Chief of Staff to the CTO

About Pearl Pearl is shaping the future of dentistry with a suite of AI solutions developed to establish higher standards of quality and care for patients worldwide. Since 2019, our team has engineered FDA-cleared computer vision capabilities for interpretation of 2D and 3D dental imagery; industry-leading capabilities which clinicians, practice owners, labs, and insurers use to elevate the efficiency, accuracy, and consistency of dental care around the world. Who We're Looking For The Chief of Staff partners with the CTO to drive velocity, quality, and strategic clarity across Product and Engineering. This role is the CTO's force multiplier on technical execution and product strategy — owning the operating system of the Product org, keeping high-priority programs on track, and translating complex technical and organizational challenges into clear decisions and accountable plans. This is a highly visible, cross-functional role for someone who has lived inside SaaS product and engineering teams and understands what it actually takes to ship great software in a regulated, high-stakes environment like the dental industry. You are equally comfortable parsing a sprint backlog and presenting a roadmap to the board.

Key Responsibilities

• Technical Program Management: Own the execution of the CTO's highest-priority cross-functional programs from kickoff through delivery. Identify scope, milestones, dependencies, and risks. Run the structured program cadence — status reviews, escalation paths, and decision logs — that keeps engineering teams unblocked and leadership informed without adding bureaucratic drag.
• Product, and Engineering Operating Cadence: Build and steward the rhythm of the Product org. Own the planning process, quarterly roadmap processes, and organizational OKR process, align Product and Engineering on priorities, and create a culture of accountability without micromanagement.
• Cross-Functional Coordination: Serve as the connective tissue between Identify where handoffs break down, own the resolution, and build the durable processes that prevent the same failures from recurring.
• Engineering Operations and Metrics: Define and instrument the leading indicators of Product health: delivery predictability, cycle time, incident rates, technical debt burn-down, and team capacity. Build the dashboards and review cadences that give the CTO and engineering leadership a clear, real-time view of where the org is healthy and where it needs intervention.
• Strategic Projects for the CTO: Run the highest-priority ad hoc initiatives end to end, leadership offsites, and the one-off unlocks that do not fit neatly anywhere else in the org.
• Complex customer onboarding initiatives
• International expansion
• Customer relationship management
• Represent the CTO in internal and external meetings when required

Qualifications

• 5+ years of experience in technical program management, product operations, or a Chief of Staff role embedded in a product or engineering organization
• Hands-on background working within SaaS product and engineering teams — you understand the software development lifecycle, agile methodologies, and what it takes to ship in a fast-moving environment
• Experience in healthcare technology, digital health, or a similarly regulated industry strongly preferred; familiarity with FDA software/AI regulatory frameworks
• Proven track record managing complex, cross-functional programs with multiple workstreams, stakeholders, and time horizons simultaneously
• Strong analytical and structured thinking skills — you can take an ambiguous problem, break it down, and drive to a clear recommendation or plan
• Exceptional communication skills; able to translate technical complexity for executive and board audiences and operational detail for engineering teams
• Detail oriented and highly organized, with a demonstrated ability to prioritize ruthlessly and maintain momentum across many competing demands
• Fluent in modern AI and productivity tools; eager to find leverage through tooling and automation rather than headcount
• Experience in a high-growth startup or technology company preferred

What Success Looks Like

• Product development programs land on time and on scope, with fewer surprises and faster escalations when things go sideways
• The CTO spends more time on the highest-leverage decisions and less time on coordination overhead
• Product and Engineering operate with a shared, well-instrumented cadence that scales as the team grows
• Cross-functional relationships between Engineering, Product Management, Design, Technical Support and GTM are tighter and more productive

What We Offer

• Competitive Benefit and Compensation Offerings
• Ongoing Training and Development Opportunities
• Unaccrued, Flexible PTO
• Remote Work

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