Chief of Staff

Chief of Staff

Philadelphia, PA

About the Client

The company builds an AI-powered estimating and proposal platform for specialty construction contractors. Its software-plus-services offering 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 an early-revenue, growth-stage company. Backed by leading early-stage investors and headquartered in Philadelphia.

About the Role

The company is on a steep growth path 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 fundraising 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 tooling, dashboards, and internal systems hygiene
• Serve as the connective tissue between engineering, sales, customer success, and the executive team

First 90 Days

Success in the first 90 days will be measured against three core deliverables:

• Payroll and compliance SOP built and operational
• Executive Assistant hired and onboarded
• Company knowledge base built and organized to support rapid onboarding and scaling

Requirements

Must-Haves

• 4 to 8 years of experience with a strong track record of execution
• Backgrounds may include top-tier management consulting, private equity portfolio operations, prior Chief of Staff experience at a high-growth company, Capitol Hill staffing experience with a follow-on MBA, or junior military officer experience followed by an operating role
• Exceptional organizational skills with the ability to manage multiple priorities simultaneously
• Builder mentality — focused on creating systems and executing, not over-planning
• Comfortable owning broad operational scope end-to-end in a highly hands-on environment
• Strong written and verbal communication skills with the ability to represent the CEO and company externally
• Fluency with modern AI tooling including Claude, Claude Code, agents, and AI-native workflows

Nice-to-Haves

• Veteran or prior service background
• Operating experience at an early-stage startup, especially in vertical SaaS or AEC-tech
• MBA from a top-tier program such as Wharton, HBS, or similar institutions

Compensation & Benefits

• Base Salary: $150K–$200K
• Equity: early-employee equity grant with significant upside tied to company growth trajectory

Philadelphia preferred, with an in-person presence expected the majority of the week.

Open to NYC-based candidates who can travel to Philadelphia two days per week.

Remote-only candidates are not a fit for this role.