Senior Learning & Development Leader - Insurtech

About Reserv

Reserv is an insurtech creating and incubating cutting-edge AI and automation technology to bring efficiency and simplicity to claims. Founded by insurtech veterans with deep experience in SaaS and digital claims, Reserv is venture-backed by Bain Capital and Altai Ventures and began operations in May 2022. We are focused on automating highly manual tasks to tackle long-standing problems in claims and set a new standard for TPAs, insurance technology providers, and adjusters alike. We have ambitious (but attainable!) goals and need people who can work in an evolving environment. If building a leading TPA and the prospect of tackling the long-standing challenges of the claims role sounds exciting, we can't wait to meet you.

About The Role

You'll own Reserv's L&D function end-to-end — foundation training, technical/systems training, leadership development, and professional development — across claims and the broader org.

This role is the architect of that next chapter of L&D. You'll set the roadmap, set the bar for quality, and partner with senior leaders across claims, operations, and further to make sure we're training the right things, the right way, at the right time.

We're open to two backgrounds for this role and excited about either: an experienced L&D leader with strategic chops, or an experienced ex-MBB consultant with deep interest or background in learning, capability-building, and org transformation. You don't need to be both — you need to be deeply strong in one and curious about the other.

What You'll Do

• L&D Strategy & Roadmap: Own the prioritized training roadmap across the four pillars. Read two input streams — evaluation outcomes from below and continuous-learning priorities from leadership above — and translate them into what we build next, what we sunset, and what we scale. The "we're not just doing what's asked — we're choosing what matters most" call.
• L&D Standards & Quality: Set Reserv's playbook for how good L&D gets built — general guidelines for instructional design, modality selection, evaluation frameworks, and quality bar. You're not making per-program modality calls, but you're the standards owner and the final word on whether a program is ready to ship.
• Team Leadership & Capability Building: Lead the L&D team — supporting the team members’ continued growth, leveraging their existing expertise, and building the bench as the function scales.
• Cross-Functional Partnership & Needs Identification: Embed with claims leadership and non-claims leaders across the company — actively surfacing where training needs and gaps exist before they become problems. Run structured needs assessments when major initiatives launch.
• Learning Outcomes & Continuous Improvement: Own the "did the training work?" loop. Build the measurement framework (completion, competency, business impact); feed PDP-aggregate gaps and post-training data back into the roadmap; sunset programs that don't move the needle.
  
  

Interested in remote work opportunities in Development & Programming? Discover Development & Programming Remote Jobs featuring exclusive positions from top companies that offer flexible work arrangements.

Qualifications

• Either (a) 6+ years of L&D / talent development leadership in a complex, scaling org, or (b) 4+ years top-tier strategy consulting (MBB or equivalent) with substantive exposure to or background in org transformation, capability-building, or learning workstreams.
• Track record of owning a function — has built or restructured a team and a roadmap.
• Strong instructional instincts — knows what good adult learning looks like, or has the curiosity to absorb it fast.
• Senior stakeholder fluency — comfortable with execs and line leaders; translates business priorities into a training agenda without being asked twice.
• Outcomes orientation — uses data to decide what to invest in, kill, or scale.
• Player-coach mentality — sets strategy AND rolls up sleeves. Scaling-startup pace, not Fortune 500.
  
  

Benefits

• Generous health-insurance package with nationwide coverage, vision, & dental
• 401(k) retirement plan with employer matching

Browse our curated collection of remote jobs across all categories and industries, featuring positions from top companies worldwide.

• Competitive PTO policy – we want our employees fresh, healthy, happy, and energized!
• Generous family leave policy after 8 months of continuous work
• Work from anywhere to facilitate your work life balance
• Apple laptop, large second monitor, and other quality-of-life equipment you may want. Technology is something that should make your life easier, not harder!
  
  

Additionally, We Will

• Listen to your feedback to enhance and improve upon the long-standing challenges of an adjuster and the claims role
• Work toward reducing and eliminating all the administrative work from an adjuster role
• Foster a culture of empathy, transparency, and empowerment in a remote-first environment
  
  

At Reserv, we value diversity in backgrounds, perspectives, and life experiences and believe that diversity in viewpoints and critical thinking drives innovation, first-principles thinking, and success. We welcome applicants from all backgrounds and encourage those from all walks of life to apply. If you believe you are a good fit for this role, we would love to hear from you!