SignNow vs Dropbox Sign (HelloSign) in 2025: Which Gives Small Teams More Value for the Money?

If you’re picking between SignNow and Dropbox Sign (formerly HelloSign), you’re already on the right track. Both are mature, reliable e‑signature platforms with everything you need to send documents, collect legally binding signatures, and keep a clean paper trail. The real differences show up in pricing, plan limits (like template caps), workflow depth, and how each fits into the broader ecosystems around them—airSlate for SignNow and Dropbox for Dropbox Sign.

The quick answer: if value per dollar is your top priority, SignNow usually offers more capability at a lower price. If your team already lives in Dropbox and wants the smoothest file-centric experience with minimal setup, Dropbox Sign can be worth the premium—especially if your volume is very light and you can live on its free plan.

Quick recommendation

• Choose SignNow if:
  • You want the lowest cost per user.
  • You need unlimited templates without jumping to higher tiers.
  • You care about conditional fields, if-then routing, and more flexible workflows.
  • You plan to grow into automation with airSlate and tools like pdfFiller.
• Choose Dropbox Sign if:
  • Your team already runs on Dropbox.
  • You want a permanent free option (3 documents per month).
  • You prefer a slick, minimal interface with seamless file-based workflows.
  • You’d benefit from the Dropbox + eSign bundle for all-in-one storage and signatures.

Pricing and plans in 2025: what you’ll actually pay

You can do great work on both tools without overspending. The key is how their tiers line up with your volume and workflow needs. Here’s what to expect this year based on commonly available pricing.

SignNow pricing overview

• Business (entry tier): about $8 per user per month with annual billing. You get the core items most teams need—unlimited templates, cloud storage integrations, and standard e‑sign features.
• Business Premium: roughly $15 per user per month (annual). Adds advanced features and admin controls better suited for growing teams.
• Enterprise: commonly around $30 per user per month, with top-tier security, controls, and advanced capabilities.
• airSlate Business Cloud bundle: around $50 per user per month. Combines SignNow with pdfFiller, document generation, and no-code workflow automation—a strong package if you’re moving beyond basic signing.
• Free trial: 7 days on any paid plan. SignNow typically doesn’t offer a permanent free plan for ongoing use.
• Pay-as-you-go: a Site License option at approximately $1.50 per signature invite, useful for very light, occasional needs.

Dropbox Sign (HelloSign) pricing overview

• Essentials (single user): about $15 per user per month with annual billing (around $20 month-to-month). Includes unlimited signature requests, reminders, audit trails, and up to 5 templates.
• Standard (2+ users): roughly $25 per user per month (annual; about $30 monthly). Increases template limits (up to 15) and adds branding, more integrations (like Salesforce, SharePoint), and stronger admin features.
• Premium: enterprise/API plan with custom pricing. Adds SSO, SMS authentication for signers, advanced reporting, multi-team management, and HIPAA with a BAA.
• Dropbox + eSign bundle: approximately $18 per month (annual) for 3 TB of Dropbox storage plus e‑sign features—a strong value if you’d otherwise be paying for Dropbox separately.
• Free options: a permanent free tier lets you send 3 documents per month; paid features often come with a 30‑day trial.

Value snapshot

• Where SignNow wins for small teams:
  • Lower per-user cost at entry and mid tiers.
  • Unlimited templates on the base plan—no caps to outgrow.
  • More built-in workflow depth without forcing an upgrade.
• Where Dropbox Sign makes sense:
  • You work in Dropbox all day and want the smoothest file-centric flows.
  • You need a true free plan (3 docs/month) for very light use.
  • You value polished UX above all and don’t mind paying more per seat.

Tips before you buy

• Confirm annual vs monthly pricing at checkout. Vendors promote “per month” rates that assume annual commitments.
• Look for promotions and bundles (especially if you already pay for Dropbox).
• Model your total cost at your next headcount milestone. Moving from 3 to 10 users can magnify a small per-user price difference into a big annual gap.
• Map your template needs. Template caps are easy to overlook and can force a plan upgrade later.
• Test your real workflow end-to-end (see the two-day test plan below). A quick, fair trial will tell you more than spec sheets.

Core features and day-to-day experience

Both tools are reliable for sending documents, collecting signatures, and tracking status. The biggest differences appear in templates, workflow customization, and how each tool feels during setup and everyday use.

Ease of use and interface

• Dropbox Sign: Known for a clean, minimal UI and almost no learning curve. It “just works” with a predictable, polished feel. Teams that value simplicity often prefer this experience right out of the box.
• SignNow: Also easy to learn, with clear signing flows and sensible defaults. Some users find the interface a bit less refined visually, but most get productive quickly after a brief onboarding.

Templates and reusable forms

• SignNow: Unlimited templates on the basic plan. If you use many standard agreements (NDAs, SOWs, onboarding packets) or variations by client/team, unlimited templates remove friction and surprise upgrade fees.
• Dropbox Sign: Template limits by plan—up to 5 on Essentials and 15 on Standard. This is fine if you keep a small, tight library. It’s limiting for teams handling many contract variants or multi-department needs.

