Senior Product Manager, AI

atPaychexRemoteUS flagArizonaFull-timeProduct ManagerSenior$110k – $140k/year

Posted Aug 28

This is a fully remote position, open to applicants in Arizona.

📋 Description

• Take charge of product strategy and roadmap for AI-driven capabilities, workflow automation, data insights, integrations, and platform enhancements.

• Convert customer challenges, business objectives, technical opportunities, and operational limitations into product priorities.

• Establish MVPs, phased rollout strategies, success metrics, deployment plans, risk management strategies, and business cases.

• Determine when AI provides sustainable value compared to when rules-based or deterministic automation is more suitable.

• Collaborate with engineering teams to design, test, and launch AI features, copilots, assistants, agents, conversational interfaces, and intelligent workflows.

• Outline user journeys, permissions, tool interactions, guardrails, fallback mechanisms, escalation processes, confidence thresholds, and human-review requirements.

• Draft requirements that encompass prompts, context engineering, structured outputs, retrieval processes, workflow orchestration, model limitations, evaluation criteria, and release readiness.

• Create natural-language experiences over complex data with structured, defensible outputs.

• Set criteria for AI release readiness, including handling hallucinations, PII protection, audit trails, observability, rollback strategies, and user transparency.

• Utilize modern AI tools for research, synthesis, requirement gathering, analysis, and prototyping.

• Gain insights into customer workflows in areas such as screening, compliance operations, document management, monitoring, integrations, and regulated environments.

• Identify opportunities to unify fragmented workflows, data sources, partner systems, and customer operations.

• Collaborate with clients and internal teams on workflows, exceptional cases, compliance needs, operational challenges, and buyer priorities.

• Conduct customer discovery, stakeholder interviews, workflow analyses, competitive research, and market evaluations.

• Leverage feedback, support trends, usage data, sales insights, implementation challenges, and market signals to shape priorities.

• Monitor foundation model releases, agent frameworks, AI evaluation methodologies, and trends in workflow automation.

• Define personas, jobs-to-be-done, user journeys, problem statements, product hypotheses, and adoption risks.

• Lead cross-functional initiatives involving engineering, UX, operations, implementation, compliance, customer success, sales, and marketing.

• Manage risks associated with sensitive data, PII, bias, explainability, auditability, and human oversight.

• Establish AI governance protocols that include evaluation, monitoring, documentation, transparency, audit trails, and release controls.

• Define KPIs and AI-specific metrics for adoption, workflow completion, time savings, quality, satisfaction, risk reduction, efficiency, revenue impact, task success, acceptance, escalation, hallucination rates, trust, cost, and time saved.

• Develop evaluation strategies such as golden datasets, offline assessments, human reviews, LLM-as-judge, regression checks, shadow mode, staged deployments, and online experiments.

• Deliver a prioritized AI roadmap, risk-managed MVPs, customer-validated outcomes, production improvements, and enhanced post-launch AI practices within the first 6–12 months.


⛳️ Requirements

• 7+ years of experience in product management within B2B SaaS, workforce technology, compliance software, transportation technology, enterprise workflow software, data products, automation products, or a similar field.

• 1 to 2+ years of experience delivering AI/ML, generative AI, intelligent automation, conversational analytics, agentic workflows, or data-driven workflow solutions to actual users.

• Proven ownership of at least one AI-powered or agent-based feature.

• Strong technical proficiency in LLMs, prompt design, context engineering, retrieval-augmented generation, structured outputs, agent frameworks, evaluation methodologies, and the trade-offs between cost, latency, quality, and safety.

• Experience in defining product strategy, requirements, user stories, acceptance criteria, success metrics, rollout strategies, and post-launch iterations.

• Strong product judgment regarding the distinction between AI and deterministic workflow automation.

• Familiarity with sensitive data, regulated workflows, compliance-heavy products, high-trust customer environments, or enterprise systems.

• Excellent analytical, written, and verbal communication skills.

• Bachelor’s degree in business, computer science, engineering, data science, human-computer interaction, or a related field; equivalent experience will also be taken into account.

• Must have a dedicated, ergonomic workspace at home.

• Access to stable, reliable high-speed internet.

• Adequate lighting and minimal background noise for professional video calls and meetings.

• Ability to lift and carry up to 5 pounds occasionally.

• Ability to work effectively in an ergonomically suitable home environment.

• Successful completion of a background investigation and drug screening.

• Familiarity with AI tools, platforms, evaluation systems, APIs, integrations, data contracts, workflow orchestration, privacy, security, auditability, and enterprise data access patterns is preferred.


🏝️ Benefits

• Medical (with company contribution)

• Dental (with company contribution)

• Vision

• Employer-paid Life Insurance and Long-Term Disability

• Short-Term Disability

• 401(k) (with company match)

• Paid holidays

• Paid time off (PTO)

• Sick Time

• Pet insurance

• Fully remote work

• Opportunity to engage in AI, automation, integrations, and data-driven insights

• Direct collaboration with executive product leadership

• Background investigation and drug screening as part of the conditional employment offer

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