Sitreps
SaaS
ChiefofStaff
Neural analysis suggests this role is
optimal for Senior candidates.
“Chief of Staff at Sitreps. Skills: Process management, Cross-functional coordination, Vendor management, Stakeholder management. Run operating cadence. Manage weekly staff meetings”
What You'll Achieve.
Build and operationalize payroll and compliance SOP; Hire and onboard Executive Assistant; Build and organize company knowledge base
Industry & Context.
What They're Looking For.
Must Have
4 to 8 years of experience, Exceptional organizational skills, Builder mentality, Owning broad operational scope, Written and verbal communication skills, Fluency with modern AI tooling
Nice to Have
Veteran or prior service background, Operating experience at early-stage startup, MBA from top-tier program
What You'll Do.
Run operating cadence
Manage weekly staff meetings
Track meeting actions
Coordinate with state agencies
Hire Executive Assistant
Manage administrative support
Design operating system
Document operating system
Codify successful workflows
Partner on fundraising preparation
Manage investor updates
Develop Series A narrative
Quarterback hiring efforts
Coordinate candidate screening
Coordinate interview scheduling
Coordinate interview prep
Coordinate debrief processes
Stand up internal tooling
Stand up AI-native operations tooling
Stand up internal systems hygiene
Serve as connective tissue
How You'll Work.
Team & Collaboration
Connective tissue across engineering; Connective tissue across sales; Connective tissue across customer success; Connective tissue with executive team
Communication Scope
Investor updates; External representation
Process & Methodology
OKRs
Full Job Description
Chief of Staff Philadelphia, PA About the Client The company builds Virtual Bid Assistants for commercial glazing and architectural metals contractors. Their software plus services pulls scope out of RFPs, manages RFIs, and generates proposals so estimators stop missing deadlines and start winning the work they actually want. The business is currently at roughly $2M ARR, targeting $5M by the end of 2026 and $30M by the end of 2027. Backed by leading early-stage investors and headquartered in Philadelphia. About the Role The company is on the path from ~$2M to $30M ARR over the next twenty-four months. That kind of growth requires a real operating system underneath it. The Chief of Staff will serve as the CEO's partner in building and running that system: the cadence, the back-office, the recruiting pipeline, the investor reporting, and the connective tissue across engineering, sales, and customer success. This is the operator who turns founder velocity into company velocity. Responsibilities Run the operating cadence. Weekly staff meetings, agendas, action tracking, dashboards, and OKRs Own the finance and compliance stack. QuickBooks cleanup, payroll, state filings, and coordination with state agencies to ensure proper filings and compliance Build SOPs that allow future hires to operate systems independently Hire and manage an Executive Assistant and additional administrative support as the company scales Design and document the operating system that takes the company from startup stage to a scalable organization Codify successful workflows into repeatable processes across the business Partner with the CEO on fundraising preparation, including investor updates, KPI tracking, data room management, and Series A narrative development Quarterback hiring efforts across the company in partnership with external recruiting firms Coordinate candidate screening, scheduling, interview prep, and debrief processes Stand up internal tooling, including AI-native operations toolin
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