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Chief of Staff to the CEO at Venture-Backed AI Startup

Big Wave Digital

Montreal, Quebec, Canada · Full Time

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Experience
3–10 yrs
Salary
USD 170,000 / year
Openings
1
Posted
2 weeks ago
Work mode
In office
Resume
Required to apply

Where you'll work

Job description

About the Company and Role

A rapidly expanding, venture-funded AI startup is seeking a Chief of Staff to work closely with the founder and CEO. The company is developing AI-driven software aimed at a well-established industry that has not yet been significantly served by current technology solutions. It is an early-stage enterprise with solid financial backing and growing market traction. The team is lean, driven, and advancing swiftly, providing a unique chance to join at an early phase and influence the foundation of commercial and operational functions.

Role Overview

This position transcends a typical administrative Chief of Staff role. The successful candidate will act as a versatile contributor, engaging in areas such as customer growth, partnerships, onboarding, go-to-market strategies, and key business ventures. Responsibilities include amplifying the CEO's capabilities, owning critical projects, and translating corporate strategy into practice. Daily tasks may vary from facilitating important client interactions to optimizing onboarding, crafting partnerships, testing growth avenues, or resolving operational challenges. This role has potential career progression into senior leadership roles in go-to-market, customer success, commercial operations, partnerships, or business operations.

Key Responsibilities

  • Assist in pre-sales and post-sales engagements with prospective and current customers.
  • Develop and maintain strong relationships with a variety of clients, from smaller companies to large enterprise clients.
  • Contribute to forming commercial strategies, refining customer messaging, and driving growth initiatives.
  • Represent the startup in customer meetings, industry gatherings, and strategic talks.
  • Build and enhance customer onboarding workflows to ensure quick realization of value for clients.
  • Identify and manage risks, resolve issues, and improve customer retention rates.
  • Create scalable customer success frameworks as the company expands.
  • Support and optimize growth channels including outbound sales, partnerships, events, marketing, and business development.
  • Analyze channel performance and prioritize resource allocation based on evidence and results.
  • Experiment with innovative ideas, refine successful tactics, and establish repeatable commercial processes.
  • Lead high-impact projects from initiation through to delivery.
  • Forge partnerships that accelerate revenue, distribution, or customer acquisition.
  • Collaborate across internal teams, investors, partners, and customers to ensure progress on key initiatives.
  • Serve as a trusted extension of the CEO, providing structure to undefined challenges and turning priorities into actionable plans.
  • Represent the CEO in selected engagements with customers, investors, and strategic partners.
  • Enable the CEO to concentrate on critical decisions and relationships that require their involvement.

Qualifications and Experience

  • Several years of experience in top-tier strategy consulting, investment banking, private equity, business operations, strategic or commercial roles in high-growth startups, or similar roles such as Chief of Staff or founder’s associate.
  • Prior startup experience is mandatory.
  • Strong analytical mindset and structured problem-solving capabilities.
  • Excellent communication skills, both verbal and written.
  • Comfortable engaging directly with clients and senior leaders.
  • Ability to balance strategic thinking with hands-on execution.
  • Strong commercial insight and instincts.
  • High degree of ownership and self-motivation.
  • Capable of operating without detailed procedural instructions.
  • Willingness to work on-site in San Francisco.
  • Technical, quantitative, or STEM academic background is highly regarded.
  • Must have valid authorization to work in the United States.

Desirable Background

  • Experience as Chief of Staff or in business operations.
  • Customer success background.
  • Knowledge of enterprise sales or pre-sales processes.
  • Expertise in customer onboarding and implementation.
  • Familiarity with go-to-market strategies and strategic partnerships.
  • Experience in startup operations.
  • Involvement in launching new products, markets, or commercial channels.

Personal Attributes

The ideal candidate is highly capable, commercially savvy, and proactive. They thrive on proximity to customers, founders, and critical business decisions. Comfortable navigating ambiguity, taking full ownership, and acting swiftly without perfect information, this individual focuses on results beyond job titles or rigid roles. The role offers significant responsibility and an exceptional chance to learn rapidly, collaborate directly with seasoned founders, and progress into meaningful leadership opportunities as the company expands.

Compensation and Benefits

  • Annual base salary up to $170,000.
  • Significant early-stage equity options.
  • Flexible balance between salary and equity for suitable candidates.
  • Health insurance and retirement benefit plans.
  • Paid time off.
  • Direct engagement with founders, investors, and the company-building process.

Why Participate?

This opening presents a chance to join a well-backed AI enterprise while the team size remains small enough for a standout individual to make a profound impact. The role includes shaping customer relationships, commercial strategies, operational systems, and future growth trajectories. For the right candidate, this opportunity extends beyond a Chief of Staff position, serving as a stepping-stone to become one of the company’s future senior leaders.

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