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Principal Technologist, Strategic Initiatives

22 hours, 15 minutes ago
United States
Full-time
Lead
Product Manager
Software Development
LLM Machine Learning System Design
Apply Now
Clover Health

Clover Health

Clover Health is a data-focused health insurance company that is revolutionizing the Medicare Advantage space by integrating innovative technology into its plans. With a focus on optimizing medical outcomes and reducing costs, Clover Health uses analyt...

Insurance
251-1K
Founded 2014
$925M raised
View All Jobs 40

Description

  • Own the product strategy, technical strategy, and delivery for a strategic initiative end-to-end.
  • Translate high-level business goals into concrete work streams, milestones, and success metrics.
  • Drive system design, technology selection, and architecture decisions, including AI-forward systems.
  • Build and ship the initiative’s systems personally while coordinating support from engineers, data analysts, and other specialists.
  • Define experiments and success criteria, and use data to guide product and technical tradeoffs.
  • Develop deep subject-matter expertise in the business domain, user needs, operational workflows, and data landscape.
  • Establish a delivery cadence and ship incremental progress quickly and consistently.
  • Build durable, well-documented systems and patterns that can support long-term business value.
  • Communicate progress clearly to executive leadership and cross-functional stakeholders.

Requirements

  • Proven engineering experience and strong product judgment, with experience as a tech lead, staff engineer, or senior PM with deep technical fluency.
  • Demonstrated experience shipping complex programs or products end-to-end and owning outcomes, not just deliverables.
  • Recent, hands-on experience with AI/LLM systems, including building, shipping, or operating AI-backed features, agentic workflows, or ML-driven products.
  • Strong technical background in system design, distributed systems, data pipelines, and cloud infrastructure.
  • Fluency in data and experimentation for product and engineering decision-making.
  • Ability to work effectively in ambiguity and create structure when no playbook exists.
  • Ability to lead without positional authority and build alignment through clarity, quality, and velocity.
  • Comfort making pragmatic tradeoffs between speed and durability while maintaining engineering quality.
  • Experience in a regulated or data-rich environment is preferred.
  • Interest in and opinions about the direction of AI/LLM technology are preferred.

Benefits

  • Competitive base salary of $225,000 to $325,000.
  • Equity opportunities, including an Employee Stock Purchase Plan (ESPP) with discounted equity.
  • Performance-based bonus program and regular compensation reviews.
  • 401(k) matching.
  • Comprehensive medical, dental, and vision coverage.
  • Generous flexible time-off policy, including No-Meeting Fridays and monthly company holidays.
  • Remote-first culture that supports collaboration and flexibility.
  • Learning programs, mentorship, professional development funding, and regular performance feedback.
  • Paid parental leave for all new parents.
  • Monthly cell phone and internet stipend, plus office setup reimbursement.

Interested in this position?

Apply directly on the company website

Apply Now

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