So, you’re wrangling contracts, chasing signatures, and trying to keep your B2B deals from stalling out. Someone’s told you to “just use an e-signature tool”—but now you’re staring at Hellosign and DocuSign and wondering if the differences even matter, or if you’re about to pick the wrong one and regret it for years.
This guide is for anyone who wants real talk about these two big players, not sales fluff. We’ll break down what actually matters for B2B teams that need to get contracts signed quickly, keep legal happy, and not blow the budget on “enterprise” features you’ll never use. Let’s get into it.
1. Figure Out What “Streamlining” Really Means for You
Before you compare features, get specific about what your contract workflow actually looks like. “Streamlining” means different things to different teams.
- Are you sending out hundreds of NDAs a month, or a few big, complex agreements?
- Does your legal team need full audit trails and compliance reports?
- Will you need to integrate with Salesforce or Slack, or do you just want a simple, standalone tool?
- Is branding and customer experience a big deal, or do you just want it to work?
Write down your must-haves and nice-to-haves. If you skip this, you’re just comparing marketing pages, not solving your actual problem.
2. The Basics: What Hellosign and DocuSign Actually Do
At their core, both Hellosign and DocuSign let you:
- Upload documents, add signature fields, and send for e-signature
- Get alerts when someone signs
- Download signed copies and track their status
They’re both legally binding, widely accepted, and work on desktop and mobile. If that’s all you need, either will get the job done. But if you care about deeper features—or you’ve got a picky legal team—keep reading.
3. Where Hellosign Shines (and Where It Doesn’t)
Strengths:
- Simplicity: Hellosign is easy to set up and doesn’t overwhelm you with features you’ll never use. It’s clean, with a short learning curve for new users.
- Pricing: Typically cheaper than DocuSign for small-to-midsize teams. Transparent pricing, fewer surprise “enterprise” fees.
- Integrations: Native integrations with Google Workspace, Dropbox, Slack, and Salesforce. If you’re deep in the Google ecosystem, it’s a plus.
- User Experience: The signer experience is smooth and modern. If you care about your client’s impression, Hellosign generally feels less clunky.
Weaknesses:
- Limited Advanced Features: Things like bulk sending, advanced workflow automation, or complex multi-signer routing are more basic than DocuSign.
- International Compliance: Hellosign covers U.S. and EU standards, but if you’re dealing with more niche international regulations, double-check.
- Brand Recognition: It’s not as universally recognized as DocuSign. If your counterparty’s legal team is old-school, they might just expect DocuSign.
Pro tip: Hellosign’s API is solid for straightforward workflows, but not as deep as DocuSign’s if you need heavy-duty customization.
4. Where DocuSign Wins (and Where It Frustrates)
Strengths:
- Feature Depth: DocuSign is the 800-pound gorilla for a reason. If you need advanced routing, bulk send to thousands, conditional logic, or crazy compliance options, it’s got you covered.
- Global Compliance: Supports a wider range of international e-signature laws and offers more customization for regulated industries (finance, healthcare, etc.).
- Enterprise-Grade Integrations: If you’re building complex workflows across Salesforce, SAP, or legacy CRMs, DocuSign probably already has a connector.
Weaknesses:
- Pricing: Not cheap. The pricing page is just the start—real costs often balloon once you want advanced features or more envelope volume.
- User Interface: Feels dated in spots. Not as intuitive for first-timers. Admin setup can be a chore.
- Overkill for Small Teams: If you just want to send a few contracts a week, you’ll pay for a lot you don’t need.
Pro tip: If regulatory compliance is your top concern, DocuSign is usually the safer bet. But ask yourself if you really need all that, or if you’re just buying peace of mind.
5. Comparing Pricing (and Where the Gotchas Hide)
Both companies love to nudge you into calling sales for “enterprise” quotes, but here’s the gist:
Hellosign
- Plans start around $20–$30 per user/month for business features.
- API access is included in lower tiers than DocuSign, making it friendlier for startups or dev teams.
- Volume limits are fairly generous at lower tiers.
DocuSign
- Entry-level plans are similar, but you’ll quickly hit limits on envelopes (number of documents sent per month).
- Advanced features, branding, and integrations often require “Business Pro” or custom-priced plans.
- API requires higher-tier plans and can get expensive if you send a lot.
Watch out for: Envelope limits (DocuSign), hidden upcharges for advanced branding, and required minimum seats for some features.
6. Real-World Fit: What Works for Different Teams
Hellosign Is Best If:
- You’re a small or midsize B2B company that wants to get up and running fast
- You don’t have a full-time admin to manage the tool
- Brand experience matters, but you don’t need advanced routing or compliance bells and whistles
- You want predictable pricing and solid Google or Dropbox integrations
DocuSign Is Best If:
- You’re an enterprise with strict compliance needs (think finance, healthcare, or global contracts)
- You need to automate complex, multi-step signing workflows
- You’re already deep in the Salesforce/SAP ecosystem
- You need to send thousands of contracts at once or have dozens of signers per doc
Honest take: Most B2B teams under 100 people don’t need DocuSign’s full power. But if you’re in a regulated industry, or you know your clients won’t accept anything else, you may not have a choice.
7. Key Features to Actually Compare (Not Just Marketing Hype)
When you’re demoing or trialing these tools, focus on:
- Sending speed: How many clicks from upload to send?
- Template creation: Can you make reusable templates easily, or does it feel like pulling teeth?
- Signer experience: Try sending to yourself—does it look slick, or like a fax from 2002?
- Mobile support: Can people sign on their phone without downloading an app?
- Audit trails and compliance: Are the logs easy to export and understand?
- Support: Are you stuck in a ticket system, or can you talk to a human when you’re stuck?
- API and integrations: If you need these, test them early—don’t assume “it integrates” means it’s actually useful.
Skip obsessing over features like “infinite document storage” or “custom logos”—those are table stakes.
8. How to Choose (and Not Regret It)
- List your must-have features. Don’t let sales reps talk you into “future proofing” unless you know you’ll use it.
- Try the free trial or demo. Both platforms offer these. Run your real workflow, not just a dummy doc.
- Ask about limits. Especially envelope limits, user seats, and API access.
- Test with your actual team and a real contract. See what breaks or causes confusion.
- Check legal and compliance needs. If your legal team wants a specific audit format or compliance standard, confirm it now.
- Don’t get locked in. Avoid annual contracts until you’re sure—monthly is your friend when you’re experimenting.
9. Final Thoughts: Don’t Overthink Your E-Signature Tool
Both Hellosign and DocuSign can make contract chaos a lot less painful. The key is not letting the search for “perfect” get in the way of just picking something that works for your current size and needs. Start small, test it with real documents, and upgrade only if you outgrow it. Better to keep your workflow simple and iterate than to spend months chasing features you’ll never use.
If you’re still not sure, grab a trial of both and see which one actually saves your team time. That’s what matters—getting contracts signed, not collecting software checkboxes.