Strategic Engagement Partner

About the role

As the Forward Deployed Partner, you will take ownership of new customer relationships the moment we sign a contract. Your mandate from day one is customer success, product innovation, account management, and relationship expansion. You’ll be the primary face of DeweyLearn for some of our largest enterprise customers, working alongside a small, fast, highly-agile, multi-disciplinary DeweyLearn team.

Responsibilities

• Drive enterprise customer excellence by building and maintaining strong relationships with large, complex accounts, establishing a tight executive cadence, and identifying adoption friction and churn signals early.
• Develop and refine playbooks, health frameworks, and expansion motions to inform and improve future engagements.
• Manage customer relationships through strategic consultation, change management, and long-term planning rather than short-term wins.
• Leverage AI tools natively to enhance effectiveness and efficiency, critically evaluating outputs rather than accepting them unquestioningly.
• Apply domain expertise in higher education, technical education, workforce development, clinical practice, or related fields to coach customers in learning science and assessment design.
• Facilitate structured discovery, working sessions with senior teams, and shape rubrics and frameworks that anchor successful engagements.
• Coach customers through change, challenge assumptions, and adopt lean, experimental approaches to build solutions with—not for—customers.
• Manage complex engagements, surface risks early, and own outcomes when plans shift through structured check-ins, executive readouts, and adoption troubleshooting.
• Partner with implementation engineers on delivery and provide structured product feedback to the DeweyLearn team.

Requirements

• Proven experience in enterprise customer excellence, including relationship-building, executive engagement, and account management for large, complex accounts.
• Fluency in AI tools and agentic systems, with strong instincts for model capabilities and critical evaluation of outputs.
• Domain expertise in higher education, technical education, workforce development, clinical practice, or related fields; fluency in learning science and assessment design is preferred.
• Experience in coaching, consulting, and change management, including facilitating working sessions and guiding customers through transformation.
• Strong project and product management skills, with a track record of delivering complex engagements on time and adapting to shifting plans.
• Demonstrated judgment, executive presence, and self-direction from prior experience at this level, without requiring managerial oversight.

Benefits

• Salary range: $130,000 to $165,000 per year.
• Medical benefits.
• Flexible PTO.
• Remote-first work environment with 10-25% travel for customer engagements.

About the team

DeweyLearn is a small, close-knit team moving fast with a deep conviction in the impact our platform can have on learning and learners. We emphasize collaboration, fun, and accountability while hiring based on ability and judgment, not pedigree. We value straight talk, delivering on commitments, and treating play and curiosity as essential to discovery. We refuse to ship work we wouldn’t be proud of.