Chief of Staff to the CTO
Pearl · United States
- Hybrid
- Full-time
- $150,000 / year
- United States
Job highlights
- Partner with CTO for Product and Engineering.
- Drive technical execution and product strategy.
- Own operating system for Product organization.
- Manage high-priority programs and cross-functional coordination.
- Define and track key engineering metrics.
About the role
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
Key skills/competency
- Chief of Staff
- CTO
- Product Management
- Engineering Operations
- Technical Program Management
- SaaS
- AI
- Healthcare Technology
- Agile Methodologies
- Cross-functional Coordination
Skills & topics
- Chief of Staff
- CTO
- Product Management
- Engineering Operations
- Technical Program Management
- SaaS
- AI
- Healthcare Technology
- Agile Methodologies
- Cross-functional Coordination
- Startup
- Leadership
- Remote
How to get hired
- Tailor your resume: Highlight experience in technical program management, SaaS, and regulated industries. Quantify achievements related to program execution and operational efficiency.
- Showcase strategic thinking: Emphasize your ability to translate complex technical issues into actionable plans and communicate effectively with diverse stakeholders, including executives.
- Demonstrate operational excellence: Provide examples of building and managing operating cadences, defining metrics, and improving cross-functional collaboration in fast-paced environments.
- Align with Pearl's mission: Express your understanding of their AI solutions in dentistry and your passion for improving healthcare through technology.
- Prepare for technical discussions: Be ready to discuss software development lifecycle, agile methodologies, and relevant AI/FDA regulations.
Technical preparation
Behavioral questions
Frequently asked questions
- What is the primary focus of the Chief of Staff to the CTO role at Pearl?
- The Chief of Staff to the CTO at Pearl acts as a force multiplier for the CTO, driving velocity, quality, and strategic clarity across Product and Engineering. This role involves owning the operational cadence, managing high-priority programs, and ensuring effective cross-functional collaboration within a regulated, high-growth environment.
- What kind of experience is most valuable for this Chief of Staff position at Pearl?
- Pearl is looking for candidates with 5+ years in technical program management, product operations, or a Chief of Staff role within SaaS product and engineering teams. Experience in healthcare technology, digital health, or regulated industries, along with a proven track record in managing complex cross-functional programs, is highly valued.
- How does this Chief of Staff role contribute to Pearl's mission in dentistry?
- This Chief of Staff role is critical to accelerating Pearl's mission by ensuring efficient and effective product development and engineering operations. By improving execution, strategic clarity, and cross-functional alignment, the role directly supports the delivery of AI solutions that enhance dental care quality and patient outcomes.
- What are the key responsibilities of the Chief of Staff to the CTO at Pearl?
- Key responsibilities include owning high-priority cross-functional programs, building and managing the Product and Engineering operating cadence, driving engineering operations and metrics, and executing strategic projects for the CTO. This involves deep involvement in technical program management, planning processes, and cross-functional coordination.
- Is this a remote position, and what are the benefits of working at Pearl?
- Yes, this is a remote work position. Pearl offers competitive compensation and benefits, ongoing training and development opportunities, and flexible Paid Time Off (PTO). They foster a culture that values growth, innovation, and improving dental care through technology.