Head of Enterprise Accounts / Regional Lead

About the role

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 hiring sellers who can manage sellers later — once they have personally proven the motion.

What 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.

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
• 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
• 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
• Scale the team, when the deals justify it

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
• 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, API