Job Description:

The Sr. Associate, Engagement Strategist is the market-facing owner of engagement outcomes for Cityblock’s attributed populations. In this role, you will design and execute AI-enabled, digitally-driven, human-supported engagement strategies that drive measurable clinical, financial, and member experience impact.

Strategists sit at the center of Cityblock’s Member Experience model -- partnering closely with local market leadership, Member Engagement Operations (inbound + outbound), Digital Communications, and Care teams. You will translate market goals, contract incentives, and segmentation insights into clear weekly, monthly, and quarterly engagement plans, and ensure those plans are executed smoothly across digital and human channels.

This role is ideal for someone who is highly organized, analytical, collaborative, and energized by connecting digital workflows, operational execution, and market-level strategy.

The Engagement Strategist will

Serve as the primary interface between our local markets and the centralized Member Experience engagement engine.

• Build trusted relationships with Market MVPs, Ops partners, and clinical leaders.

• Communicate engagement priorities, program plans, timelines, and results.

• Consolidate market needs and translate them into briefs for digital and human channels.

• Ensure consistent, coordinated messaging and execution across all MX modalities.

​Own the end-to-end engagement strategy and program orchestration for assigned markets, ensuring digital and human engagement work as a unified system.

• Translate market goals, segmentation insights, and contract requirements into coordinated, multi-modal engagement programs.

• Partner with Digital Strategy (Marketing Ops + Digital Comms) to build sequenced digital workflows (SMS, email, webforms, routing) that warm members before human outreach.

• Work closely with Engagement Operations (inbound + outbound) to align calling strategies, scripts, timing, and capacity to the digital plan.

• Collaborate with Data and Analytics to understand segment behavior, channel performance, and readiness signals that inform prioritization.

• Integrate guidance from Behavioral Change & Program Design (BCD) to ensure messaging and interventions are behaviorally informed, accessible, and tailored to specific populations.

• Collaborate with Product and Analytics teams to operationalize AI-driven programs -- including propensity models, digital behavior signals, and automated routing -- into day-to-day engagement strategy.

• Ensure that digital and human channels work together -- not in parallel -- with clear sequencing, consistent messaging, and smooth member handoffs.

• Troubleshoot issues in workflows, routing, messaging, or operational execution quickly and collaboratively across all teams.

Monitor performance and drive continuous improvement.

• Review dashboards and performance signals daily and weekly.

• Identify friction points across the funnel (digital → human → care).

• Recommend strategy shifts, new segments, new sequencing, or new test designs.

• Run structured test-and-learn cycles with clear hypotheses and measurement.

• Partner with Data and Analytics on segmentation performance and insights.

• Surface insights from care teams, call center teams, member feedback, and market dynamics.

• Ensure insights translate into product, workflow, and message improvements across MX.

Work Experience

• 3–5 years of relevant professional experience in healthcare engagement, lifecycle marketing, operations strategy, or applied human-centered design

• Cross-functional project management

  • Ability to coordinate work across multiple teams (Digital Strategy, Engagement Operations, Data & Analytics, Behavioral Change & Program Design, Market Ops, Care Teams).

  • Strong organization and task management skills; able to manage multiple simultaneous workstreams.

  • Skilled at building workbacks, timelines, briefs, and launch checklists.

  • Excellent communicator who ensures alignment between digital and human channels.

  • Experience facilitating meetings, clarifying roles, and maintaining accountability across stakeholders.

  • Proactive issue identification and resolution -- “connective tissue” between teams.

  • High attention to detail with strong QA instincts (logic, routing, content, sequencing).

• Engagement strategic planning

  • Ability to translate market goals, contract levers, and member insights into actionable omnichannel engagement plans.

  • Comfort with segmentation logic and prioritizing cohorts based on readiness, value, or performance.

  • Skilled at designing multi-modal strategies that combine digital workflows with human outreach.

  • Understanding of behavior-change principles and how they apply to messaging and sequencing.

  • Ability to create structured briefs that guide digital builds, content, and operational execution.

  • Systems thinking: sees how digital, operational, and clinical elements fit together.

  • Capacity to balance short-term needs with long-term engagement strategy.

• Program analysis

  • Ability to read dashboards, interpret early signals, and identify performance issues.

  • Skilled at evaluating engagement funnels (digital → human → care) to identify friction points.

  • Familiarity with common engagement metrics (reachability, conversion, action rates, downstream outcomes).

  • Ability to partner with Analytics to understand segment opportunities and channel performance trends.

  • Comfortable forming hypotheses, running controlled tests, and evaluating results.

  • Experience translating findings into clear recommendations and next steps for iteration.

  • Strong written and verbal storytelling skills to communicate performance to senior leaders.

We take into account an individual’s qualifications, skillset, and experience in determining final salary. This role is eligible for health insurance, life insurance, retirement benefits, participation in the company’s equity program, paid time off, including vacation and sick leave. The actual offer will be at the company’s sole discretion and determined by relevant business considerations, including the final candidate’s qualifications, years of experience, skillset, and geographic location. The expected salary range for this position is:

Cityblock values diversity as a core tenet of the work we do and the populations we serve. We are an equal opportunity employer, indiscriminate of race, religion, ethnicity, national origin, citizenship, gender, gender identity, sexual orientation, age, veteran status, disability, genetic information, or any other protected characteristic.

We do not accept unsolicited resumes from outside recruiters/placement agencies. Cityblock will not pay fees associated with resumes presented through unsolicited means.