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Head of Sales

Job in Northern, Floyd County, Kentucky, USA
Listing for: Trusteai
Full Time position
Listed on 2026-10-10
Job specializations:
  • Sales
    B2B Sales, IT / Software Sales, Technical Sales, Business Development
Salary/Wage Range or Industry Benchmark: 180000 - 300000 USD Yearly USD 180000.00 300000.00 YEAR
Job Description & How to Apply Below
About eAI

eAI is building the governed execution layer for enterprise AI
.

As banks and regulated enterprises move AI agents from experimentation into production, they need infrastructure that controls what AI can access, what actions it can take, when human approval is required, and how every action is governed, monitored and audited.

eAI provides the governance and control infrastructure required to deploy AI safely across regulated environments.

We are looking for an exceptional Head of Sales to build our enterprise sales engine across financial services.

The Role

This is a hands‑on sales leadership role for someone who knows how to create pipeline, open strategic accounts and close complex enterprise technology contracts.

We are not looking for someone who only manages people who sell.

You will sell.

You will work directly with the CEO and technical leadership to identify target institutions, activate executive relationships, prospect into new accounts, lead discovery, develop opportunities, navigate complex buying processes, negotiate and close.

As revenue scales, you will build the sales organization around a repeatable enterprise sales motion.

What You'll Own
  • Own enterprise sales and new ARR generation.
  • Build qualified pipeline across banks, credit unions, fintechs and other regulated financial institutions.
  • Personally source and close strategic enterprise opportunities.
  • Leverage existing financial‑services relationships to create executive‑level conversations.
  • Develop new relationships within target accounts.
  • Sell to CIOs, CTOs, CISOs, Chief Risk Officers, Chief Data Officers, Chief AI Officers and other senior executives.
  • Lead executive discovery, product positioning and commercial conversations.
  • Navigate complex technical, security, risk, compliance, procurement and legal processes.
  • Build strategic account plans for priority institutions.
  • Develop a repeatable land‑and‑expand sales motion.
  • Maintain disciplined pipeline management and accurate forecasting.
  • Work with product and technical leadership to refine positioning, use cases, pricing and go‑to‑market strategy.
  • Develop strategic partnerships capable of generating qualified opportunities.
  • Recruit and build the broader sales organization as revenue scales.
What We're Looking For

We are deliberately setting a high bar.

You should have:

  • 10+ years of enterprise technology sales experience.
  • Significant experience selling into banks and regulated financial institutions.
  • A strong network of senior executives across financial services.
  • A demonstrated history of personally generating multi‑million‑dollar enterprise pipeline
    .
  • A demonstrated history of personally sourcing and closing six‑ and seven‑figure enterprise contracts
    .
  • Experience selling AI, SaaS, data infrastructure, cybersecurity, governance, risk, compliance, lending, core banking or other mission‑critical enterprise technology.
  • Strong technical fluency and the ability to engage credibly with sophisticated technology buyers.
  • Experience navigating complex, multi‑stakeholder enterprise sales cycles.
  • Strong executive presence and commercial negotiation skills.
  • Excellent pipeline management and forecasting discipline.
  • Experience operating in an early‑stage or high‑growth environment.
  • The ability and willingness to operate without a large existing SDR, marketing or sales organization.
The Profile

The strongest candidates combine four characteristics:

Connected — You have genuine relationships across financial services and can create conversations with senior executives.

Technical — You can credibly discuss AI, governance, data, risk, security and enterprise technology.

Hungry — You will prospect, follow up, travel, demo, negotiate and personally drive opportunities forward.

A Closer — You have repeatedly turned complex…

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