Founding Account Executive

Found AI; Chicago (IL); Hybrid; USD 130,000 - 155,000; Full time

Benefits offered by this job

Equity

Ramp support

Benefits

Job summary

Found AI is seeking an experienced enterprise salesperson in Chicago to lead new revenue from first contact to signed contract. You will co-sell with the founder on live deals and convert design-partner conversations into paid engagements, building a repeatable motion for the team.

You’ll operate in a hybrid downtown Chicago office, travel up to 40%, and leverage your AI knowledge to discuss ROI and value with C-level buyers. A quota-driven, early-stage startup sale mindset is essential.

Qualifications

• 5+ years closing complex, multi-stakeholder mid-market deals from first touch to signature with verifiable quota attainment.
• Experience selling highly technical products and early/ambiguous offerings.
• Ability to hold substantive business conversations with C-level leaders (CIO, CFO) and secure the next meeting.
• Knowledge of AI technology and ability to discuss ROI vs alternatives.

Responsibilities

• Own new enterprise revenue from first conversation to signed contract.
• Convert design-partner conversations into paid engagements and build repeatable sales motion.
• Create a forecast leadership can plan against and develop an early sales playbook.

Skills

5+ years B2B sales

C-level conversations

ROI selling

AI knowledge

Job description

Location

Downtown Chicago, hybrid - 3 days a week (flexible)

Reports to

Go-To-Market Lead, works closely with the Co-Founders

Compensation

$130K–$155K base, $270K–$310K OTE (roughly 50/50 base and variable) + ramp support + equity + benefits

About Found

Companies run on complex, invisible context— institutional knowledge that standard internal systems miss. Without this context, enterprise AI becomes an expensive generator of generic responses that fail to scale. Found captures your unique business context (your data, decisions, and frameworks) and builds it into a compounding Context Graph, resulting in more accurate, secure, and cost-efficient intelligence. From this foundation, our Solutions Team deploys autonomous AI systems into key business functions to capture slipped value. Our success aligns with yours as we focus on outcomes generated, not seats or tokens. We're venture-backed, working with early design partners, and selling into the office of the CFO and CIO.

Why this role exists

Today the founders run every deal. That works for the first handful of design partners and breaks the moment we want to grow faster than one calendar allows. This is the first dedicated sales seat. You take the design-partner conversations we’re already in, turn them into paid engagements, and build the repeatable motion the next sellers will run. If you do this well, Found stops being founder-gated on revenue.

What You’ll Deliver

First 90 days

• Co-sell second chair with the founder on live deals, then take the active design-partner pipeline end to end, running discovery and audit-scoping conversations yourself.
• Convert at least one design partner into a paid engagement.
• Write down the buyer, the real objections, and what moves a CFO from interest to signature.

First 12 months

• Carry and hit a quota built on closed audit engagements and the platform expansion that follows them.
• Turn the founder-led pitch into a playbook two new reps can run without you in the room.
• Self-source qualified pipeline that covers the number with room to spare, without waiting on marketing or the founders.

What You’ll Own

• New enterprise revenue, from first conversation to signed contract.
• Design-partner conversion: turning access-for-shaping relationships into paid engagements.
• The deal motion for a C-level (CIO, CFO), audit-led enterprise sale.
• The feedback loop from the field into product and pricing decisions.
• The early sales playbook and the data that proves it repeats.
• A forecast the leadership team can plan against.

Must-haves

• 5+ years of B2B sales experience, closing complex, multi-stakeholder mid-market deals from first touch to signature, with quota attainment you can state and back up.
• You have recent but substantial experience selling highly technical products
• You’ve sold something early or ambiguous, before the category or the playbook existed.
• You can hold a substantive business conversation with a C-Level leader or head of operations and earn the next meeting.
• You sell on ROI against the customer’s real alternative, including doing it themselves, and you hold price under discount pressure.
• You tell the truth about where a deal actually stands, including the deals that are dying.
• You are knowledgeable about AI technology.
• Must be able to work a 3-day flexible hybrid schedule in a downtown Chicago office.
• Must be able to travel up to 40%, starting in the Midwest.

Nice-to-haves

• You’ve sold into technology, data, finance, or operations teams.
• You’ve been a first or early sales hire before.
• You understand enterprise AI or data infrastructure well enough to go deep with a technical buyer.
• You use AI in your day-to-day work.
• You have successfully sold AI solutions.
• You have worked in an early-stage startup in a sales capacity

Equal opportunity

Found AI is an equal opportunity employer. We hire on evidence of the work and the values above, not pedigree. If you read the must-haves and you’re close but not a perfect match, apply anyway and tell us why you’d be good at this. The calibration above means we’d rather assess than screen you out. We’ll provide reasonable accommodation in the hiring process on request.