Head of Strategic Operations

About Monstro

Monstro is a governed AI platform for regulated financial institutions. We give banks and wealth managers a way to deliver trusted advice digitally — to every client, not just the top tier.

Institutions already have the relationships, data, and context to understand each client. Monstro turns that understanding into advice. It gives every client the experience of a personal advisor: bringing together their full financial picture, identifying what matters, and delivering personalized guidance across investments, tax, retirement, insurance, legal, and more.

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. Every recommendation reflects the institution's own views, policies, and permissions. Every output is auditable, traceable, and reversible, and client data stays under the institution's control. Generative AI shapes how advice is designed; at runtime, execution is deterministic — so every output can be explained and stood behind, not just trusted.

The work

We are building for a high-stakes industry where the work has real consequences. The challenge is to make advice more personal and more available without making it less trusted — to build AI that institutions can audit, explain, and reverse, in a domain where being wrong carries real cost. That is a hard problem, and it is the reason to be here.

You will work on technology that brings real financial advice to people who have rarely had access to it. You will be expected to think clearly, move with urgency, hold a high bar, and take responsibility for work that matters. We are an early team building something ambitious, and what you do here will shape both the product and the company.

About the Role

The Head of Strategic Operations is one of the most influential roles at Monstro. Working as a strategic partner to the Executive team, you'll help turn company strategy into execution, ensuring priorities stay aligned, decisions are implemented, and the business continues to scale with speed and precision.

This is not an exec assistant role, but it is also not a role for someone who only advises from the sidelines. You will be expected to get into the details when needed — from preparing an exec meeting and coordinating follow-up, to resolving a cross-functional blocker or rebuilding a broken process.

As Monstro continues its rapid growth, there will be more opportunities than time. Your role is to ensure the leadership team is focused on the work that creates the greatest impact. You will take an ambiguous priority, structure it, identify the real decision makers and blockers, create the plan, keep pressure on the work, and make sure it gets finished.

You'll work across Product, Engineering, Commercial, Operations, People, Finance, Customer Success and Marketing — helping each function stay connected to the company's objectives while acting as an extension of the Executive Team in driving accountability and momentum.

No two weeks will look the same. You might be structuring a new strategic initiative, resolving an operational bottleneck between departments, rebuilding a broken process, improving executive decision-making, or coordinating the launch of a major client deployment. If you enjoy variety, solving difficult problems, and helping exceptional teams perform at their highest level, you'll thrive in this role.

What You'll Own

• Operating Rhythm: Own the company’s source of truth (priorities, owners, deadlines, dependencies). Implement and maintain a "Company Gantt Chart" that provides true transparency across Product, GTM, Recruiting, and Delivery.
• Execution & Accountability: Don't just track tasks; push for completion. Ensure that decisions made in executive meetings are translated into clear, actionable, and tracked workstreams. Push back when plans lack rigor or feasibility.
• Commercial/GTM Support: Act as the operational backbone for our commercial expansion—keeping track of banks, advisors, and conferences, and managing the operational mechanics behind the scenes.
• Special Projects: Lead high-impact, confidential initiatives ranging from hiring and fundraising support to legal and operational process rebuilding.
• Operational Efficiency: Identify bottlenecks before they impact delivery. Improve how we work by applying an "AI-native" mindset to our internal workflows, reporting, and knowledge management.

What Success Looks Like

• The executive team operates with clarity, alignment and consistent execution against company priorities
• There is one clear, current source of truth for what matters, who owns it, and where it stands
• Strategic initiatives move quickly from discussion to delivery with clear ownership and measurable outcomes
• Cross-functional collaboration becomes a competitive advantage, with fewer bottlenecks and faster decision-making
• Company objectives remain visible across the organisation, with progress tracked transparently and proactively
• Operational processes scale alongside company growth without introducing unnecessary bureaucracy
• The Executive team is able to focus on the highest-value strategic opportunities, knowing execution across the organisation is being driven effectively

What We're Looking For

• 6 –10+ years' experience in high-growth startups or scale-ups, with experience in a Founder’s Office, Chief of Staff, Business Operations, Strategy, Operating, Investing, or top-tier Management Consulting environment. You’ve operated in fast-moving businesses before and understand what it takes to scale.
• Trusted partner to founders and executives, with experience working directly alongside CEOs, founders, executive leadership teams, boards, and investors on high-priority strategic initiatives.
• Exceptional operator with outstanding organisational and project management skills. You can orchestrate multiple complex, business-critical initiatives simultaneously without losing attention to detail.
• Comfortable thriving in ambiguity. You enjoy environments where priorities evolve quickly, ownership is high, and there isn't a playbook to follow. You naturally bring structure to complexity.
• Strategic thinker with an execution mindset. You can move seamlessly between high-level business strategy and hands-on execution, building scalable processes rather than simply managing tasks.
• Outstanding communicator with exceptional written and verbal communication skills. You have the confidence to challenge ideas, influence senior stakeholders, and engage effectively with executives, investors, partners, and board members.
• High urgency, grit, and relentless follow-through. You are driven to see work through to completion, maintaining momentum until outcomes are delivered. You thrive in high-performance environments where speed and quality are equally important.
• Strong analytical capability, using data and structured thinking to solve problems, improve operational efficiency, and support informed business decisions.
• Influential without authority. You build trusted relationships across all levels of an organisation and consistently drive alignment, accountability, and execution.
• Externally credible and highly polished, with the presence and professionalism to represent Monstro with financial institutions, strategic partners, advisors, investors, and other senior stakeholders.
• AI-native mindset, with enthusiasm for leveraging modern AI tools to improve productivity, communication, decision-making, and operational effectiveness.
• Experience within AI, fintech, SaaS, BankingTech, or another regulated technology environment is highly desirable.
• Bachelor's degree required. An MBA or equivalent experience in strategy consulting or executive-level business operations is advantageous.

• Ownership & Impact: Shape the future of AI-powered finance—building a category-defining product used by consumers and institutions around the world.
• Experienced Team: Join a team with leadership that has a track record of scaling companies from early stage to major exits.
• Principles-Driven Culture: Work in a culture that values speed, ownership, and impact—what most companies achieve in 90 days, we do in 45.
• Comprehensive Compensation Package: Competitive salary, equity, and robust benefits package, including paid health, vision, dental, and disability coverage.

Base Compensation Range for New York City: $156,750 - $268,850

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

If you’re excited to contribute to a high-bar team building something meaningful, we love to hear from you!