[Hiring] Director, Academy Product & AI @Guild

Role Description

Guild is hiring a Director of Product & AI to lead our Academy Product team. Guild's Academy product delivers short-form, employer-customized learning programs to frontline teams. Completion rates top 80%, customer NPS is strong, and the product is available globally. You'll own the full product and engineering org — setting vision, rapidly shipping features, and coaching a small, AI-fluent team that punches well above its weight.

You will lead both Product and Engineering/AI across both the learner and administrator experience, with five direct reports. This team will research, prototype and write production-grade software in close partnership with AI coding tools: using them to move faster, think bigger, and spend more time on the problems that actually require human judgment. You will play a critical role in continuing to champion this model, build a team culture around it, and lead with adaptability in an environment where the craft of both product and engineering is evolving in real time.

Outcomes You Will Drive:

• Academy completion & behavior change rates exceed 80%
• Academy customer NPS exceeds 80
• New product features are directly linked to revenue growth

What You’ll do to Achieve those Outcomes:

• Deeply understand the key inputs to your product vision: learner voice, administrator voice, evolving external landscape and opportunities to innovate and leverage AI.
• Deliver and evangelize (internally and externally) a product vision that reflects a thesis on what drives behaviour change in an organization and tangible differentiation from competitors.
• Make thoughtful prioritization decisions in both the long and short term.
• Drive alignment on product strategy, including engaging teams at all levels across Academy Success, Go-To-Market, and cross-functional executives.
• Champion the Academy product externally at conferences and events, internally within Guild, and directly with our customers.
• Lead and develop a high-performing, AI-fluent team of product managers and engineers.
• Champion and shape the team's AI-first culture.
• Guide the team's operating cadence, including planning, status updates, and retrospectives.

Qualifications

• Have shipped AI-workflow centered product in the last year and shown that it delivers value.
• Experience owning a holistic product roadmap and managing both product managers and engineers.
• A track record of shipping high-quality, production-ready software from discovery and design through implementation, rollout, and iteration.
• Genuine enthusiasm for AI-assisted design, prototyping and development.
• A knack for building cross-functional relationships across organizational boundaries.
• Strong collaboration and communication skills.
• A demonstrated commitment to inclusive, psychologically safe, engaged teams.
• A builder's mindset.

Requirements

• You're comfortable with ambiguity, energized by defining the playbook rather than following one, and willing to share what you learn — including what doesn't work.

Benefits

• Access to low-cost, high-quality health care options through Collective Health and Kaiser (due to coverage limitations, Kaiser is currently only available in CA & CO).
• Access to a 401k to help save for the future.
• Vacation policy to rest and recharge.
• 8 days of fully-paid sick leave, to take the time to heal and or recover.
• Family-friendly benefits, including 12 weeks of parental leave for non-birthing parents and 18-20 weeks for birthing parents.
• Well-rounded wellness benefits including free and low-cost mental health resources and financial wellbeing support services.
• Education benefits and tuition assistance to help your future development and growth.