Follow Up Email for Contract Signing: 7 Templates, a Day-by-Day Cadence, and the Mistakes Killing Your Deals

You know the moment. The prospect says "Yes! Send over the contract, I'll sign it tonight." You hang up, fire off the agreement within five minutes, and then... nothing. Day one passes. Day three. By day five, you're staring at your inbox wondering if the whole conversation was a fever dream.

This isn't a you problem. It's a pattern. In one analysis, 42% of closed-won revenue started as a non-response thread that was revived through follow-up. Yet only 8% of sales reps follow up more than five times, and 40% give up after the first "no." The gap between "verbal yes" and "signed contract" is where deals go to die - and most reps don't have a system for bridging it, starting with a follow up email for contract signing that actually gets a response.

What You Need (Quick Version)

Here's the contract follow-up cadence you'll build in this article:

• Day 1: Same-day confirmation email with the contract link
• Day 2-3: Gentle nudge that proactively addresses sticking points
• Day 5-7: Value-add follow-up with new information
• Day 10-14: Deadline-driven urgency email
• Day 21: Break-up email that leaves the door open

The #1 tactic that prevents all of this: get the signature while you're still on the call.

You'll also get 15 subject lines grouped by tone, the 5 mistakes that tank contract follow-ups, and a quick guide to using your e-signature tool's built-in reminders.

Why Contracts Stall (And What You Can Actually Do About It)

The hardest part about a stalled contract isn't the waiting. It's not knowing why they've gone quiet. Your brain defaults to "they changed their mind" or "they went with a competitor," but the reality is usually more mundane - and more fixable - than that.

Here's what's happening behind the silence.

The excitement faded

During the call, your prospect was bought in. They could see the ROI, feel the urgency, picture the implementation. Then they hung up, opened Slack, got pulled into three fires, and your contract became one of 47 tabs they'll "get to later." The emotional momentum that drove the verbal yes evaporates fast. As one r/sales poster put it: "I've realized that when they say yes, I NEED to get them to sign RIGHT THERE." That's not paranoia - it's pattern recognition. 68% of B2B buyers choose a vendor that demonstrates understanding of their unique needs, and that understanding has a half-life measured in hours, not days.

Internal stakeholders entered the picture

Your champion said yes. But the CFO needs to approve anything above a certain threshold. Legal wants to redline the indemnification clause. Procurement needs three competing quotes. The average B2B deal involves 6-10 stakeholders, and your champion may not have the authority - or the energy - to shepherd the contract through all of them. That's exactly why your follow-up email after contract sent needs to account for multiple decision-makers, not just your main point of contact. (If you want a full playbook here, build multi-threading into your process.)

Your email got buried

One CFO asked for a contract "by Friday," then ghosted. She finally replied on the seventh follow-up, saying the first email "sank beneath 600 unread messages." Your contract isn't being ignored. It's competing with hundreds of other emails for attention.

Your email bounced or went to the wrong person

They're comparing you to a competitor

Sometimes the silence isn't about internal process. It's about a competing proposal that landed on their desk the same week. They won't tell you this - they'll just go quiet while they evaluate. Your follow-up cadence needs to account for this possibility by reinforcing your value, not just asking for a status update. (This is where a tight competitive intelligence loop pays off.)

They simply forgot

This one stings, but it's the most common reason.

Your deal isn't their top priority. They have their own quotas, their own fires, their own boss breathing down their neck. A well-timed follow-up isn't annoying - it's a service. 81% of customers welcome post-meeting follow-up emails. One r/smallbusiness founder described this happening "every few months" - prospects who were genuinely excited just drifted. A timely contract signing reminder is often all it takes to bring them back.

Look, 10-20% of deals that reach the contract stage still fail to close. That's a lot of revenue left on the table for something that's theoretically already sold. The good news: most of these deals are recoverable with the right follow-up system.

Before You Send the Contract - A Pre-Send Checklist

The best follow-up email is one you never have to send. Here's what to do before the contract leaves your outbox:

☐ Ask about their internal review process. "Who else needs to sign off on this?" and "What does your approval process look like?" aren't just forecast questions - they're deal-saving questions. If you know legal needs two weeks, you won't panic on day three.

☐ Get a timeline commitment. Don't end the call with "I'll send it over." End with "When can I expect this back?" A specific date gives you permission to follow up without feeling awkward.

