Principal, Executive Operations & AI Enablement

Requirements: Bachelor’s degree in Business, Computer Science, Engineering, or a related field preferred. Familiarity with the operational, regulatory, and compliance considerations within value-based healthcare or high-growth technology environments is a strong plus. Overall Experience: 8+ years of progressive experience in Chief of Staff functions, strategic operations, management consulting, or high-level executive operations within fast-paced, high-growth environments. Executive Operations Expertise: Proven experience supporting executive leadership teams and Board governance processes, including executive meetings, Board administration, agenda management, executive communications, and confidential leadership operations. AI Technical Literacy: Advanced hands-on proficiency with modern generative AI tools and platforms (e.g., OpenAI, Claude, custom GPTs, Microsoft Copilot, AI-enabled workflow automation tools such as Zapier or Make, and productivity-enhancing AI applications). Tooling Expertise: Mastery of modern productivity and collaboration platforms including Google Workspace, Microsoft 365, Slack, Notion, Asana, ClickUp, Jira, Monday.com, or similar operational systems. Communication & Presence: Exceptional verbal and written communication skills with the professional presence required to comfortably influence senior executives, investors, and Board members. Execution Style: An unwavering ownership mindset with obsessive attention to detail, strong systems thinking, and a calm demeanor under high-stakes pressure. 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: $125,000.00 - $165,000.00 Annual 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. Cityblock Health is the first tech-driven provider for communities with complex needs—bringing better care to where it’s needed most, block by block. Founded in 2017 on the premise that “health is local” and based in Brooklyn, we are backed by Alphabet’s Sidewalk Labs along with some of the top healthcare investors in the country. Our mission is to improve the health of underserved communities. Importantly, our solutions are designed specifically for Medicaid and lower-income Medicare beneficiaries, and we meet our members where they are, bringing care into the home and neighborhoods through our community-based care teams and Virtual Care offerings. In close collaboration with community-based organizations, local providers, and leading health plans, we are reorganizing the health system to focus on what matters to our members. Equipped with world-class, custom care delivery technology, we deliver personalized primary care, behavioral health, and social services to deliver a radically better experience of care for every member and community we serve. Over the next year, we’ll grow quickly to bring better care to many more members and their communities. To do this, we need people who, like us, believe that everyone should have good care for what matters to them, in their community. Our work is grounded in a belief in the power of a diverse community. To close gaps in care and advance equity in the communities we serve, we have to start with making our own team diverse and inclusive. Our ways of working are characterized by creativity, collaboration, and mutual learning that comes from bringing together a community from diverse backgrounds and perspectives. We strive to ensure that every person on the Cityblock team, and every Cityblock member, feels supported and included as a part of our community. Our Values: Aim for Understanding Be All In Bring Your Whole Self Lean Into Discomfort Put Members First About our Team: We employ a field-based, home-based care model and are committed to meeting members where they are--in their homes, in their community, and in our Hubs. We will go above and beyond to connect with Cityblock members in a non-judgmental, respectful and empathic manner, to meet their needs, and to provide feedback to the system as a whole as we strive to do better every day.

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