Forward Deployed Specialist, CRM - Central at Whirl AI in Chicago

Company Description

Whirl AI helps Enterprise IT organizations deliver business change faster. Our platform gives enterprise teams AI agents grounded in a deep, continuously updated understanding of how their systems actually work - compressing discovery and documentation from weeks to hours without sacrificing quality or control. We are early-stage, moving fast, and building the team that will define how Enterprise IT operates in the AI era.

Please note: We are prioritizing candidates in the Chicago metro area for this role. Candidates within Central Time will be considered.

Key Responsibilities

Solutions / Pre-Sales:

• Value Selling: Partner with Sales leadership on complex enterprise deals. Handle deep technical and AI security objections and show how Whirl's agentic AI platform solves the customer's specific problems to move deals to close.

• Tailored Demos & Workshops: Build and deliver demos using the customer's real scenarios, and run technical workshops that tie Whirl's capabilities to clear business outcomes for IT and business leaders.

• Solution Design: Lead technical discovery, map the customer's enterprise systems and priorities to the right Whirl use cases, and define POC scope and success criteria with the customer.

Customer Engineering:

• Technical Deployment: Connect Whirl to customer systems and lead security and AI governance reviews with IT and security teams, covering access, data handling, and how agents operate. Troubleshoot issues in live environments.

• Custom Solutions: Design and build custom workflows, artifacts, and playbooks for each customer's use cases. Turn what works into repeatable templates that can be reused across teams and customers.

• POC Delivery: Run 30-to-90 day proof-of-value sprints against agreed success criteria to prove Whirl's value before contract.

• Rollout & Enablement: Roll Whirl out across teams and roles. Train users, build enablement materials, and coach champions so teams build Whirl into their daily work.

• Account Management & Growth: Own the post-sale relationship and run regular value reviews. Partner with Sales to drive renewals and expansion into new teams and use cases.

• Partner Delivery: Work with implementation partners and system integrators on joint projects and build handoff playbooks so delivery can scale.

Voice of the Customer:

• Field Feedback: Capture customer priorities, friction, and unfiltered feedback from day-to-day work with users and leaders.

• Product Input: Combine that feedback with usage data to turn it into prioritized, evidence-backed requests. Work directly with product and engineering to shape the roadmap and test new capabilities with customers.

Required Experience & Competencies

• Experience: 5+ years in a client-facing Customer Engineering, Solutions Engineering, Enterprise Architecture, or business-aligned Forward Deployed Engineer/Specialist role.

• Technical Fluency: Strong enough grasp of enterprise systems, integrations, and data to earn credibility with architects and engineers, and to understand how a customer's business actually runs on their systems.

• Commercial Polish: Proven track record of navigating complex corporate structures, commanding the room with CXOs, managing intense timelines, and translating complex technology into clear commercial value.

Preferred Qualifications

• Education: Degree in computer science, engineering, or a related field, or equivalent practical experience.

• AI Expertise: Hands-on experience building with or deploying LLMs and agentic AI systems.

• Workflow Automation: Familiarity with AI coding tools like Claude Code and building AI-powered workflows.

• Enterprise Ecosystems: Proficiency with enterprise platforms such as Salesforce or Oracle Fusion.

Why Join us

• Own meaningful technical decisions at the ground floor of an AI company targeting a massive market

• Work directly with founders and have immediate, visible impact

• Competitive compensation including equity and benefits (100% employer-paid health plan coverage for employees)

Whirl AI is committed to equal employment opportunity. All hiring decisions are made on the basis of qualifications, merit, and business need - never on race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status, or any other characteristic protected by law.

We build better products because our team doesn't all think the same way, and we want that to keep being true. Show up as yourself. We can't wait to meet you.