☐ Tie to an implementation deadline. "If you want to go-live by March 15th, I need paperwork back by March 1st." This reframes the contract as a logistics step, not a decision point. The decision was already made on the call.

☐ Use e-signature tools so they can sign while on the call. This is the single highest-leverage tactic in this entire article. The gap between the call and the inbox is where deals die. If you're using DocuSign, PandaDoc, or Dropbox Sign, send the link while you're still talking. "I just sent it over - do you see it? Let's walk through it together." I've seen teams cut their contract-to-close time in half with this one change.

☐ Collect payment method at signing (freelancers/service providers). If you're a solo operator or small agency, don't separate the contract from the payment step. Use tools like HoneyBook or Dubsado to bundle the agreement and payment authorization into one flow. This eliminates the second stall point that kills freelancer deals.

☐ Verify the signer's email address. Especially if the contract is going to someone different from your main contact. Verify before you send - a bounced contract email is a silent revenue leak you'll never know about. (If you need a step-by-step workflow, see how to verify an email address.)

☐ Send the contract within 5 minutes of verbal agreement. Not "later today." Not "after lunch." Five minutes. Every minute of delay erodes the momentum from the call.

How to Build a Contract Follow-Up Cadence - Day by Day

Cold outreach cadences and contract follow-up cadences are fundamentally different animals. Cold outreach data says 6-8 touchpoints are needed to engage a B2B buyer. A 2026 study of 16.5 million emails found the sweet spot for cold outreach is one initial email plus one follow-up - after that, each additional follow-up sees diminishing returns. (If you're building the cold side too, start with an email cadence framework.)

But contract follow-ups are warmer. The prospect already said yes. You have a relationship. The rules are different.

Here's the framework:

Day 1: Same-Day Confirmation

Send within 5 minutes of the call. Confirm what was discussed, attach or link the contract, and set expectations for the timeline. This isn't a follow-up - it's the handoff. Warm contract follow-ups get roughly 40-60% response rates at this stage for deals with genuine intent. Reps who send just one follow-up lift their reply rate from 16% to 27% - so even if you do nothing else, do this.

Day 2-3: First Follow-Up (Gentle Nudge)

If they haven't signed, send a short email that proactively addresses common sticking points. Don't ask "did you get it?" - assume they got it and might have questions. Offer a quick call. This is also the day to make a phone call. Email + phone on the same day is significantly more effective than either channel alone. (More on timing in when should I follow up on an email.)

Day 5-7: Second Follow-Up (Add Value)

This is where most reps fail.

In our experience, the Day 5-7 value-add follow-up is where the biggest gains are - and where most people default to "just checking in" and wonder why it doesn't work. Instead, add something new: a case study, an ROI calculation, a resource that addresses a concern from the original call. Give them a reason to re-engage beyond guilt. Consider sending a 60-second Loom video walking through the contract highlights - video follow-ups can boost click rates by 300%.

Day 10-14: Third Follow-Up (Create Urgency)

Tie to a deadline. Implementation calendar, pricing expiration, team availability - whatever creates a real (not manufactured) reason to move now. If you're in enterprise sales with legal review cycles, extend this to Day 14-17. Layer in a second phone call here.

Day 21: Break-Up Email

If you've heard nothing after three weeks and multiple touchpoints, send the break-up. "Should I close your file?" works because it triggers loss aversion. But if you're past five follow-ups on a single contract, the deal isn't stalled - it's dead. Send the break-up and redirect your energy.

Multi-channel note: Don't rely on email alone. Layer in a phone call at Day 3 and Day 10. Use your e-signature tool's built-in reminders (more on that in a later section). The combination of email + phone + platform reminder is significantly more effective than any single channel. If you're on HubSpot, Sequences can automate the entire cadence - set it up once and it fires each follow-up on schedule. (For more structure, use a follow up email sequence strategy.)

Here's the thing: if you're sending more than five follow-ups on a single contract, the deal isn't stalled - it's dead. The break-up email is your exit ramp, not your last Hail Mary.

7 Follow-Up Email Templates for Contract Signing

Every template below is designed to do one thing: give the recipient a reason to respond that goes beyond "I feel guilty for not replying." Copy, paste, customize the bracketed placeholders, and send.

Template 1 - Same-Day Confirmation (Day 1)

When to use: Within 5 minutes of the verbal agreement. This isn't a follow-up - it's the handoff.

