Chief of Staff

Job Title: Chief of Staff, Office of the Chief Commercial Officer

Location: Fully Remote

Reports to: Chief Commercial Officer

Drips is seeking a strategic, execution-minded Chief of Staff to serve as a trusted partner to our Chief Commercial Officer (CCO). This role is critical to amplifying the CCO’s impact by ensuring seamless coordination of commercial strategy, internal execution, and strategic follow-through across multiple high-growth functions including Voice of the Customer, Sales, Corporate Strategy, Marketing, and Product Marketing.

This is not an Executive Assistant position—this is a strategic operational role suited for someone who can balance influence without authority, navigate complex priorities, and bring ruthless clarity and follow-through to the commercial team’s most important initiatives.

Core Responsibilities

Strategic Enablement & Execution:

• Drive alignment and execution on key commercial initiatives by managing cross-functional follow-ups, task assignments, and progress tracking—primarily in ClickUp.
• Partner with the CCO on strategic planning cycles, including managing the corporate strategy calendar, strategic initiative mapping, and board-level deliverables.
• Proactively coordinate and surface project risks, resource constraints, and communication gaps to maintain momentum and accountability.
  
  

Time & Attention Optimization

• Own calendar optimization for the CCO, ensuring strategic priorities are reflected in how time is allocated across staff management, thinking time, travel, and external engagement.
• Manage email and Teams prioritization, filtering signals from noise, initiating first-line responses where appropriate, and escalating only what requires executive decision-making.
• Track and prepare materials for internal and external meetings—ensuring pre-read alignment, stakeholder readiness, and post-meeting follow-through.
  
  

Operational Cadence & Performance

• Manage and maintain Commercial team OKRs, metrics that matter
• Ensure the CCO’s calendar, meeting cadence, and priorities align with strategic outcomes.
• Lead weekly business rhythm—commercial team standups, cross-functional syncs, pipeline, and planning forums—driving clarity on next actions and owners.
• Build out and maintain internal Click up dashboards or project trackers summarizing workstream progress and outcomes for executive visibility.
  
  

Scaling Commercial Excellence

• Help codify and operationalize the CCO’s knowledge and leadership models into SOPs, playbooks, and onboarding guides for Sales, Marketing, and Solution Consulting.
• Coordinate training alignment across Product Marketing and Solution Consulting to enable scalable growth and reduce over-reliance on executive pursuit support.
  
  

Strategic Analysis & Competitive Intelligence

• Drive competitive vendor analysis and synthesize insights into executive-ready presentations for internal discussion and go-to-market planning.
• Serve as the connective tissue between the Commercial org and broader Drips teams (Finance, Product, CS), keeping lines of communication crisp and forward-moving.
  
  

Ideal Profile

• 5–8 years of experience in a fast-paced commercial operations, management consulting, Chief of Staff, or strategy & planning role.
• MBA required
• Executive presence, judgment, and discretion—you can anticipate needs and manage up effectively.
• Exceptional written and verbal communication skills; highly organized and detail-oriented.
• Experience with tools like ClickUp, Salesforce, PowerPoint, and Excel.
• Highly resourceful, bias for action, thrives in ambiguity, and a strong sense of ownership.
  
  

About Drips

Drips is a fast-growing, tech-enabled managed service transforming how health plans engage their members at scale. As the pioneer of Conversational AI-as-a-Service, Drips helps healthcare organizations connect with hard-to-reach members to drive measurable outcomes across the member journey- including Stars, HEDIS, HOS, medication adherence, care gap closure, acquisition, and retention.

Unlike traditional SaaS solutions, Drips is a fully integrated service partner. Our intelligent outreach solutions deliver proven administrative and medical cost savings while directly impacting quality scores, member experience, revenue protection, and operational efficiency. With strong momentum and trusted partnerships across national, regional, and local health plans, Drips is positioned as an indispensable ally in today’s value-driven healthcare landscape.