Managing Director, Enterprise Accounts, Financial Services AI

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."

Why this role matters

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 commitments that establish Monstro as a trusted enterprise standard in the segment.