Now Hiring - Performance AI - Enterprise Account Executive in Chicago, IL

Full description of the position

Enterprise Account Executive Regulated Finance / Operations AI Performance AI i s hiring a Enterprise AE to sell Edge, our governed AI platform for regulated finance and operations-heavy companies. This is a full- cycle, net-new revenue role for a seller who can self-source pipeline, sell to CEOs/CFOs/COOs/CIOs, run discovery, demo the product, navigate IT/security review, and close $100K+ production deals. This is not an inbound closing role. This is not a management role. This is for a builder who can create demand before the sales machine is fully built. Location Fully onsite at Prudential Tower in Chicago. What Edge Does Edge helps companies turn scattered business knowledge across Microsoft 365, email, documents, spreadsheets, QuickBooks, databases, and internal systems into secure, usable answers and reports. Customers use Edge to reduce manual search, reporting work, audit prep, document review, and operational knowledge bottlenecks. The Sales Motion We sell direct production deployments, not vague free pilots. The right candidate can identify real business pain, qualify hard, build urgency, manage multi-stakeholder deals, and package clean commercial scope without overpromising custom work or roadmap features.

What You Will Do

• Build your own outbound pipeline into regulated finance and operations-heavy companies.
• Prospect CEOs, CFOs, COOs, CIOs, CTOs, and IT leaders.
• Run discovery calls and quantify business pain.
• Demo Edge around real customer use cases.
• Navigate IT, security, procurement, and multi-stakeholder buying processes.
• Package $100K+ production deals using approved software, rollout, connector, training, and security line items.
• Maintain clean CRM hygiene, accurate forecasts, and clear next steps.
• Push back on bad-fit customers, vague pilots, excessive discounting, and unapproved custom requests.
• Work with Product and Implementation to ensure sold scope matches delivered scope. Target First-Year Outcomes
• $600K+ in new ARR.
• $1M+ in first-year new-logo TCV.
• 5+ net-new production customers.
• $2.4M+ in qualified pipeline created.
• Clean scope discipline with no unapproved custom promises. Required Experience
• 5+ years of B2B SaaS closing experience.
• Proven success closing $100K+ ACV or first-year TCV deals.
• Must have self-sourced meaningful pipeline, not just closed inbound or SDR-generated opportunities.
• Experience selling into regulated, complex, or operationally heavy industries.
• Experience selling to executive buyers and technical evaluators.
• Strong discovery, qualification, and deal-control discipline.
• Ability to sell business outcomes, not just software features.
• Comfort discussing data access, permissions, integrations, IT review, security review, and implementation scope.
• Ability to run a credible demo without engineering on every call.
• Strong CRM and forecast discipline. Strong-Fit Backgrounds You may be a strong fit if you have sold finance workflow, compliance/GRC, BI/reporting, analytics, enterprise search, document automation, RPA, cybersecurity, vertical SaaS, AI, data, or workflow automation into mid-market or enterprise buyers. Not a Fit This role is probably not a fit if you:
• Need SDRs to create most of your pipeline.
• Mainly close inbound or partner-generated deals.
• Prefer mature brand demand over early-market selling.
• Rely on sales engineers for most technical conversations.
• Dislike outbound prospecting.
• Discount early instead of creating urgency through business pain.
• Sell roadmap features as live capabilities.
• Want to manage a team before personally closing revenue.
• Avoid CRM hygiene, next steps, deal notes, and forecast discipline.

Compensation

Base: $120K$130K OTE: $250K Commission: based on eligible new-logo cash collected

Benefits

: Health, Dental, vision, life, 401K, PTOs, sick leaves, Gym Why This Role Matters Companies want AI, but regulated buyers cannot use uncontrolled tools against sensitive business data. Edge gives them a safer way to use AI across approved systems, documents, spreadsheets, and workflows. The right seller will help Performance AI turn Edge into a repeatable enterprise sales motion. Pay: $120,000.00 - $130,000.00 per year

Benefits

:

• 401(k)
• Dental insurance
• Health insurance
• Life insurance
• Paid time off
• Vision insurance Location:
• Chicago, IL 60601 (Preferred) Ability to Commute:
• Chicago, IL 60601 (Preferred) Work Location: In person