Despite the operational chaos, the mission to serve marginalized populations keeps us deeply connected.

A value-based healthcare provider focused on marginalized communities, currently wrestling with the painful transition from idealistic startup to a rigid, profitability-driven corporate structure.
Clear culture with defined traits
The Movement
Toyin Ajayi
CEO & Co-founder
Cityblock Health is a healthcare company with 1,000+ employees headquartered in New York, NY, founded in 2017. A profound mission struggling under the weight of hyper-growth and corporate maturation.
Innovation
Cityblock Health leans toward boundary-pushing with a score of 70/100.
Hierarchy
Cityblock Health leans toward structured & clear with a score of 80/100.
Collaboration
Cityblock Health takes a balanced approach to collaboration with a score of 45/100.
Work-Life Balance
Cityblock Health leans toward always-on hustle with a score of 25/100.
Mission
Cityblock Health leans toward purpose-driven with a score of 95/100.
Growth
Cityblock Health leans toward hypergrowth with a score of 65/100.
Toyin Ajayi
CEO & Co-founder
Enforces 'intentional culture' and is driving the pivot from messy startup to mature, structured corporate entity.
Alberto Lopez Toledo
CTO
Appointed to scale AI investments and automate administrative friction across the care platform.
Michael Roaldi
President
Brought in during a period of massive executive expansion to scale operations and standardize care.
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Despite the operational chaos, the mission to serve marginalized populations keeps us deeply connected.
Care management faces unreal caseloads and intense micromanagement.
Constant layoffs and restructurings happen 2-3 times a year, causing high anxiety.
The welcoming startup vibe is gone, replaced by a cold, siloed corporate environment.
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