Chief of Staff Greater New York City, NY Area

About Monstro

Monstro provides the AI-powered Financial Intelligence System for regulated financial institutions. It enables banks and wealth managers to deliver continuous, personalized, governed Financial Guidance to every client, not just the top tier, across their entire financial life: saving, borrowing, investing, planning, protecting, and preparing.

Meaningful Financial Guidance has only ever been available to a small portion of people. We are changing that, through the institutions people already trust. Institutions already have the relationships, the data, and the context to understand each client; Monstro turns that understanding into guidance that helps each person understand, decide, and act. For clients, that means clearer decisions, proactive support when life changes, and a better view of their financial lives. For institutions, it means deeper relationships, more clients served consistently, and more of each client’s financial life managed in one place.

What makes this possible is how the system is built. Governance is not an added feature; it is foundational. Every recommendation reflects the institution’s own views, policies, and permissions. Every output can be audited, traced, and reversed, and client data stays under the institution’s control. Generative AI is used to build and configure the system; at runtime, execution is deterministic, so every output can be explained and stood behind, not just trusted.

About the Role

We're looking for an exceptional Chief of Staff to play a pivotal role in Monstro's next phase of growth.

Driving company-wide execution, operational excellence and cross-functional accountability will be at the heart of your remit.

This is a hands-on, execution-focused Chief of Staff role, working closely with the founder and executive team to translate business priorities into coordinated, measurable outcomes.

You will establish and manage the company's operating cadence, improve cross-functional delivery, build scalable execution frameworks and ensure critical initiatives progress from decision to completion.

You'll work across Product, Engineering, Commercial, Finance, People, Recruiting and Client Delivery, bringing structure, accountability and operational discipline to a fast-moving startup environment.

This role is distinct from day-to-day Business Operations. Its primary focus is ensuring Monstro's highest-priority initiatives are executed effectively across the organisation, with clear ownership, measurable progress and consistent delivery.

While you will serve as a trusted partner to the founder and executive team, this is not a role centred on advising from the sidelines. We need someone who is comfortable getting into the detail, solving operational problems personally and taking direct ownership of outcomes.

You'll be expected to identify what needs to happen, determine how best to make it happen, engage the right stakeholders and drive execution through to completion.

What You'll Own

1. Company-Wide Execution & Operating Cadence

Establish and manage a consistent company-wide operating rhythm, including leadership reviews, cross-functional planning, progress reporting and decision follow-through.

Own a central source of truth for strategic priorities, milestones, accountable owners, dependencies and delivery commitments.

Build practical dashboards, project plans and reporting frameworks that provide clear visibility into progress and execution risks.

Ensure executive decisions translate into actionable plans with defined responsibilities and measurable outcomes.

Maintain momentum across business-critical initiatives, proactively addressing delays and gaps in accountability.

1. Cross-Functional Delivery & Accountability

Drive the execution of company-wide priorities across Product, Engineering, Commercial, Recruiting and Client Delivery.

Translate complex objectives into structured workstreams, realistic timelines and clear deliverables.

Identify operational dependencies, resource constraints and competing priorities before they affect delivery.

Challenge unrealistic plans, resolve blockers and ensure commitments are followed through.

Take direct ownership of complex initiatives that span multiple functions.

Create transparency and accountability without introducing unnecessary bureaucracy.

1. Commercial & Institutional Execution

Coordinate the internal execution of strategic commercial initiatives, institutional engagement activities and market expansion priorities.

Ensure stakeholder engagement, internal resources, deadlines and follow-up actions are organised and tracked.

Partner with commercial leadership to improve coordination and execution readiness across the institutional pipeline.

Support cross-functional preparation for institutional onboarding and client deployments.

Ensure critical commercial initiatives receive the operational attention and internal coordination needed to progress effectively.

This is an execution and operational enablement responsibility, not a direct sales or revenue-closing role.

1. Operational Excellence & Process Improvement

Identify inefficiencies and execution bottlenecks that affect company-wide performance.

Design and implement scalable processes, workflows and reporting mechanisms that improve speed, quality and accountability.

Leverage AI-enabled tools and automation to reduce manual work and improve organisational productivity.

Establish practical standards for documentation, knowledge sharing and cross-functional collaboration.

Work alongside existing operational functions to improve how teams coordinate and deliver, without duplicating routine administrative responsibilities.

1. Strategic Initiatives & Special Projects

Lead high-priority, cross-functional initiatives on behalf of the founder and executive leadership team.

Own projects involving organisational readiness, hiring coordination, business scaling, internal systems and operational transformation.

Support the coordination of fundraising, board and investor-related activities where required.

Bring structure to ambiguous challenges, identify decision-makers and dependencies, and drive projects through to completion.

Personally step in to resolve business-critical problems when needed.

1. Executive Partnership & Execution

Act as a trusted Chief of Staff to the founder and executive team, ensuring strategic priorities translate into effective execution.

Provide clear, actionable reporting on progress, risks, resource constraints and decisions requiring leadership attention.

Improve the effectiveness of leadership meetings through structured agendas, clear decisions and rigorous follow-through.

Offer objective, data-informed insights to support prioritisation and resource allocation.

Challenge constructively, influence across functions and independently drive agreed actions through to completion.

