---
title: 'Portfolio CEO: Commercial Roofing Company at American Operator'
canonical: 'https://feeny.ai/job/portfolio-ceo-commercial-roofing-company-american-operator-boston-zd4bw9we3vtb'
type: 'job'
last_seen: '2026-09-09'
---

# Portfolio CEO: Commercial Roofing Company at American Operator

- **Company:** American Operator
- **Location:** Boston, MA
- **Employment:** full-time
- **Work type:** onsite
- **Posted:** 2026-08-20
- **Last confirmed live:** 2026-09-09
- **Apply:** https://jobs.ashbyhq.com/americanoperator/9fd98e70-dded-486e-beca-e89994354a6d

## Job description

## ABOUT AMERICAN OPERATOR

American Operator exists to keep the American Dream alive through small-business leadership and ownership. We place experienced operators into businesses of retiring owners who want their life's work placed in the hands of leaders who care. Over time, our CEOs follow a clear pathway to earn significant equity in the business they lead.

## ABOUT THE ROLE

We are looking for an experienced operator to lead a commercial roofing company as CEO in partnership with American Operator. This is a rare opportunity to step into an entrepreneurial opportunity where the business is already profitable, has a strong reputation, a loyal customer base, and an experienced team already in place. This business has found a niche in an institutional market which leads to recurring repair and service work.

As CEO, you'll assume full responsibility for day-to-day operations, team leadership, and P&L performance. This is not a turnaround situation, it's an opportunity to build on a solid foundation. Your focus will be on developing and growing a great team, driving revenue through project expansion, executing with operational discipline, and scaling the business from a position of strength.

American Operator will be your partner from day one, providing strategic support, resources, and guidance while empowering you to lead independently. Most importantly, you'll have a clear path to earning significant equity ownership in the business you grow and lead.

## WHAT YOU'LL DO

- Own the day-to-day operations and P&L of a commercial roofing company
- Step in as the next leader of a newly acquired business and lead the team and customers through the ownership transition
- Own accurate job estimating and stand up an estimating function to win new commercial business
- Steward the institutional and commercial relationships that anchor the business, earning repeat work through trustworthy, responsive service
- Recruit, manage, and develop a high-performing field team to expand the company’s project capacity
- Partner with American Operator on strategy, budgeting, and growth planning

## REQUIREMENTS

- 10+ years of leadership experience running a construction, contracting, or specialty-trade business
- Proven experience owning P&L performance and driving project-level margin and profitability
- Estimating experience with the ability to price and win institutional and commercial work
- Experience leading and scheduling field crews to deliver projects safely, on time, and on budget
- Experience building high performance teams with accountability for hiring and firing
- Experience personally owning and growing high-trust customer relationships in an institutional, municipal, commercial, or other referral-driven market
- Entrepreneurial leader who can set the vision and lead a business through an ownership transition

## WHAT SETS YOU APART

- Estimated commercial, institutional, or specialty roofing projects
- Stepped in as the new leader after an ownership or leadership transition and earned the trust of a long-tenured team
- Worked on historic or institutional buildings and know the specialty materials and codes they demand
- Grown a trades business by adding crews and labor capacity, and brought basic systems (CRM, job costing) into a shop that ran on word of mouth
- You have scaled a founder-led contracting or trades business
- Hold, or the ability to obtain, a Massachusetts Construction Supervisor License (CSL) and Home Improvement Contractor (HIC) license

## COMPENSATION

Base salary: $170,000, plus a 20% performance-based bonus opportunity, distributions, and meaningful equity participation beginning at 10% ownership, with the potential to increase ownership based on performance and value creation. Total compensation varies by portfolio company, individual performance, and deal structure, and includes a comprehensive benefits package.

## LOCATION

This opportunity is located in the greater Boston metro area. The exact location of this business will be revealed during the interview process. Relocation will be required if you are not currently in or near the market of the opportunity.

Ready to lead the next chapter? Before you apply, we encourage you to visit americanoperator.com http://americanoperator.com to learn more about who we are, how we work, and what our operators have to say about the experience. When you are ready, apply today to start the conversation.

## About American Operator

## Company Overview
- **One-liner**: American Operator acquires small businesses from retiring owners and partners with experienced industry operators to lead as CEO, with a clear path to earn majority ownership.
- **Entity Type**: Private (backed by institutional investors; funding stage not disclosed)
- **Headquarters**: Austin, TX, USA
- **Founded**: Not publicly available
- **Founders**: William Fry (CEO, Founder)

## Core Business
- Primary industry: Small business acquisition and operation (search fund / “acquire-and-operate” model)
- Target customers: Retiring small business owners (sellers) and high-capacity industry operators (buyers/CEOs); serves B2B/B2C across multiple verticals
- Mission or purpose statement: “Reviving the American Dream” by creating a new path to small business ownership for the next generation of hardworking Americans.

