Chief of Staff

Monstro•New York, NY

11h•$220,000 - $302,000•Onsite

About The Position

Monstro is seeking an execution-focused Chief of Staff to help lead the company’s next phase of growth. Working closely with the founder and executive team, this hands-on role translates company priorities into coordinated, measurable outcomes and ensures that critical initiatives progress from decisions through completion. The position establishes the company-wide operating cadence, strengthens cross-functional delivery and accountability, and develops scalable execution frameworks. The Chief of Staff works across Product, Engineering, Commercial, Finance, People, Recruiting and Client Delivery. Responsibilities include maintaining visibility into strategic priorities and delivery risks; coordinating institutional and commercial initiatives; improving processes and workflows; leading strategic projects; and providing clear, actionable reporting to leadership. This is an operational leadership and execution role, not a direct sales, executive assistant, or primarily advisory position, and it complements rather than replaces Business Operations. Success involves building reliable systems for planning, reporting, decision tracking and follow-through; improving execution speed and coordination; and enabling leadership to focus more time on strategic priorities and company growth. The role is based at The Spiral in Hudson Yards, New York City, with four days per week in the office. The stated base salary range is $220,000–$302,000. Monstro describes its product as an AI-powered financial intelligence system for regulated financial institutions, with governance and deterministic runtime execution foundational to the system.

Requirements

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 in high-growth startups or scale-ups, ideally supporting a transition from early-stage development into commercial growth.
Hands-on operating experience with direct accountability for complex initiatives and measurable business outcomes.
Experience establishing operating cadences, planning frameworks, execution dashboards and accountability mechanisms.
Exceptional organisational and programme management skills, including managing 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, including identifying root causes and implementing practical solutions.
Ability to work across technical, commercial and operational functions and influence stakeholders without formal authority.
Resourcefulness, urgency and accountability, with a record of delivering in ambiguous, fast-changing environments.
Excellent communication skills and confidence constructively challenging senior stakeholders.
Experience implementing AI tools, automation or technology-enabled workflows to improve internal efficiency.
Business judgment, discretion and ability to manage confidential initiatives.
Bachelor's degree required.
Ability to work four days per week in the New York City office, as specified for the role.

Nice To Haves

Experience in AI, fintech, enterprise SaaS, banking technology or another regulated technology environment is highly desirable.
MBA or equivalent relevant experience is advantageous.
Execution-focused Chief of Staff experience within a founder-led technology company.
Track record of driving company-wide initiatives with direct delivery accountability and measurable results.
Experience establishing cross-functional operating frameworks and delivery accountability.
Experience working in lean, resource-constrained environments with personal responsibility for solving problems and execution.
Experience supporting the transition from product development into commercial launch and enterprise client delivery.

Responsibilities

Establish and manage a company-wide operating rhythm, including leadership reviews, cross-functional planning, progress reporting and decision follow-through.
Maintain a central source of truth for strategic priorities, milestones, owners, dependencies and delivery commitments.
Build dashboards, project plans and reporting frameworks that show progress and execution risks.
Turn executive decisions into actionable plans with defined responsibilities and measurable outcomes; maintain momentum and address delays or accountability gaps.
Drive company-wide priorities across Product, Engineering, Commercial, Recruiting and Client Delivery.
Translate complex objectives into workstreams, timelines and deliverables; identify dependencies, resource constraints and competing priorities.
Challenge unrealistic plans, resolve blockers, follow up on commitments and directly own complex initiatives spanning multiple functions.
Coordinate strategic commercial initiatives, institutional engagement, market expansion, stakeholder activities and follow-up actions.
Partner with commercial leadership on institutional pipeline coordination and execution readiness, and support preparation for institutional onboarding and client deployments.
Identify execution bottlenecks and implement scalable processes, workflows and reporting mechanisms that improve speed, quality and accountability.
Use AI-enabled tools and automation to reduce manual work and improve productivity; establish practical standards for documentation, knowledge sharing and collaboration.
Lead high-priority cross-functional initiatives for the founder and executive leadership team, including projects involving organisational readiness, hiring coordination, scaling, internal systems and operational transformation.
Support coordination of fundraising, board and investor-related activities when required.
Structure ambiguous challenges, identify decision-makers and dependencies, and drive projects to completion; personally address business-critical problems when needed.
Provide leadership with actionable reporting on progress, risks, resource constraints and decisions requiring attention.
Improve leadership meetings with structured agendas, clear decisions and follow-through; offer objective, data-informed insights for prioritisation and resource allocation.
Influence across functions, constructively challenge stakeholders and independently drive agreed actions through to completion.
Take ownership of operational challenges so the executive team can focus on strategic priorities, institutional relationships and company growth.