Top 6 Invoicing & Proposal Tools Freelancers Use to Turn Late-Paying Clients Into On-Time Payers

For freelancers, managing cash flow is just as critical as delivering great work. One of the major roadblocks to a healthy freelance business is dealing with *late-paying clients*. Late payments disrupt planning, create stress, and could even steer you away from projects that originally seemed promising. Fortunately, technology is on your side. With the right invoicing and proposal tools, you can encourage clients to pay on time — if not early.

TLDR:

Freelancers can put an end to late payments by using the right invoicing and proposal software. The best tools offer features like automated reminders, client portals, e-signature enabled proposals, and integrated payments to simplify the billing process. Top platforms include Bonsai, FreshBooks, AND.Co, and more. These tools don’t just make invoicing easy — they also help establish professionalism and boundaries.

1. Bonsai – All-In-One Platform for Freelancers

Bonsai is widely known in the freelancing world for its complete business suite – it covers time tracking, contracts, invoicing, tax prep, and proposals. One of its standout features is the ability to automatically add late fees to invoices that aren’t paid by the due date, encouraging clients to pay on time from the outset.

• Automated reminders that nudge clients as deadlines approach
• Deposit requests integrated into proposals and invoices
• Payment methods include ACH, credit card, and PayPal

Freelancers particularly love Bonsai’s customizable proposal templates that include the option for e-signatures, eliminating delays caused by back-and-forth emails. Once a proposal is approved, it seamlessly transitions into an invoice.

2. FreshBooks – Invoicing Powerhouse with Time Tracking

FreshBooks has built its reputation on simplicity, but don’t let that fool you — this is a robust platform perfect for freelancers and small business owners alike. Its intuitive dashboard and automation tools help create, send, and manage invoices effortlessly.

• Schedule recurring invoices to retainers or long-term clients
• Late payment penalties can be added automatically
• Online payment support that includes Stripe and bank transfers

FreshBooks also has one of the most detailed client reporting dashboards, so you can see which clients consistently pay late — and take action. Time tracking integrates into invoices directly, reducing friction and making billing more accurate.

3. HoneyBook – Professional Proposals with a Personal Touch

HoneyBook is designed for creative freelancers who want to blend sleek design and functionality. Known for its stunning proposals, this all-in-one platform includes contracts, payments, and client communication in a single ecosystem. Its proposal tool is a secret weapon for setting payment expectations right from the start.

• Client portal allows clients to view, approve, and pay all in one place
• Smart payment scheduling lets you break payments into milestones
• Automatic follow-ups reduce the need for awkward reminders

Freelancers using HoneyBook report fewer ghost clients thanks to its integrated proposal-approval-invoice workflow. Payment plans help you set expectations early and avoid vague “net 30” terms that often lead to delays.

4. AND.Co – Simplicity That Gets You Paid

Now part of Fiverr’s suite of freelancer tools, AND.Co offers a free and premium version that strips invoicing and proposals down to what matters most: clarity and ease. Designed for solo freelancers, it’s one of the simplest tools to operate.

• Quick contracts and proposals that are legally sound
• Smart invoicing that detects billable hours and suggests invoices
• Auto-reminders that let you “set and forget” billing follow-ups

The platform also lets clients pay directly from the invoice using multiple payment options, removing any friction during the process. For freelancers tired of chasing payments and juggling tools, AND.Co is a breath of fresh air.

5. PayPal Invoicing – Convenient and Familiar

While not a dedicated freelancing platform, PayPal’s invoicing system remains one of the top-used tools due to its sheer convenience and client familiarity. Nearly every client has a PayPal account or at least trusts the platform, making it a fast and non-intimidating choice to get paid.

• Instant invoice sending and real-time payment status updates
• Built-in tax and discount options for streamlined negotiation
• Integrated tipping options that encourage more generous clients

One standout feature is the ability to send invoices via a link—which can be texted, emailed, or even sent through social media. While PayPal doesn’t have robust recurring invoice support or complex proposal features, it works especially well for freelancers offering one-off services or working internationally.

6. Proposify – Serious Proposal Automation for Bigger Deals

If your work involves pitching large-scale or long-term projects, Proposify specializes in building proposal documents that *win* contracts and set expectations right away. The platform is known for its collaborative editing, detailed metrics, and incredible design flexibility.

• Interactive proposals with embedded pricing tables, upsells, and videos
• Analytics showing which parts of your proposal clients linger on
• Seamless digital signatures and auto-conversion into invoices

This tool is especially powerful for freelancers who constantly find themselves explaining terms or getting approval on complex deliverables. The structured flow means clients understand timelines and payment terms better, minimizing miscommunication that often leads to late payment.

How These Tools Help Ensure On-Time Payments

It’s not just about creating a nicer-looking invoice — these tools are about setting expectations and eliminating friction in every step of the client relationship. Here’s how they do it:

• Upfront payment scheduling: Milestones, deposits, and clear terms eliminate ambiguity.
• Automated reminders: No need for awkward follow-ups or emotional labor.
• Integrated payments: Fewer delays due to “check’s in the mail” excuses.
• Built-in penalties: Late fees and terms of service deter delays from the start.
• Professionalism: When your proposal and invoice look sharp and organized, clients take you seriously.

Tips for Getting Paid Faster Every Time

In addition to using these tools, make sure you follow these practical tips:

1. Request deposits: Always get a percentage upfront before starting work.
2. Set due dates clearly: “Due upon receipt” often works better than net-30 for freelancers.
3. Communicate expectations: Discuss payment terms during the proposal stage, not after sending the invoice.
4. Use automated systems: Let the software handle follow-ups and late fee tracking.
5. Vet your clients: Check previous reviews or ask for references if possible, especially for big projects.

Conclusion

Freelancing gives you flexibility and independence — but only if financially sustainable. If chasing payments is your part-time job, it’s time to let powerful invoicing and proposal tools do the heavy lifting. These six platforms each bring unique features to the table, but all focus on the same goal: helping you get paid *on time*. Whether you’re just starting out or scaling your solo business, choosing the right billing tools is one of the smartest business moves you’ll make.