## Products & Services
- **Operate-to-Own Model**: American Operator funds the acquisition of a small business, partners with a proven operator to lead as CEO, and provides hands-on support and governance. The operator receives meaningful day-one ownership and can incrementally buy back equity until they become majority owner. [americanoperator.com](https://www.americanoperator.com/)
- **America’s Small Business Stock (future offering)**: The company is working toward a public offering that would allow everyday Americans to invest in a portfolio of small businesses, democratizing ownership. [americanoperator.com/about-us](https://www.americanoperator.com/about-us)

## Market Standing
- **Valuation/Market Cap**: Not publicly available
- **Key Metric**: Total funding not disclosed; recent acquisition of Greenway Painting (Jackson, MS) completed. [americanoperator.com](https://www.americanoperator.com/)
- **Notable Investors/Partners**: Board includes Joe Lonsdale (co-founder of Palantir, 8VC) and Baris Akis; advisor network of current and former business owners across multiple industries. [americanoperator.com/about-us](https://www.americanoperator.com/about-us)
- **Growth Signals**: Active hiring for multiple roles (VP of Investments, VP of Portfolio Performance, Business Development Associate); expanding portfolio with announced acquisition; building out advisor network for scaling across industries. [builtin.com](https://builtin.com/company/american-operator)

## Competitive Advantages
- **Operate-to-Own Model**: Differentiates from traditional private equity by offering operators a clear path to majority ownership rather than permanent minority stake.
- **Hands-On Support**: Operators receive a dedicated industry advisor, governance structure, and access to American Operator’s back-office resources.
- **Local Focus**: Keeps businesses locally owned and operated, preserving community relationships and reputation.
- **Strong Advisor Network**: Experienced operators and former owners provide sector-specific guidance (home services, manufacturing, landscaping, painting, etc.).

## Strategic Focus
- Scale acquisition pipeline across multiple industries (home services, manufacturing, landscaping, logistics, etc.)
- Build a portfolio of enduring small businesses and work toward a public “small business stock” offering
- Expand the operator candidate pool and continue refining the operate-to-own playbook

## Why Work Here
- **Culture**: Tight-knit, mission-driven team focused on high-impact work; “your voice is heard, your impact is real.” [americanoperator.com/careers](https://www.americanoperator.com/careers)
- **Work Policy**: In-office collaboration at the Austin, TX headquarters (on-site work expected, with snacks and team connection). [americanoperator.com/careers](https://www.americanoperator.com/careers)
- **Benefits**: Comprehensive medical/dental/vision, 401k with company match, generous parental leave, flexible time off (“Use What You Need”). [americanoperator.com/careers](https://www.americanoperator.com/careers)
- **Growth Exposure**: Hands-on work with live deals, critical operations, and strategic portfolio support – ideal for candidates seeking fast learning and real ownership experience.
- **Values**: “Operator First,” “American Roots,” “High-Impact” – emphasis on building strong local businesses and supporting operators taking the bold step into ownership.

## Sources
1. [americanoperator.com](https://www.americanoperator.com/)
2. [americanoperator.com/careers](https://www.americanoperator.com/careers)
3. [americanoperator.com/about-us](https://www.americanoperator.com/about-us)
4. [builtin.com](https://builtin.com/company/american-operator)

## Other roles at American Operator

- [Vice President, Portfolio Performance](https://feeny.ai/job/vice-president-portfolio-performance-american-operator-austin-da3y16dr8a6w) — Austin, TX
- [Vice President, Investments](https://feeny.ai/job/vice-president-investments-american-operator-austin-h3xqfv4zzysc) — Austin, TX
- [Portfolio CEO: Event Production and Rental Company](https://feeny.ai/job/portfolio-ceo-event-production-and-rental-company-american-operator-san-diego-ds3kvd7d948r) — San Diego, CA
- [VP, Operator Selection & Experience](https://feeny.ai/job/vp-operator-selection-experience-american-operator-austin-fc7vagczn1c8) — Austin, TX
- [Portfolio CEO Network: Commerical Distribution](https://feeny.ai/job/portfolio-ceo-network-commerical-distribution-american-operator-allen-town-9kzsx4x9nm0d) — Allen Town
- [Deal Sourcing Analyst](https://feeny.ai/job/deal-sourcing-analyst-american-operator-austin-bs3ejt7w4bbk) — Austin, TX
- [Portfolio CEO: Tent & Event Rental Company](https://feeny.ai/job/portfolio-ceo-tent-event-rental-company-american-operator-philadelphia-wj48vz4nznjq) — Philadelphia, PA
- [Portfolio CEO Network](https://feeny.ai/job/portfolio-ceo-network-american-operator-united-states-v6mvggz17jm5) — United States