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 of Strategic Banking Accounts to lead our expansion into the largest financial institutions in the U.S. This is a senior individual contributor role — a quota-carrying operator-seller who personally closes platform deals and helps define the strategic GTM motion as it scales. It is not a sales management role at the outset.
This role is built for an established banking commercial operator who brings deep, current executive relationships within the top 5–100 U.S. banks. You must have working fluency in how procurement, security, risk, and compliance operate at national scale, and the ability to navigate the executive buying process of a large regional or national institution. We are looking for a true, hands-on operator who treats cycle length as something to compress, not a constant to accept.
A warm bank network is a real accelerant here — but it's a complement to active, current 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 Strategic Accounts build-out, focused exclusively on the top 5–100 U.S. banks. These large regional and national institutions need governed financial intelligence to maintain decision relevance. The first wave of $10M+ platform commitments defines Monstro as the strategic standard for the industry. This hire's early wins define the playbook for the national accounts organization.
The specific value this role brings is institutional navigation: the ability to get a deal through a bank — past procurement, InfoSec, risk, and compliance — without becoming captive to the bank's own pace and process. Beyond near-term bookings, this hire surfaces strategic 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 strategic organization that grows from here.
What You'll Do
Personally close platform deals
- Own a quota. Personally lead pursuit and close of $10M+ platform commitments with US middle-market and regional financial institutions.
- 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 motion
- Generate qualified pipeline through deliberate outbound, executive briefings, partner channels, events, and targeted content — not solely through your personal network.
- Use existing relationships as accelerants; build new ones from cold where they don't exist. Demonstrate that you can produce pipeline in accounts where you start with zero warmth.
- Maintain disciplined account plans with named economic buyers, identified internal champions, documented compelling events, and mutual close plans.
Help define the strategic 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 leadership 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 strategic 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 scale
- 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.
Represent Monstro externally
- Be a credible voice with strategic 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 strategic 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: Institutional credibility and navigation — the ability to get a deal through a bank's process, not just to a bank's door.
You bring deep bank credibility: current executive relationships, and a working fluency in how procurement, security, risk, compliance, and the executive buying process actually operate inside a bank — fluency specific enough that you can describe the mechanics (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 the generalities. You use that fluency to translate what Monstro does into language that makes a bank comfortable moving.
This role is valuable only if you remain a true operator — someone who personally runs discovery, negotiation, and deal orchestration, not someone who opens a door and expects the deal team to take it from there. In diligence, we will specifically test whether your value is a live, current network you can still activate and work — not a historical Rolodex — and whether you have a track record of compressing bank sales cycles rather than simply surviving them or becoming captive to the bank's own process and pace. We are looking for someone who can point to a specific deal where they moved a bank from first meeting to signature meaningfully faster than that institution's norm, and can explain exactly how: who they identified as the real economic buyer early, how they ran security and business workstreams in parallel rather than sequentially, how they pre-wired the procurement path before formal RFP stage.
The known risk with this profile is becoming captive to bank process — accepting the bank's timeline and caution as fixed rather than something to actively manage down. We are hiring specifically to counter that risk: this is a seller who uses institutional credibility as leverage to move faster, not as a reason to slow down.
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.
- Within 12 months: multiple closed platform agreements at $10M+ in usage commitments, generated through a balanced mix of existing relationships and new pipeline built 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 strategic 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.
What We're Looking For
- A senior individual contributor, not a sales manager. You have personally carried a number and closed $3M–$5M ACV deals (contributing to $10M+ multi-year platform commitments) into Tier-1 or large regional financial institutions. Former bank-side leadership experience is a significant plus, but only if you have subsequently proven you can originate, negotiate, and close enterprise technology deals from a cold start.
- Demonstrated repeatable sales motion. You can walk through how you build pipeline from cold, how you qualify, how you advance, and how you close — with specifics, not slogans. You have closed deals in accounts where you had no pre-existing relationship at the start of the cycle.
- Operator mindset. You are energized by ambiguity. You have sold at an early-stage or new-category company before — ideally where the deck, the case studies, and the pricing model didn't fully exist yet — and you helped build them. You write your own follow-ups, run your own discovery, and don't wait for enablement to ship.
- Financial services depth. Real working knowledge of bank infrastructure, operational realities, security posture, and regulatory regimes. You have personally walked deals through bank procurement, InfoSec, and risk review, and lived to tell about it — and you can talk about compressing that process, not just enduring it.
- Executive credibility. You hold your own in C-suite engagements with CEOs, Presidents, CIOs, CTOs, Chief Digital Officers, Chief Risk Officers, and Heads of Wealth or Trust at US middle-market and regional financial institutions. You translate technical and regulatory value into commercial outcomes the executive cares about.
- Technical literacy. Comfortable engaging substantively on cloud, data architecture, APIs, AI governance, and security frameworks. You can hold a technical conversation without a sales engineer in the room.
- Data-driven self-management. You run your own pipeline like an operator runs a P&L: clean stages, honest forecasts, weekly inspection, and ruthless prioritization of where your time goes.
- Comfortable building the playbook, not just executing one. You are excited about helping shape narrative, pricing, segmentation, and motion alongside leadership — and producing the artifacts that the next ten sellers will use.
- US travel readiness. Willing to travel substantially across the US to lead executive engagements and deal orchestration as the pipeline demands. New York-based with regular travel to major US financial hubs (Charlotte, Atlanta, Dallas, Chicago, Minneapolis, San Francisco, and regional markets where target banks and credit unions are headquartered).
How We Will Evaluate You
Because we have seen the failure mode before — sellers whose primary asset is a network they no longer actively work, or who accept long bank cycles as immovable rather than something to engineer around — the process is calibrated specifically to distinguish a current operator-seller from a relationship-only hire. Expect to:
- Walk us through 2–3 specific deals end-to-end from the last 12–18 months, including how pipeline was built, 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 bank's typical sales cycle, and explain the specific mechanism — not general effort, but what you actually changed about the sequencing, the stakeholders involved, or the procurement path.
- 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.
- Describe what happens after you make an introduction — who runs discovery, who negotiates, who owns the close — to confirm you remain hands-on through the full cycle.
- 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 a long-tenured relationship seller whose primary value is a historical Rolodex, or for someone who arranges an introduction and expects the company to run the deal from there. A warm network is a real accelerant — but only alongside someone still energized to personally originate, negotiate, and close.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 brand that opens every door before they can perform.
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.
A Note on Interviewing: We sometimes use AI note-takers to help us transcribe interview notes, so we can be more present in your interview. If you’d like to opt out of us using automatic transcribers, please note this in the free text field in your application; otherwise we’ll take your application as confirmation that you’re happy for us to use note-takers (whether added to video calls or in the background).
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.