Subject line: [Company Name] agreement - ready for your signature

Email:

Hi [First Name],

Great talking today. As discussed, here's the agreement for [project/service name]: [contract link]

Quick recap of what we covered:

• [Key term 1, e.g., "12-month engagement starting April 1"]
• [Key term 2, e.g., "$4,500/mo with quarterly reviews"]
• [Key term 3, e.g., "Dedicated CSM assigned within 48 hours of signing"]

If everything looks good, you can sign directly in the link above. If you need to loop in [legal/finance/anyone else they mentioned], happy to jump on a quick call with them.

What's a realistic timeline for getting this back?

Best, [Your name]

Why it works: It confirms the terms (so they don't have to re-read the whole contract to remember what they agreed to), provides the signing link immediately, and asks for a timeline - which gives you permission to follow up later.

Template 2 - The Gentle Nudge (Day 2-3)

When to use: 2-3 days after sending the contract with no response. This is your first follow-up email after contract sent, so don't ask "did you see my email?" - assume they did and might have questions.

Subject line: Questions on the [Company Name] agreement?

Email:

Hi [First Name],

Wanted to make sure nothing's holding up the [project name] agreement. A few things that sometimes come up at this stage:

• Pricing or payment terms - happy to walk through the structure
• Implementation timeline - we can adjust the start date if needed
• Compliance or security review - I can send our SOC 2 report / DPA / [relevant doc] directly to your team

If any of these apply (or something else entirely), a 15-minute call would sort it out. [Calendar link]

Otherwise, the signing link is here whenever you're ready: [contract link]

[Your name]

Why it works: Instead of a generic "checking in," you're proactively naming the objections they might be wrestling with. This saves them the effort of articulating the problem and makes it easy to respond with "actually, it's the compliance thing - can you send that over?"

Template 3 - The Value-Add Follow-Up (Day 5-7)

When to use: When the gentle nudge didn't get a response. Each follow-up needs to bring something new to the table - bumping without new information is the #1 follow-up mistake.

Subject line: [Relevant resource] + your [Company Name] agreement

Email:

Hi [First Name],

While your agreement is in review, thought this might be useful - [one of the following]:

• "Here's a case study from [similar company] who saw [specific result] within [timeframe]"
• "I put together a quick ROI estimate based on the numbers you shared: [link or 2-3 bullet points]"
• "Our implementation team just published this onboarding checklist - figured it'd help you plan internally: [link]"

The agreement is still here whenever you're ready: [contract link]

Any questions I can answer in the meantime?

[Your name]

Why it works: You're demonstrating continued investment in their success, not just chasing a signature. The resource also gives them something to forward to internal stakeholders who might be part of the decision.

Template 4 - The Scheduling Reframe (Day 7-10)

When to use: When you need to follow up but "just checking in" feels desperate. This reframes the follow-up as a logistics question.

Subject line: Finalizing my implementation calendar - quick question

Email:

Hi [First Name],

I'm locking in my implementation calendar for [month/next two weeks] and wanted to confirm whether [date you discussed] still works for your team's kickoff.

To hit that date, I'd need the signed agreement back by [specific date - 3-5 business days before kickoff].

Does that timeline still work on your end? If things have shifted, no problem - just let me know and I'll adjust.

[Your name]

Why it works: You're not asking "have you signed yet?" You're asking a scheduling question that assumes the deal is moving forward. It's a subtle but powerful reframe - and it creates a natural deadline without manufactured urgency.

Freelancer/SMB variation: "I'm booking my project calendar for [month] and have a slot reserved for your [project type]. Want to confirm it's still a go - the agreement is here whenever you're ready: [contract link]"

Template 5 - The Stakeholder Check-In (Day 10-14, Enterprise)

When to use: When you suspect the delay is internal - legal review, CFO approval, procurement process. This is especially common in enterprise deals where 6-10 stakeholders touch the decision.

Subject line: Anyone else need to review the agreement?

Email:

Hi [First Name],

Totally understand these things take time on your end. Quick question: is there anyone else on your team who needs to review the agreement before it can move forward?

If it's helpful, I'm happy to:

• Jump on a 10-minute call with your legal/finance team to walk through terms
• Send over our [SOC 2 report / security questionnaire / vendor assessment form] directly
• Provide a redlined version if there are specific clauses to discuss

Just let me know who to loop in and I'll reach out directly.

