Hi, I am Zachary Caswell

Product-minded operations leader and founder of Estimate Fox, with 12+ years in the insurance industry. I lead a district handling $500M+ in annual assignments and serve as the primary point of contact for 140+ contractor offices.

About Me

Zachary Caswell

Hi There! I'm Zachary Caswell

Product-Minded Operations Leader | Founder, Estimate Fox

I am a product-minded operations leader with 12+ years in P&C claims and residential repair. I founded and ran Estimate Fox, a nationwide virtual SaaS-based service that helped residential repair contractors with estimating and insurance claims handling. As founder and product owner, I worked with engineers to develop the product, set pricing, drove growth, conducted market and competitor research, onboarded customers, and turned their feedback into product and service improvements—about three years of product management experience. As District Manager at Crawford & Company (Contractor Connection), I lead a district handling $500M+ in annual assignments and serve as the primary point of contact for 140+ contractor offices, most of them small and mid-size residential repair businesses. I started on the claims side at USAA, first resolving complex member issues and later as a desk property adjuster.

Location:Virginia Beach, VA
Product:Founder & product owner, Estimate Fox (2019–2022)
Experience:12+ years in P&C claims and residential repair
Education:B.S. Business Administration – Finance, Liberty University (2011)
Learning:IBM AI Product Manager Professional Certificate (in progress)
Connect on LinkedIn

Building Estimate Fox

About three years of product management experience

August 2019 – August 2022

Residential repair contractors have to produce estimates and work through insurance claims documentation to get jobs documented and paid. I founded Estimate Fox to help with that work: a nationwide virtual SaaS-based service that helped residential repair contractors with estimating and insurance claims handling.

As founder and product owner, I worked with engineers to develop the product, bringing estimating and claims expertise from my years as a USAA desk property adjuster so the service was shaped around real contractor workflows. I worked directly with small and mid-size contractor business owners, onboarded customers, and walked them through those workflows.

I set pricing, drove business growth, and conducted market and competitor research to position the offering. I also gathered customer feedback and turned it into product and service improvements. I count this as about three years of product management experience, from August 2019 to August 2022.

01 — Skill

Customer Discovery & User Empathy

As a former USAA desk property adjuster, I already understood how estimates and claims get reviewed and paid. I then worked directly with small and mid-size contractor business owners, listening to their needs as I onboarded them and walked them through estimating and claims workflows.

02 — Skill

Working with Engineers

I worked with engineers as founder and product owner, bringing estimating and claims expertise to shape the product around real contractor workflows and to decide what to build next from customer feedback.

03 — Skill

Pricing & Packaging

I set pricing for the service and positioned the offering for residential repair contractors, tying the price to the estimating and insurance claims help the product provided.

04 — Skill

Market & Competitor Research

I conducted market and competitor research to understand the landscape and to position Estimate Fox for residential repair contractors.

05 — Skill

Go-to-Market & Growth

I drove business growth for a nationwide virtual service, building relationships with contractor business owners and taking the offering to market.

06 — Skill

Customer Onboarding & Feedback Loops

I onboarded new customers and walked them through estimating and claims workflows, serving as a trusted advisor on getting jobs documented and paid. I gathered their feedback and turned it into product and service improvements that made the service easier to use and more valuable to contractors.

12+ years in the insurance industry
140+ contractor offices in the district I lead
$500M+ in annual assignments
#1 of 12 districts on cycle time, estimate upload time, and customer surveys

What I Do

Product Ownership

I founded and ran Estimate Fox as founder and product owner, working with engineers to develop a nationwide virtual SaaS-based service for residential repair contractors.

Customer Discovery & Feedback

I bring user empathy from years as a desk property adjuster, and I turned conversations with contractor owners—during onboarding and day-to-day work—into product and service improvements.

Pricing, Research & Growth

At Estimate Fox I set pricing, drove business growth, and conducted market and competitor research to position the offering for residential repair contractors.

Contractor Network Management

I lead and support 140+ contractor offices as the primary point of contact in Contractor Connection’s managed repair program for insurance carrier clients.

Partner Success & Onboarding

I onboard new contractor offices, run virtual trainings, coach owners and their teams on program workflows, and build trusted relationships through regular check-ins, meetings, and visits.

Operations Leadership

I use performance data and KPIs to improve processes, hold offices accountable to SLAs, and help the district consistently rank #1 of 12 districts on cycle time, estimate upload time, and customer surveys.

Experience

  1. Dec 2022 – Present Virginia Beach, VA (Remote)

    District Manager

    Crawford & Company (Contractor Connection)

    • Lead a district handling $500M+ in annual assignments as the primary point of contact and relationship owner for 140+ contractor offices in Contractor Connection’s managed repair program for insurance carrier clients.
    • Onboard new contractor offices, coach owners and their teams on program workflows, and build trusted relationships through regular check-ins, virtual meetings, and in-person visits.
    • Use performance data and KPIs to monitor office health, and hold offices accountable to SLAs, program timeframes, and documentation standards.
    • District consistently ranks #1 of 12 districts on cycle time, estimate upload time, and customer surveys.
  2. 2014 – 2019 Chesapeake, VA

    Desk Property Adjuster

    USAA

    • Handled residential property claims end to end, from investigation and coverage determination through estimating, negotiation, and payment.
    • Negotiated with contractors and policyholders to reach fair, well-documented resolutions on repair scopes and estimates.
  3. 2012 – 2014 Phoenix, AZ

    Executive Resolutions Senior

    USAA

    • De-escalated and resolved complex member issues with empathy, diplomacy, and patience, delivering effective solutions while maintaining customer satisfaction.
    • Mentored colleagues on handling difficult situations, strengthening team problem-solving capabilities.

Education & learning

B.S. in Business Administration – Finance

Liberty University, Lynchburg, Virginia · 2011

AI Product Manager Professional Certificate

IBM (Coursera) · In progress

Interests

Running, mountain biking, kayaking, pickleball, indoor rock climbing

My Skills

Strengths shaped by founding Estimate Fox, leading a contractor network, and running claims operations.

These are the areas I built as founder and product owner of Estimate Fox, and that I use every day as District Manager at Crawford & Company (Contractor Connection).

Product Ownership & Development
Customer Discovery & Feedback
Pricing, Research & Growth
Contractor Network Management
Partner & Customer Success
Operations Leadership

What I’m Looking For

I’m open to management, operations, and product management roles, especially at tech-forward, startup-style companies where I can build, iterate, and own outcomes.

Contact

Let’s talk about management, operations, or product management roles — especially in a tech-forward, startup-style environment. Send a message and I’ll get back to you. I’m based in Virginia Beach, VA.

Or find me on LinkedIn