Director, Chief of Staff
The Opportunity Wrapbook is looking for a Director, Chief of Staff to serve as a strategic partner to our CEO and Senior Leadership Team. This is a high-impact role for someone who wants to operate at the center of company strategy and execution. You'll help drive company priorities, lead critical cross-functional initiatives, and ensure our leadership team is aligned and moving quickly. We're looking for an operator - someone with strong business acumen who understands complex industries, builds strong points of view, turns ambiguity into clarity, and drives work forward.
What You'll Do
Be AI Native
- Use AI as a core operating tool - not a supplement.
- Own and evolve the CEO's AI-powered operating system.
- Build and maintain agentic workflows that extend the CEO's and SLT's leverage.
- Be a force multiplier for the company's AI adoption: model best practices, share what works, and help the broader organization develop fluency with AI tools and workflows.
- Stay on the frontier. Continuously evaluate new AI tools, techniques, and capabilities - and translate what's relevant into practical leverage for the CEO and leadership team.
Strategic Partner to the CEO
- Develop a deep understanding of Wrapbook's business, priorities, and operating model.
- Synthesize information from across the company, escalating the most urgent items to the CEO and creating clear recommendations.
- Help shape and clarify company-level strategy and priorities.
- Proactively identify risks, gaps, and opportunities.
- Leverage AI and emerging tools to increase executive and company-wide leverage - improving synthesis, decision-making speed, and operating efficiency.
Drive Cross-Functional Outcomes
- Own and lead high-priority, cross-functional initiatives from scoping through execution.
- Align stakeholders, clarify decision-making, remove blockers and ensure follow-through.
- Step into ambiguous areas and create structure where needed.
Improve How We Operate
- Own company-level planning and communication processes (annual planning, OKRs, MBRs, All Hands).
- Design and facilitate leadership meetings that drive clear decisions and accountability.
- Continuously improve operating rhythms and cross-team coordination.
What We're Looking For
- 7+ years of experience in a high-performance environment (consulting, banking, operating role, etc.).
- A systems-level thinker who leverages AI as a force multiplier in planning, analysis, and executive workflows.
- Demonstrated experience owning complex, cross-functional initiatives.
- Strong analytical skills and business judgment.
- Ability to form independent points of view and make clear recommendations.
- Excellent, executive-level written and verbal communication skills.
- High agency, curiosity, and a bias toward action.
- Comfort working directly with senior leaders and navigating ambiguity.
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! #LI-Remote Apply tot his job Apply To this Job