
Job Description
Own the white space. Operate with CEO mandate. Drive the programs that move the company.
We’re hiring a high-agency operator into the Office of the CEO to drive Clover’s most important cross-functional initiatives from ambiguity to execution.
This is a rare role designed for someone who thrives at the intersection of strategy, systems design, and executional rigor. You’ll operate as a force-multiplier to the CEO and executive team: orchestrating execution across organizational boundaries, structuring problems that don’t yet have owners, and driving initiatives that directly shape Clover’s growth and operational leverage.
As a Special Project Lead, you will:
- Architect Strategic Programs: Translate high-level goals into MECE work-streams with clear interfaces, owners, and timelines.
- Drive Execution with CEO-Standard Rigor: Own initiatives from kickoff through outcomes. Set the pace. Maintain altitude and detail without losing either.
- Align Stakeholders Across Levels and Functions: Influence without authority. Drive accountability through clarity, not escalation.
- Translate Ambiguity Into Action: When no playbook exists, build one. When priorities are unclear, ...
The Real Dill ☘️
Clover Health IPO'd back in 2021 by merging with a special purpose acquisition company (SPAC) and has been in and out of the news for various reasons over the past few years. What's clear, however, is their reach is massive - over 250,000 customers combined on it's insurance and non-insurance products. One other thing to note - they operate in the Medicare Advantage space, an area with lots of competition from both startups and traditional insurers. (November 2023)
Jon Lee, PT, DPT, OCS, FAAOMPT, MBA
Pickle co-founder
About Clover Health
Medicare Advantage insurance provider, combining coverage and flexible care model for seniors
MissionImprove every life
Wow FactorServes over 250,000 customers across its insurance and non-insurance offerings
Company benefits
- 🔐 Health insurance
- 🦷 Dental
- 👀 Vision
- 🏡 WFH stipend
- 🐣 Maternity/paternity leave
Pickle is not affiliated with listed companies unless otherwise noted.
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