Senior Director, AI Product Strategy

Why Ryan?

• Hybrid Work Options

• Award-Winning Culture

• Generous Personal Time Off (PTO) Benefits

• 14-Weeks of 100% Paid Leave for New Parents (Adoption Included)

• Monthly Gym Membership Reimbursement OR Gym Equipment Reimbursement

• Benefits Eligibility Effective Day One

• 401K with Employer Match

• Tuition Reimbursement After One Year of Service

• Fertility Assistance Program

• Four-Week Company-Paid Sabbatical Eligibility After Five Years of Service

Ryan, LLC is an award-winning global tax firm that liberates its clients from the burden of being overtaxed. By freeing our clients’ capital, we make it possible for them to invest, grow, and thrive – concentrating on what they do best. In 2021, Ryan was named as One of the Best Places to Work by Glassdoor. Ryan has also been named one of the Fortune 100 Best Companies to Work For the past five years in a row.
We are on a mission to become the world’s trusted platform for tax, seamlessly delivering the right combination of software and expertise to become an intuitive extension of our clients’ tax capability.
This senior leader will be responsible for defining and delivering transformative AI-enabled solutions across multiple product lines. This individual will lead a cross-functional team driving machine learning, automation, and generative AI innovations that improve operational efficiency and create scalable value for clients. This role is perfect for a strategic thinker and operator who excels at converting advanced technology into business outcomes.
We are on a mission to become the world’s trusted platform for tax, seamlessly delivering the right combination of software and expertise to become an intuitive extension of our clients’ tax capability.
The Senior Director, AI Product Strategy is responsible for assisting with delivering a class-defining experience for the public facing look, feel and navigation for Ryan. They work as part of a team that defines, creates and lead the implementation and execution of innovative strategies that deliver a consistent and trusted experience for Ryan clients.
This role is perfect for a leader who has an ownership mentality for driving impact, pursues data-informed insights, focuses on customer empathy and product craft, and loves to learn and execute. To be successful in this role, you need to have a bias for action, and be comfortable guiding decision-making based on a combination of hard data and incomplete or ambiguous information. You understand how to balance long-term bets with quick wins.

Duties and responsibilities, as they align to Ryan’s Key Results:

• Lead the product strategy and roadmap for AI-first features, including ML-powered document processing, GenAI use cases (e.g., AskRyan), and decision automation tools.
• Partner with Data Science, Engineering, and UX teams to bring scalable and explainable AI capabilities to market.
• Drive discovery, experimentation, and delivery of AI models and LLM applications embedded into Ryan’s tax and compliance platforms.
• Define hypotheses and measurable KPIs for AI solutions; ensure model outcomes align with business goals.
• Own product lifecycle for AI features: data readiness, prototyping, testing, launch, post-release iteration.
• Guide the development of human-in-the-loop systems, AI safety protocols, and governance workflows.
• Collaborate with stakeholders on responsible AI principles (ethics, privacy, interpretability).
• Manage cross-functional delivery teams; build and prioritize backlogs for AI features and platform enablers.
• Communicate technical concepts, risks, and value clearly to both executive and non-technical stakeholders.
• Represent Ryan in AI partnerships, vendor selection, and thought leadership efforts.

Education and Experience:

• 10+ years in product management, with at least 3 years in AI/ML-enabled product development.
• Track record of launching AI features in enterprise SaaS, compliance tech, or data-intensive domains.
• Familiarity with NLP, classification models, embeddings, vector search, prompt engineering, and GenAI tools.
• Experience defining and monitoring AI model KPIs (precision, recall, confidence, bias).
• Proven ability to translate complex technical concepts into intuitive customer experiences.
• Skilled at balancing speed to market with regulatory compliance, data security, and ethical AI practices.
• Strong cross-functional leadership and product storytelling skills.

Bachelor’s degree or equivalent required. Minimum of 10 years of direct work experience in a product management capacity. Experience breaking problems down into component parts, analyzing data and creating hypotheses and MVPs against stated goals. Experience working across agile-based Software Development Lifecycle and processes.

               

Preferred Qualifications:

• Anticipates and proactively delivers expected results for executive leadership team
• Effectively solves problems
• Streamlines and improves processes
• Demonstrates initiative and provides complete follow-through on areas of responsibility
• Advanced written, visual and verbal communication skills
• Superior attention to detail
• Demonstrates accuracy and thoroughness
• Sense of urgency
• Demonstrates willingness to be flexible and adaptable to changing priorities
• Thrives working both independently and in a team-based environment
• Strong multitasking and organizational skills

Supervisory Responsibilities:

Requires supervisory responsibilities, including managing projects, training employees, assigning work, and making sound business decisions while representing the Firm.

Work Environment:

• ​ Standard indoor working environment.
• Occasional long periods of sitting while working at computer.
• ​ Must be able to lift, carry, push, or pull up to 30 lbs.
• ​ Position requires regular interaction with employees at all levels of the Firm, clients, and interface with external vendors as necessary.

Travel:

Standard indoor working environment.

Occasional long periods of sitting while working at computer. Must be able to lift, carry, push, or pull up to 30 lbs.

Position requires regular interaction with employees at all levels of the Firm, clients, and interface with external vendors as necessary.

Independent travel requirement: 25%.

Equal Opportunity Employer: disability/veteran