Chief of Staff to the CEO

Chief of Staff to the CEO - Montreal, Canada Montreal, Canada About Human Agency We're scaling rapidly and have a growing pipeline of opportunities that demand exceptional talent across disciplines. Our mission is to bring on individuals, from creative producers to technical experts to entrepreneurial leaders, who can help us realize this next chapter of growth. We are a company of doers. Leaders roll up their sleeves, teams work flat, and everyone contributes to what ships. Titles don't insulate us from feedback or basics. We invite critique, learn quickly, and keep raising the bar. The best ideas win here, no matter where they come from, because clients trust us to deliver the strongest outcomes every time. Our clients' missions, products, and bottom lines are sacred. We immerse ourselves in their world, becoming stewards of their goals and partners in solving big problems. Every product, strategy, or asset we create must be both beautiful and functional; practical, usable, and designed for real-world impact. Humans are our most valuable resource, and we only grow by hiring people who push us forward. Across strategy, engineering, design, data, and operations, we seek out teammates who raise the bar and make us better. Always hire up, never down. We partner with organizations of all sizes to explore, design, and implement AI strategies that are secure, scalable, and human-centered. We believe AI should amplify human potential, not replace it and we build with that conviction in every engagement. From advisory and tooling to implementation and education, we meet clients where they are and help them integrate AI in ways that align with their mission and values. Our goal is to empower teams to work smarter, move faster, and unlock new possibilities through thoughtful, responsible innovation. And through it all, we lead with purpose, love, and adventure. We do meaningful work with people we care about, and we make the ride an adventure worth taking. Because at Human Agency, who we are and how we work are one and the same. The Opportunity We are seeking an exceptional Chief of Staff to serve as a force‑multiplier to our CEO, Caroline Hoogland. Sitting within our Creative Services team, you will be tapped for both internal and external work with clients. Rather than being hired for a predetermined set of tasks, you will be brought on to solve complex, evolving challenges. Success in this role requires self‑direction, proactive value creation, and the ability to thrive without constant oversight. Over the coming year, your responsibilities will be tailored to both organizational needs and your individual strengths, potentially including: Supporting marketing strategy at client organizations Managing CEOs at client organizations Leading communications, PR, brand building, or content strategy Leading fundraising efforts for funds or clients Driving sales initiatives at Human Agency You’ll own special projects, drive organizational initiatives from concept to completion, and build the infrastructure that allows Human Agency to grow sustainably. If you thrive on turning ambitious ideas into reality and building the scaffolding that makes a fast‑growing startup actually work, this is your role. Key Responsibilities Strategic Execution & CEO Partnership Partner with the CEO to translate initiatives and special projects into sequenced plans with clear owners, timelines, and success metrics Own end‑to‑end execution of CEO‑level special projects and organizational initiatives, from scoping and planning through delivery and measurement Maintain focus and accountability across the CEO's portfolio of priorities; proactively identify conflicts, dependencies, and risks before they become problems Produce high‑quality executive materials (strategy briefs, decision memos, board materials, organizational roadmaps) that drive alignment and enable confident decision‑making Serve as a strategic thought partner to the CEO, pressure‑testing ideas, surfacing options and trade‑offs, and ensuring initiatives align with company strategy and capacity Internal Systems & Operations Build and continuously improve the internal operating systems that allow Human Agency to scale: hiring infrastructure, resource allocation processes, team capacity planning, and cross‑functional coordination mechanisms Design and implement hiring systems that support our 25‑30+ person growth target in 2026 without overwhelming the existing team, including interview frameworks, candidate evaluation rubrics, and onboarding processes Own resource allocation and capacity planning across the organization—ensuring the right people are working on the right priorities at the right time, and that key team members aren't stretched unsustainably thin Establish organizational rhythms that create alignment without bureaucracy: leadership meeting cadences, decision‑making frameworks, communication protocols, and reporting structures Identify operational bottlenecks and inefficiencies; design and implement solutions that increase organizational velocity while maintaining quality Cross‑Functional Leadership & Coordination Orchestrate complex, cross‑functional initiatives that require coordination across leadership and multiple teams Manage staffing assignments and contributions across concurrent workstreams; keep tools current (Asana/Notion, Google Workspace, Slack) Serve as a neutral coordinator and problem‑solver when initiatives span multiple departments or require difficult trade‑offs between competing priorities Represent the CEO's office in key internal discussions, ensuring the CEO's priorities and perspective are understood even when they can't be in every meeting Build strong working relationships across the organization; earn trust as someone who gets things done without ego and acts in the company's best interest Establish shared dashboards for organizational health (timeline, risk, capacity, dependency status) and run tight meeting cadences Communications & Organizational Transparency Prepare agendas, briefings, and executive‑ready presentations; synthesize complex information into actionable insights Ensure crisp internal communication on company strategy, priorities, and decisions, translating CEO‑level thinking into clear, actionable guidance for the broader team Prepare the CEO for key meetings, presentations, and decisions; provide relevant context, background materials, and recommended talking points Provide clear, timely reporting to the CEO and stakeholders on progress, risks, and decisions Maintain visibility on organizational health metrics and key initiatives; proactively surface issues and opportunities to leadership Who You Are Experience & Skills 5‑7+ years in high‑performing environments such as Chief of Staff roles, strategic operations, management consulting, venture capital/private equity, or startup leadership positions Demonstrated success taking ambiguous, complex initiatives and driving them to completion—you're the person who makes hard things happen Strong systems thinking and process design capability—you don't just execute tasks, you build the infrastructure that makes future execution easier and more scalable Exceptional project management and coordination skills across multiple concurrent workstreams with competing priorities and timelines High proficiency with modern collaboration tools (Google Workspace, Asana/Notion, Slack) and comfort with AI‑powered productivity tools Outstanding written and verbal communication—you can synthesize complex information into clear, actionable briefs for different audiences Bonus: Experience in high‑growth startups, venture studios, or AI/tech companies; background in talent operations or organizational design; exposure to board‑level strategy and operations Mission‑driven operator with deep commitment to Human Agency's values and vision Systems builder, not just task executor—you think about sustainable processes, not one‑off solutions High agency and bias for action—you see what needs to happen and make it happen without waiting for permission Calm under pressure with excellent judgment about when to escalate vs. solve independently Ego‑free collaborator who earns trust through delivery, not title or authority Intellectually curious with strong learning agility—comfortable moving between strategic thinking and tactical execution Comfortable operating in ambiguity—you thrive when there's no playbook and create clarity from complexity Able to hold strategic context while driving tactical execution Considerations Education: Bachelor's degree or equivalent experience; an advanced degree in a relevant field is a plus Ethics: Commitment to ethical practices and responsible business operations Travel: Occasional (10–25%) for company offsites, key events, and leadership meetings Location: Remote‑friendly with preference for candidates in major tech hubs and strong preference for overlap with EST business hours Compensation This role offers a competitive base salary with performance‑based bonuses and potential equity participation. Final compensation will vary based on experience, performance, and location. Why Join Human Agency Join a team of thinkers and builders creating meaningful impact across sectors—with autonomy to lead, the resources to succeed, and room to grow. This role offers direct partnership with our CEO and outsized impact on the company's trajectory during a critical growth phase. Equal Opportunity Commitment Human Agency is an Equal Opportunity Employer. We value diverse backgrounds and strive to build an inclusive culture where everyone feels welcomed and empowered. Voluntary Self‑Identification For government reporting purposes, we ask candidates to respond to the below self‑identification survey. Completion of the form is entirely voluntary. Whatever your decision, it will not be considered in the hiring process or thereafter. Any information that you do provide will be recorded and maintained in a confidential file. 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