Create capacity for the executive team by taking ownership of operational challenges and ensuring business-critical initiatives continue to progress.

What Success Looks Like

Within the first 30–60 days:

Develop a clear understanding of Monstro's strategic priorities, operating model, key dependencies and execution challenges.

Establish a reliable company-wide view of priorities, owners, timelines and progress.

Identify and begin resolving significant cross-functional bottlenecks.

Introduce a consistent cadence for leadership reporting, decision tracking and accountability.

Within the first 3–6 months:

Implement an effective company-wide execution framework supporting planning, visibility and delivery.

Improve coordination across Product, Engineering, Commercial, Recruiting and Client Delivery.

Introduce practical process improvements and AI-enabled efficiencies.

Demonstrate measurable improvements in execution reliability, transparency and speed.

Establish repeatable coordination processes supporting institutional engagement and commercial growth.

Within the first 12 months:

Build a scalable execution framework supporting Monstro's next phase of growth.

Ensure leadership has consistent visibility into strategic priorities, progress and delivery risks.

Create an environment where decisions translate into action, ownership is clear and critical initiatives are delivered reliably.

Enable the founder and executive team to focus more time on strategic priorities, institutional relationships and company growth.

What We're Looking For

6–10+ years of relevant experience in execution-focused Chief of Staff, strategic operations, startup operations, programme leadership or similar cross-functional leadership roles.

Demonstrable experience within high-growth startups or scale-ups, ideally helping businesses move from early-stage development into commercial growth.

A proven hands-on operator, with direct accountability for driving complex initiatives and delivering measurable business outcomes.

Strong experience establishing operating cadences, planning frameworks, execution dashboards and accountability mechanisms.

Exceptional organisational and programme management skills, with the ability to manage multiple business-critical priorities simultaneously.

Experience working directly with founders, CEOs and senior leadership teams, combining strategic judgment with personal execution.

Strong analytical and problem-solving capabilities, with the ability to identify root causes and implement practical solutions.

Confidence working across technical, commercial and operational functions, influencing stakeholders without formal authority.

A high degree of resourcefulness, urgency and accountability, with a track record of delivering results in ambiguous, fast-changing environments.

Excellent communication skills and the confidence to challenge senior stakeholders constructively.

Experience implementing AI tools, automation or technology-enabled workflows to improve internal efficiency.

Strong business judgment, discretion and the ability to manage confidential initiatives.

Experience within AI, fintech, enterprise SaaS, banking technology or another regulated technology environment is highly desirable.

Bachelor's degree required. An MBA or equivalent relevant experience is advantageous.

Particularly Relevant Backgrounds

We would be especially interested in candidates who have:

Served as an execution-focused Chief of Staff within a founder-led technology company.

Driven company-wide initiatives with direct accountability for delivery and measurable results.

Established cross-functional operating frameworks and delivery accountability.

Worked in lean, resource-constrained environments where they were personally responsible for solving problems and getting things done.

Supported the transition from product development into commercial launch and enterprise client delivery.

We will prioritise evidence of operational ownership and execution over advisory experience, seniority of title or strategy credentials alone.

What This Role Is Not

A Chief of Staff who only advises: This is a true Chief of Staff position, but one defined by execution rather than advisory support alone. You'll be expected to move beyond recommendations and take direct responsibility for turning decisions into action, removing obstacles and delivering tangible business outcomes.

Not an executive assistant position: Executive coordination may occasionally be required, but the primary responsibility is company-wide execution and operational leadership.

Not a purely strategic role: Developing plans matters, but implementing them and ensuring delivery matters more.

Not a passive programme management role: You will be expected to challenge, intervene, solve problems and take ownership rather than simply report progress.

Not a replacement for Business Operations: The role complements existing operational functions by focusing on cross-functional execution, strategic priorities and delivery accountability.

Why Monstro?

Meaningful Impact: Help build a company bringing trusted, AI-powered financial guidance to millions of people.

Real Ownership: Take responsibility for business-critical initiatives and see the direct impact of your work on company performance.

Founder-Level Exposure: Work closely with experienced leadership and play an influential role in how the business develops and scales.

Early-Stage Opportunity: Help shape the execution frameworks and operating culture of a company entering an exciting phase of institutional growth.

AI-Native Environment: Work in a business where modern technology and intelligent automation are central to both the product and how we operate.

Collaborative Culture: Join an ambitious, high-accountability team that values direct communication, sound judgment, speed and exceptional execution.

New York City: Based at The Spiral in Hudson Yards, with four days per week in the office.

Benefits: Competitive compensation and meaningful equity, 100% employer-paid medical, dental and vision coverage, disability coverage, flexible PTO, paid parental leave and catered meals.

Compensation

New York City Base Salary: $220,000–$302,000

Final compensation will depend on experience, skills, internal leveling and market conditions, and will be offered within the stated range in accordance with applicable pay transparency laws.

A Note on Interviewing

We sometimes use AI note-taking tools to help transcribe interview conversations so we can remain fully engaged. Candidates may request that automated transcription not be used during their interview.

Ready to Build With Us?

We're looking for a Chief of Staff who takes ownership, creates clarity, removes obstacles and makes things happen.

If you're energised by working closely with a founder, driving company-wide execution and helping build an ambitious technology company, we'd love to hear from you.