Principal Technologist, Strategic Initiatives

Job Application for Principal Technologist, Strategic Initiatives at Clover Health

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. Whether it's safeguarding our environment, accelerating innovation, or unlocking efficiency, we sit at the intersection of technology and impact across the entire company.

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. If you're an engineering leader looking to get back to building with the strategic scope and seniority you've earned, this is that role.

We are building a technology organization where empowered individuals own business outcomes, not tasks. Our Technologists are the single-threaded owners who make that model work. You operate with high autonomy and a direct line to executive leadership. You ship incremental progress in a fast cadence: define a goal, land it, demo it, measure it.

Responsibilities:

• 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.

You should get in touch if:

• You have proven engineering experience and product judgment, having operated as a tech lead, staff engineer, or senior PM with deep technical fluency.
• You have shipped complex programs or products end-to-end — not just advised on them or managed parts of them. You've owned outcomes, not just deliverables.
• You have recent, hands-on experience with AI/LLM systems: building, shipping, or operating AI-backed features, agentic workflows, or ML-driven products. You have opinions about where the field is going.
• You are technically strong: comfortable with system design, distributed systems, data pipelines, and cloud infrastructure. You can hold your own in architecture discussions and make sound technical tradeoffs.
• You are fluent in data and have used data and experimentation to make product and engineering decisions.
• You thrive in ambiguity. When no playbook exists, you build one. When priorities conflict, you force-rank them. When coordination breaks down, you fix it.
• You don't need positional authority to lead. You earn trust and create alignment through clarity, quality, and velocity.

Benefits Overview:

• Financial Well-Being: Our commitment to attracting and retaining top talent begins with a competitive base salary and equity opportunities. Additionally, we offer a performance-based bonus program, 401k matching, and regular compensation reviews to recognize and reward exceptional contributions.
• Physical Well-Being: We prioritize the health and well-being of our employees and their families by providing comprehensive medical, dental, and vision coverage. Your health matters to us, and we invest in ensuring you have access to quality healthcare.
• Mental Well-Being: We understand the importance of mental health in fostering productivity and maintaining work-life balance. To support this, we offer initiatives such as No-Meeting Fridays, monthly company holidays, access to mental health resources, and a generous...