Director, Academy Product ­& AI

Guild

6h • Remote

About The Position

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.

Requirements

• 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. You use AI tools daily in the flow of work, understand their strengths and failure modes, and you're excited to help a team continue to stay ahead of the curve
• A knack for building cross-functional relationships across organizational boundaries, influencing peer leaders in other business domains
• Strong collaboration and communication skills, including the ability to translate technical concepts for non-technical audiences and drive alignment across a broad range of senior stakeholders.
• A demonstrated commitment to inclusive, psychologically safe, engaged teams and sufficient technical depth to engage effectively in key technical decisions, while empowering the team to own those decisions.
• A builder's mindset. 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.

Responsibilities

• Deeply understand the key inputs to your product vision: learner voice, administrator voice, evolving external landscape and opportunities to innovate and leverage AI. You’ll listen deeply to learners, administrators, internal Academy success teams, competitors, and L&D experts, collate those findings, and develop your own strong perspective at what accelerates team transformation.
• 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. You will own the long-term vision but be constantly belief-updated and seeking new opportunities as the landscape evolves.
• Drive alignment on product strategy, including engaging teams at all levels across Academy Success, Go-To-Market, and cross-functional executives, and crafting narratives that create urgency
• Champion the Academy product externally at conferences and events, internally within Guild, and directly with our customers - always in learning and feedback-gathering mode to continue to iterate and improve.
• Lead and develop a high-performing, AI-fluent team of product managers and engineers, providing clear expectations, regular feedback, and meaningful growth opportunities through effective 1:1s, performance management, and career development — including helping the team build strong instincts for working effectively with AI tools.
• Champion and shape the team's AI-first culture — establish norms around how AI tools are used in the research, design and development workflow and help the team continuously refine their judgment about when to trust, when to verify, and when to go deeper than the AI.
• Guide the team's operating cadence, including planning, status updates, and retrospectives.

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; 2-week ramp-up period for when employees return from a leave of 6 weeks or more; as well as employer-paid short-term and long-term disability, employer-sponsored life insurance, fertility and caregiving benefits.
• 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
• variable compensation
• stock options

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed