Before:
- Manual 1099 processing across encrypted, siloed systems
- Daily file transmission requirements—even with no payments
- Multiple payments per contractor due to rigid vendor code structure
- Ongoing support load from contractors without self-serve visibility
After:
- Automated 1099 generation with real-time EIN matching
- On-demand, consolidated payments for 1,000+ monthly contractors
- Instant payouts delivering funds within minutes
- Reduced support volume thanks to contractor self-service portal
Company Overview
Safeguard Properties, headquartered in Cleveland, Ohio, is the largest privately held mortgage field services company in the U.S. Working on behalf of mortgage lenders, servicers, and government-backed investors, Safeguard manages a nationwide network of independent contractors who inspect and maintain vacant homes throughout the foreclosure lifecycle.
Each month, Safeguard processes hundreds of thousands of work orders that must be quickly and accurately paid out.
“We don’t own a single hammer or lawnmower. Everything we do relies on a vast network of subcontractors across the country, and Wingspan helps us keep that running.”
— Jennifer Anspach, AVP of Finance
The Challenge
Prior to Wingspan, Safeguard used a legacy multi-party payment setup that was rigid, error-prone, and highly manual:
- Payment rigidity: Work Orders submitted with multiple work codes led to vendors and subcontractors receiving separate payments, resulting in extra processing, errors, and frustration.
- Daily file submission required: Even if no payments were due, a zero-dollar “dummy file” had to be sent to avoid process failures.
- Manual check processing: Contractors who opted out of electronic payments triggered costly, time-consuming paper checks.
- No 1099 or EIN support: Tax season required hours of manual work and data stitching across encrypted systems.
“Before Wingspan, we were manually compiling 1099s from multiple systems with encrypted EINs and ridiculous passwords—it was like an arts and crafts project.”
— Jennifer Anspach, AVP of Finance
Results
$36.9M in Payout Volume in 4 Months
Between April and July 2025, Safeguard processed over $36.9 million in contractor payments through Wingspan—enabling seamless payments to over 1,000 contractors monthly.
“We process thousands of invoices per month, which we then consolidate and send to Wingspan for payment processing.”
— Jennifer Anspach
2,300+ Instant Payouts for Contractors
Contractors opted for 2,301 instant payouts during this period, totaling more than $4 million in accelerated payments—demonstrating demand for immediate, flexible access to funds.
- July alone: 791 instant payouts totaling over $1.3M
- Instant payouts increased 86% from April to July
20% Drop in Contractor Support Calls
Safeguard’s finance team saw a clear decline in inquiries thanks to Wingspan’s contractor portal, where vendors can view and manage their payment history independently.
“Wingspan reduced our support calls by at least 20%. It’s made life easier for vendors—and our finance team.”
— Jennifer Anspach
60+ Hours Saved During Tax Season
By automating 1099 processing and IRS validation, Safeguard dramatically reduced year-end lift for its team.
“Wingspan handles the heavy lifting. I don’t have to troubleshoot every week. We just review the data. I can’t imagine going back to the old way.”
— Jennifer Anspach
Why Wingspan
Safeguard had already seen Wingspan in action at a subsidiary, National Safety & Risk, and the finance team chose to expand its use based on proven results. The deciding factors:
- Flexible payment workflows, including consolidated payouts across contractor codes
- Automated 1099 generation and real-time EIN validation
- A user-friendly contractor portal and self-service payment visibility
- The ability to scale: 1,000+ contractors and 250,000+ monthly invoices
“It was quick, easy, and intuitive for vendors to log in and get paid how they want. That’s a huge shift.”
— Jennifer Anspach, AVP of Finance
Implementation
Safeguard opted for a cautious, phased rollout—beginning with high-volume contractors to validate the process. Satisfied with the process for their first group of contractors, they moved quickly to migrate their remaining thousands of contractors. Wingspan's flexible and customized implementation process allowed Safeguard to move at the best pace for their business.
- Responsive support: Wingspan’s team was highly available throughout onboarding.
- Simple setup: Even team members with no accounting background found it easy to configure and manage.
- Minimal disruption: No outages, rework, or escalations during implementation.
“Anybody can use it with very little knowledge. It’s that easy to understand.”
— Pari Prata, Business Analyst
Looking Ahead
With a full 1099 cycle ahead and strong contractor adoption, Wingspan is now a foundational part of Safeguard’s contractor operations, trusted to support high-volume payouts and year-round compliance.
“Once they're up and running, they're just running. We're not having to troubleshoot and fix things every week. That’s been great from my perspective.”
— Jennifer Anspach, AVP of Finance
Contractor finance at scale doesn’t have to be complex.
See why leading operations teams trust Wingspan to handle weekly payments, 1099s, and vendor support at volume. Request a Demo →