Chief of Staff to COO
Pearl · United States
- Hybrid
- Full-time
- $150,000 / year
- United States
Job highlights
- Drive revenue growth across marketing and sales.
- Optimize SMB funnel and customer retention.
- Build scalable customer success operations.
- Execute strategic projects for the COO.
- Utilize AI tools for GTM acceleration.
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 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
Key skills/competency
- Chief of Staff
- COO
- Revenue Growth
- Go-to-Market Strategy
- SMB Sales
- Customer Success
- AI Tools
- Operations Management
- Strategic Initiatives
- Cross-functional Leadership
Skills & topics
- Chief of Staff
- COO
- Strategic Leadership
- Revenue Growth
- Go-to-Market Strategy
- Sales Operations
- Marketing Operations
- Customer Success
- AI Tools
- Startup
- Remote
How to get hired
- Tailor your resume: Highlight strategic leadership, cross-functional project management, and AI tool fluency.
- Craft a compelling cover letter: Emphasize your experience in high-growth startups and your ability to drive results.
- Prepare for behavioral questions: Showcase your problem-solving, communication, and leadership skills.
- Research Pearl's mission: Understand their AI-driven approach to dentistry and their commitment to patient care.
- Demonstrate analytical prowess: Be ready to discuss how you've used data to optimize funnels and retention.
Technical preparation
Master CRM and sales automation tools.,Practice analyzing funnel conversion metrics.,Familiarize with GTM AI tools.,Prepare data-driven strategy examples.
Behavioral questions
Describe a complex cross-functional initiative.,How do you handle ambiguous problems?,Give an example of driving accountability.,How do you influence stakeholders at all levels?
Frequently asked questions
- What are the key responsibilities for the Chief of Staff to COO at Pearl?
- The Chief of Staff to COO at Pearl is responsible for driving revenue and growth across Marketing, Sales, and Customer Success. This includes optimizing the SMB funnel, intervening in churn, scaling customer success operations, managing partner economics, supporting international growth, owning the operating cadence, adopting AI tools, and executing strategic projects for the COO.
- What qualifications are essential for the Chief of Staff role at Pearl?
- Essential qualifications include 5+ years of strategic leadership experience (preferably Chief of Staff), a background in investment banking, management consulting, or commercial roles, a proven track record of leading complex initiatives, strong analytical and problem-solving skills, exceptional communication abilities, detail-orientation, and fluency in AI tools. Experience in a high-growth startup is preferred.
- How does Pearl leverage AI in its go-to-market strategy for this Chief of Staff role?
- Pearl utilizes AI tools like Claude and Clay to compound output, reduce manual work, and accelerate the SMB funnel. The Chief of Staff will evangelize and support the adoption of these tools, identify high-leverage workflows, design agentic patterns, and measure their impact on GTM efficiency.
- What kind of impact can I expect to make as Chief of Staff at Pearl?
- Success in this role contributes to a measurable lift in Net Revenue Retention (NRR) through churn intervention and expansion programs. You will also be instrumental in improving overall Go-To-Market (GTM) efficiency.
- What is the work arrangement for the Chief of Staff position at Pearl?
- Pearl offers a remote work arrangement for this Chief of Staff position, providing flexibility for employees.
- What are the benefits of working as Chief of Staff at Pearl?
- Pearl offers competitive benefits and compensation, ongoing training and development opportunities, unaccrued flexible PTO, and the advantage of a remote work environment.
- How does Pearl approach international growth for its Chief of Staff role?
- The Chief of Staff will drive Pearl's commercial expansion outside the US, focusing on strategic partners and enterprise accounts in regions like Northern Europe and Australia. This involves partnering with regional leaders on commercial strategy and market entry sequencing.
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