Principal Technologist, Strategic Initiatives

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<