Director of Strategy & Operations, Wrapbook
$164-263.8k
US Salary is dependent on location. Canada rates: $164,000 - $223,500 (CAD)
Media production payroll & insurance solution
Be an early applicant
Media production payroll & insurance solution
201-500 employees
Be an early applicant
$164-263.8k
US Salary is dependent on location. Canada rates: $164,000 - $223,500 (CAD)
201-500 employees
Company mission
To make the lives of those working in production better.
Role
Who you are
- 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
- 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
- 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
What the job involves
- 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
- 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
- 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, 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 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
Our take
Payroll systems for the production industry are long outdated, with the vast majority of administration still being completed manually, in person, and on paper. This forces cast and crew members to loose many hours in unpaid work and drives up production costs.
Wrapbook's app helps cast and crew complete onboarding, submit timecards and track payments. It offers touch and face ID and helps users track various filings as they pass through the system. Its position as one of the country’s only entertainment-compliant companies of its kind has given it a strong head start in its field.
The company's product is used by well-known production companies such as CollegeHumor, Creative Blood and JN, and serves over 1,000 companies in total. The company has earned Unicorn status, and continues to enhance the capabilities of its payroll platform such as through the acquisition of scheduling platform Cinapse.
Kirsty
Company Specialist at Welcome to the Jungle
Insights
230% employee growth in 12 months
Company
Funding (last 2 of 4 rounds)
Sep 2024
$20m
LATE VC
Nov 2021
$100m
SERIES B
Total funding: $150.5m
Company benefits
- Health & Benefits - choose from several customizable plans, including vision and dental
- Minimum Time Off - Everyone is encouraged to take at least 3 weeks off annually
- 401K & RRSP
- Work Remotely
- IT Setup for Your Home
- Lifestyle Perks - Wrapbook employees get a monthly stipend to treat themselves
- Stock Options
- Parental Leave
Company HQ
Midtown Manhattan, New York, NY
Leadership
Cameron Woodward
(Co-founder)Director of Interactive Marketing at Invisible Children. Next, Co-founded and Executive produced Sprinkle Lab for 8 years. Went on to Found and serve as CEO of Film Casualty Insurance Agency.
Ali Javid
(CEO & Co-founder)Formerly VP of Business Development at Body Labs, Business Development Manager at Intel Corporation and Director of Strategy and Finance at WebTuner Corp.
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