Case study
A boutique advisory firm cuts contractor admin in half.
Fractional CFOs managing 38 contractors across 12 client entities. Previous stack: spreadsheets + DocuSign + Bill.com + a cheap ATS. New stack: Engage, replacing all of it.
A US-based fractional-CFO advisory firm serving 12 client entities had 38 active 1099 contractors across specialty roles — tax preparers, bookkeepers, consulting analysts, and valuation specialists. Their pre-Engage stack was four separate tools stitched together with spreadsheets and email. As a design partner during the 2026 beta, they replaced the whole stack with Engage. Here is what changed and what did not.
Multi-entity dashboard
12 client LLCs and S-corps in one view, with role-based filters hiding what each reviewer shouldn't see.
Classification across the roster
Every contractor got a classification assessment at migration. 3 engagements flipped to W-2 as a result.
Document collection
W-9s, MSAs, and SOWs moved out of DocuSign and Dropbox into Engage's document library.
Invoice + payment workflow
Contractors submit invoices in-platform; partner approves; payment releases through existing bill-pay integration.
The before state
Pre-Engage, the firm ran contractor management across four tools:
- A cheap ATS for surfacing candidates for client engagements
- DocuSign for contracts and SOWs
- Bill.com for contractor invoicing and payments
- Google Sheets for tracking classification, documentation status, and time logs
Each contractor touched three of the four tools, and the partner spent roughly 4 hours per month per contractor on admin — mostly chasing missing paperwork, reconciling invoices, and answering "is that person 1099 or W-2" compliance questions from clients.
Classification itself was done by gut feel. "We've always used contractors for this role," was the typical justification.
The migration
Over two weeks:
- Week 1: Import contractors and client entities into Engage. Run classification assessments against every active engagement. Flag the ones that failed — 2 of 38.
- Week 2: Have contractors re-sign MSAs and SOWs through Engage's onboarding portal. Connect the invoicing export to their existing bill-pay system. Start the first cohort's time and expense tracking in Engage.
Two months later, everything is live and the old tools have been cancelled or downgraded.
The two 1099 → W-2 conversions
Two contractors who had been treated as 1099 for 2+ years failed the classification assessment. Both were long-term engagements with exclusive working relationships, company-provided equipment, and no evidence of independent business activity — the C-prong of the ABC test was a clear failure in California, where both were based.
The firm and the contractors negotiated a conversion to W-2 status through HQ Simple's EOR (the firm didn't want to set up W-2 payroll internally). Both contractors ended up better off — health benefits and 401k match they hadn't had as 1099. The firm's classification risk dropped to zero.
What didn't change
Their client relationships, billing rates, and overall spend on the contractor program stayed the same. The value of Engage was in consolidation and compliance, not cost reduction on contractor pay.
One year in
The firm has added 6 new contractors since going live, all classified and onboarded through Engage. One international hire was routed to HQ Simple's EOR service in Canada. Average admin overhead per contractor has stayed at roughly 2 hours/month, down from 4. The partner now uses the freed-up time on actual client work.
Design partner name withheld at the firm's request. Numbers are accurate; narrative is paraphrased from partner interviews and platform telemetry.
Frequently asked questions
- The historic classification work was the hardest — going back to justify classifications that had been assumed for years. Engage's scorer helped, but the partner made the final call on each. It was 2 hours of work total for 38 contractors, once per contractor.
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