Senior Product Manager

Red Oak

31d•Onsite

About The Position

We're looking for a Senior Product Manager to own the AI workstream within our flagship product, but more importantly, drive us toward AI-first delivery and capabilities. This is not a role about bolting a chatbot onto existing features. It's about reimagining how compliance reviews are done, how to surface insights for content authors and compliance reviewers, and how firms stay ahead of regulators — all powered by intelligent, supervised Agentic automation. You'll work at the intersection of cutting-edge AI capabilities and the highly regulated, relationship-driven world of wealth management. You'll partner daily with teams across engineering, strategy, and the go-to-market. And you'll have a direct line to our clients — compliance officers, marketers, sales, and heads of operations who will use what we build under your direction.

Requirements

Experience: 5+ years of product management experience, with at least 2 years directly shipping AI/ML-powered products in a B2B enterprise SaaS environment.
AI Fluency: Working knowledge of LLMs, RAG architectures, agentic workflows, and prompt engineering — you don't need to write code, but you need to speak the language fluently with engineers.
Discovery Skills: Strong discovery and research instincts — comfortable running user interviews, shadowing operational workflows, and synthesizing insights into crisp product strategy.
Impact: Demonstrated track record of AI features that users actually adopted — you have before-and-after impact stories to tell. Comfortable operating in a fast-moving, resource-focused environment at ~125 people.
Communication: Excellent written and verbal communication; able to produce clear PRDs, executive briefs, and business cases, and present confidently to C-suite stakeholders.

Nice To Haves

Experience with compliance, supervision, or RegTech products; financial services, fintech, or wealth management; multi-agent AI systems; data pipelines, vector databases, or document intelligence platforms; or enterprise AI sales cycles including security reviews and vendor risk assessments.

Responsibilities

Product Strategy & Roadmap: Own the AI product roadmap end-to-end — from discovery through delivery — for our Compliance solution. Evaluate and prioritize AI opportunities based on client impact, technical feasibility, regulatory risk, and business value.
Success Metrics: Define, track, and communicate success metrics for AI features: accuracy, adoption, time-to-insight, exception rates, and model drift.
Discovery & Client Engagement: Conduct ongoing discovery with wealth managers, compliance officers, sales, and technology buyers to understand their workflows, pain points, and AI readiness. Translate client needs into clear product direction — including PRDs, opportunity assessments, and executive-ready narratives.
Responsible AI Practices: Champion responsible AI practices in client conversations — addressing bias, hallucination risk, data privacy, and auditability proactively. Design for human-in-the-loop workflows where AI accelerates and humans supervise.
Cross-Functional Execution: Partner with engineering to shape AI system design and ensure requirements are technically grounded. Collaborate with design to create AI-native UX patterns with appropriate confidence indicators, exception queues, override controls, and audit trails.
GTM Partnership: Work closely with sales and marketing to position AI capabilities competitively, enable the field, and support enterprise deals involving AI use cases.
Regulatory Stewardship: Navigate the regulatory environment (SEC, FINRA, ERISA, state regulators) to ensure AI features are designed with compliance, auditability, and human oversight baked in.
Vendor Evaluation: Evaluate AI/LLM vendors, APIs, and infrastructure partners with an eye toward data residency, governance, and contractual risk. Stay current on AI regulatory developments affecting financial services.