Workflow and routing depth

• Both platforms handle the essentials: multiple signers, sequential signing, reminders, and expiration deadlines. That’s enough for most straightforward processes.

- Where SignNow goes deeper:

• Conditional logic and branching: Show fields or route documents based on user input (if-then flows).
• Conditional fields: Reveal or hide fields dynamically (for example, only show a W‑9 section if “US contractor” is selected).
• Editor role: Collaboratively prep a document before sending for signature.
• Attachment requests: Ask signers to upload files (like a photo ID, insurance certificate, or license).
• Payment collection: Collect payments during signing through supported integrations.
• These features are valuable for finance, HR, education, healthcare administration, and any process with variable paths.

- Dropbox Sign is excellent for linear flows:

• Standard routing is smooth and reliable.
• More advanced branching or conditional behavior may require workarounds or additional tools.

Mobile and offline use

• Both have capable iOS and Android apps for sending and signing on the go.
• SignNow adds offline signing: prepare, sign, and sync when back online. This is a practical advantage for field teams, travel, or spotty connectivity. SignNow also supports biometric app security (Face ID/Touch ID) for extra protection on mobile devices.

Notable extras

• SignNow highlights:
  • PDF merging inside the app.
  • Kiosk mode for in-person events or walk-up signing.
  • Collaboration via an editor role.
  • Conditional field logic, attachment requests, and payment options.
  • Strong value at lower tiers for teams that need more than “just sign.”
• Dropbox Sign highlights:
  • Deep Dropbox integration and file-centric workflows.
  • Tamper-proofing and clean audit trails.
  • Dropbox Forms for data capture.
  • Unlimited self-signing by the account owner (outbound requests to others are what count).
  • Works smoothly alongside DocSend for tracked sharing in sales or investor relations.

Security, compliance, and reliability

Both tools are designed for legally valid e‑signatures and enterprise-grade security. For most small teams, you won’t choose between them on security alone—but you should pick the right plan level for your obligations.

Legal validity and audit trails

• Both comply with ESIGN and UETA in the U.S. and eIDAS in the EU.
• Both generate detailed audit trails and certificates of completion, which you’ll need for internal audits or legal enforcement.

HIPAA, GDPR, and data privacy

• HIPAA: Both vendors can support HIPAA-compliant use on appropriate business/enterprise plans with a signed Business Associate Agreement (BAA).
• Dropbox Sign: HIPAA support typically starts on Standard/Premium with a BAA.
• SignNow (airSlate): Supports HIPAA with a BAA for customers who need it.
• GDPR/CCPA: Both outline GDPR compliance for EU data and alignment with CCPA. Data processing addenda are available so you can meet privacy requirements.

Security controls and certifications

• Expect strong encryption in transit and at rest, role-based access controls, and two-factor authentication.
• Dropbox Sign benefits from Dropbox’s broader security posture (including SOC 2).
• SignNow (airSlate) maintains common certifications and publishes security practices; enterprise deployments can include private cloud options when tighter control is required.
• Signer verification: Dropbox Sign offers SMS-based verification at higher tiers. SignNow supports options such as one-time passwords and knowledge-based authentication (KBA) for regulated contexts.

Reliability and SLAs

• Both run on mature cloud infrastructure with high uptime and optional enterprise SLAs at upper tiers.
• Reports of downtime are uncommon in normal use.

Practical takeaway

If you’re an SMB, both tools will meet standard security and compliance expectations. Your decision should focus more on pricing, workflows, template limits, and ecosystem fit. If you handle PHI, make sure you’re on a HIPAA-ready plan and sign a BAA.

Ecosystems compared: airSlate vs Dropbox

SignNow within the airSlate ecosystem

• airSlate Business Cloud bundles SignNow with pdfFiller (PDF editing), document generation, and no-code workflow automation.
• This is compelling if you want end-to-end automation: generate contracts from form inputs, route approvals based on conditions, push data to your CRM/accounting, and archive automatically.
• For small teams growing into more complex processes, the airSlate path can remove manual steps without needing engineering resources.

Dropbox Sign within the Dropbox ecosystem

• If your files live in Dropbox, Dropbox Sign delivers the smoothest file-centric experience:
  • Send for signature directly from a stored file.
  • Have signed copies auto-save to the right folder.
  • Pair with DocSend for tracked, secure sharing—useful for sales decks, investor updates, or sensitive documents.
• For teams that live in Dropbox and Slack all day, this tight integration reduces context switching and setup time.

Bottom line on ecosystems

• Process automation advantage: SignNow with airSlate.
• Content storage and collaboration advantage: Dropbox Sign with Dropbox.

What real users say (summarized)

Dropbox Sign (HelloSign)

• Praised for polish and ease of use. Teams regularly describe it as “frictionless” and quick to adopt.
• Common trade-offs: higher pricing than alternatives, and more limited support options on lower tiers (email/help center over hands-on support).