[Your name]

Why it works: You're acknowledging the reality of enterprise buying without making your champion feel bad about the delay. And you're offering to do the work of selling internally - which is exactly what a stalled deal needs.

SMB variation: Skip this template entirely. If you're selling to a solo founder or small team, the stakeholder check-in feels tone-deaf. Jump straight to Template 6.

Template 6 - The Deadline Urgency Email (Day 14)

When to use: When you have a legitimate deadline - implementation capacity, pricing expiration, team availability. Don't manufacture fake urgency. Buyers can smell it.

Subject line: [Company Name] agreement - timing update

Email:

Hi [First Name],

Quick heads-up on timing: [choose the one that applies]

• "Our implementation team has capacity to start your onboarding on [date], but I need the signed agreement by [date] to hold that slot."
• "The pricing in the current agreement is locked through [date]. After that, I'd need to re-quote based on our updated rates."
• "To hit your [goal they mentioned - e.g., 'Q2 launch'], we'd need to kick off by [date], which means paperwork by [date]."

None of this is a hard stop - just want to make sure you have the full picture so nothing catches you off guard.

Agreement link: [contract link]

[Your name]

Why it works: Real deadlines create urgency without pressure. The key phrase is "just want to make sure you have the full picture" - it positions you as helpful, not pushy.

Freelancer variation: "I have one project slot open for [month] and wanted to give you first priority since we've already scoped everything out. If you're still interested, the agreement is here: [contract link]. If timing has changed, totally understand - just let me know either way."

Template 7 - The Break-Up Email (Day 21)

When to use: After 3-4 follow-ups with no response. This is your last email in the contract signing sequence.

Subject line: Should I close your file?

Email:

Hi [First Name],

I've reached out a few times about the [project/service name] agreement and haven't heard back, so I want to respect your time.

I'm going to assume the timing isn't right and close out your file on my end. If anything changes down the road, you've got my info - happy to pick the conversation back up.

If I've got it wrong and you're still interested, just reply and I'll keep things open.

Either way, no hard feelings. Appreciate the conversations we've had.

[Your name]

Why it works: "Should I close your file?" is one of the highest-performing subject lines in sales - it triggers loss aversion. The email itself is gracious and low-pressure, which makes it easy to respond to. 80% of prospects say "no" four times before saying "yes," and this email often gets the "no, wait, I'm still interested" reply.

Freelancer variation: Soften the tone slightly: "Hey [First Name], I know things get busy. I'm going to close out the [project name] proposal on my end, but if you want to revisit in a few weeks or months, just shoot me a note. No pressure either way."

15 Subject Lines for Contract Follow-Up Emails

64% of recipients open emails based on subject line alone. The sweet spot is 3-7 words (roughly 41 characters) for highest engagement, and with 42% of emails opened on mobile, shorter lines avoid truncation on small screens. (If you want more options, pull from these reminder email subject lines.)

Friendly / Warm

1. Questions on the [Company Name] agreement?
2. Your [Project Name] contract is ready
3. Quick question about next steps
4. Following up: [Project Name] agreement
5. Anything I can clarify on the agreement?

Urgent / Action-Oriented

6. Finalizing my calendar - quick question
7. [Company Name] agreement - timing update
8. Implementation slot for [month] - confirming
9. Pricing locked through [date]
10. Ready to finalize the [Company Name] agreement?

Break-Up / Final

11. Should I close your file?
12. Still interested in [Project Name]?
13. Closing the loop on your agreement
14. Last note from me on [Project Name]
15. Yay or nay?

Best practices: Reply to your original email thread for follow-ups 1-3 (keeps context visible). Switch to a new subject line for follow-ups 4-5 - a fresh subject line can re-engage someone who's been ignoring the thread. Never use the same subject line twice in a sequence. Each one should signal that this email is different from the last.

Preview text matters too. Keep it to 35-40 characters so it renders cleanly on mobile. Most email clients pull the first line of your email body as preview text, so make that first sentence count - don't waste it on "Hi [Name]."

5 Mistakes That Kill Contract Follow-Ups

Bumping without new information

"Just wanted to make sure you saw my last email" is the laziest follow-up in sales. It adds zero value and puts the burden entirely on the recipient. Every follow-up needs to bring something new - a resource, a deadline, a question, a reframe. If you can't think of something new to add, you're not ready to send.

