Chief of Staff to the Founder

Location: US or Canada
Type: US Applicants - Full-Time; Canadian Applicants - Independent Contractor
The Opportunity

We are seeking an exceptional Chief of Staff to serve as a force multiplier to our founder, Brendan Lind. You'll be the engine that translates the founder's vision and initiatives into executable plans, builds the systems that allow our leadership team to operate at their highest level, and ensures nothing critical falls through the cracks as we scale rapidly.

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:

• Leading AI transformation projects with clients
• Managing CEOs at client organizations
• Driving sales initiatives at Human Agency
• Partnering with Recruiting to help us find and close top-tier talent
• Managing client project delivery
• Driving value through data and analytics for clients
• Leading go-to-market initiatives for clients

You'll own special projects, drive organizational initiatives from concept to completion, and build the infrastructure (GTM motions, resource allocation, operational rhythms) that allows Human Agency to grow while maximizing our greatest strength - our people. 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 & Founder Partnership

• Partner with the founder to translate priorities, initiatives, and strategic vision into sequenced plans with clear owners, timelines, and success metrics
• Own end-to-end execution of founder-level special projects and organizational initiatives, from scoping and planning through delivery and measurement
• Maintain focus and accountability across the founder's portfolio of priorities; proactively identify conflicts, dependencies, and risks before they become problems
• Prepare 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 founder, 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 no one is 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
• Serve as a neutral coordinator and problem-solver when initiatives span multiple departments or require difficult trade-offs between competing priorities
• Represent the founder's office in key internal discussions, ensuring the founder'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

Communications & Organizational Transparency

• Ensure crisp internal communication on company strategy, priorities, and decisions-translating founder-level thinking into clear, actionable guidance for the broader team
• Prepare the founder for key meetings, presentations, and decisions; provide relevant context, background materials, and recommended talking points
• 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, business development, or startup leadership positions
• AI-native, not AI-curious. Before you do almost anything manually, you've already asked yourself whether AI can do it better. You're constantly tinkering, building small tools, automating your own workflows, and sharing what you find.
• Demonstrated success in 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 work-streams with competing priorities and timelines
• High proficiency with modern collaboration tools (Google Workspace, Asana/Notion, Slack) and intermediate to advanced 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; proven success driving business development in B2B environments; exposure to board-level strategy and operations

Mindset & Traits

• 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

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