Senior Site Success Manager.

City Bureau is seeking a Senior Site Success Manager to join our Documenters team and serve as a trusted partner, strategic advisor, and hands-on problem-solver for a portfolio of Documenters sites across the country. This is a senior-level role for someone who brings deep expertise in nonprofit revenue generation and development alongside a strong background in coaching and consulting; someone who thrives in complex multi-stakeholder environments and can lead difficult conversations with confidence and care.

You’ll manage a portfolio of up to six sites with a high degree of autonomy, owning relationships and outcomes across the full program lifecycle, from incubation and launch through growth, intervention, and, when necessary, offboarding. You’ll also contribute meaningfully to the broader strategy and systems that make the Documenters Network work at scale.

We’re looking for someone who combines the instincts of a skilled coach with the rigor of a strategic analyst - someone who can read a situation, identify what a site really needs, and design a path forward even when the terrain is complicated. The ideal candidate is comfortable leading organizational change conversations, synthesizing data into actionable insights, and contributing to team-wide learning and capacity building.

This role reports to the Director of Site Success and collaborates closely with cross-functional partners across product, communications, and operations.

• $80,000 annual salary. City Bureau uses a universal compensation system.
• Full-time with a benefits package including health care, dental, vision, and life insurance.
• Employer-sponsored 401k with 100% employer match up to 2% of salary.
• $1,000 combined annual technology and work tools and professional development allowance.
• 15 days paid vacation, not including health days.
• 11 company holidays each year, which may be exchanged for employees who celebrate other holidays.
• A 4.5-day week for most of the year; during three summer months, City Bureau operates on a 4-day work week.
• Remote, with occasional travel to Chicago and partner communities; Chicago-area staff are expected to participate periodically in in-person City Bureau community events.
• A culture of intentional professional development and organizational learning.
• This position is represented by the Chicago News Guild, TNG-CWA Local 34071 (City Bureau Workers Guild).