Clover Health - Principal Technologist, Office of the CTO

• 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: • 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 Some have been replaced by strategic systems; others are still running and that's fine.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. • effortlessly approachable • 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.