Head of Enterprise Accounts / Regional Lead

Head of Enterprise Accounts / Regional Lead

New York City, Hybrid
About Monstro

Monstro is a governed AI platform for regulated financial institutions. We give banks and wealth managers a way to deliver trusted advice digitally — to every client, not just the top tier. Institutions already have the relationships, data, and context to understand each client. Monstro turns that understanding into advice, delivering personalized guidance across investments, tax, retirement, insurance, legal, and more. For clients, this means clearer decisions and proactive support when life changes. For institutions, it means deeper relationships and more clients served consistently, with client data under the institution’s control. Every recommendation reflects the institution’s views, policies, and permissions. Every output is auditable, traceable, and reversible, and runtime execution is deterministic so outputs can be explained and stood behind.
The Role

While our Strategic Accounts team handles the largest transformational engagements, the Enterprise Accounts motion drives broad platform adoption across US middle‑market and regional financial institutions — community and regional banks, super-regional banks, credit unions, mid‑sized wealth and asset managers, and trust companies — with enterprise platform commitments of $10M+ in usage. We are hiring two Directors, Enterprise Accounts to build this motion from the ground up. These are senior individual contributor roles — quota‑carrying operator-sellers who personally close platform deals and help define the enterprise GTM motion as it scales. They are not sales managers at the outset.
We are deliberately hiring two complementary profiles:
A proven, modern enterprise technology seller

who sells cloud, data, AI, infrastructure, cybersecurity, fintech, or another complex platform into major banks. Highly driven, technically fluent, disciplined in building and managing pipeline, and accustomed to personally driving deals from origination through close.
An established banking commercial leader

who brings executive relationships and industry credibility inside financial institutions — but only if they are still a true operator.
What we are not hiring for: traditional, long‑tenured relationship sellers whose primary value is a historical Rolodex but who are no longer hands‑on or willing to grind through early‑stage work. A warm network is an accelerant, not a substitute for being a current, active operator.
Hiring additional sellers or managers under either of these profiles is a downstream outcome, not the current job. The bar to progress is closed revenue. We are not hiring managers who will hire sellers; we are hiring sellers who can manage sellers later — once they have personally proven the motion.
Why This Role Matters

This is Monstro's first dedicated Enterprise Accounts build‑out. US middle‑market and regional financial institutions represent thousands of addressable buyers needing governed financial intelligence that can’t wait for a Tier‑1 transformation. The first wave of $10M+ platform commitments will define the enterprise standard across this segment. The sellers who land those deals will define the playbook for all who follow.
Beyond near‑term bookings, these hires surface enterprise requirements back to Product, simplify large‑deal complexity, and create the first version of the repeatable platform motion—qualification, pricing, security posture, deployment shape, and expansion patterns. 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 and 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 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.
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.
The Two Profiles We're Hiring

Profile 1: Modern Enterprise Technology Seller

You are currently succeeding at a strong technology company — cloud, data, AI, infrastructure, cybersecurity, fintech, or a comparable complex platform — selling into major banks. Representative archetypes include current top performers at companies like Datadog, Palantir, Oracle, Snowflake, AWS, Google Cloud, Microsoft, and ServiceNow, among other data, AI, infrastructure, security, and fintech businesses selling into financial institutions.
What you are doing right now matters more than total years of experience:
What have you personally originated in the last 12–18 months?
Which banking buyers do you sell to, and how technical is the sale?
How do you create pipeline — and can you do it without a large‑company machine behind you?
Are you prepared to build, not just execute inside a system someone else built?
You bring executive relationships and industry credibility inside financial institutions. This profile 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 others to take it from there. In diligence, we will test whether your value is a live, current network you can still activate and work — not a historical Rolodex.
Both profiles share the same bar: personal origination, personal ownership of the deal cycle, and comfort operating without a mature sales machine underneath them.
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, sponsor, and next steps.
Within 12 months: multiple closed platform agreements at $10M+ in usage commitments, from a 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: upsell or cross‑sell from at least one closed account within 12 months of signature.
First version of the enterprise playbook shipped: ICP, qualification framework, discovery model, objection library, pricing posture, and security response templates.
At least two product enhancements influenced by your deal cycles, prioritized into the roadmap within 12–18 months.
What We're Looking For

Senior individual contributors, not a sales managers.

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 your role.
Demonstrated repeatable sales motion.

You can walk through how you build pipeline from cold, qualify, advance, and close with specifics.
Operator mindset.

You are energized by ambiguity, have built or sold at an early‑stage company, and write your own follow‑ups and discovery.
Financial services depth.

Real working knowledge of bank infrastructure, security, regulatory regimes, and procurement.
Executive credibility.

Comfortable in C‑suite engagements and translating technical value into commercial outcomes.
Technical literacy.

Comfortable discussing cloud, data architecture, APIs, AI governance, and security frameworks without a sales engineer.
Data‑driven self‑management.

You manage pipeline with clean stages and honest forecasts.
Comfortable building the playbook, not just executing one.

You help shape narrative, pricing, and motion and produce reusable artifacts.
Background.

Likely an early or top‑performing enterprise seller in software for US middle‑market/regional banks (examples: nCino, Q2, Alkami, Jack Henry, FIS, Fiserv, Finastra, Hyland, MeridianLink, Backbase, Snowflake/Databricks FS verticals, Palantir Foundry, Oracle FSGBU, etc.).
US travel readiness.

Willing to travel across the US to lead executive engagements. New York‑based with regular travel to major US financial hubs.
What Success Looks Like

Within 6 months: a qualified pipeline across 20–30 named accounts with identified buyers and next steps.
Within 12 months: multiple $10M+ platform deals closed.
How We Will Evaluate You

Expect a process designed to identify current operator‑sellers. You may be asked to:
Walk through 2–3 specific deals end‑to‑end from the last 12–18 months, including pipeline origins, buyers, challenges, and your role.
Show a 90‑day plan for a named bank with no pre‑existing relationships.
Discuss pricing posture, qualification criteria, and artifacts to build in your first 6 months.
What These Roles Are Not

Not a head‑of‑sales role. Authority is earned through closed revenue.
Not a role for someone whose value is a Rolodex; relationships are an accelerant, not the strategy.
Not a role for someone who relies on introductions and expects others to run the deal.
Not a role for someone needing a finished deck or polished materials before acting.
Why Monstro?

Ownership & Impact:

Shape the future of AI‑powered finance and the enterprise GTM motion that takes it to market.
Experienced Team:

Leadership with a track record of scaling companies from early stage to major exits.
Principles‑Driven Culture:

Speed, ownership, and impact—what others achieve in 90 days, we do in 45.
Compensation

Senior individual contributor roles with executive‑level total compensation, 50/50 base/variable, with uncapped accelerators. In New York: On‑Target Variable: $225,000 – $275,000; On‑Target Earnings: $450,000 – $550,000; Realistic Top‑Performer: $1,000,000 – $1,500,000+; Equity: 0.10% – 0.20% (pre‑Series A; vesting per policy). Commission accelerates above 100% and again above 150% with no cap. Additional milestone kickers apply for marquee logos and multi‑year commitments. The plan rewards closed ACV, not activity, with 8–12 closed deals per year in the $5M–$15M ACV range.
Benefits include paid health, vision, dental, and disability coverage.
Why Monstro

Ownership & Impact:

Shape the future of AI‑powered finance and the enterprise GTM motion.
Experienced Team:

Leadership with a track record of scaling.
Principles‑Driven Culture:

Speed, ownership, and impact.
*The posted ranges reflect base salary and on‑target earnings for this role in New York. Final compensation will depend on experience, skills, and market conditions.

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