How do I get customers to actually sign without me chasing them every time?

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The honest truth about unsigned documents is that most delays aren't about hesitation over the deal itself, they're about priority. Your contract is the most important thing in your day; it's a small task on a long list in theirs, easy to open, mean to get back to, and then genuinely forget. A reminder isn't nagging, it's just making sure your task reappears on their list before it falls off entirely. Automating that removes the part where you have to personally remember to chase, which is the step that actually tends to slip on your end too.

The no-tool way: a calendar reminder to follow up yourself

Set a calendar reminder for two or three days after sending any document, and manually send a short, friendly follow-up if it's still unsigned. This costs nothing and works fine if you're disciplined about actually checking and acting on that reminder every single time, for every document, which is exactly the habit that tends to break down once you're juggling more than a handful of open deals at once. The honest failure mode here isn't the customer forgetting, it's you forgetting to remind them, which is exactly the inconsistency an automated system removes once it's set up. To see which ones are still open, read how to track which proposals and contracts are still unsigned.

SignWell

SignWell, an e-signature tool built for sending documents without requiring recipients to create an account, includes reminders on its standard tiers, confirmed live, including the Free plan at $0 a month, though that tier's 3-document-a-month cap makes it tight for active, ongoing use. The Light plan, at $12 a month ($10 a month billed annually), adds unlimited documents alongside the same reminder functionality.

Dropbox Sign

Dropbox Sign, formerly known as HelloSign before Dropbox rebranded it after acquiring the company, is an e-signature tool built into Dropbox's broader product ecosystem, with reminder functionality as a standard part of its sending workflow. I wasn't able to load its current pricing page live this session to confirm exact plan names and current dollar figures, so check dropboxsign.com's pricing page directly for current plan details before comparing it against the options confirmed here.

Signeasy

Signeasy, an e-signature and document tracking tool for individuals and teams, confirmed live: Personal runs $10 a month ($120 a year), Business runs $20 a user a month ($240 a year), and Business Pro runs $30 a user a month ($360 a year), with reminder functionality included as part of its standard document tracking across these tiers, which makes it a reasonable option if you're already comparing it for other reasons, like its broader document tracking features, rather than picking a tool on reminders alone.

QuickSigner

QuickSigner is an e-signature tool built around a flat price per user with no document caps, aimed at being simpler and cheaper than larger established platforms for everyday signing needs. Reminders, automatic or manual nudges sent to anyone who hasn't signed yet, are included on its Business plan, confirmed live at $5 a month per user ($48 a year), and above, but not on the Free tier. For anyone building reminders into a custom workflow or app rather than using QuickSigner's own interface directly, its Professional-tier API includes a specific remind endpoint, confirmed live, that triggers a reminder for a given recipient programmatically.

Setting it up, four steps

1. Send the contract with a clear deadline stated in the document or the sending message itself, since "sign whenever" invites exactly the indefinite delay you're trying to prevent.
2. Turn on reminders in whichever tool you're using, confirming the cadence (how often, starting when) matches how urgent this particular deal actually is.
3. Check the list each morning for anything still unsigned past a reasonable point, rather than assuming the automated reminders alone will close every deal without any human follow-up. A monthly view helps too, see how to get a monthly list of signed and unsigned jobs.
4. Call on high-value deals rather than relying on reminders alone. A phone call signals the deal actually matters to you, which an automated email, however well-timed, simply can't replicate.

A worked example

Say you send a $12,000 contract and it's sitting unsigned after four days with two automated reminders already gone out. At this point, an automated system has done its job, it's surfaced that this specific document needs attention, and the next step is a judgment call, not another automated email. For a deal this size, a direct call ("just checking you got the contract, any questions before you sign?") both re-surfaces the task and gives you a chance to catch any last-minute hesitation before it becomes a stalled deal. The reminders got it back on their radar; the call is what actually closes it.

Writing a reminder that doesn't feel naggy

The tone of the reminder itself matters more than how it's triggered. A reminder that just says "you haven't signed yet" reads as a nag, even when it's completely automated and not personal at all. A better version offers something useful alongside the nudge: "just checking you got this, let me know if you have any questions before signing" does the same job of resurfacing the task, but gives the customer an easy, face-saving reason to respond even if the real answer is simply "I forgot." Most e-signature tools let you customize the reminder's wording rather than using a generic default, and it's worth the five minutes to write one that doesn't sound like a collections notice. A narrower guide, how to send a reminder to a customer who has not signed, covers the same job.

Where automated reminders fall short

Here's what I'd tell a client directly: reminders work great for the customer who genuinely just forgot, which is most of them, but they do nothing for the customer who's gone quiet because they're having second thoughts, are waiting on someone else's approval, or found a cheaper alternative while your contract sat in their inbox. An automated system can't tell the difference between "I forgot" and "I'm stalling," and treating both the same way, with more automated emails, often makes the stalling case worse rather than better. If a deal's gone quiet past the point where "they just forgot" is still a believable explanation, that's your cue to pick up the phone rather than wait for one more reminder to land.

When to skip the tool entirely

For high-value deals specifically, lead with a phone call before the document even goes out, confirming they're ready to sign, then send it as the formal step rather than the first contact. Reminders are genuinely useful as a safety net for the rest of your pipeline, the smaller, routine deals where a phone call for each one isn't a reasonable use of your time, but they're not a substitute for a personal touch on the deals that matter most to your business.

How many reminders before it stops helping

There's a point of diminishing returns, usually somewhere around the second or third automated reminder, past which more nudges stop producing signatures and start producing irritation instead. If someone hasn't responded to two reasonably spaced reminders, a third identical one rarely changes the outcome. That's the signal to switch channels entirely, a call, a text, a different person on your team reaching out, rather than simply increasing the frequency of the same email that's already been ignored twice, since repeating an approach that's already failed rarely produces a different result the third time. When several people send documents, you can see what staff send so nobody gets two reminders.

How I'd approach this

When a client's biggest issue is deals stalling in the signing stage, I look at whether the problem is actually reminders, or whether it's that too many deals are being treated identically regardless of size, with the same hands-off automated follow-up for a $500 deal and a $50,000 one. Get in touch if you want a signing follow-up process built properly, sized to how much each deal actually matters.