If you’ve ever tried to get a bunch of people to sign the same document—think HR onboarding, NDAs, or waivers—you know the pain of sending and tracking each signature request one by one. If you’re using Hellosign, there’s a better way: Bulk Send. This isn’t a magic wand, but it can save hours of mind-numbing admin work. Here’s how to use it properly, what to watch out for, and how to avoid shooting yourself in the foot.
Who Should Use Bulk Send—and Who Shouldn’t
Bulk Send is for anyone who needs a lot of people to sign the same document, but not to negotiate or fill out a bunch of unique info. Think:
- HR teams sending out employee policies to 200 staffers.
- Event organizers sending a waiver to every participant.
- Small business owners collecting updated W-9s from contractors.
It’s not for:
- Sending out customized contracts (unless they only need a few variable fields).
- Anything requiring multiple signers on the same copy.
- Use cases where you want recipients to see each other’s info (they won’t).
If your needs are more complex, you’ll hit Bulk Send’s limits fast.
Before You Start: What to Have Ready
Don’t jump in yet. Here’s what you’ll need to avoid a bunch of “uh oh” moments later:
- A Hellosign account with Bulk Send: This isn’t on the free plan. You need a paid plan that supports Bulk Send—check your plan first or you’ll hit a wall right away.
- A finalized document: PDF or DOCX works best. Don’t send out a half-baked draft.
- A list of recipients: Usually in a CSV file (Excel or Google Sheets export works fine).
- Any info you want filled in per person: For example, “First Name” or “Department” fields.
Pro tip: Clean your recipient list before you upload it. Typos in emails or missing names will blow up your send and waste time.
Step 1: Prep Your Document Template
The document you upload will go out to everyone, so make it generic, but not thoughtless. Here’s how to set it up:
- Open Hellosign and head to Templates.
- Click “Create Template.”
- Upload your ready-to-sign document.
- Drag and drop signature, date, and any other fields where you want recipients to sign or fill in info.
- If you want to personalize each doc (like auto-filling “Name” or “Team”), add “merge fields.” These will pull info from your CSV later.
Don’t: Add fields for info you can’t provide in your CSV. Every merge field you add needs a matching column in your recipient file, or the send will fail.
Reality check: Merge fields sound fancy, but they’re just mail merge. If you want logic or dynamic content, this isn’t that.
Step 2: Build Your CSV Recipient List
Hellosign’s Bulk Send eats CSV files—nothing else. Here’s the minimum you need:
- Email: The address you’re sending to.
- Any merge fields: If your template has a “First Name” field, your CSV needs a “First Name” column.
A simple CSV might look like:
Email,First Name,Department jane@example.com,Jane,Finance bob@example.com,Bob,Engineering
Checklist before uploading:
- No blank rows or weird characters.
- Every email is valid (typos are the #1 cause of failed sends).
- Merge field columns exactly match what you set up in the template (case-sensitive).
Heads up: If you have hundreds of recipients, double-check for spam traps or role-based emails (info@, admin@). These often get blocked or ignored.
Step 3: Start the Bulk Send Process
Now for the part that feels like magic—if you did your homework.
- Go to the Template you just made.
- Click “Use Template” and look for the Bulk Send option.
- Upload your cleaned CSV file.
- Map each column in your file to the right field in Hellosign. If something’s mismatched here, stop and fix your CSV.
- Review the email message and subject line. This is what your recipients will see, so make it clear and direct—nobody opens vague “Action required” emails.
- Preview a sample of what each recipient will see (Hellosign lets you check a few). If it looks off, fix it now.
- Hit send.
After you send: Each recipient gets their own copy to sign. They can’t see each other’s info. You’ll get notified as people sign, and you can track who’s still outstanding.
Step 4: Track Status and Handle Reminders
You’re not done yet—people forget, emails go to spam, and some folks just need a nudge.
- Dashboard: Hellosign’s dashboard shows the status for every request—signed, viewed, or waiting. Use filters to find the stragglers.
- Automatic reminders: Hellosign can send reminders, but they’re generic. If someone’s ignoring you, a personal follow-up usually works better.
- Download results: Once everyone’s signed (or you’ve given up), you can download all completed documents as a batch.
Pro tip: Keep your CSV handy. If you need to resend to just the non-signers, filter them out and run a new Bulk Send.
What Works Well (and What Doesn’t)
The good:
- Saves a ton of time if you have 20+ people to reach.
- Decent tracking for who’s done and who’s lagging.
- Merge fields help you personalize (a little).
The rough edges:
- Any errors in your CSV (even a single typo) can tank the whole send. The error messages aren’t always clear.
- Limited flexibility—if you need conditional logic, custom workflows, or multiple signers per doc, this isn’t it.
- Bulk Send can hit email limits—if you’re sending to thousands, some emails may get flagged as spam.
Ignore the sales pitch: This isn’t “set and forget.” You still need to prep, check, and follow up.
Common Gotchas and How to Avoid Them
Some things you’ll only learn by messing up (or by reading this):
- Test before a big send. Run a Bulk Send to yourself and a couple of colleagues. Catch formatting or merge field issues early.
- Don’t over-personalize. The more fields you add, the bigger the chance something breaks.
- Keep it legal. If your doc needs to comply with local laws (like GDPR), make sure your message covers privacy and data use.
- Watch your plan limits. Some plans cap Bulk Sends per month. If you’re sending thousands, check your contract so you don’t get a surprise bill.
Quick FAQ
Can I cancel a Bulk Send after it’s started?
Not really. Once it’s out, it’s out. You can cancel individual requests, but you can’t “unsend” everything.
What about attachments?
You can’t bulk-attach personalized files. Everyone gets the same doc.
Can I use this for contracts with multiple signers?
Nope. Bulk Send is one signer per document, per send.
Do recipients need a Hellosign account?
No, they can sign as guests in their browser.
Final Thoughts: Don’t Overcomplicate It
Bulk Send is a solid time-saver—if you stick to what it’s good at. Don’t try to hack it into doing stuff it wasn’t built for. Clean your files, test with a small batch, and keep your templates simple. Fix one thing at a time, and you’ll spend less time chasing signatures and more time on real work.