Wrapbook

Director, Strategy & Operations

Wrapbook

full-time

Posted on:

Location Type: Remote

Location: United States

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Salary

💰 $164,000 - $263,800 per year

Job Level

Lead

About the role

  • 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
  • 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
  • Own Executive-Level Communications
  • Own Board, All Hands, Monthly State of the Business, and leadership offsite materials

Requirements

  • 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.
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 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
Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools
strategic planningoperational planningKPI managementprogram managementresource mappinggoal-setting frameworksinitiative sequencingAI applicationautomationperformance reviews
Soft Skills
leadershipstakeholder alignmentcross-functional collaborationdecision-makingcommunicationteam buildingrisk managementsynthesis of insightsclaritydecisiveness