Principal Technologist, Office of the CTO
Confirmed live in the last 24 hours
Clover Health
Job Description
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:
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