Senior Product Manager - AI Applications

Reynolds and Reynolds is seeking an experienced Senior Product Manager to drive the vision, strategy, and execution of AI-powered features in our CRM and DMS applications. Your work will shape core tools that dealership staff rely on daily. You'll influence decisions about AI model selection, hosting architecture, cost structures, and delivering business impact at scale.

You'll collaborate closely with engineering and data science teams, evaluating and selecting between open-weight models, hosted solutions, and emerging AI capabilities. This individual contributor position offers significant scope and autonomy. As our subject matter expert on applied AI, you will shape our product roadmap, steer vendor decisions, and help define pricing strategies.

Core Responsibilities

Own and execute the roadmap for AI-enabled features across our CRM and DMS platforms

Evaluate and compare open weight and hosted models on metrics including quality, latency, cost, and risk

Lead build-versus-buy decisions for hosting and fine-tuning AI/ML models

Define objective evaluation methods to measure feature effectiveness for automotive dealers

Develop clear requirements and provide guidance to engineering teams, facilitating collaborative decision-making

Manage relationships with model and infrastructure vendors, including alignment, negotiation, and escalation

Collaborate with Legal to navigate data usage, privacy compliance, and AI disclosure regulations

Integrate cost and efficiency analysis into product recommendations and business cases

Mentor and support early-career product managers through feedback and review (no direct reports)

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Requirements

5+ years of product management experience, with at least 3 years directly owning AI or machine learning products

Deep understanding of open weight models and the trade-offs between self-hosting and API-based solutions

Proven experience delivering LLM-based features: prompt engineering, retrieval augmentation, tool integrations, and implementing guardrails

Demonstrated expertise in model evaluation (test sets, benchmarking, quality metrics)

Ability to converse fluently with engineers about technical factors such as latency, rate limits, and context windows (no coding required)

Strong grasp of usage-based economics and cost structures

Experience in automotive retail technology or dealership software (highly valued but not required)

Benefits

Medical, dental, vision, life insurance, and a health savings account

401(k) with up to 6% matching

Professional development and training

Promotion from within

Reynolds offers a hybrid work schedule, based on position eligibility. Following completion of your training period, eligible associates may work-from-home up to two days per week.

Paid vacation and sick days

Eight paid holidays

Referral bonuses

Reynolds and Reynolds promotes a healthy lifestyle by providing a non-smoking environment. Reynolds and Reynolds is an equal opportunity employer.

5+ years of product management experience, with at least 3 years directly owning AI or machine learning products. Deep understanding of open weight models and the trade-offs between self-hosting and API-based solutions. Proven experience delivering LLM-based features: prompt engineering, retrieval augmentation, tool integrations, and implementing guardrails. Demonstrated expertise in model evaluation (test sets, benchmarking, quality metrics). Ability to converse fluently with engineers about technical factors such as latency, rate limits, and context windows (no coding required). Strong grasp of usage-based economics and cost structures. Experience in automotive retail technology or dealership software (highly valued but not required)

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