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:

• 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.
• 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