Strategy & Operations Lead, People

We’re hiring a Strategy & Operations Lead to build and run the people systems that will support Prosper as we grow from approximately 800 to 1,500+ clinicians.

This is an operating role for someone who excels at turning ambiguous, high-complexity problems into simple, reliable systems. You’ll own the clinician journey from signed offer through start, compensation and benefits strategy, clinical organization design and talent development, People Ops service delivery, and core people systems for our HQ team.

You’ll be accountable for outcomes including signed-offer-to-start conversion, clinician total-rewards satisfaction, People Ops service levels, and HQ engagement and retention. You’ll also partner with Provider Operations on early clinician retention.

You do not need to arrive as a career HR leader. We’re open to exceptional operators from consulting, investment banking, business operations, strategy and operations, general management, or similar backgrounds. What matters most is your ability to learn quickly, exercise sound judgment, and own consequential work from diagnosis through execution.

You’ll initially receive support on complex employee-relations, compliance, and termination decisions. As you build domain expertise and demonstrate judgment, your ownership will expand.

• Own clinician onboarding success: Lead the clinician journey from signed offer through start, building scalable processes that improve conversion, day-one readiness, learning and development, and early retention..
• Own compensation and benefits strategy: Develop compensation frameworks, conduct market benchmarking, lead plan design and renewals, oversee implementation, and communicate total rewards clearly to employees.
• Shape the clinical organization: Partner with clinical leadership on role definitions, leveling, career pathways, talent development, and the effectiveness of clinician learning and development.
• Build scalable People Operations system: Manage accommodations, complaints, escalations, investigations, and terminations with clear service levels, escalation paths, and legally defensible documentation. Design simple, reliable workflows with clear ownership, handoffs, controls, documentation, and escalation paths that can support 1,500+ clinicians.
• Build HQ people systems: Partner directly with the CEO on HQ onboarding, performance management, structured feedback, engagement, retention, and leveling frameworks. Create playbooks, templates, decision tools, and guidance that help managers navigate people decisions earlier and more consistently.
• Lead the People Operations team: Manage and develop the existing team, ensuring recurring work is accurate, timely, visible, and continuously improving.

• You have approximately 5-7 years of experience, ideally including:
  
  • 3-4 years in consulting or investment banking, followed by 2-3 years in a strategic operating role at an early- to mid-stage startup, such as Business Operations, Strategy and Operations, General Management, Chief of Staff, or Clinical or Provider Operations.
• You have owned consequential, cross-functional work from problem definition through implementation and measurable results.
• You are comfortable moving between strategic questions—such as compensation frameworks and organization design—and hands-on operational execution.
• You can work confidently with operational data, build useful models or trackers, detect issues, and translate analysis into decisions.
• You communicate clearly and can bring structure to sensitive or ambiguous situations.
• You have experience managing, coaching, or developing others, either directly or through cross-functional leadership.

Prior healthcare or people operations experience is not required. Exposure to a distributed, regulated, marketplace, or high-volume workforce is helpful but not necessary.

• High ownership: You own consequential work end-to-end, create visibility, follow through on details, and escalate risks before they become problems.
• First-principles problem-solving: You structure ambiguous problems, test assumptions, identify the key driver, and build solutions for the actual context rather than copying a generic playbook.
• Builds for scale: You design simple systems with clear handoffs, controls, edge cases, and a path from the first version to significantly higher volume.
• Data proficiency: You manipulate operational data, build useful models and trackers, identify issues, and translate analysis into decisions.
• Learning agility: You enter unfamiliar domains quickly, identify what must be learned, seek expert input intelligently, and improve your judgment through feedback.
• Practical judgment and communication: You balance speed, empathy, consistency, confidentiality, and risk; explain decisions clearly; and know when not to act alone.

• We understand why clinicians drop off between signing and starting, address the highest-impact causes, and improve signed-offer-to-start conversion.
• Clinicians understand and value their compensation and benefits, reflected in stronger total-rewards satisfaction and lower regrettable attrition attributable to compensation or benefits.
• Clinical roles, levels, and career pathways are clear, and learning and development programs measurably prepare clinicians to succeed.
• Accommodations, complaints and escalations are acknowledged, investigated, documented, and resolved within clear service levels.
• People Operations workflows remain reliable as clinician volume and organizational complexity increase while the People Operations team operates with strong prioritization, accuracy, visibility, and follow-through.