Director, Enterprise Accounts - US Middle-Market & Regional Banking

Job Description

Job Description

About Monstro

Monstro is the operating system for governed financial intelligence. We build governance and intelligence infrastructure that enables artificial intelligence to operate safely, explainably, and at institutional scale.

We exist because the level of financial guidance historically available to a small group should be accessible to many more people. By combining AI with deep institutional infrastructure, we help financial institutions deliver more personalized, responsible, and life-changing financial support to millions of individuals.

We're building mission-critical systems in a highly regulated domain, and we care deeply about doing it right. If you're motivated by meaningful problems, high standards, and shaping infrastructure that improves financial outcomes, you'll feel at home here.

While our Strategic Accounts team pursues Monstro's largest transformational engagements with Tier-1 global banks, the Enterprise Accounts motion drives broad platform adoption across US middle-market and regional financial institutions — community and regional banks, super-regionals, credit unions, mid-sized wealth and asset managers, and trust companies — through enterprise platform contracts in the $5M–$15M ACV range.

We are hiring a Director, Enterprise Accounts to be the first dedicated platform seller on this motion. 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.

Hiring under this role is a downstream outcome, not the job. As Monstro grows, this seller may have the opportunity to scale into a player-coach or organizational leadership role. The bar to get there is closed revenue. We are not hiring a manager who will hire sellers; we are hiring a seller who can manage sellers later — once they have personally proven the motion.

This is Monstro's first dedicated Enterprise Accounts hire. US middle-market and regional financial institutions represent thousands of addressable buyers — banks, credit unions, wealth managers, and trust companies — that need governed financial intelligence but cannot wait for, or justify, a Tier-1-scale transformation program. The first wave of $5M–$15M ACV platform agreements is what converts Monstro from a capable solution into a trusted enterprise standard across this segment. The seller who lands those deals defines the playbook for everyone who follows.

Beyond near-term bookings, this hire surfaces enterprise 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.

Personally close platform deals

• Own a quota. Personally lead pursuit and close of $5M–$15M ACV platform agreements with US middle-market and regional financial institutions — community and regional banks, super-regionals, credit unions, mid-sized wealth and asset managers, and trust companies.
• 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 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, CRO, 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 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.

Represent Monstro externally

• Be a credible voice with enterprise 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.

• 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: 8–12 closed platform agreements in the $5M–$15M ACV range, generated through a balanced mix of existing relationships and new pipeline you 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 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.

• Senior individual contributor, not a sales manager. You have personally carried a number and personally closed $3M–$15M+ ACV platform deals into Tier-1 or large regional financial institutions. References will validate that you, specifically, drove those wins.
• 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.
• 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.
• Background. Likely an early or top-performing enterprise seller at a company that sells platform, core banking, or data infrastructure software into US middle-market and regional financial institutions (e.g., nCino, Q2, Alkami, Jack Henry, FIS, Fiserv, Finastra, Hyland, MeridianLink, Backbase, Snowflake/Databricks FS verticals, Palantir Foundry, Oracle FSGBU, or a comparable financial-services-focused enterprise software business). The pattern we care about is what you closed and how, not the logo on your resume.
• 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).

Because we have seen the failure mode before, the process is calibrated specifically to distinguish operator-sellers from relationship-only hires. Expect to:

• Walk us through 2–3 specific deals end-to-end, including how pipeline was built, who the economic buyer was, what nearly killed the deal, and what your specific role was in saving it.
• 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.

• It is not a head-of-sales role. Team-building authority is earned through closed revenue.
• It is not a role for a seller whose pipeline plan is entirely a Rolodex. Relationships are an accelerant; they are not the strategy.
• 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.

This is a senior individual contributor role with executive-level total compensation, structured as a true closer's seat — 50/50 base/variable split, with uncapped accelerators designed so that top performers materially out-earn OTE on the strength of closed deals.

New York

• Base Salary: $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 at sustained over-attainment against the 8–12 closed-deal year-one plan
• Equity: 0.10% – 0.20% (pre-Series-A; subject to Board approval and standard four-year vesting with a one-year cliff)

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 $5M–$15M ACV range, a top performer is on a clear path to seven-figure total cash earnings.

Benefits include paid health, vision, dental, and disability coverage.

• Ownership & Impact: Shape the future of AI-powered finance — and the enterprise GTM motion that takes it to market — building a category-defining product used by 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: Speed, ownership, and impact. What most companies achieve in 90 days, we do in 45.

*The posted ranges reflect base salary and on-target earnings for this role in New York. Final compensation will depend on a variety of factors including experience, skills, internal leveling, and market conditions, and will be offered within the stated ranges in accordance with applicable pay transparency laws.

If you're a senior enterprise seller who would rather close the next bank than manage the people who do — and who is energized by building the motion alongside leadership in the US middle-market and regional segment — we'd like to meet you.