About Careertakes

👉 Important disclosure: Careertakes is a third-party recruiting platform supporting this hiring process. If selected, you will be employed directly by our client, Technology, Information and Internet.

Applicants for this role may also receive access to additional matched opportunities through the Careertakes platform.

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What You’ll Do

Confidential Client is hiring a Forward-Deployed Technical Product Manager who will sit at the intersection of client-facing strategy and engineering delivery. You will embed with enterprise clients to turn ambiguous AI requests into production systems that change how teams operate.

• Own the client relationship for complex, high-value engagements — earn trust across org charts and keep expectations grounded.
• Translate fuzzy business goals into clear outcomes and engineerable requirements; own the outcome through delivery.
• Rapidly prototype solutions (we use Claude and similar models) to test assumptions with real users before committing engineering effort.
• Serve as the bilingual bridge between ops and engineers — explain tradeoffs (RAG pipeline vs. rules engine, etc.) and drive pragmatic technical decisions.
• Run multiple engagements (2–3) concurrently, prioritizing client needs and shielding engineering focus when required.
• Build internal AI-driven tooling and agents to automate project management, risk detection, and repetitive workflows.
• Help define how the firm runs engagements and scales its services — you’ll shape the practice, not just execute projects.

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What You’ll Bring to the Team

• 2+ years in a hybrid product/technical role (product management, technical project management, solutions engineering, or an engineering role with heavy stakeholder ownership). Consulting/services experience counts.
• Strong technical fluency — you can read code, understand system architecture, and discuss build-vs-buy tradeoffs credibly.
• Comfortable leading client conversations and navigating scope/tradeoff discussions with clarity and candor.
• AI-native: you’ve built with AI tools, prototyped solutions (Claude or similar), and automated parts of your workflows — not just experimented.
• Outcome-oriented: you measure success by the change delivered to the client, not by deliverables produced.
• Scrappy, curious, and willing to iterate quickly. Domain knowledge in wealth management/financial services is optional — we’ll teach the domain.

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Compensation & Requirements

• All-cash compensation range: $130,000 to $200,000 per year.
• Employment type: Full-time.
• Work location: Hybrid from Chicago with openness to fully remote candidates outside Chicago.
• Requires US work authorization; we cannot sponsor visas.

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Our Workplace

Confidential Client operates like a small, high-rigor engineering firm focused on delivering production AI systems for wealth-management clients. Expect a collaborative environment with frequent pairing, blameless postmortems, and a culture that values learning, candor, and operational excellence.

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Hiring Process

We keep the process fast and respectful of your time:

• Intro call (45 minutes).
• Team interview with founders, including a working session on a realistic engineering problem.
• Decision and offer.

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Keywords & Fit

This role is best for technically fluent product leads who enjoy embedded client work, rapid prototyping with AI, and owning outcomes end-to-end. If you’re excited to shape a growing practice and move quickly, apply even if you don't match every bullet.

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Equal Opportunity & Hiring Transparency

Careertakes and our client are Equal Opportunity Employers committed to building a diverse and inclusive workforce. We prohibit discrimination or harassment of any kind. To support a fair and efficient hiring process, AI tools may be used to assist with application review or resume screening. These tools do not replace human decision-making. Final hiring decisions are made by people.

If you have questions about how your data is used, please contact us directly.