Operations Training Manager, Delivery

About the role

Lead and manage the Operations learning delivery function, ensuring consistent, high-quality delivery of onboarding ~200 new hires annually, and continuous learning programs for our existing front line teams.

Own and manage the Operations training calendar and team capacity, aligning training schedules with hiring plans, operational priorities, and program capacity.

Partner with Operations leaders to identify knowledge gaps, emerging skill needs, and opportunities for targeted learning interventions.

Translate operational feedback and performance trends into actionable training improvements and new learning initiatives, while running continuous evaluation of all programs and team members.

Collaborate with the Instructional Design Manager on course strategy, content structure, and learning methodology.

Monitor trainee performance trends and operational metrics to evaluate training effectiveness and continuously improve programs, along with ensuring 100% CE completion across our teams.

Support and contribute to leadership development initiatives for Operations leaders and emerging managers.

Facilitate training sessions ~30% of time to support trainer capacity or high-priority initiatives.

Responsibilities

• Lead and manage the Operations learning delivery function, ensuring consistent, high-quality delivery of onboarding ~200 new hires annually, and continuous learning programs for our existing front line teams.
• Own and manage the Operations training calendar and team capacity, aligning training schedules with hiring plans, operational priorities, and program capacity.
• Partner with Operations leaders to identify knowledge gaps, emerging skill needs, and opportunities for targeted learning interventions.
• Translate operational feedback and performance trends into actionable training improvements and new learning initiatives, while running continuous evaluation of all programs and team members.
• Collaborate with the Instructional Design Manager on course strategy, content structure, and learning methodology.
• Monitor trainee performance trends and operational metrics to evaluate training effectiveness and continuously improve programs, along with ensuring 100% CE completion across our teams.
• Support and contribute to leadership development initiatives for Operations leaders and emerging managers.
• Facilitate training sessions ~30% of time to support trainer capacity or high-priority initiatives.

Requirements

5+ years of experience in training, learning and development, operations enablement, or a related field.

2+ years of experience in a leadership role with direct reports.

The capacity to thrive within a high-speed, evolving landscape while managing ambiguity effectively.

Experience working in a highly regulated industry such as insurance, finance, health care, or other related field.

Experience managing training programs or learning initiatives across multiple teams or operational functions.

Proven ability to lead and develop trainers or facilitators in a performance-driven environment.

Strong facilitation and coaching skills with experience delivering engaging virtual or in-person learning experiences.

The capacity to translate operational needs and performance data into effective learning solutions.

Strong cross-functional collaboration skills and the ability to partner effectively with business leaders.

Excellent organizational and program management skills, including experience managing complex training calendars or initiatives.

Qualifications

Graduate degree in a related field preferred.

Skills

Strong facilitation and coaching skills with experience delivering engaging virtual or in-person learning experiences.

The capacity to translate operational needs and performance data into effective learning solutions.

Strong cross-functional collaboration skills and the ability to partner effectively with business leaders.

Excellent organizational and program management skills, including experience managing complex training calendars or initiatives.

Benefits

Competitive salary and company equity through Restricted Stock Units (RSUs), granted as part of our standard compensation package and based on role and level.

401(k) with company match up to 4% of eligible earnings.

Multiple medical plan options, plus dental and vision coverage.

Company-funded HSA contributions (based on medical plan selection).

Company-paid life insurance and short-term disability.

Health & Wellbeing: A variety of supplemental benefit options, including long-term disability, critical illness, accident, legal, and pet insurance.

Access to mental health support and confidential counseling resources.

Flexible PTO for exempt employees (most employees take 15–20 days per year), plus 8 company-observed holidays.

Paid parental leave, including up to 14 weeks at 100% pay for birthing parents and 8 weeks at 100% pay for non-birthing parents.

Growth & Development: Career mobility and internal growth opportunities across the organization.

Professional development budgets for certifications, conferences, and learning available, subject to management approval.

Pay

Competitive salary and company equity through Restricted Stock Units (RSUs), granted as part of our standard compensation package and based on role and level.

Schedule

Remote-first employer with offices in Chicago, IL and St. Petersburg, FL where teams can come together for collaboration.

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