Principal Technologist, Office of the CTO at Cloverhealth

We're hiring a Principal Technologist into the Office of the CTO. This is a hands-on problem-solver role for someone who can walk into any room in the company, listen to what's broken, and ship a working solution — not a perfect one, but a good one that gets people moving. While the CTO and CEO are building the long-term technical and strategic vision and drive the company's most transformative initiatives, your job is to handle everything that would otherwise pull them off that focus. Business stakeholders have real problems that need real solutions now — not in six months when the grand architecture is ready. You are the person who listens, scopes the pragmatic path, and builds the thing that gets them through it. You build the bicycle, not the race car. This is not a managerial or bureaucratic role. You ship software. You build lightweight applications, automations, integrations, and workflows that solve real operational problems. You are technical, you are pragmatic, you are allergic to red tape, and you know when good enough is exactly right. You are also a counterweight. When leadership is tempted to overengineer a solution or boil the ocean, you're the voice that says: not yet. Let me get this to decent. You come back later and make it great. You have the judgment and discipline to build interim solutions that don't become permanent technical debt. As a Principal Technologist, Office of the CTO, you will: • Be the CTO and CEO's technical complement. Handle the problems, conversations, and stakeholder relationships that would otherwise consume their time and attention. • Listen to business stakeholders — operations leaders, department VPs, cross-functional partners — understand their pain, and scope pragmatic solutions. You are effortlessly approachable and people trust you to help. • Ship working solutions — sometimes personally, sometimes by marshaling the right engineers, analysts, or vendors across the department. You know when to build it yourself and when to pull in the right people. Either way, you are accountable for the result. • Exercise disciplined judgment about scope. You know the difference between a focused interim solution and a sprawling system that takes years to unwind. You build things that are easy to replace when the long-term architecture arrives. • Manage a portfolio of tactical problems across the organization. You context-switch fluently across domains and stakeholders, keeping multiple workstreams moving without letting any of them expand beyond their mandate. • Partner closely with the CTO to ensure interim solutions converge toward the long-term technical vision. You flag what's working, what's stuck, and what needs to graduate from "good enough" to "built right." Success in this role looks like: • First 90 days: • Build relationships across the organization. Earn the trust of operations leaders, department heads, and cross-functional partners. People start coming to you with problems instead of escalating to the CTO. • Identify and deliver your first 2-3 quick wins — working solutions to real problems that demonstrate the model. • Develop a clear understanding of the CTO's long-term technical vision so your tactical solutions are directionally aligned. • First 6 months: • Business stakeholders have a reliable path for getting pragmatic technology solutions without waiting for strategic initiatives to deliver. You are their first call. • You have shipped multiple solutions across different domains. Each one is scoped tightly, solves the problem, and doesn't create sprawling dependencies. • The CTO is measurably freed up. Problems that would have pulled leadership into tactical firefighting are handled before they escalate. • First year: • You have built a track record of delivering focused solutions that work. Some have been replaced by strategic systems; others are still running and that's fine. None have become regrettable technical debt. • You are a trusted voice in leadership conversations, known for pragmatism and good judgment about what to build, what to defer, and what to let be imperfect. • The organization operates faster because stakeholders have a responsive technical partner who meets them where they are. You should get in touch if: • You have a background in consulting, systems integration, or a generalist technical role where you regularly shipped solutions across multiple domains and stakeholders. Big Three, Big Four, or SI experience is a plus, but what matters is the pattern: walk in, understand the problem, deliver something that works. • You can ship software. You build apps, automations, integrations, and workflows. You're not a project manager with a technical vocabulary — you are a builder who happens to be great with people. • You are effortlessly approachable. You build rapport naturally. People want to work with you, confide in you, and trust you to help them solve their problems. You bring warmth and good humor to difficult conversations. • You have excellent judgment about scope. You know when something needs to be "built right" and when it needs to be "built now." You have the discipline to build focused solutions that don't sprawl, and you instinctively avoid vendor commitments that take years to unwind. • You have hands-on experience with AI/LLM tools and use them to accelerate your own work. You are the kind of person who reaches for automation and AI instinctively. • You thrive on variety. You are energized by context-switching across domains, stakeholders, and problem types. You don't need a single initiative to 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. 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. A reasonable estimate of the base salary range for this role is:$190,000—$275,000 USD