Principal of Executive Operations & AI Enablement, Cityblock Health
$125-165k
+ Equity Program
Healthcare for underserved communities
Be an early applicant
Healthcare for underserved communities
1001+ employees
Be an early applicant
$125-165k
+ Equity Program
1001+ employees
Company mission
To reduce costs, improve the experience and the quality of care, and transform the health of communities.
Role
Who you are
- 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
What the job involves
- The Principal, Executive Operations & AI Enablement serves as the primary operational catalyst, executive governance lead, and AI enablement partner for the Executive Leadership Team (ELT) and Board operations
- This is not a traditional administrative role; it is a high-impact, forward-looking position designed for an elite operator with exceptional executive presence, operational rigor, AI fluency, and judgment
- The role combines three critical dimensions:
- AI-enabled executive workflow transformation and operational optimization
- End-to-end governance and executive operations management for the ELT and Board of Directors
- Strategic execution support for high-priority initiatives and executive priorities
- Acting as a trusted advisor and execution partner to senior leadership, this individual orchestrates executive and Board governance processes, drives operational excellence, and continuously identifies opportunities to leverage AI and automation to increase organizational efficiency and executive leverage
- Success in this role requires obsessive attention to detail, exceptional organizational discipline, executive maturity, professionalism in high-stakes environments, and a relentless commitment to quality, precision, and follow-through
- This individual must thrive in a fast-paced environment while seamlessly balancing strategic thinking with hands-on execution
- AI Prototyping & Workflow Transformation: Act as the internal benchmark for AI productivity. Partner 1:1 with ELT leaders to build custom AI assistants, engineer advanced prompts, automate legacy manual tasks, and introduce modern, scalable operating practices to maximize executive leverage
- Executive Governance & Board Operations: Own the end-to-end strategy and precision execution of all ELT and Board of Directors meetings. Manage complex calendars, design high-impact agendas, track action items, and maintain absolute version control over critical governance assets
- Materials & Communications QA: Serve as the final line of defense for executive outputs. Author, edit, and rigorously quality-assure Board decks, investor presentations, and strategic briefs for absolute polish, accuracy, and clarity
- Strategic Initiatives & Special Projects: Partner directly with the CEO and C-suite to independently drive high-priority cross-functional initiatives under tight deadlines, proactively surfacing operational risks and clearing execution bottlenecks
- Discretion & Trust: Handle highly confidential business matters with exceptional judgment, professionalism, and executive maturity
Our take
Cityblock Health partners with local health insurance providers and professional health practitioners to bring better healthcare to marginalized populations in the US with complex, unmet needs.
While there’s been a groundswell of startups in healthcare, and in particular the value based healthcare space, Cityblock Health sets itself apart through its focus on underserved communities in the US, rather than the wealthy. In doing so, it is helping to drive equity at a time when people need it most.
It's pulled in some serious funding and hasn't wasted a second putting it to work, rolling out its services in new cities and states across the US. The company has set its sights on reaching 10M members by 2030, and it's certainly moving with purpose to get there. Since 2021 funding, it's rolled out its community-focused, value-based care model, opening new offices and locking in key partnerships to bring its vision to more people, faster.
Kirsty
Company Specialist at Welcome to the Jungle
Insights
4% employee growth in 12 months
Company
Funding (last 2 of 8 rounds)
Sep 2021
$400m
LATE VC
Mar 2021
$192m
SERIES C
Total funding: $915m
Company benefits
- Employee connectedness - Time to retreat and connect with teammates to shape our culture and set goals together
- Great health insurance - Comprehensive medical, mental health, dental, and vision coverage for employees and their families, including 12 free therapy or psychiatry sessions per year
- Financial savings - 401(k), HSA, FSA, and Commuter benefits to support you now and for the future
- Paid time off - Up to 9 weeks of paid time off, including vacation, sick & safe time, and holidays
- Parental leave - Up to 16 weeks of paid leave for new parents, and a flexible work culture for everyone, including parents
- Learning and development - Access to LinkedIn Learning and weekly professional development classes, with reimbursement for clinical CEUs
Company HQ
Dumbo, NY
Leadership
Toyin Ajayi
(Co-Founder & CEO)Board certified Physician. Served as President of Cityblock in 2017, becoming CEO in 2022. Previously served as Chief Medical Officer at Commonwealth Care Alliance (CCA), as well as Chief Health Officer at Sidewalk Labs.
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