Principal Technologist, Strategic Initiatives

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.

The work is technically demanding and strategically important. You'll operate in a data-rich, regulated environment where AI is reshaping what's possible, from agentic systems that reason over business data to AI-assisted workflows that compress build cycles from months to minutes. You should be excited by that shift, not intimidated by it.

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.

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 flexible time-off policy. Additionally, we embrace a remote-first culture that supports collaboration and flexibility, allowing our team members to thrive from any location. 
• Professional Development: Developing internal talent is a priority for Clover. We offer learning programs, mentorship, professional development funding, and regular performance feedback and reviews.

Additional Perks:

• Employee Stock Purchase Plan (ESPP) offering discounted equity opportunities
• Reimbursement for office setup expenses
• Monthly cell phone & internet stipend
• Remote-first culture, enabling collaboration with global teams
• Paid parental leave for all new parents
• And much more!

About Clover: We are reinventing health insurance by combining the power of data with human empathy to keep our members healthier. We believe the healthcare system is broken, so we've created custom software and analytics to empower our clinical staff to intervene and provide personalized care to the people who need it most.

We always put our members first, and our success as a team is measured by the quality of life of the people we serve. Those who work at Clover are passionate and mission-driven individuals with diverse areas of expertise, working together to solve the most complicated problem in the world: healthcare.

From Clover’s inception, Diversity & Inclusion have always been key to our success. We are an Equal Opportunity Employer and our employees are people with different strengths, experiences, perspectives, opinions, and backgrounds, who share a passion for improving people's lives. Diversity not only includes race and gender identity, but also age, disability status, veteran status, sexual orientation, religion and many other parts of one’s identity. All of our employee’s points of view are key to our success, and inclusion is everyone's responsibility.

#LI-REMOTE

Pursuant to the San Francisco Fair Chance Ordinance, we will consider for employment qualified applicants with arrest and conviction records. We are an E-Verify company.

A reasonable estimate of the base salary range for this role is $195,000 to $315,000. Final pay is based on several factors including but not limited to internal equity, market data, and the applicant’s education, work experience, certifications, etc.