Chief of Staff, AI Special Projects

Lakeview Loan Servicing•New York, NY

5d•Remote

About The Position

The Chief of Staff, AI Special Projects is a high-agency operating role that reports to the Head of Engineering and helps a rapidly growing AI team operate with speed, clarity, and follow-through while building AI-enabled platforms inside a complex, high-stakes investment and financial services environment. This role is designed for a highly capable, technically curious operator who wants to work directly with Engineering leadership, learn quickly through close mentorship, and grow into materially broader ownership as the team scales. The expectation is not that this person has all the answers on day one; the expectation is that they bring strong judgment, learning velocity, organization, follow-through, and comfort operating in uncertainty. This role is a force multiplier for product development, Engineering leadership leverage, daily execution, and the operating rhythm required to scale quickly. Sitting at the epicenter of Engineering, Product, and domain Subject Matter Experts (SMEs), this person will help organize priorities, capture context, run the operating cadence, support platform health, source critical talent, and unblock work. Few roles offer this combination of access, urgency, mentorship, and learning curve: a front-row seat to technology, startup-style AI product building, and a cutting-edge financial services environment. You will see how ambiguous business problems become prototypes, evaluations, production launches, and scaled workflows, while learning directly from Engineering leadership and a founding AI team. Whether you are a recent graduate, early in your career, or coming from a different professional path with limited direct exposure to tech, startups, institutional finance, or hedge funds, this role is designed to be a growth accelerator and a credible bridge into multiple future paths, including engineering, product, strategy, operations, or other high-leverage technology-adjacent roles. The role will start with strong execution support, context capture, follow-through, and operating cadence, and is expected to grow into broader ownership of special projects, decision visibility, and cross-functional execution.

Requirements

Hunger to learn, high agency, excellent organization, and excellent written and verbal communication skills
Strong technical fluency and comfort using AI tools and platforms to accelerate research, synthesis, documentation, analysis, planning, workflow design, and communication. A coding, computer science, engineering, quantitative, analytical, operational, or self-taught technical background is helpful, but a traditional CS degree or conventional technology resume is not required
Comfort operating in ambiguous environments where priorities change, context is incomplete, and the next step needs to be created
Exceptional learning velocity and comfort growing into broader responsibility quickly; you may not have direct experience in every area, but you can absorb context, ask good questions, build judgment, and take on increasingly ambiguous work over time
Strong follow-through: you remember details, close loops, keep people accountable, and make sure important work does not get dropped
Strong curiosity about AI, product development, engineering, platform operations, financial markets, startup-style execution, complex workflows, and how technology teams build and scale products
Strong judgment, discretion, and maturity when working in a regulated, high-stakes environment
Ability to work well with technical, product, business, operational, recruiting, and vendor stakeholders
Bias toward action and continuous improvement; you are energized by learning quickly, improving systems, and making the team more effective

Nice To Haves

Exposure to startups, consulting, operations, product, engineering, AI tools, automation, recruiting, team-building, or workflow improvement
Experience using AI tools for research, writing, analysis, coding, automation, project management, or workflow acceleration
Experience working with operators, domain experts, customers, executives, technical teams, candidates, or external partners
Experience organizing teams, programs, labs, communities, side projects, events, operational initiatives, or other complex workstreams

Responsibilities

Own and run many of the team's daily operational tasks: agendas, notes, action items, follow-ups, trackers, decision logs, recurring rituals, operating checklists, and meeting preparation
Run a clear rhythm for priorities, standups, demos, stakeholder check-ins, feedback loops, launches, and post-launch follow-through
Keep docs, task boards, timelines, status updates, operational checklists, and open questions current so everyone knows what matters and who owns it
Play a significant role in ensuring healthy day-to-day operations of all critical technology platforms and services, partnering with Engineering to track service health, releases, incidents, escalations, risks, and follow-through
Maintain lightweight dashboards, runbooks, operating checklists, escalation paths, service-review notes, and post-incident action items so platform work stays visible and accountable
Help coordinate platform rollouts, issue triage, stakeholder communications, user feedback loops, reliability follow-through, and operational improvements across critical systems
Partner directly with the Head of Engineering on high-priority AI special projects that need structure, urgency, and follow-through
Convert broad goals into plans with owners, milestones, risks, decisions, and next actions
Jump into gaps across discovery, demos, rollout coordination, hiring support, vendor sourcing and engagement, talent sourcing, documentation, and stakeholder communication
Learn investment, operational, and technology workflows by working with SMEs, operators, product managers, engineers, and users
Turn messy domain context, feedback, edge cases, and constraints into notes, requirements, maps, FAQs, and action plans
Highlight where AI, automation, or better workflow design can create leverage for users and the team
Draft crisp briefs, research summaries, roadmap updates, launch notes, recaps, and executive-ready updates
Keep stakeholders aligned on priorities, tradeoffs, timelines, ownership, decisions, and follow-through
Build lightweight docs, onboarding materials, knowledge hubs, and playbooks that help the team scale
Build trust through responsiveness, discretion, judgment, and clear communication
Use modern AI tools and platforms every day to speed up research, synthesis, planning, documentation, analysis, project management, workflow design, and communication
Experiment with AI-assisted ways to improve knowledge capture, reporting, process automation, recruiting workflows, service-health visibility, and team operations
Identify bottlenecks, manual work, dropped handoffs, and unclear processes; help fix them
Help source critical talent and build out the team by identifying promising candidates, organizing outreach lists, preparing candidate context, coordinating interview loops, and driving fast follow-through
Support onboarding and team rituals as the AI organization scales, turning repeated questions, handoffs, and processes into clear playbooks
Represent the team with professionalism, urgency, and strong written communication in candidate and stakeholder interactions
Contribute to a founding-team culture of ownership, curiosity, urgency, low ego, customer obsession, technical curiosity, and learning
Take on unglamorous work when it matters and turn repeated work into scalable systems over time