Director, Strategy & Operations

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 - Director, Strategy & Operations (Remote - USA / Canada) As the Director, Strategy & Operations, you are the execution engine and strategic operator for Client Operations. This is a genuine leadership role, not an advisory or support function. You will hold end-to-end ownership of how a 100+ person organization plans, executes, communicates, and continuously improves, translating the SVP’s strategic direction into disciplined, measurable execution at scale.Your mandate spans the full operational lifecycle of Client Operations — from multi-year strategy through annual planning, quarterly priorities, and weekly execution rhythms. You will serve as the connective tissue between the SVP, the Client Operations leadership team, and senior partners across Finance, Sales, Marketing, Product, and Engineering: strengthening structure, surfacing cross-functional dependencies, driving alignment, and ensuring the organization executes with clarity and velocity. You will serve as a proxy for the SVP when appropriate, influencing senior stakeholders without formal authority and representing Client Operations in cross-functional forums.You will also shape how the organization communicates as it scales- proactively drafting and socializing key materials ahead of formal announcements, ensuring leaders are aligned and prepared before a message lands broadly. Over time, you will build and lead a small Strategy & Operations team, developing direct reports to program management departmental and cross-functional work while you retain personal ownership of the highest-stakes work.This role is best suited for a proven Chief of Staff, senior Business Operations leader, or executive-level strategic operator who has moved beyond advising into genuine ownership — someone who translates ambiguity into structure, holds senior leaders accountable, and drives measurable outcomes at scale. Candidates with executive consulting backgrounds are welcome; however, this role requires deep operational ownership and a demonstrated ability to execute strategy sustainably.What you'll doOwn the End-to-End Planning EngineDesign and own the annual planning process: timeline, stakeholder alignment, trade-off structuring, resource mapping, goal-setting frameworks, and initiative sequencingBuild and run 6-month and multi-year planning cycles in close partnership with the SVPTranslate strategic direction into clear, actionable operating plans with accountability mechanisms and measurable milestonesPressure-test priorities and trade-offs across the leadership team, surfacing risks and driving decisionsCoordinate cross-functional planning inputs from Finance, Sales, Product, and EngineeringRun the Operating Cadence of Client OperationsDesign and drive weekly, monthly, and quarterly leadership rhythmsLead monthly KPI and performance reviews; elevate the quality, clarity, and decisiveness of all leadership forumsIdentify and prioritize opportunities to apply AI and automation to improve how Client Operations runs- from reducing manual work in reporting and communications to accelerating program executionEnsure disciplined follow-through on commitments across senior leadersAttend Client Operations leadership team staff meetings, representing the SVP’s perspective, identifying cross-functional dependencies and risks, and synthesizing insights into coordinated action plansContinuously assess and improve how Client Operations sets goals, measures performance, and executes at scaleBuild the Team and Drive Cross-Functional ProgramsBuild, develop, and direct a small team of Program Managers who lead and drive projects within Client Operations and across the Wrapbook organizationThis team will Program manage initiatives end-to-end: scoping, planning, stakeholder alignment, risk management, and outcomes measurementYou will retain personal ownership of the highest-stakes strategic work while directing the team on large operational programsOwn Executive-Level CommunicationsOwn Board, All Hands, Monthly State of the Business, and leadership offsite materialsProactively draft and socialize key communications to ensure leadership alignment ahead of broad announcementsPartner with SVP of Ops to drive the cascading communications motion across Client Operations — from CO SLT alignment, to StratOps and frontline leaders, through to ICs via their respective Slack channels — ensuring the right message reaches the right audience in the right sequenceWhat you'll have8–12+ years in strategy, business operations, executive operations, consulting, or operational leadership rolesPrior experience as a Chief of Staff, VP/Director of Business Operations, or senior strategic operator supporting an SVP, COO, or CEO in a complex organizationProven track record running annual and multi-year planning processes — including coordinating executive stakeholders, structuring trade-offs, aligning resources, and translating strategy into measurable operating plansExperience managing and developing direct reports; comfort hiring for, building, and leading small teamsTrack record of program managing large, cross-functional initiatives from ambiguity through sustained execution and measurable outcomesExperience operating in high-growth, cross-functional environments with executive visibilitySkills & CompetenciesStrong executive presence and the ability to influence senior stakeholders without direct authorityExceptional written and verbal communication skills, including executive-level narrative development and board-ready materialsStructural thinking — able to bring order to ambiguity and build systems that scaleHigh business judgment: able to distinguish what matters from what is merely urgent, and make sound trade-offs without perfect informationA bias toward action — equally comfortable shaping strategy and driving it to completionWhy Join UsAt 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 OffWork from anywhere in Canada and USAHealth and Dental benefitsUp to $1,500 USD/ $2,025 CAD towards IT set up for your homeUp to 2% matching RRSP / 401KLearning and Development opportunitiesUp to $50 USD/ $67.50 CAD towards Internet/Cell phone serviceOur 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 NowHave we got your attention? Submit your application today and a member of our Talent team will be in touch with you shortly!#LI-Remote

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