About Us:
Wrapbook is a smart, intuitive platform that makes production payroll and accounting easier, faster, and more secure. We provide a unified payroll platform that seamlessly connects your entire team—production, accounting, cast, and crew—all in one place. Wrapbook empowers production teams to manage projects, pay cast and crew, track expenses, and generate data-driven insights, while enabling workers to manage timecards, track pay, and onboard to new projects from any device. Wrapbook brings clarity and dependability to production payroll, while increasing the productivity of your whole team.
Trusted by companies of all sizes, Wrapbook powers payroll for some of the industry’s top production companies, including SMUGGLER, Tuff, and GhostRobot. Our growing team of 250+ people across the USA and Canada, including entertainment and technology experts from SAG-AFTRA, DGA, IATSE, Teamsters, Amazon, Microsoft, Facebook, and more. Wrapbook is backed by top-tier investors, including Jeffrey Katzenberg’s WndrCo, Andreessen Horowitz, and A* Capital. We have raised $130M and are in a strong financial position.
The Opportunity
Wrapbook is looking for a Director, Chief of Staff to serve as a strategic partner to our CEO and Senior Leadership Team.
This is a high-impact role for someone who wants to operate at the center of company strategy and execution. You’ll help drive company priorities, lead critical cross-functional initiatives, and ensure our leadership team is aligned and moving quickly.
We’re looking for an operator — someone with strong business acumen who understands complex industries, builds strong points of view, turns ambiguity into clarity, and drives work forward.
What You’ll Do
Be AI NativeUse AI as a core operating tool — not a supplement.
Own and evolve the CEO's AI-powered operating system.
Build and maintain agentic workflows that extend the CEO's and SLT's leverage.
Be a force multiplier for the company's AI adoption: model best practices, share what works, and help the broader organization develop fluency with AI tools and workflows.
Stay on the frontier. Continuously evaluate new AI tools, techniques, and capabilities — and translate what's relevant into practical leverage for the CEO and leadership team.
Develop a deep understanding of Wrapbook’s business, priorities, and operating model.
Synthesize information from across the company, escalating the most urgent items to the CEO and creating clear recommendations.
Help shape and clarify company-level strategy and priorities.
Proactively identify risks, gaps, and opportunities.
Leverage AI and emerging tools to increase executive and company-wide leverage - improving synthesis, decision-making speed, and operating efficiency.
Own and lead high-priority, cross-functional initiatives from scoping through execution.
Align stakeholders, clarify decision-making, remove blockers and ensure follow-through.
Step into ambiguous areas and create structure where needed.
Own company-level planning and communication processes (annual planning, OKRs, MBRs, All Hands).
Design and facilitate leadership meetings that drive clear decisions and accountability.
Continuously improve operating rhythms and cross-team coordination.
What We’re Looking For
7+ years of experience in a high-performance environment (consulting, banking, operating role, etc.).
A systems-level thinker who leverages AI as a force multiplier in planning, analysis, and executive workflows.
Demonstrated experience owning complex, cross-functional initiatives.
Strong analytical skills and business judgment.
Ability to form independent points of view and make clear recommendations.
Excellent, executive-level written and verbal communication skills.
High agency, curiosity, and a bias toward action.
Comfort working directly with senior leaders and navigating ambiguity.
Why Join Us
At Wrapbook, creativity meets technology — and not just in the product.
In addition to a competitive salary and all the benefits you can expect from a fast-growing technology company, you’ll get access to a team of creative problem solvers and the chance to see your contributions make large impacts. Benefits include:
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
Our Pledge to Fostering an Inclusive and Safe Workplace:
Wrapbook pledges to be a harassment- and discrimination-free space for everyone, regardless of age, disability, ethnicity, gender identity or expression, nationality, neurotype, personal appearance, political affiliation, professional background, race, religion, or sexual identity or orientation.
Apply Now
Have we got your attention? Submit your application today and a member of our Talent team will be in touch with you shortly!
#LI-Remote
Top Skills
What We Do
Employers in media production and the entertainment industry are constantly hiring. Freelance employees move between projects and could get onboarded 30 or more times in a single year. And yet, much of the industry uses physical paperwork with no easy way to track payments, often struggling with compliance (due to ever-changing laws and union rules), and has few automation processes in place when it comes time to send payroll reports to their accountants. Wrapbook is an intuitive payroll and insurance solution for those balancing multiple projects. With digital solutions, simplified compliance, and comprehensive reporting, we take the stress away so employers and project-based workers can focus on the big picture. Commercial producers, filmmakers, and anyone creating media deserve robust solutions to meet their unique demands. With Wrapbook, you only have to ask for documents from cast and crew once. Our platform lets you move all the onboarding forms associated with any crew from a project to any future ones, giving you back hours. By swapping out paper timecards with digital ones, approving payroll is now a piece of cake. Crew can log into Wrapbook from any device to enter their hours and expenses. Providing producers with the right tools to onboard crew and process payments helps them put routine work on auto-pilot. That way, they can focus on more compelling tasks. Let us tackle paperwork, payroll, and insurance, so you can continue creating the work that matters.
