Managing Director, Enterprise Accounts, Financial Services AI

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.

The Work

We are building for a high-stakes industry where the work has real consequences. Guidance only matters if people can trust it and institutions can govern it. The challenge is to make Financial Guidance 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 what makes the problem hard, and the work meaningful. This is not a simple AI problem; it takes product judgment, technical depth, regulatory discipline, design quality, and a team that moves quickly without lowering the bar.

Monstro is moving from vision to market: launching with financial institutions, growing the team, and building for the enterprise in one of the most regulated industries. You will be expected to think clearly, communicate directly, move with urgency, hold a high standard, 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

We are hiring a Managing Director, Enterprise Accounts, Financial Services AI to build this motion from the ground up. This is a senior individual contributor role — a quota-carrying operator-seller who personally closes platform deals and helps define the enterprise GTM motion as it scales. It is not a sales management role at the outset.

This role is built for a modern enterprise/AI seller: someone who currently sells data, AI, cloud, or infrastructure platforms into financial institutions, brings genuine 0→1 / category-creation DNA, is technically fluent, and is comfortable operating without a mature playbook or a long bench of reference customers. You are willing to challenge how banks traditionally buy — rather than accepting six months of workshops, a formal RFP, and a small POC that never becomes commercially meaningful, you push the deal toward a real decision: faster to yes where the fit is real, and just as importantly, faster to know where it isn't, so cycles resolve instead of drifting.

We are explicitly not looking for someone who can arrange a meeting and then expect the company to carry the deal from there, and not looking for someone whose answer to "why does this take 12–18 months" is "that's just how banks work." Category-creation instincts are a real accelerant here, but they are a complement to disciplined, hands-on selling — not a substitute for it. (See "What This Role Is Not" below for the full picture.)

Why This Role Matters

This is one of the first hires in Monstro's Enterprise Accounts build-out. The larger top U.S. bank universe — banks sized 5-100 in the country — represent thousands of addressable buyers that need governed financial intelligence but cannot wait for, or justify, a Tier-1-scale transformation program. The first wave of $10M+ platform commitments is what converts Monstro from a capable solution into a trusted enterprise standard across this segment. This hire's early wins define the playbook for everyone who follows.

The specific value this role brings is the ability to get a genuinely new category bought by a regulated institution — moving a deal through procurement, InfoSec, risk, and compliance at real speed, without letting the bank's default pace and process set the timeline. Beyond near-term bookings, this hire surfaces key requirements back to Product, simplifies large-deal complexity, and writes the first version of the repeatable platform motion — qualification, pricing, security posture, deployment shape, expansion patterns. Done well, the artifacts produced in the first 12 months become the foundation of the enterprise organization that grows from here.

What You'll Do

Personally close platform deals

• Own a quota. Personally lead pursuit and close of $10M+ platform usage commitments with the larger top U.S. bank universe (banks sized 5-100 in the country).
• Run the full cycle: prospecting and pipeline development, discovery, technical evaluation, security and procurement review, commercial negotiation, and close.
• Maintain a clean, honest forecast. Inspect your own pipeline before anyone else has to.

Build pipeline through a repeatable, self-directed motion

• Generate qualified pipeline through deliberate outbound, executive briefings, partner channels, events, and targeted content. This is a self-generation role — you are expected to produce pipeline in accounts where you start with zero warmth, not to rely on inbound or inherited relationships.
• Maintain disciplined account plans with named economic buyers, identified internal champions, documented compelling events, and mutual close plans.

Help define the enterprise GTM motion

• Translate every deal into reusable assets: ICP and account segmentation, qualification criteria, discovery frameworks, objection libraries, ROI models, security and compliance response templates, and competitive playbooks.
• Partner with the CEO and Product on pricing, packaging, and positioning. Bring the institutional buyer's voice into the building.
• Help establish the forecasting cadence, pipeline review rhythm, and deal-stage definitions that the enterprise organization will run on.

Drive expansion inside closed accounts

• Convert initial platform deployments into broader adoption — additional divisions, additional use cases, deeper integration — through coordinated expansion plans with Customer Success and Product.
• Build the early reference base. Your first wins create the proof points for the next ten.

Navigate regulated procurement at speed

• Drive InfoSec, regulatory, legal, and procurement processes in parallel with commercial negotiation. Anticipate the gates; don't get caught by them.
• Coordinate Legal, Security, and Compliance internally to clear approvals on first submission wherever possible.
• Multi-thread deliberately: build simultaneous relationships across risk, technology, and business-line stakeholders so no single gatekeeper can stall a deal, rather than relying on one champion to carry it alone.
• Push stalled or non-real deals to a fast, clear "no" rather than letting them drift through workshops and pilots that never convert.

Represent Monstro externally

• Be a credible voice with senior buyers — executive briefings, industry forums, selective public speaking, and customer references that compound pipeline.

Scale the team, when the deals justify it

• As closed revenue and pipeline justify it, help recruit additional enterprise AEs and supporting roles — initially as a player-coach, and over time, potentially as a sales leader. Team-building is earned by sold pipeline, not the other way around.

The Profile We're Looking For

Primary value: Current quota-carrying commercial operator with deep banking fluency and current executive relationships. You have a willingness to reshape how the deal gets bought, rather than accepting the bank's default process.

You're currently selling data, AI, cloud, or infrastructure platforms into financial services at a company where that motion is real and current today — not