Chaser is the best pick for owner-run or bookkeeper-run B2B firms on Xero, QuickBooks, or Sage — it auto-chases overdue invoices by email, SMS, calls, and letters, publishes its pricing from $259 a month, and offers a done-for-you collector add-on. Upflow is the best pick for B2B companies with a dedicated finance person — it leans mid-market, prices by quote, and offers more agentic AI, including a Collections Agent whose autonomy you can dial from suggest-only to fully autonomous. Both replace the "who's emailing the late payers this week?" routine with software that follows up on a schedule.
The two, in one line each
Chaser is receivables software that auto-chases overdue invoices by email, SMS, calls, and letters, with AI payment prediction and cash-flow forecasting.
Upflow is an AR platform that automates multi-channel invoice follow-up with AI collection agents and a free analytics tier; paid plans are quote-only.
Where each one actually wins
Chaser wins on transparency and hands-off help. Its Compact plan is $259 a month on monthly billing ($233 annual) for four users, 30 follow-up templates, and four automated workflows, with Core at $779 ($700 annual) and Complete at $1,169 ($1,050 annual). Its AI is real but modest, layered on a rules-based dunning engine: an AI email generator, a Late Payment Predictor, recommended chasing times, debtor risk insights, and an AI revenue forecast. For businesses that would rather not chase at all, an optional Care add-on assigns a dedicated AR specialist who chases on your behalf, at a much higher price. There's a free trial but no free tier.
Upflow wins on AI depth and seats. Every paid plan includes unlimited seats, and its agents include an Insights Agent on all plans, a Collections Agent that drafts outreach grounded in your AR history (Scale plan and up), a Cash Application Agent (Accelerate and up), and an MCP connection for Claude and ChatGPT. It also has a free "Discover" tier, though that is an analytics dashboard with AR benchmarks, not a collections tool. The catch for small businesses: all paid plans are quote-only and tiered by annual invoiced revenue, starting with a plan for up to $10 million in revenue, and the Collections Agent isn't on the two cheapest tiers.
If you're a small B2B firm that wants a published price and optional outsourced chasing, Chaser is the more direct fit. If you have a finance person and want AI agents and unlimited seats, Upflow's platform is built for that, but expect a sales conversation.
Quick comparison
| Tool | Starting price | Core job | Best fit |
|---|---|---|---|
| Chaser | $259/mo (Compact, monthly billing); free trial | Automated invoice chasing + AI payment prediction | Small B2B firms and accountancies on Xero, QuickBooks or Sage |
| Upflow | Quote-only (free analytics tier available) | AR automation + AI collection agents | B2B teams with a finance person, roughly $2M-$50M revenue |
*Prices as listed by each vendor in October 2026. The video above is Chaser's own product introduction; no recent head-to-head video of the two exists.*
Which one should you use?
Choose Chaser if you want a published price, a free trial, and the option to outsource the chasing. Choose Upflow if you have a finance team and want AI collection agents with configurable autonomy and unlimited seats.
FAQ
Do these tools connect to QuickBooks and Xero? Yes — both integrate with QuickBooks Online and Xero and chase by email, SMS, calls, and letters. Chaser also lists Sage, SAP, Odoo, Stripe, and Dynamics 365 Business Central; Upflow also lists NetSuite, Sage Intacct, Pennylane, Chargebee, Stripe Billing, and Zuora.
Is the AI actually deciding who to chase? In Chaser, AI predicts which invoices are likely to be paid late and recommends chasing times, while the chasing itself runs on rules you set. In Upflow, the Collections Agent can draft or send outreach, with autonomy you configure from suggest-only to fully autonomous.
Does Upflow really have a free plan? Its free "Discover" tier is an analytics dashboard with AR health benchmarks and insights. The collections automation itself is on paid, quote-only plans.
Will automated reminders hurt customer relationships? Tone and timing matter. Both tools let you set templates and escalation steps, and Chaser's AI email generator helps draft messages — reviewing the sequence before turning it on is worth the time.
What does Upflow claim it can do for payment speed? Upflow's homepage claims an average 30% reduction in days sales outstanding within three months, which is a vendor claim not independently verified.
Related guides
- Best AI Invoicing Tool for Freelancers in 2026
- How to Write an Invoice and Get Paid on Time in 2026
- Best AI Accounts Payable Automation in 2026
- Explore Business tools
*Ratings and pricing reviewed monthly. Last updated October 2026.*
Bogdex · Founder & editor, woska
Bogdex builds and curates woska, testing AI tools against real workflows to judge which ones actually save time rather than which have the longest feature list.