Sumly

Sumly offers bookkeeping software aimed exclusively at self-employed professionals, freelancers and solopreneurs. The product connects to a user's bank accounts and automatically sorts transactions into categories, flagging tax-deductible and partially deductible items (for example, meals at 50%) so that deductions are identified without manual receipt collection or spreadsheets. Alongside expense tracking and ongoing bookkeeping, the service calculates quarterly estimated tax payments, supports tax filing handled by a licensed tax professional, and offers business setup such as LLC formation, with human support available for questions.

The company positions the product against general small-business accounting tools that it characterizes as designed for firms with employees and an outside accountant, arguing those require lengthy setup and ongoing weekly admin. Sumly's stated alternative is quick bank connection, automatic categorization for user review, and read-only bank access through Plaid with encryption. Marketing materials cite roughly 50 hours a year saved and refunds in a $2,000-$18,000 range, and customer testimonials reference individual savings figures.

Founding story

Co-founders Maggi Heneghan and Maximo Librandi met at a pitch competition at Columbia University, where Librandi was completing a Master's in Engineering and Heneghan was at the Business School. Heneghan had worked in consulting and fintech and observed friends going independent and losing time to receipts and quarterly taxes; Librandi, a software engineer and former freelancer, had experienced the same administrative burden. They built Sumly as a simpler way for independent workers to track expenses, keep books and handle taxes.

Business model

Sumly sells a self-serve subscription in three tiers: a free Starter plan, Strive at $49 per month (or $399 billed annually, about $33 per month), and Thrive at $149 per month (or $999 billed annually, about $83 per month). Higher tiers add bookkeeping, payroll and a dedicated tax pro, layering human tax-professional services on top of the software.

Recurring monthly or annual software subscriptions, with a free entry tier and paid plans that bundle bookkeeping, payroll and tax professional services.

Traction

The website features customer testimonials from named users, including a B2B brand strategist citing $13,533 saved, a fractional CFO citing $2,918 saved, and an events manager/creator citing $1,295 saved.