Chief of Staff to the Managing Director of AI

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

**A note before you read further**

The world is changing fast, and so is this role. We can't fully tell you what this job looks like in six months. That's true of every role at Human Agency right now. What we need from you, no matter what: accountability, curiosity, and a builder-first mindset. If that sounds exciting, keep reading. If it sounds intimidating but you're still interested, let's talk. If none of that sounds like you, that's okay. This probably isn't your spot.

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 at 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 for our Managing Director of AI—someone who combines strategic vision in AI with hands-on execution and technological know-how. You'll be both a force-multiplier and a transformation architect: designing AI-enabled processes, building automated engines that run independently, leading organizational rollouts, and ensuring crisp execution across our AI solutions practice.

This role goes beyond traditional Chief of Staff responsibilities. You'll design processes that leverage AI, build repeatable systems that scale, and lead entire client transformations from discovery to sustained adoption. You have the potential to grow into leading organizational-level AI implementations as the practice expands.

Key Responsibilities

Strategic & Executive Leadership

Partner with the Managing Director of AI and the executive team to translate priorities into sequenced plans, resourcing, and measurable outcomes

Lead Human Agency's AI transformation methodology: define offerings, build repeatable frameworks, and establish best practices for AI-enabled workflows

Design end-to-end processes that embed AI tools (LLMs, automation platforms, knowledge assistants) into client workflows and internal operations

Translate complex AI capabilities into clear business cases, use cases, and implementation roadmaps for executive audiences

Produce high-quality executive materials (briefings, roadmaps, decision memos) that drive alignment and decisions

Identify where AI creates leverage across client engagements and surface strategic opportunities to leadership

AI Process Design & Automated Engines

Design and build AI-powered systems that operate independently with minimal ongoing intervention—automated engines that scale beyond individual engagements

Create repeatable processes for AI implementation: discovery frameworks, solution architectures, evaluation routines, and governance models

Design prompts, playbooks, and knowledge bases optimized for reliability, consistency, and reusability across multiple clients

Implement lightweight automation using no/low-code tools (Zapier, Make, Airtable) integrated with AI capabilities

Establish monitoring and feedback loops that enable self-correcting, continuously improving systems

Document patterns and best practices that can be deployed at scale

Client Service Delivery & Organizational Rollouts

Own end-to-end delivery on multiple client engagements involving AI-enabled solutions (e.g., knowledge assistants, workflow automations, content summarization, research copilots), from discovery through launch and sustained adoption

Lead company-wide and client-wide AI adoption initiatives—managing stakeholder alignment, training, governance, and measurement across entire organizations

Run comprehensive discovery to surface use cases, success metrics, risks, change-management needs, and technical requirements; translate findings into scopes, timelines, and clear acceptance criteria

Coordinate solution build-outs with internal teammates and external partners: data/connectivity needs, tool selection, integration planning, prompt engineering, and rollout choreography

Design change-management approaches that address skill gaps, cultural resistance, workflow disruption, and organizational readiness

Partner with client leadership to sequence rollout phases, manage dependencies, and demonstrate ROI

Quality, Governance & Evaluation

Set lightweight evaluation routines: accuracy metrics, latency benchmarks, cost tracking, quality assurance processes, and continuous improvement cycles

Establish prompt/playbook management, basic safety/guardrail checks, and UAT plans

Build governance frameworks that enable responsible, scalable AI adoption across organizations

Implement monitoring systems that track performance, usage, and business impact

Stakeholder Management & Enablement

Lead standing client check-ins, executive presentations, demo readiness, decision logs, and release notes, presenting succinct options and recommendations

Create comprehensive enablement materials: user guides, FAQs, training programs, and governance playbooks that empower client teams to operate AI systems independently

Build lasting client relationships through proactive communication, anticipation of needs, and consistent delivery quality

Present to executive audiences with clarity and confidence, addressing concerns about accuracy, security, and adoption

Operations & Project Management

Design and continuously improve the operating system for AI work: intake → triage → prioritization → delivery → QA → launch → measurement

Manage staffing assignments and subcontractor contributions across concurrent workstreams; keep tools current (Asana/Notion, Google Workspace, Slack)

Budget & scope control: track time against SOWs, flag changes early, manage vendors, and ensure on-budget delivery with clear documentation

Establish shared dashboards for delivery health (timeline, risk, burn, dependency status) and run tight meeting cadences

Communications & Reporting

Prepare agendas, briefings, and executive-ready presentations; synthesize complex information into actionable insights

Provide clear, timely reporting to the Managing Director of AI and stakeholders on progress,