[Hiring] Principal Technologist, Strategic Initiatives @Clover Health

Role Description

Our Corporate Technology organization is the engine behind how Clover works—and how we scale. Bringing together IT, Security, Corporate Data, and Corporate R&D, we focus on making the employee experience seamless, secure, and genuinely delightful. From building resilient infrastructure to enabling smarter decision-making through data, we power the systems and tools that keep our business running and evolving.

We're hiring a Principal Technologist to own one of our most important strategic initiatives end-to-end. This is a senior individual contributor role that spans product and engineering. You set the product direction, design the systems, ship the software, and own the outcome.

You won't write requirements and hand them to engineering. You won't architect systems and hand them to a PM. You will do both. You own the strategy, define the metrics, and build the systems.

As a Principal Technologist, you will:

• Be fully accountable for your initiative's outcomes. Own the product strategy, technical strategy, and delivery.
• Translate high-level goals into concrete work streams with clear milestones and metrics that connect operational progress to financial impact.
• Drive system design, technology selection, and architecture decisions, including AI-forward systems.
• Make pragmatic tradeoffs between speed and durability, holding the line on engineering quality while keeping velocity high.
• Own delivery personally. You will pull in engineers, data analysts, and other specialists as needed, but you are the one building — not managing the building of — your initiative's systems.
• Become your initiative's subject matter expert. Go deep on the business domain, user needs, operational workflows, and data landscape.
• Influence across teams through clarity and the expertise you cultivate.
• Design experiments, define success criteria, and use data to guide product and technical tradeoffs.
• Make progress legible to leadership as a byproduct of your methodology.

Success in this role looks like:

• First 90 days: Deeply understand the business model, technology landscape, and your initiative's strategic context. Build key relationships across engineering, data, operations, and executive leadership. Own a clear 3–6 month product and technical plan aligned to business objectives. Establish a delivery cadence and ship your first measurable increment.
• First 6 months: You have shipped multiple increments with measurable impact on your initiative's core metrics. Progress is visible, incremental, and consistent. You have established yourself as the single-threaded owner of your initiative. Leadership and operations teams trust your judgment; stakeholders are aligned.
• First year: Your initiative has delivered fundamental business value you can quantify and stand behind. The systems and patterns you've built are durable and well-documented. You've raised the bar for what outcome-driven Principal Technologistership looks like at Clover.

Qualifications

• Proven engineering experience and product judgment, having operated as a tech lead, staff engineer, or senior PM with deep technical fluency.
• Experience shipping complex programs or products end-to-end — not just advising on them or managing parts of them.
• Recent, hands-on experience with AI/LLM systems: building, shipping, or operating AI-backed features, agentic workflows, or ML-driven products.
• Technically strong: comfortable with system design, distributed systems, data pipelines, and cloud infrastructure.
• Fluent in data and have used data and experimentation to make product and engineering decisions.
• Ability to thrive in ambiguity; capable of building playbooks, force-ranking priorities, and fixing coordination breakdowns.
• Ability to lead without positional authority; earns trust and creates alignment through clarity, quality, and velocity.

Benefits

• Financial Well-Being: Competitive base salary, equity opportunities, performance-based bonus program, 401k matching, and regular compensation reviews.
• Physical Well-Being: Comprehensive medical, dental, and vision coverage.
• Mental Well-Being: Initiatives such as No-Meeting Fridays, monthly company holidays, access to mental health resources, and a generous flexible time-off policy.
• Professional Development: Learning programs, mentorship, professional development funding, and regular performance feedback and reviews.
• Additional Perks: Employee Stock Purchase Plan (ESPP), reimbursement for office setup expenses, monthly cell phone & internet stipend, remote-first culture, paid parental leave for all new parents.