Chief of Staff to the Managing Director of AI

Chief of Staff to the Managing Director of AIChicago, ILLocation: US or CanadaType: US Applicants - Full-Time; Canadian Applicants - Independent ContractorAbout Human AgencyWe'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 OpportunityWe 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 ResponsibilitiesPartner with the Managing Director of AI and the executive team to translate priorities into sequenced plans, resourcing, and measurable outcomesLead Human Agency's AI transformation methodology: define offerings, build repeatable frameworks, and establish best practices for AI-enabled workflowsDesign end-to-end processes that embed AI tools (LLMs, automation platforms, knowledge assistants) into client workflows and internal operationsTranslate complex AI capabilities into clear business cases, use cases, and implementation roadmaps for executive audiencesProduce high-quality executive materials (briefings, roadmaps, decision memos) that drive alignment and decisionsIdentify where AI creates leverage across client engagements and surface strategic opportunities to leadershipDesign and build AI-powered systems that operate independently with minimal ongoing intervention—automated engines that scale beyond individual engagementsCreate repeatable processes for AI implementation: discovery frameworks, solution architectures, evaluation routines, and governance modelsDesign prompts, playbooks, and knowledge bases optimized for reliability, consistency, and reusability across multiple clientsImplement lightweight automation using no/low-code tools (Zapier, Make, Airtable) integrated with AI capabilitiesEstablish monitoring and feedback loops that enable self-correcting, continuously improving systemsDocument patterns and best practices that can be deployed at scaleOwn end-to-end delivery on multiple client engagements involving AI-enabled solutions, from discovery through launch and sustained adoptionLead company-wide and client-wide AI adoption initiatives—managing stakeholder alignment, training, governance, and measurement across entire organizationsRun comprehensive discovery to surface use cases, success metrics, risks, change-management needs, and technical requirements; translate findings into scopes, timelines, and clear acceptance criteriaCoordinate solution build-outs with internal teammates and external partners: data/connectivity needs, tool selection, integration planning, prompt engineering, and rollout choreographyDesign change-management approaches that address skill gaps, cultural resistance, workflow disruption, and organizational readinessPartner with client leadership to sequence rollout phases, manage dependencies, and demonstrate ROISet lightweight evaluation routines: accuracy metrics, latency benchmarks, cost tracking, quality assurance processes, and continuous improvement cyclesEstablish prompt/playbook management, basic safety/guardrail checks, and UAT plansBuild governance frameworks that enable responsible, scalable AI adoption across organizationsImplement monitoring systems that track performance, usage, and business impactLead standing client check-ins, executive presentations, demo readiness, decision logs, and release notes, presenting succinct options and recommendationsCreate comprehensive enablement materials: user guides, FAQs, training programs, and governance playbooks that empower client teams to operate AI systems independentlyBuild lasting client relationships through proactive communication, anticipation of needs, and consistent delivery qualityPresent to executive audiences with clarity and confidence, addressing concerns about accuracy, security, and adoptionManage 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 documentationEstablish shared dashboards for delivery health (timeline, risk, burn, dependency status) and run tight meeting cadencesPrepare agendas, briefings, and executive-ready presentations; synthesize complex information into actionable insightsProvide clear, timely reporting to the Managing Director of AI and stakeholders on progress, risks, and decisionsContribute to Human Agency's AI thought leadership through documentation of best practices, case studies, and insightsWho You AreExperience & Skills5-7+ years in operations, client services, product/program/project management, strategic support, consulting, or transformation roles with direct ownership of client-facing deliveryDemonstrated 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 vendorsStrong understanding of AI capabilities and limitations, when to use AI, how to design for reliability, and how to manage risks responsiblyProven ability to design repeatable processes and systems that scale beyond individual projectsExperience with no/low-code automation platforms (e.g., Zapier/n8n), knowledge bases, and modern AI toolingHigh proficiency with Google Workspace, Asana/Notion, Slack, and comfort with modern web and content tools; experience preparing polished executive documents and presentationsExceptional ability to translate complex technical concepts into clear business value for non-technical audiencesBonus: 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 developmentBuilder and operator: You design systems that work without constant oversight, not just execute tasksStrategic and tactical: Comfortable setting vision while rolling up sleeves for hands-on implementationAI pragmatist: Excited about possibilities but grounded in what actually delivers measurable valueMission-driven; systems thinker with bias for actionClear, persuasive communicator who can influence executive stakeholders and earn trust through deliveryCalm under pressure with excellent judgment about when to escalation versus solving independentlyAble to hold strategic context while driving tactical execution across multiple concurrent engagementsIntellectually curious with strong learning agility, you stay current on AI capabilities and translate findings into practical applicationsComfortable operating in ambiguity and creating structure where none existsConsiderationsEducation: Bachelor's degree or equivalent experience; an advanced degree in business, technology, or a related field is a plusEthics: Commitment to ethical practices and responsible AI (transparency, human oversight, privacy, bias mitigation)Travel: Regular (20–40%) for client activities, organizational rollouts, and eventsLocation: Remote-friendly with preference for candidates in major tech hubsCompensationThis 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 AgencyJoin 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 the opportunity to shape how organizations integrate AI at scale, with clear pathways to increased leadership responsibility as our practice expands.Equal Opportunity CommitmentHuman Agency is an Equal Opportunity Employer. We value diverse backgrounds and strive to build an inclusive culture where everyone feels welcomed and empowered.J-18808-Ljbffr