Insightly vs Square POS: which one fits your business?
Side-by-side comparison of Insightly and Square POS — fees, features, ease, support, and which one fits your business. Scored on the same rubric.
Short answer: Square POS wins on our scorecard (7.3/10 vs 6.9/10).
| Scored on | Insightly | Square POS |
|---|---|---|
| Right fit for small biz | 7 | 8 |
| Ease of use | 8 | 7 |
| Fees & pricing | 6 | 7 |
| Customer support | 5 | 6 |
| Features | 8 | 8 |
| Plus Plan (Annual) | $29/user/mo | — |
| Professional Plan (Annual) | $49/user/mo | — |
| Enterprise Plan (Annual) | $99/user/mo | — |
| Success Plan (Support) | Varies by tier | — |
| Standard Processing (Swiped) | — | 2.6% + $0.10 |
| Keyed-in Transactions | — | 3.5% + $0.15 |
| Monthly Software Fee (Basic) | — | $0 |
| Square for Restaurants Plus | — | $60/mo per location |
Insightly in one paragraph
A powerful bridge between sales and operations that is great for professional services, provided you watch out for the tiered pricing traps.
Skip it if: You are a solo-founder who only needs a basic digital Rolodex or if you require instant phone support without paying extra.
Square POS in one paragraph
Square POS is the gold standard for startups and small retailers who want a zero-cost entry point into professional sales tracking, provided they can handle the risk of automated account holds.
Skip it if: Skip it if you process high-ticket items (over $5,000 per sale) or have a high-risk business model that could trigger frequent automated account freezes.
Frequently asked questions
Which is better, Insightly or Square POS?
On our five-axis scorecard, Square POS scores higher (7.3/10 vs 6.9/10). Square POS is the gold standard for startups and small retailers who want a zero-cost entry point into professional sales tracking, provided they can handle the risk of automated account holds.
Who should skip Insightly?
You are a solo-founder who only needs a basic digital Rolodex or if you require instant phone support without paying extra.
Who should skip Square POS?
Skip it if you process high-ticket items (over $5,000 per sale) or have a high-risk business model that could trigger frequent automated account freezes.