Remote Content Designer Jobs in Boston, MA (NOW HIRING)

Drips helps organizations build stronger customer and member relationships through personalized, two-way conversations at scale. We combine AI-powered engagement with strategy, design, and managed execution to help people take meaningful next steps across the customer journey.

Our User Experience team turns business goals, user needs, operational realities, and performance insights into clear, useful conversation experiences across channels and use cases.

We're hiring a UX Content Strategist to join our User Experience team as a full-ownership strategist, driving UX strategy, content direction, conversation design, and client-facing delivery for complex programs from discovery through launch and optimization.

Your primary (but not only) focus will be healthcare, designing member-facing experiences for health plans and healthcare organizations. You'll bring enough healthcare fluency to know the difference between a message that's merely accurate and one that's useful, respectful, motivating, compliant, and appropriate for the moment a member receives it. Payer experience is strongly preferred, but we're open to candidates with other meaningful healthcare experience and a demonstrated ability to learn complex domains quickly.

You'll also flex into other verticals when demand requires it. We're looking for a strategist who can take a problem from ambiguity to a clear, defensible, measurable experience and explain the reasoning behind the work.

• Lead discovery and translate client goals, audience needs, operational realities, and program constraints into a coherent UX strategy.
• Develop conversation designs, scripts, content guides, journey maps, kickoff materials, and optimization recommendations ready for implementation and client review.
• Make decisions that balance business outcomes, feasibility, brand voice, privacy, legal, and compliance requirements.
• Own deliverables through review, revision, approval, launch, and post-launch learning, not just the first draft.

• Translate complex clinical, payer, benefit, and program information into plain, empathetic, action-oriented language.
• Recognize when a healthcare message needs additional validation, escalation, or careful handling of privacy and protected health information.
• Work confidently with client subject-matter experts and internal partners when requirements are incomplete, conflicting, or evolving.
• Build reusable patterns, frameworks, and guidance that make high-quality healthcare experiences easier to produce consistently.

• Serve as a trusted UX partner to Client Success, Solutions Consulting, Implementation, Project Management, Production, Data, and other cross-functional teams.
• Facilitate or contribute to discovery sessions, kickoffs, conversation design reviews, and optimization discussions.
• Present your work clearly, explain your rationale, and guide stakeholders toward decisions.
• Close loops on open questions, surface risks early, and keep work moving without waiting for perfect information.Help improve intake, handoffs, templates, documentation, and operating practices across the UX function.

• Connect content and journey decisions to measurable outcomes: engagement, completion, click-through, response, transfer, appointment, conversion, satisfaction, or other program-specific metrics.
• Interpret performance signals and client feedback to recommend changes to message strategy, cadence, sequencing, calls to action, and journey structure.
• Frame hypotheses and split tests that are practical to implement and useful for learning.
• Use emerging tools, including AI-assisted workflows, thoughtfully, with human judgment and rigorous review for quality, brand alignment, privacy, and compliance.

• Meaningful professional experience in healthcare, health insurance, health services, digital health, patient or member engagement, or a closely related domain.
• Strong experience in UX content strategy, content design, or a comparable discipline.
• Demonstrated ability to own complex work from discovery through delivery: strategy, writing, review, stakeholder alignment, and iteration.
• Experience turning complex or regulated information into clear, human, action-oriented content.
• Strong writing and editing judgment across conversational channels such as SMS, IVR, voice, email, web, and surveys.
• Comfort facilitating meetings and presenting work to clients and internal stakeholders.
• Ability to work across multiple concurrent programs, prioritize under pressure, and communicate clearly about scope, tradeoffs, timing, and risk.
• A collaborative approach and a willingness to help improve the system, not just complete individual assignments.

• Experience with health plans, payers, Medicare, Medicaid, quality programs, risk adjustment, HRA or AWV programs, medication adherence, care management, transitions of care, or member engagement.
• Experience designing for populations with different health literacy, accessibility, language, age, or care needs.
• Familiarity with healthcare privacy, PHI-sensitive workflows, regulatory review, or client approval processes.
• Experience with multi-step journeys, branching logic, personalized content, transfer flows, surveys, or conversational AI.
• Experience using performance data or experimentation to improve content and journey outcomes.
• Experience creating reusable frameworks, templates, or playbooks that help a team scale.
• Comfort using AI-assisted tools as a force multiplier while maintaining high standards for human review and accountability.

To be considered for this role, you must submit a brief cover letter that explains your interest in the UX Content Strategist role at Drips. In your letter, highlight your relevant experience in content strategy, content design, healthcare, customer or member engagement, or related fields. Additionally, describe your experience collaborating with cross-functional teams. Please include one example that illustrates your approach to solving a complex content or experience challenge.