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 COO to drive revenue and growth across Marketing, Sales, and Customer Success. This role is the COO's force multiplier on go-to-market strategy and execution, owning the highest-leverage initiatives end to end and translating ambiguous problems into operational systems that scale. This is a highly visible, cross-functional role for a builder who thrives at the intersection of strategy, analytics, and execution, and who is comfortable moving from a board-ready model in the morning to a partner negotiation in the afternoon to a churn save war room in the evening.

Key Responsibilities Include:

• SMB Revenue Acceleration and Funnel Optimization: Monitor the end-to-end SMB self-serve funnel from lead generation through close, onboarding, and first expansion. Partner with Marketing, Sales, and our channel partners to lift conversion at every stage, sharpen attribution, raise MQL quality, and shorten time to revenue. Build the analytics and feedback loops that turn the SMB funnel into a system rather than a series of disconnected handoffs.

• Churn Intervention and Retention: Stand up the playbook and cross-functional motion across Customer Success (CS), Product, and RevOps to identify at-risk accounts early across both the SMB and Enterprise books, run a disciplined save process, and convert retention wins into expansion. Own the leading indicators of churn and the closed-loop feedback into product and pricing.

• Customer Success Operations at Scale: Assist in building the systems, tooling, instrumentation, and metrics that let Customer Success keep pace as Pearl roughly doubles revenue year over year. Define the operating model across SMB and Enterprise CS, the data infrastructure that powers it, and the AI-enabled workflows that compound capacity over headcount.

• Partner Economics: Diagnose unit economics across the channel and partner programs that power our SMB motion. Recommend and execute restructures (fee architecture, attach incentives, motion ownership) that improve margin, partner ROI, and the long-term defensibility of the relationship.

• International Growth (Partners and Enterprise): Drive Pearl's commercial expansion outside the US, with a primary focus on strategic partners and enterprise accounts across Northern Europe, Australia, and beyond. Partner with regional leaders on commercial strategy, sequence market entry by opportunity size and time to revenue, and build the operating cadence that holds international teams accountable to the plan.

• Operating Cadence and Business Reviews: Own the rhythm of business across the commercial org. Build the QBRs, weekly business reviews, and OKR processes that surface issues early across both the SMB and Enterprise motions, keep leadership focused on the metrics that matter, and create accountability without bureaucracy.

• AI Deployment and Adoption: Evangelize and support the broader GTM organization in adopting AI tools (Claude, Clay, and the rest of the modern GTM stack) to compound output, reduce manual work, and accelerate the SMB funnel. Partner with team leads to identify high-leverage workflows, design agentic patterns, and measure the lift.

• Strategic Projects for the COO: Run the highest-priority ad hoc bets end to end. Board and investor prep, leadership offsites, GTM org design, M&A diligence support, and the one-off unlocks that do not fit anywhere else on the org chart.
  

Qualifications

• 5+ years of experience in a strategic leadership role- preferably as a Chief of staff or similar position.

• Investment banking, management consulting, or commercial background.

• Proven track record leading complex, cross-functional initiatives from inception to completion.

• Strong analytical and problem solving skills with the ability to think strategically and drive results in a fast paced environment.

• Exceptional communication and interpersonal skills with the ability to influence stakeholders at all levels and build trust quickly.

• Detail oriented and highly organized with a proven ability to prioritize tasks, manage multiple projects simultaneously, and meet deadlines in an evolving environment.

• Demonstrated leadership capabilities, including ability to motivate teams, drive accountability, and foster a culture of collaboration and innovation.

• Fluent in AI tools used to accelerate analysis, prototype workflows, and scale output.

• Experience in a high growth startup or technology company preferred

What Success Looks Like

• Contribute to measurable lift in NRR through churn intervention and expansion programs you help to stand up.

• Improve GTM efficiency

What We Offer

• Competitive Benefit and Compensation Offerings

• Ongoing Training and Development Opportunities

• Unaccrued, Flexible PTO

• Remote Work