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 do

Own the End-to-End Planning Engine

• Design and own the annual planning process: timeline, stakeholder alignment, trade-off structuring, resource mapping, goal-setting frameworks, and initiative sequencing

• Build and run 6-month and multi-year planning cycles in close partnership with the SVP

• Translate strategic direction into clear, actionable operating plans with accountability mechanisms and measurable milestones

• Pressure-test priorities and trade-offs across the leadership team, surfacing risks and driving decisions

• Coordinate cross-functional planning inputs from Finance, Sales, Product, and Engineering

Run the Operating Cadence of Client Operations

• Design and drive weekly, monthly, and quarterly leadership rhythms

• Lead monthly KPI and performance reviews; elevate the quality, clarity, and decisiveness of all leadership forums

• Identify 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 execution

• Ensure disciplined follow-through on commitments across senior leaders

• Attend Client Operations leadership team staff meetings, representing the SVP’s perspective, identifying cross-functional dependencies and risks, and synthesizing insights into coordinated action plans

• Continuously assess and improve how Client Operations sets goals, measures performance, and executes at scale

Build the Team and Drive Cross-Functional Programs

• Build, develop, and direct a small team of Program Managers who lead and drive projects within Client Operations and across the Wrapbook organization

• This team will Program manage initiatives end-to-end: scoping, planning, stakeholder alignment, risk management, and outcomes measurement

• You will retain personal ownership of the highest-stakes strategic work while directing the team on large operational programs

Own Executive-Level Communications

• Own Board, All Hands, Monthly State of the Business, and leadership offsite materials

• Proactively draft and socialize key communications to ensure leadership alignment ahead of broad announcements

• Partner 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 sequence

What you'll have

• 8–12+ years in strategy, business operations, executive operations, consulting, or operational leadership roles

• Prior experience as a Chief of Staff, VP/Director of Business Operations, or senior strategic operator supporting an SVP, COO, or CEO in a complex organization

• Proven track record running annual and multi-year planning processes — including coordinating executive stakeholders, structuring trade-offs, aligning resources, and translating strategy into measurable operating plans

• Experience managing and developing direct reports; comfort hiring for, building, and leading small teams

• Track record of program managing large, cross-functional initiatives from ambiguity through sustained execution and measurable outcomes

• Experience operating in high-growth, cross-functional environments with executive visibility

Skills & Competencies

• Strong executive presence and the ability to influence senior stakeholders without direct authority

• Exceptional written and verbal communication skills, including executive-level narrative development and board-ready materials

• Structural thinking — able to bring order to ambiguity and build systems that scale

• High business judgment: able to distinguish what matters from what is merely urgent, and make sound trade-offs without perfect information

• A bias toward action — equally comfortable shaping strategy and driving it to completion

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!

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