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Human Agency · 4 days ago

Chief of Staff to the Managing Director of AI - Boston, MA

Boston, MA

Full-time

Hybrid

Lead/Staff, Director/Executive

5+ years exp

Human Agency is a rapidly scaling company focused on integrating AI strategies into organizations. They are seeking a Chief of Staff for the Managing Director of AI to lead AI transformation initiatives, design processes leveraging AI, and ensure effective execution across client engagements.

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Responsibilities

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

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

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

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

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

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

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, risks, and decisions

Contribute to Human Agency's AI thought leadership through documentation of best practices, case studies, and insights

Qualification

AI fluencyClient servicesProcess designProject managementNo/low-code automationGoogle WorkspaceStakeholder managementCommunication skillsStrategic thinkingTeam collaboration

Required

5-7+ years in operations, client services, product/program/project management, strategic support, consulting, or transformation roles with direct ownership of client-facing delivery

Demonstrated success leading multi-stakeholder projects and organizational change initiatives end-to-end (scope, timelines, budgets, risk, and change management)

Deep AI fluency: hands-on experience implementing LLM-enabled solutions, prompt engineering, workflow automation, and knowledge management systems; can shape prompts/playbooks, evaluate quality, and choose appropriate tools or vendors

Strong understanding of AI capabilities and limitations, when to use AI, how to design for reliability, and how to manage risks responsibly

Proven ability to design repeatable processes and systems that scale beyond individual projects

Experience with no/low-code automation platforms (e.g., Zapier/n8n), knowledge bases, and modern AI tooling

High proficiency with Google Workspace, Asana/Notion, Slack, and comfort with modern web and content tools; experience preparing polished executive documents and presentations

Exceptional ability to translate complex technical concepts into clear business value for non-technical audiences

Builder and operator: You design systems that work without constant oversight, not just execute tasks

Strategic and tactical: Comfortable setting vision while rolling up sleeves for hands-on implementation

AI pragmatist: Excited about possibilities but grounded in what actually delivers measurable value

Mission-driven; systems thinker with bias for action

Clear, persuasive communicator who can influence executive stakeholders and earn trust through delivery

Calm under pressure with excellent judgment about when to escalate vs. solve independently

Able to hold strategic context while driving tactical execution across multiple concurrent engagements

Intellectually curious with strong learning agility, you stay current on AI capabilities and translate findings into practical applications

Comfortable operating in ambiguity and creating structure where none exists

Education: Bachelor's degree or equivalent experience; an advanced degree in business, technology, or a related field is a plus

Ethics: Commitment to ethical practices and responsible AI (transparency, human oversight, privacy, bias mitigation)

Travel: Regular (20–40%) for client activities, organizational rollouts, and events

Location: Remote-friendly with preference for candidates in major tech hubs

Preferred

Bonus: Experience leading organizational-level technology rollouts, background in management consulting, familiarity with responsible AI considerations (privacy, data handling, consent, bias mitigation), or experience in AI/ML product development