Sitreps

SaaS

ChiefofStaff

$150–200k Philadelphia, Pennsylvania, United States; New York, New York, United States FULL TIME
Market Sentiment
HIGH DEMAND

Neural analysis suggests this role is
optimal for Senior candidates.

The Brief

“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.

SaaS

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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