Director Guide Training and Readiness

Devoted Health • Waltham, MA

3d • $182,000 - $216,000 • Remote

About The Position

Within Member Experience Operations, the Director of Guide Training and Readiness owns the Guide Training function’s strategy, operating plan, budget, team, and results. The Director will organize the function around Learning Design, Training Delivery, and Measurement and Readiness, leading through managers. The role is accountable for Guide readiness at graduation and proficiency through the first 90 days, while building a scalable training operation for a growing population, seasonal peaks, and new products and market segments.

The Director sets readiness standards and go/no-go decisions for internal and vendor populations; owns learning design, content architecture, delivery quality, measurement, and continuous improvement; and prioritizes training intake against business risk and available capacity. The role also builds facilitator capacity for peak periods, develops managers and specialists, partners on career pathways and mobility, and manages budget, headcount, vendors, and tools. The position is remote with onsite expectations multiple times per year.

Requirements

• 8+ years of operational, training, or enablement leadership, including managing managers; preferably in a dynamic, fast-paced environment requiring flexibility and speed.
• Experience owning a function’s plan, budget, and headcount, with accountability for committed outcomes rather than activity measures.
• Track record of building a function or program from an underbuilt state into a measured and predictable operation.
• Experience defining and using outcome metrics for learning or operational programs, including an example where data changed program design.
• Experience prioritizing demand that exceeds capacity, including declining senior stakeholders with defensible reasons.
• Strong influence in a matrixed environment and ability to move leaders toward a direction they did not initially support.
• Experience in high-volume, high-accuracy member- or customer-facing operations.
• Fluency with AI tools to increase team output and improve measurement, with sound judgment about where they are useful.
• Transparent communication, including reporting successes and problems and raising risks early.
• Service mindset toward members and the Guides being trained.

Nice To Haves

• Experience in Medicare Advantage, healthcare, or another regulated service environment.
• Experience with contact center or member services operations at scale, including vendor or outsourced populations.
• Understanding of instructional design principles and modern learning tools sufficient to set direction and assess work quality.
• Experience standing up training for a new product, market segment, or line of business.
• Experience building a mentorship or on-the-job coaching program with defined outcomes.

Responsibilities

• Own and evolve a published Guide Training operating plan, including ramp design, learning modalities, delivery standards, mentorship, AI-assisted practice, and dated commitments.
• Own Guide readiness from training completion through day 90, setting standards for provisioning, systems access, competency verification, success measures, and rollback plans; exercise go/no-go authority for internal and vendor populations.
• Diagnose early performance gaps, determine whether they are training-related, provide targeted remediation and practice, and partner with Guide Supervisors on structured graduation handoffs and floor reinforcement.
• Set outcome targets for quality and accuracy at 30, 60, and 90 days, speed to proficiency, workflow adherence, escalation rates, learner experience, and early attrition; partner with Quality and Workforce Management on measurement and cohort reviews.
• Conduct retrospective reviews of every cohort and use results to improve program design.
• Run intake across the Guide organization and cross-functional partners; scope requests with owners, effort estimates, dates, and success measures; sequence work against business risk and explicitly decline or defer work where appropriate.
• Own curriculum development, competency architecture, proficiency definitions, assessment validity, and content standards, including content developed outside the function.
• Ensure content is reusable across populations and plan years, with practice simulations built in Orinoco and learning built in Rise and delivered through Workday Learning.
• Ensure cohorts start on schedule with certified facilitators, including during the September–December peak and for vendor and seasonal populations; establish facilitator certification and flex capacity through Guide subject matter experts.
• Lead and develop managers and specialists; set standards, build bench depth and coverage, and hire for future capability needs.
• Stand up training for new products, market segments, and Guide functions; extend training to adjacent member- and prospect-facing populations where justified by the business case.
• Partner with Talent Management on career pathways, competency frameworks, and internal mobility for Guides.
• Own the function’s budget and headcount plan, including vendors and tools, and grow scope based on demonstrated return.

Benefits

• Employer-sponsored health, dental, and vision plans with low or no premium.
• Generous paid time off.
• $100 monthly mobile or internet stipend.
• Stock options for all employees.
• Parental leave program.
• 401K program.
• Bonus eligibility for roles below Director level; Director and above are excluded.
• Total rewards package is for full-time employees only; interns and contract positions are not eligible.

What This Job Offers

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