Chief of Staff to the CEO – Integrator

This is a fully remote position, open to applicants in Canada, +1 more country.

📋 Description

• Collaborate with the CEO to establish and monitor quarterly objectives.

• Maintain the Vision/Traction Organizer in alignment with the CEO.

• Serve as the CEO's thought partner and provide balance when necessary.

• Clarify trade-offs, resolve interdepartmental tensions, and unify the leadership team.

• Prepare the CEO for meetings with partners, negotiations, and decision-making processes.

• Oversee the operational aspects of customer and partner relationships.

• Monitor and fulfill commitments made to customers and partners.

• Transform customer and partner insights into organizational priorities and roadmap contributions.

• Translate these priorities into accountable owners, milestones, and outcomes across technology, product, and customer experience.

• Link technology, product, and leadership teams effectively.

• Ensure timely delivery of high-priority work that meets customer standards.

• Lead the EOS implementation as Integrator in collaboration with the CEO, who acts as Visionary.

• Facilitate the weekly Level 10 leadership meeting and take ownership of the company Scorecard.

• Develop a scalable operational model.

• Create self-improving AI loops across various functions.

• Integrate AI agents into Scorecards, Rock tracking, and meeting preparations.

• Establish a repeatable revenue channel through CRM and platform partnerships.

• Manage customer onboarding to ensure demonstrated value and successful reference outcomes.

• Maintain a cohesive product roadmap and predictable delivery schedule.

• Implement operational discipline for expansion across Canada and into the US.

⛳️ Requirements

• Previous experience as CEO, COO, CPO, general manager, or senior functional leader.

• Over 15 years of experience in the software industry.

• Proven history of scaling companies or substantial functions, particularly in founder-led, high-growth settings.

• Demonstrated capability to convert strategy into cross-functional execution while maintaining priorities with calm authority.

• Experience as a trusted advisor to founders; direct, candid, and committed to their success.

• Proficient in using AI agents; utilizes them daily, constructs workflows, and designs self-improving processes.

• Commercially astute and knowledgeable about products.

• Comfortable navigating revenue, partnerships, and customer success dynamics.

• Capable of engaging credibly with engineers on technical trade-offs.

• Experience in B2B SaaS or within the wellness, fitness, and health sectors is advantageous.

• Must be eligible to work remotely from Canada or the US.

🏝️ Benefits

• Equity incentive or equity stake commensurate with an executive role.

• Initially fractional, with a pathway to full-time employment.

• Fully remote positions available across Canada and the US.

• Direct, daily collaboration with the founder and involvement in every key decision.

• Access to an advisory board comprising exited founders and senior operators.

• Flexible engagement structure.

• Equal opportunity employer.

• Accommodations available upon request during the selection process.