Chief of Staff

Monstro•New York City, NY

13d•Hybrid

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 role turns business priorities into coordinated, measurable outcomes by establishing the company’s operating cadence, improving cross-functional delivery, building execution frameworks and ensuring critical initiatives progress from decision to completion. The role works across Product, Engineering, Commercial, Finance, People, Recruiting and Client Delivery, bringing structure, accountability and operational discipline to a fast-moving startup. The position focuses on execution of the company’s highest-priority initiatives rather than routine Business Operations, advisory work alone, executive assistance or passive programme management. The Chief of Staff is expected to personally solve operational problems, take direct ownership of complex outcomes, engage stakeholders and drive work through to completion. Responsibilities include company-wide planning and reporting, cross-functional delivery, commercial and institutional coordination, process improvement, strategic projects, and executive partnership. The role is based at The Spiral in Hudson Yards, New York City, with four days per week in the office. The stated New York City base salary range is $220,000–$302,000, with final compensation dependent on experience, skills, internal leveling and market conditions. Benefits include meaningful equity, employer-paid medical, dental and vision coverage, disability coverage, flexible PTO, paid parental leave and catered meals.

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 experience helping a business move from early-stage development into commercial growth.
A hands-on operating track record with direct accountability for driving complex initiatives and delivering measurable business outcomes.
Experience establishing operating cadences, planning frameworks, execution dashboards and accountability mechanisms.
Exceptional organisational and programme management skills, including 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, 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 track record of delivering in ambiguous, fast-changing environments.
Excellent communication skills and confidence constructively challenging senior stakeholders.
Strong business judgment, discretion and ability to manage confidential initiatives.
Bachelor’s degree required.
Evidence of operational ownership and execution is prioritised over advisory experience, title seniority or strategy credentials alone.

Nice To Haves

Experience in AI, fintech, enterprise SaaS, banking technology or another regulated technology environment is highly desirable.
MBA or equivalent relevant experience.
Experience implementing AI tools, automation or technology-enabled workflows to improve internal efficiency.
Experience as an execution-focused Chief of Staff in a founder-led technology company.
Experience 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 getting things done.
Experience supporting the transition from product development into commercial launch and enterprise client delivery.

Responsibilities

Establish and manage the 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 make progress and execution risks visible.
Translate executive decisions into actionable plans with clear responsibilities and measurable outcomes; maintain momentum and address delays or accountability gaps.
Drive execution of company-wide priorities across Product, Engineering, Commercial, Recruiting and Client Delivery.
Translate complex objectives into workstreams, realistic timelines and deliverables; identify dependencies, resource constraints and competing priorities.
Challenge unrealistic plans, resolve blockers, ensure commitments are followed through and take ownership of complex cross-functional initiatives.
Coordinate internal execution of strategic commercial initiatives, institutional engagement and market expansion priorities.
Organise and track stakeholder engagement, internal resources, deadlines and follow-up actions; partner with commercial leadership on institutional pipeline coordination and execution readiness.
Support cross-functional preparation for institutional onboarding and client deployments; provide operational coordination for critical commercial initiatives.
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 organisational productivity.
Establish practical standards for documentation, knowledge sharing and cross-functional collaboration while working alongside existing operational functions.
Lead high-priority cross-functional initiatives and special projects for the founder and executive leadership team, including organisational readiness, hiring coordination, scaling, internal systems and operational transformation.
Support coordination of fundraising, board and investor-related activities where required.
Bring structure to ambiguous challenges, identify decision-makers and dependencies, and personally resolve business-critical problems as needed.
Provide actionable reporting on progress, risks, resource constraints and decisions requiring leadership attention.
Improve leadership meeting effectiveness through structured agendas, clear decisions and rigorous follow-through.
Offer objective, data-informed insights for prioritisation and resource allocation; constructively challenge stakeholders and independently drive agreed actions.
Take ownership of operational challenges to create capacity for the executive team and keep business-critical initiatives progressing.
Establish a scalable execution framework and consistent leadership visibility into strategic priorities, progress and delivery risks. Facilitate reliable delivery and enable the founder and executive team to focus more on strategic priorities, institutional relationships and company growth.