Not addressing the real objection

There are really only five reasons a prospect stalls: they don't see the need, the cost doesn't match the perceived value, there's no urgency, they don't actually want it, or they don't trust you. Your follow-up should probe for which one it is - not just repeat the ask. Template 2 above does this by naming common sticking points upfront.

Making follow-ups look automated

Plain text. Short paragraphs. Sent as replies to the original thread.

That's what a real email from a real person looks like. The moment your follow-up has a banner image, a formatted signature block with six social icons, and a "sent via [platform]" footer, it screams automation. We've tested both approaches - plain text consistently outperforms formatted HTML in contract follow-ups. Personalized emails generate 6x higher transaction rates than generic templates, and personalized follow-ups achieve roughly 18% response rates vs. 9% for generic ones. The difference is real and it compounds across your cadence. (To systematize this without sounding robotic, use conditional sequences.)

Using the same subject line every time

If your first three follow-ups all say "Following up on [Company Name] agreement," the recipient's brain starts filtering them out before they even open. Vary your subject lines. Switch between friendly, urgent, and reframed angles. A new subject line signals new information - even before they read the body.

Following up too aggressively (or not enough)

Four or more cold emails triples the spam complaint rate. But contract follow-ups aren't cold - you have a relationship. The sweet spot is 3-5 follow-ups over 21 days for warm deals. More than that and you're annoying. Fewer than that and you're leaving money on the table - 27% of small businesses never follow up at all, even though one follow-up lifts reply rates from 16% to 27%.

Real talk: stop trying to write better follow-up emails. Start preventing the need for them. The pre-send checklist - getting timeline commitments, identifying stakeholders, signing on the call - eliminates more stalled contracts than any template ever will. The templates are your safety net, not your strategy.

Use Your E-Signature Tool's Built-In Reminders

Your manual follow-up cadence should have a "set it and forget it" layer running underneath it. Most e-signature platforms have built-in reminder features that complement your email sequence.

PandaDoc: Navigate to Manage > click the recipient's name > Send reminder. You can send one reminder per 24 hours, and it's available on all plans - including free. Reminders show up in the document's activity log, so you can see whether they were opened.

DocuSign: Set automatic reminders at customizable intervals (e.g., every 3 days, every 5 days). You can configure these when sending the envelope or update them after the fact. Available on paid plans.

Dropbox Sign (formerly HelloSign): Basic auto-reminders on paid plans. Less configurable than DocuSign, but functional for simple contracts.

The key insight: These platform reminders come from the e-signature tool, not from your email address. That means the recipient gets a notification that feels like a system prompt ("You have a document waiting for signature") rather than a sales follow-up. It's a different psychological trigger - and it stacks nicely with your personal email cadence.

Layer in email tracking tools like HubSpot's free sales tools or Mixmax to see when the recipient opens the contract. If they've opened it three times but haven't signed, that's a signal - they're probably stuck on a specific clause and need a nudge, not a reminder. (If you're evaluating tooling, start with these sales tracking software options.)

FAQ

How many times should I follow up on an unsigned contract?

Three to five follow-ups over 21 days is the sweet spot for warm contract follow-ups. Beyond five, the deal is likely dead - send a break-up email and redirect your energy. Reply rates jump from 16% to 27% with just one follow-up, so even a single nudge makes a meaningful difference.

How long should I wait before sending a follow up email for contract signing?

Send a confirmation email the same day you get the verbal yes - ideally within five minutes. First follow-up at Day 2-3, then Day 5-7, Day 10-14, and a final break-up at Day 21. For enterprise deals with legal review, extend each interval by 2-3 days.

What do I say instead of "just checking in"?

Reframe as a scheduling question ("I'm finalizing my implementation calendar - does next Tuesday still work?") or add new value like a case study, a deadline, or a relevant resource. Each follow-up should give the recipient a reason to respond beyond guilt. Templates 3 and 4 above are built specifically for this.

Why do clients ghost after saying they'll sign?

The excitement from the call fades once the prospect is alone with the document. Internal stakeholders (legal, finance, procurement) create delays, emails get buried under hundreds of others, or they're quietly comparing alternatives. The average B2B deal involves 6-10 stakeholders, and any one of them can slow things down.

How do I make sure my contract follow-up emails reach the signer?

Verify the signer's email address before starting your sequence - especially if the contract goes to someone other than your main contact. Prospeo verifies emails with 98% accuracy and offers 75 free verifications per month, which is enough to cover every stakeholder on a deal before you send a single follow-up.