Chief of Staff/Executive Assistant

Meds.com is a rapidly growing consumer technology firm operating a suite of healthcare businesses, including our flagship brand BlueChew. Our mission is to better patients' lives through innovative healthcare solutions. With a team of 300 professionals across various specialties, we've built scalable pharmacy, telemedicine, and e-commerce platforms using cutting-edge technology. As we continue our accelerated growth trajectory, we're launching new products to expand our patient base and accelerate growth. Join us in tackling exciting challenges at the intersection of healthcare and technology.

We are seeking a highly proactive and experienced Director of Compliance to lead our regulatory framework. As we expand our product offerings and enter new markets, this role is critical in ensuring that our telehealth platform, pharmacy partnerships, and prescription fulfillment processes adhere to the highest standards of safety, ethics, and legal compliance. You will serve as the primary liaison between our operational teams and state/federal regulatory bodies.

Join our team in Austin, TX - we're looking for someone who truly values and enjoys working in the office, not just tolerates it.

Responsibilities

What This Role Offers

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• Direct Access: Full alignment and daily collaboration with experienced, successful tech founders.
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• High Leverage: The autonomy to manage executive workflows, clear roadblocks, and eliminate administrative red tape.
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• Strategic & Operational Scope: A seat at the table for high-level meetings, paired with the responsibility to drive follow-through.
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• Trust & Impact: A position of deep trust, acting as an extension of the leadership team.

Executive Support & Workflow Optimization (EA Responsibilities)

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Communication Synthesis: Monitor, triage, and draft high-level correspondence, ensuring the founders are briefed on critical matters and that external partners receive timely responses.

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Meeting Preparation: Organize agendas, compile background research, and prepare briefs ahead of critical leadership meetings, board reviews, and external partner presentations.

Strategic Execution & Project Management (Chief of Staff Responsibilities)

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Drive Accountability: Attend executive meetings alongside the founders to capture action items, track deliverables, and hold cross-functional teams accountable to deadlines.

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Operational Liaison: Act as a central point of contact connecting the founders with internal departments (Product, Growth, Legal, Ops) and external stakeholders to ensure alignment.

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Special Projects: Own and execute discrete, complex initiatives tasked by the founders—ranging from market research deep-dives to operational process improvements.

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Dashboard & KPI Tracking: Help the founders monitor key metrics across DTC platforms, organizing data and status reports so leadership can make real-time, informed decisions.

What We’re Looking For

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The Ultimate Operator: You are a key operator who excels in highly dynamic environments. You love bringing order to chaos and building repeatable workflows where things are not yet fully "figured out."

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Execution over Ideation: While you are a sharp problem-solver, you are deeply enthusiastic about the execution stage of business—turning ideas into structured project plans and seeing them through to completion.

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High-Level Discretion: Ability to handle sensitive financial, strategic, and personnel data with absolute confidentiality and flawless judgment.

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Anticipatory Thinking: The ability to operate independently, foresee scheduling conflicts or project bottlenecks before they happen, and move fast to resolve them without waiting for instructions.

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Cross-Functional Fluency: Experience wearing multiple hats and communicating confidently across product, growth, and business operations teams.

Qualifications

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5+ years of experience as a Chief of Staff, Executive Assistant to C-Suite founders, or Senior Project Manager—ideally within digital health, e-commerce, or fast-paced startup environments.

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Proven track record of managing complex, cross-functional initiatives with extreme precision, organizational structure, and ownership.

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Master Communicator: Clear, concise, and confident written and verbal communication skills, with the ability to command respect and collaboration across teams.

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DTC & Tech Familiarity: Understanding of digital health platforms, subscription-based models, and modern productivity tools (Slack, Notion, Asana, Google Workspace).

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Analytical Ability: Skilled at synthesizing complex information, financial metrics, or operational data into digestible summaries for executive decision-making.

Perks

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• 100% company-paid Medical, Dental, and Vision premium coverage for employees, plus.
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Short-Term Disability and Life Insurance

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• 401(k) with company match
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• Complimentary daily lunch provided on-site