VS
Pilot vs Square — Which One Wins?
A detailed, side-by-side comparison of Pilot and Square to help you pick the right tool for your workflow.
TLDR
Quick Verdict
Square takes the lead with a 4.4 rating and is best for brick-and-mortar businesses and restaurants. Pilot (4.0) is the better pick if you need vc-backed startups needing professional bookkeeping.
Side-by-Side Comparison
| Criteria | Pilot | Square |
|---|---|---|
| Rating | ★★★★ 4.0(72) | ★★★★ 4.4(310) |
| Pricing Model | subscription | freemium |
| Starter Price | $599/mo (bookkeeping) | $29/mo (Plus) |
| Free Tier | Yes | Yes |
| Platforms | Web | Web, iOS, Android, Hardware |
| Learning Curve | Easy | Easy |
| API Available | No | Yes |
| Best For | VC-backed startups needing professional bookkeeping | Brick-and-mortar businesses and restaurants |
| Verdict | Best for Startups | Best POS Ecosystem |
Feature Checklist
| Feature | Pilot | Square |
|---|---|---|
| Expert Bookkeeping | — | |
| Tax Prep | — | |
| Fractional CFO | — | |
| R&D Tax Credits | — | |
| Investor-Ready Reports | — | |
| POS System | — | |
| Payment Processing | — | |
| Invoicing | — | |
| Banking | — | |
| Payroll | — |
Pilot
Pros
- ✓Understands startup accounting
- ✓R&D tax credit expertise
- ✓Investor-ready reports
Cons
- ✕Very expensive
- ✕Overkill for simple businesses
- ✕Long onboarding process
Square
Pros
- ✓All-in-one ecosystem
- ✓Beautiful hardware
- ✓Easy to set up
Cons
- ✕Higher processing fees than dedicated processors
- ✕Account stability issues reported
- ✕Can freeze funds without warning
The Bottom Line
Both Pilot and Square are solid tools in the Accounting & Finance space. Square edges ahead with a stronger overall rating (4.4 vs 4.0) and is the better choice for brick-and-mortar businesses and restaurants. However, if you prioritize vc-backed startups needing professional bookkeeping, Pilot is worth serious consideration. We recommend trying the free tier or trial of each before committing.
Frequently Asked Questions
Is Pilot better than Square?▼
Square scores higher overall with a 4.4 rating vs 4.0. However, the best choice depends on your specific needs. Pilot is best for VC-backed startups needing professional bookkeeping, while Square is best for Brick-and-mortar businesses and restaurants.
Can I switch from Pilot to Square?▼
Yes, most users can migrate between the two. Square offers a free tier to test before committing.
Which is more affordable, Pilot or Square?▼
Pilot starts at $599/mo (bookkeeping), while Square starts at $29/mo (Plus). Pilot offers a free tier. Square offers a free tier.