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 a generalist. Maybe you're on a dedicated financial-services vertical team at a modern data or cloud platform, at a category-creating company known for selling into large, complex, security-conscious institutions without a conventional playbook, at an enterprise platform company with a track record of turning a foothold deal into a much larger commitment, or at the infrastructure layer of fintech, where your buyer is a regulated institution rather than a startup. The common thread isn't the logo on your badge — it's that you own a named-account book in financial services, self-generate pipeline rather than inherit it, and are judged on velocity and account ownership rather than relationship tenure. In short: you sell modern data/AI/infrastructure into financial institutions today, you own the account, and you self-generate pipeline — wherever that happens to sit.

What you bring. Genuine 0→1 / category-creation DNA — you've sold something new into an industry that didn't yet have a category for it, and you're technically fluent enough to hold your own on architecture, data, and AI governance conversations without a sales engineer in the room.

You're comfortable operating without a mature playbook, a deep bench of reference customers, or a brand that pre-sells the meeting — because you've built those things before rather than inherited them. And you're willing to challenge how banks traditionally buy: instead of defaulting to months of workshops, a formal RFP, and a small pilot that quietly never converts into anything material, you push the deal toward a real decision — faster to yes where the fit is real, and just as importantly, faster to no where it isn't, so cycles resolve instead of drifting.

Experience bar: accomplishment over tenure. As a rough guide, ~7+ years of quota-carrying enterprise technology sales experience is a reasonable floor — but tenure is a proxy, not the bar. If you're a 9-year seller with a genuine track record of originating and closing enterprise technology sales — even without a deep bench of referenceable logos — you're much closer to what we're looking for than a 20+ year seller whose primary asset is long-accumulated banking relationships. Direct banking experience is a plus, but the proven ability to close complex technology deals is the primary requirement. We will weigh what you've actually closed and how, at what velocity, and how self-directed your pipeline generation was, well above years in seat.

The known risk with this profile is underestimating the weight of bank process — assuming velocity alone can substitute for the institutional navigation a regulated buyer requires. We're hiring specifically to counter that risk: we want someone who pairs speed and category-creation instincts with genuine respect for (and fluency in) what a bank's risk, security, and compliance functions actually need to see. We'll specifically test whether you can describe the mechanics of a bank's buying process in specific terms (how a vendor risk assessment gets triaged, what InfoSec wants to see before a POC, who actually controls budget versus who merely has to bless it) — not just generalities about banks being risk-averse.

What Success Looks Like

• Within 6 months: a qualified, advancing pipeline covering 20–30 named middle-market and regional accounts, each with an identified economic buyer, executive sponsor, and documented next steps — self-generated, not inherited.
• Within 12 months: multiple closed platform agreements representing $10M+ in usage/credit commitments, built predominantly from pipeline you generated from cold.
• Forecast accuracy within ±10% on a rolling 90-day basis from month 9 onward.
• ≥60% first-cycle clearance on InfoSec, regulatory, and procurement reviews through early alignment with Legal, Security, and Compliance.
• Reference-grade outcomes: ≥50% of closed customers willing to take peer reference calls within 6 months of go-live.
• Measurable expansion: meaningful upsell or cross-sell from at least one closed account within 12 months of initial signature.
• First version of the enterprise playbook shipped: ICP, qualification framework, discovery model, objection library, pricing posture, and security response templates — adopted by the broader team.
• At least two product enhancements influenced by your deal cycles, prioritized into the roadmap within 12–18 months.

How We Will Evaluate You

Because we have seen the failure mode before — sellers who arrive with a hot category and a fast pitch but underestimate what it actually takes to move a regulated buyer, or who accept long sales cycles as immovable rather than something to engineer around — the process is calibrated to test both halves of this profile: genuine self-generation and velocity, and real fluency in how a bank actually buys. Expect to:

• Walk us through 2–3 specific deals end-to-end from the last 12–18 months, including how pipeline was built from cold, who the economic buyer was, what nearly killed the deal, and what your specific role was in saving it.
• Describe a deal where you meaningfully compressed a sales cycle with a risk-averse or regulated buyer, and explain the specific mechanism — not general effort, but what you actually changed about the sequencing, the stakeholders involved, or the procurement path.
• Describe a deal where you pushed a stalled or drifting process to a clear "no" rather than letting it linger — what told you it wasn't real, and how you got out of it fast.
• Show how you would build a 90-day plan for a named bank where you have no pre-existing relationships.
• Pressure-test our current narrative, pricing posture, and qualification criteria — and tell us what you would change.
• Talk through which artifacts (qualification model, ROI calculator, objection library, security response, pricing framework) you would build in your first 6 months.
• Walk through the actual mechanics of a bank's procurement, security, and risk review process in specific, granular terms — not generalities about banks being risk-averse.

What This Role Is Not

It is not a head-of-sales role from day one. Hiring additional sellers or managers under this person is a natural next step as revenue grows, not the starting job — we're looking for a seller who can grow into managing sellers over time, once they've personally proven the motion themselves.It is not a role for someone leaning on a hot category or a strong brand to open doors for them. A recognizable current employer is a real accelerant — but only alongside someone still energized to personally originate, negotiate, and close from cold.It is not a role for someone who treats a 12–18 month sales cycle as an unchangeable fact of banking rather than a problem to be actively managed down.It is not a role for someone who needs a finished deck, polished case studies, and a long bench of reference customers before they can perform.It is not a role for a generalist enterprise AE with a passing exposure to financial services — real, current fluency in how banks buy is required, not just fluency in the product being sold.

Why Monstro

• Impact: Build technology that helps millions of people make better financial decisions, through the institutions they already trust, and help define the category of Financial Intelligence.
• Ownership: High trust, high ownership, high standards. You will own meaningful problems end to end from day one.
• Experienced team: Work with leadership that has a track record of scaling companies from early stage to major exits.
• Principles-driven culture: We move fast, because the opportunity is urgent. We communicate directly, because clarity saves time. We hold a high standard, because institutions and clients need to trust what we build.
• In person, in New York: We are headquartered at The Spiral in Hudson Yards and work in the office four days a week, because our pace depends on fast collaboration.
• Compensation and benefits: Competitive cash compensation and meaningful equity, plus 100% employer-paid medical, dental, and vision coverage, disability coverage, flexible PTO, paid parental leave, and catered meals.

Base compensation range for New York City: $225,000 – $275,000

• On-Target Variable: $225,000 – $275,000 (50% of OTE)
• On-Target Earnings (OTE): $450,000 – $550,000
• Realistic Top-Performer Earnings: $1,000,000 – $1,500,000+ annually based on the 8–12 closed-deal year-one plan ($3M–$5M ACV per deal).
• Equity

Plan Mechanics

• Commission accelerates above 100% of plan and accelerates again above 150%, with no cap on annual earnings.
• Additional milestone kickers apply on marquee logos, multi-year platform commitments, and named reference accounts that unlock the next wave of pursuits.
• The plan is built to reward closed ACV, not activity. At the targeted 8–12 closed deals per year in the $3M–$5M ACV range (leading to $10M+ multi-year platform commitments), a top performer is on a clear path to seven-figure total cash earnings.

*The posted range reflects the base salary for this role across the market ranges for each location. 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.

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Ready to Build With Us?

The standard is simple: do great work, own the outcome, communicate with purpose, move with urgency, raise the level. If that sounds like you, we’d love to hear from you.