Director, Strategy & Operations

Wrapbook, Inc.

Job Overview

Location

Remote

Job Type

Full-time

Full Job Description

📋 Description

• As the Director, Strategy & Operations at Wrapbook, you will serve as the execution engine and strategic operator for Client Operations, holding 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.
• You will design and own the annual planning process, build and run 6-month and multi-year planning cycles, translate strategic direction into clear, actionable operating plans with accountability mechanisms, pressure-test priorities across leadership, and coordinate cross-functional planning inputs from Finance, Sales, Product, and Engineering.
• You will run the operating cadence of Client Operations by designing and driving weekly, monthly, and quarterly leadership rhythms, leading monthly KPI and performance reviews, identifying opportunities to apply AI and automation to improve operations, ensuring disciplined follow-through on commitments, attending leadership team meetings to represent the SVP’s perspective, and continuously assessing and improving goal-setting, performance measurement, and execution at scale.
• You will build, develop, and direct a small team of Program Managers who lead and drive projects within Client Operations and across Wrapbook, retaining personal ownership of the highest-stakes strategic work while guiding the team on large operational programs, and you will own executive-level communications including Board, All Hands, Monthly State of the Business, and leadership offsite materials, proactively drafting and socializing key communications to ensure leadership alignment ahead of broad announcements.
• You will partner with the 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 Slack channels—ensuring the right message reaches the right audience in the right sequence, and over time, you will build and lead a small Strategy & Operations team, developing direct reports to program management departmental and cross-functional work while retaining ownership of the highest-stakes initiatives.
• This role is ideal 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, with experience in high-growth, cross-functional environments and executive visibility.

🎯 Requirements

• 8–12+ years of experience 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

🏖️ Benefits

• 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 setup for your home office
• Up to 2% matching RRSP / 401K
• Learning and Development opportunities
• Up to $50 USD / $67.50 CAD towards Internet/Cell phone service

Skills & Technologies

Remote

Ready to Apply?

Apply Externally

You will be redirected to an external site to apply.

Wrapbook, Inc.

Visit Website

About Wrapbook, Inc.

Wrapbook builds cloud-based payroll, onboarding, insurance and compliance software for the entertainment industry. The platform automates timecards, union reporting, tax withholding, residual payments and workers’ comp while providing digital start-work packets and e-signatures. Production accountants, studios, ad agencies and unions use the service to manage cast and crew across film, television, commercials and live events, integrating with accounting packages and banking APIs for real-time cost tracking.

View Company Profile

Get more remote jobs like this

Subscribe to the weekly newsletter for similar remote roles and curated hiring updates.

Weekly remote jobs and featured talent.

No spam. Only curated remote roles and product updates. You can unsubscribe anytime.