SignNow

• Frequently chosen for value: strong features for the price, simple implementation, and intuitive workflows.
• Common trade-offs: UI that some find less modern and support that can feel less proactive on lower tiers. Occasional minor bugs or lag are mentioned but not as systemic issues.

Which one should you choose? Recommendations by scenario

Freelancers and solo consultants

• Very light or sporadic sending:
  • Dropbox Sign’s free plan (3 docs/month) might be enough. It keeps costs at zero until your volume grows.
• Consistent or growing volume on a budget:
  • SignNow’s Business plan (around $8/user/month) is hard to beat, especially with unlimited templates that won’t force an upgrade later.

Small teams (2–10 users) focused on cost

SignNow typically offers lower per-user pricing with fewer caps and deeper workflow features at entry tiers. Savings add up quickly as you add seats.

Teams standardized on Dropbox

• Dropbox Sign integrates seamlessly with existing Dropbox storage and file workflows.
• The Dropbox + eSign bundle can simplify billing and stack value if you need 3 TB storage anyway.

Regulated workflows or complex routing

SignNow’s conditional fields, branching logic, attachment requests, kiosk mode, and offline signing provide more flexibility for finance, healthcare administration (with BAA), education, and multi-step internal approvals.

Field teams and spotty connectivity

SignNow’s offline mobile mode is an advantage for on-the-go work, construction sites, real estate showings, and any place with unreliable internet.

API and developer needs

• Both vendors offer capable APIs.
• Dropbox Sign’s API is known for a straightforward, self-serve experience with transparent pricing—popular with startups.
• SignNow’s API pairs nicely with airSlate if your long-term plan includes broader, no-code workflow automation across departments.

Try both in a weekend: a quick, fair test plan

Day 1 (morning): Define success

• Write down what “done” looks like. For example:
  • A three-signer contract with a fixed signer order.
  • Conditional fields that appear based on an earlier answer.
  • A requested attachment (e.g., photo ID) from one signer.
  • Automatic reminders and an expiration date.
  • Auto-save the signed copy to your workspace (Dropbox, Google Drive, SharePoint, or your CRM).

Day 1 (afternoon): Test Dropbox Sign

• Create a template with your fields.
• Set signer order and enable reminders.
• Send a test to two colleagues and yourself.
• Save the signed copy to Dropbox and review the audit trail.
• Note:
  • Time from signup to first successful send.
  • Any missing features or workarounds.
  • Clarity of the UI and signer experience.
  • Total projected monthly cost for your user count and template needs.

Day 2 (morning): Test SignNow

• Recreate the same template and routing.
• Add conditional fields and request an attachment from one signer.
• Try a mobile test in offline mode to confirm sync behavior.
• Export the signed copy to your current storage or app ecosystem.
• Note the same metrics: time to first send, coverage of must-haves, and projected cost.

Day 2 (afternoon): Compare and decide

• If both meet your must-haves and one is meaningfully cheaper for your team size, pick the cheaper option.
• If your team spends all day in Dropbox and wants maximum simplicity with native integration, pick Dropbox Sign even if it costs more.

FAQs

Is HelloSign the same as Dropbox Sign?

Yes. HelloSign was acquired and rebranded as Dropbox Sign. You’ll often see “Dropbox Sign (formerly HelloSign)” in documentation.

Does Dropbox Sign have a permanent free plan?

Yes. The free tier lets you send up to 3 documents per month at no cost. It’s great for very low volume but doesn’t include advanced features like larger template libraries.

Does SignNow have a free plan or only a trial?

SignNow offers a 7‑day free trial of paid plans. There isn’t a permanent free plan for ongoing use, but there is a pay‑as-you-go option for occasional documents.

Can both be HIPAA compliant, and do I need a BAA?

Both can support HIPAA-compliant use on appropriate plans. You’ll need to sign a Business Associate Agreement (BAA), typically available on business/enterprise tiers.

Do both integrate with Google Workspace, Microsoft 365, and Salesforce?

Yes. Both platforms offer popular integrations across Google, Microsoft, Salesforce, Slack, and more. Dropbox Sign is especially tight with Dropbox; SignNow integrates broadly and pairs with airSlate for workflow automation.

Which supports offline signing?

SignNow’s mobile app supports offline signing and syncs when you reconnect.

Which has more advanced workflow/conditional logic?

SignNow generally offers deeper built-in options for conditional logic, conditional fields, attachment requests, kiosk mode, and payment collection via supported integrations.

Conclusion: the better value for most cost‑conscious teams

If you’re a small team or solo pro watching spend, SignNow typically delivers more features per dollar—lower per-user pricing, unlimited templates on the entry tier, and richer workflow options when you need them. Dropbox Sign wins on polish, the generosity of its free 3‑docs/month plan for very light usage, and the smoothest experience if your business already runs on Dropbox.

Still unsure? Block off a weekend and run the two-day test above. Rebuild your real workflow in both tools, compare setup time and feature coverage, then multiply the per-user cost by the headcount you expect in the next 12 months. The right choice will be obvious—and you’ll make it based on your actual work, not a spec sheet.