So, you need two or more people to sign the same document—maybe it’s a contract, a waiver, or just something your boss dreamt up to make your life harder. Whatever it is, you want to get it done quickly, without a paper chase or endless email chains. This guide is for you.
We’ll walk through, step by step, how to collect multiple signatures on a single document using Hellosign. I’ll cover what actually works, what to avoid, and a few real-world tips you won’t find in the average help article.
Why Use Hellosign for Multiple Signatures?
Look, there are a hundred e-signature tools out there, and most of them promise the moon. Hellosign (now called Dropbox Sign, but most folks still say Hellosign) is solid, straightforward, and doesn’t bury the basics under a pile of features. It works for small teams, freelancers, and anyone who needs to wrangle a handful of signatures without throwing their laptop out the window.
Who this is for:
- You need more than one person to sign the same document.
- You don’t want to print, scan, or chase people down.
- You want a clear audit trail (no one can say, “I never saw it!”).
Step 1: Prep Your Document
Before you even open Hellosign, get your document ready. This will save you headaches later.
- Use a common format. PDF is best. Word docs work, but formatting can shift when uploaded—stick to PDF if you want things to look the same for everyone.
- Leave space for signatures. You don’t have to, since Hellosign lets you drop signature boxes anywhere, but it’ll look neater.
- Double-check for blanks. It’s a pain to realize you missed a field after someone already signed.
Pro tip: If you’re sending out a contract or agreement, make sure it’s the final version. You can’t edit it in Hellosign once it’s uploaded—if you spot a typo after sending, you’ll have to start over.
Step 2: Log Into Hellosign
Head to Hellosign and log in. If you don’t have an account, you can create one for free. The free plan has limitations (like only three documents per month), so if you’re collecting signatures often, you might outgrow it fast.
Once you’re in, click “Create” or “Send for Signature.”
Step 3: Upload Your Document
- Click “Upload File” and select your PDF or document.
- You can add multiple files if you need (they’ll get combined into one signing workflow).
- Wait for the file(s) to upload and preview to appear.
Watch out: Super-large files (think: scans with loads of images) can choke the uploader. Keep your files under 40 MB, and use PDFs rather than image files for best results.
Step 4: Add Signers
Here’s where you tell Hellosign who needs to sign, and in what order.
4.1 Enter Signer Info
- For each signer, enter their name and email address.
- Click “Add Another Signer” for as many people as you need.
- You can usually add up to 20 signers per document, even on lower-tier plans—but double-check your plan’s limits if you’re working with a crowd.
4.2 Set Signing Order (Optional)
- Sequential signing: Signers get the document one after another. Good if order matters (e.g., your boss signs first, then it goes to legal, then to the client).
- Parallel signing: Everyone gets the doc at the same time. Faster, but less control.
Set the order by dragging signers up or down in the list, or look for a toggle labeled “Set signing order” or similar.
My take: If you don’t care about order, parallel is faster. If you need approvals in a certain sequence, use sequential.
Step 5: Place Signature Fields and Other Inputs
Now you’ll put signature boxes on the document for each person.
- Drag a “Signature” box from the toolbar onto the document.
- Assign each box to a signer (you’ll see their names in a dropdown).
- Add other fields as needed: date, initials, text boxes, checkboxes, etc.
Important: Make sure every signer has at least one required field, or they’ll be able to “finish” without actually signing.
Common gotchas:
- Overlapping fields: If two people need to sign close to each other, make sure fields aren’t stacked on top of each other. Resize or nudge them apart.
- Same email for multiple signers: Hellosign doesn’t like this. If two people share an email (e.g., a generic office inbox), you’ll have issues. Each signer needs their own email address.
Step 6: Add a Message (Optional)
You can write a short message that goes out with the signature request. Keep it simple:
“Hi all,
Please review and sign this agreement. Let me know if you have questions. Thanks!”
No need for a novel—just set expectations.
Step 7: Review and Send
Double-check everything:
- Are all signers listed, and in the right order?
- Are all fields assigned correctly?
- No typos in emails?
If it looks good, hit “Send for Signature.”
Heads up: Once you send, you can’t edit the document or fields. You can cancel the request and start over (but that’s a pain).
Step 8: Tracking and Reminders
After sending, you’ll land on a status page showing:
- Who’s signed and who hasn’t
- When each person viewed or signed
- Options to remind signers with a click
Hellosign sends automatic reminders, but you can send manual nudges if someone’s dragging their feet.
Pro tip: If a signer claims they “never got it,” check if they have a typo in their email, or if it landed in spam. You can resend to the correct address if needed.
Step 9: What Happens After Everyone Signs?
Once all signatures are collected:
- Everyone gets a final, signed PDF by email.
- You can download the fully executed copy from your Hellosign dashboard.
- There’s an audit trail showing who signed when (helpful if things ever get legal).
You can’t edit or add signatures to a completed document. If you missed someone, you’ll need to start a new request.
Advanced Tips and Honest Downsides
Templates and Bulk Send
- If you send the same document to different groups often (e.g., onboarding forms), consider making a template. Saves time placing fields.
- For collecting signatures from lots of people (but each on their own copy), look at bulk send. This is not for multiple people on the same document.
Mobile Signing Works (Mostly)
Hellosign’s emails and interface are mobile-friendly. Most people can sign from their phone without issues. That said, dragging fields is harder on mobile—if someone has trouble, tell them to try on a computer.
What Doesn’t Work So Well
- Multiple signers, one device: If you’re in the same room with several signers, Hellosign isn’t ideal for “pass the laptop” signing. Each person needs their own email and receives a link.
- Signer authentication: Basic plans offer limited options (like email verification). If you need stricter ID checks, you’ll need a higher-tier plan—or another tool.
Common Mistakes to Avoid
- Wrong emails: Double-check addresses. Typos mean delays.
- Forgot to assign fields: If you don’t assign fields to the right signer, someone might not be able to sign—or worse, sign in the wrong place.
- Trying to collect signatures in-person: Hellosign is built for remote signing. For in-person, something like DocuSign’s in-person mode or old-fashioned pen-and-paper is faster.
Keep It Simple and Iterate
That’s all there is to it. Collecting multiple signatures on a single document in Hellosign doesn’t have to be complicated—prep your document, add the right people, drop the fields, and double-check before hitting send. If you get tripped up, don’t overthink it. Start over, fix the issue, and send again. With a little practice, you’ll have it down to a science.
Good luck—and don’t let paperwork slow you down.