Account Executive (Mid-Market)

Most enterprises cannot describe how their own work gets done. Fluency fixes that.

We capture how work actually happens across an organization, beneath the tools and across the systems, and turn it into structured intelligence executives can act on. Customers use Fluency to find where automation and AI should be deployed, prove whether transformation is delivering results, and see operational reality at a level that was previously invisible.

We work with Fortune 10 companies. We recently closed a US$6M seed led by Accel, with participation from DST Global Partners. We are building the team in San Francisco now.

The role

Founding mid-market AE. Full sales cycle into 1,000 to 5,000 employee enterprises.

You will sell to COOs, CIOs, and CEOs, often before they have language for the problem. There is no established category for what Fluency does. You will help create it.

What the work looks like

• Outbound-heavy pipeline generation. Inbound exists, and you will be paired with a BDR, but hunting is still a core part of the role.

• Discovery with executive and technical stakeholders, focused on identifying latent operational pain rather than running qualification checklists.

• Pilot-first sales motion. Deals start with paid, tightly scoped pilots against a specific use case. You design these with the customer and convert them to enterprise agreements.

• Post-pilot expansion. The product compounds inside organizations through new business units and new use cases. Early customers should become your biggest accounts.

• Shaping the sales motion alongside founders. Positioning, messaging, objection handling, and pricing are all unfinished. You will help build them.

• Travel for demos, workshops, and executive meetings when required. Expect monthly or more frequent travel depending on deal activity.

Deal mechanics today

• Buyers: COO, CIO, CEO, Head of Transformation, Head of Operations

• ACV: six figures minimum, expanding from there

• Sales cycle: typically two to four months through pilot, with some deals closing in under six weeks; longer for full enterprise conversion.

• Pilots are paid and scoped to a single business unit or process

• Expansion is driven by proving value in one area and rolling across the org

This will evolve. You will help shape it.

Who does well here

People who have built pipeline from nothing. Ex-founders, first or second AEs at startups. For this role, we cannot elevate someone coming from a BDR track - you need to have owned a revenue number with operating experience. People who can hold a room with a CEO and get into the weeds on pilot design. People with evidence of obsession with something.

You’ve originated and closed 6-figure plus deals.

What specifically wins in this role: executive discovery, translating technical capability into business value, pilot scoping and delivery, political navigation across multiple stakeholders, land-and-expand discipline, and creating urgency without brand or precedent.

This is not a role for someone who needs a playbook handed to them or who sells best in defined markets with known products.

Compensation

• Base: US$125K | OTE: US$250K, uncapped

• $10k annual health coverage and weekly meal stipend

• Substantial early-stage equity

Process

Resume screen → founder conversation → live deal simulation → paid work trial on a real sales motion → offer.

This role is in-person in San Francisco. No hybrid or remote.