Head of Enterprise Accounts / Regional Lead

About Monstro

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. It gives every client the experience of a personal advisor: bringing together their full financial picture, identifying what matters, and delivering personalized guidance across investments, tax, retirement, insurance, legal, and more.

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. Every recommendation reflects the institution's own views, policies, and permissions. Every output is auditable, traceable, and reversible, and client data stays under the institution's control. Generative AI shapes how advice is designed; 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. The challenge is to make advice 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 a hard problem, and it is the reason to be here.

You will work on technology that brings real financial advice to people who have rarely had access to it. You will be expected to think clearly, move with urgency, hold a high bar, 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

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 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. Neither is a sales management role at the outset.

We are deliberately hiring two complementary — not identical — profiles:

1. A proven, modern enterprise technology seller who is currently selling cloud, data, AI, infrastructure, cybersecurity, fintech, or another complex platform into major banks. Highly driven, technically fluent, disciplined in how they build and manage pipeline, and accustomed to personally driving deals from origination through close.
2. An established banking commercial leader who brings deeper executive relationships and industry credibility inside financial institutions — but only if they are still a true operator. We are explicitly not looking for someone who can arrange a meeting and then expect the company to carry the deal from there.

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, technologically current, or willing to grind through the work an early-stage company demands. A warm network is an accelerant. It is not a substitute for being a current, active operator.

Hiring additional sellers or managers under either of these people is a downstream outcome, not the job. The bar to get there 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 — 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 $10M+ platform commitments is what converts Monstro from a capable solution into a trusted enterprise standard across this segment. The sellers who land those deals define the playbook for everyone who follows.

Beyond near-term bookings, these hires surface enterprise requirements back to Product, simplify large-deal complexity, and write 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 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 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.

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 strong data, AI, infrastructure, security, and fintech businesses selling into financial institutions.

We care less about your total years of experience and more about what you are doing right now:

• 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 (SEs, marketing, implementation) behind you?
• Are you genuinely prepared to build, not just execute inside a system someone else already built?

Profile 2: Banking Commercial Leader

You bring deeper, current 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 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.

Both profiles are held to 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, 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 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.

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 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).

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 — the process is calibrated specifically to distinguish current operator-sellers from relationship-only hires. 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.
• 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.
• For Profile 2 candidates specifically: 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.

What These Roles Are Not

• 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, or whose primary value is a historical network they no longer actively work. Relationships are an accelerant; they are not the strategy.
• It is not a role for someone who arranges an introduction and then expects the company to run the deal from there.
• 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?

• Ownership & Impact: Shape the future of AI-powered finance—building a category-defining product used by consumers and 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: Work in a culture that values speed, ownership, and impact—what most companies achieve in 90 days, we do in 45.

Compensation

These are senior individual contributor roles 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.

Why Monstro

• 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.

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 notetakers (whether added to video calls or in the background).

Ready to Build With Us?

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.