk accounts, and expansion. Separate controllable from uncontrollable churn, catch risk early, and make sure success plans are in motion before customers stop running payroll. Coach the team through the hard calls rather than taking them over.

• Own executive escalations for key accounts. Be the escalation point for the commercial book’s most important customers. Turn what you learn from escalations, NPS, and customer feedback into specific changes in how the team engages, onboards, and escalates.

• Model AI use. Use Claude daily and build agents yourself, then teach the team to build their own. Hold the team accountable for using these tools to work more efficiently.

• Build relationships in person. Represent Wrapbook across the LA commercial production community, at customer offices, on set, and at industry events. Engage key decision makers, strengthen executive relationships, and model the relationship-building you expect from the team.

What You’ll Have:

• 10+ years in customer success, account management, or payroll operations, with 5+ years leading customer-facing teams.

• Experience owning a customer segment or function end to end: setting strategy, building the annual plan, and making the case for investment.

• Deep knowledge of the commercial production payroll industry: how production companies and payroll services work, union and non-union payroll, and the day-to-day workflows of producers and production accountants.

• A track record of owning and improving retention, expansion, and NPS, with the numbers to show it.

• Experience designing and leading both high-touch and scaled or digital customer success motions, including the coverage model that connects them.

• Strength as a hands-on coach who has developed subject matter experts into well-rounded CSMs and future leaders.

• Hands-on AI fluency: you use Claude (or similar tools) every day, have built skills, agents, or workflow apps that saved your team real time, and have led an AI-enabled change in how a team works. You know what to automate and what needs a person.

• Strong analytical skills: comfortable with dashboards, health scores, and churn analysis, and able to turn data into a plan.

• Credibility with customers and executives, a track record of presenting strategy to senior leadership, and the ability to influence cross-functional leaders without direct authority.

• Unlimited Paid Time Off

• Work from anywhere in Canada and USA

• Health and Dental benefits

• Up to 2% matching RRSP / 401K

• Learning and Development opportunities

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