Dropbox Sign (Formerly HelloSign) vs Docusign: Which is Best for You?

Not all eSignature tools are built the same. The question is: which one do you need?

If you’re comparing eSignature tools for your business, you’ve come across two big names: Docusign and HelloSign (now Dropbox Sign). Both are leading e-signature solutions, but with different strengths, designed for very different users and workflows.

In this guide, we’ll break down how Dropbox Sign and Docusign compare in terms of pricing, reviews, usability, integrations, security, and real-world performance. Whether you’re a solo founder or an enterprise organization, this side-by-side comparison will help you confidently choose the right tool.

What is HelloSign used for?

HelloSign, now known as Dropbox Sign, is an intuitive e-signature solution designed for simplicity and speed. It’s best known for its clean interface and seamless integration with Dropbox, making it a go-to solution for individuals, startups, and small to mid-sized businesses looking to manage document signing workflows without complexity.

HelloSign allows users to:

• Send signature requests to one or more recipients.
• Add legally binding eSignatures to PDF documents, Word docs, and other file types.
• Create reusable templates for frequently used documents, and create documents from scratch with embedded fields like NDAs, contracts, or offer letters.
• Track the status of sent documents in real-time with audit trails.
• Integrate with tools like Google Workspace, Slack, Salesforce, and Dropbox.

What is Docusign used for?

Docusign is one of the most established and feature-rich e-signature solutions available today. Designed for scalability and compliance, Docusign offers advanced features like payment collection, signer authentication, and automated document routing. These tools enable users to streamline their signing workflows with just a few clicks, whether they’re in legal, sales, or HR teams.

At its core, Docusign enables users to:

• Send, sign, and manage electronic documents securely from any device.
• Set up complex legal document review and approval workflows with multiple recipients and custom signing orders.
• Collect additional data using form fields, checkboxes, and dropdowns, enhancing your document preparation process.
• Track signing progress with detailed audit trails and real-time notifications.
• Comply with strict regulations including eIDAS, HIPAA, SOC 2, and FedRAMP.

What sets Docusign apart is its expansive ecosystem:

• It integrates with over 350 applications, including Salesforce, SAP, Microsoft 365, Google Workspace, and Workday.
• It offers up to five templates on lower-tier plans and unlimited signature requests on higher plans.
• Docusign is packed with key features like collaborative commenting, bulk sending, and seamless payment integration.
• It offers advanced options like Signer Authentication, Payment Collection, and Contract Lifecycle Management (CLM) features.
• Through the Docusign API, businesses can embed eSignatures directly into their websites or apps and automate document workflows.

Discover a full list of Docusign alternatives.

Who uses HelloSign and Docusign?

HelloSign (now Dropbox Sign) is built for lightweight use cases—think quick signatures on NDAs or offer letters. Docusign, on the other hand, supports regulated industries and complex approval workflows.

For teams that need to manage contracts from creation to renewal, not just signing, HyperStart offers a complete contract lifecycle solution.

HelloSign vs Docusign: A comparison guide

Feature lists alone don’t always reveal how tools perform in real workflows. For example, both Docusign and Dropbox Sign allow users to sign documents online. But Docusign is better suited for enterprise use. If your team relies on tools with standalone solution capabilities and robust security features, Docusign may be a better fit.

We’ve also included HyperStart contract management software in the mix—not as another eSignature tool, but as a modern solution for teams that need to do more than just sign. If you’re managing contracts across multiple tools and touchpoints today, this side-by-side will help you see what each platform can (and can’t) do.

HyperStart offers an alternative approach by bundling document management, e-signature tools, and contract workflows into one seamless platform. Unlike HelloSign or Docusign, which focus on just signing documents, HyperStart lets you manage the entire contract lifecycle in one place.

Read more on Docusign Pricing and Compare Contract Management Software Pricing.

User reviews of HelloSign vs Docusign

We’ve looked at how HelloSign, Docusign, and HyperStart CLM compare on paper—across pricing, features, support, and implementation. But numbers and specs only tell part of the story. Here’s what actual users on G2 have to say about their experience with each platform.

What users like about HelloSign (Dropbox Sign)

Tyler C

My firm uses Dropbox Sign (Formerly HelloSign) to send out templated contracts and onboarding documents to new clients. This process using Dropbox Sign has helped us grow our client base rapidly and easily.

Janella S

I love the fact that Dropbox Sign has a very user-friendly interface. Anyone could use it, and I love the updates that I receive in my email. Months Later and I still love DropBoxSign.

Penny M

I like that all you have to do is mark where clients are to sign and it is so simple – almost 99% of clients know – understand what needs to be done because of the simple instructions.

Where HelloSign falls short

Ashley S

Dropbox Sign no longer has a free option, so I’d have to pay just to send a few contracts per month. Additionally, the free version of HelloSign didn’t allow for saving a template (I use the same contract over and over again), but now that I’m on DigiSigner I can save everything and the process is much more streamlined.

Cynthia M

The only thing I dislike about Droprox Sign is you can’t change the variables once you’ve sent the item out for signature. Sometimes we’ll get a customer who wants to omit a middle name, or add an initial, and instead of fixing it, we have to scrap the whole thing and start over. It’s no big deal, but if you’re dealing with a customer who’s already a pain, having to re-do their contract might make you grumpy for a min.

Irene S

The click to sign box should be easier to identify by changing the background of the box. There should be an option to send by text to sign.

What users like about Docusign

Jennifer E

Having Docusign linked directly to Procore is extremely helpful, and makes it very easy to issue change orders or other documents quickly. It is also easy to navigate, and keep track of the status of documents that have been sent out via Docusign.

Ashley S

Docusign gives me the ability to send anything and everything we need for the hiring and HR process to be signed by needed parties. It is tracked and sends reminders when there are pending items, which takes that off my plate. Easy to then download when complete and save!

Yogita S

DocuSign is a very helpful tool that makes signing documents quick and easy. The best part is that you don’t need to print, scan, or mail anything—you can sign documents online from your phone or computer, anytime and anywhere. It saves a lot of time and keeps everything organized in one place. The platform is simple to use, secure, and legally accepted, which gives peace of mind. I also liked how it sends notifications when others sign the document, making the whole process smooth and efficient.

Where Docusign falls short

Oviya M

On the downside I’ve found with Docusign is that the pricing can be bit steep for the smaller business and individuals. More amazing features are available on higher tier plans.

Verified User in Medical Practice

I can’t say I’ve stumbled upon a bad feature or one I don’t like enough. It’s simple, fast, reliable, and it just works. DocuSign gives our business a more corporate, 21st century feel when interacting with partners and clients alike.

Damian R

Overall, the product is slow, unresponsive and difficult to use. Most importantly, we were promised certain features in our contract, which were ultimately not delivered, and customer service simply does not care.

What users like about HyperStart CLM

             We took demos of around 5 CLM vendors and chose to use HyperStart. They were the only CLM vendor that had SOC2 compliance and met the criteria of around 22 parameters, which we had evaluated them on.

Om Prakash Pandey

Head of Legal at LeadSquared

Read case study

             HyperStart has simplified tracking crucial clauses like liability, indemnity, and contract terms. Multiple teams, including finance, business, and operations, benefit from having all this data in one place. Now, we receive email reminders for contracts that are due for renewal.

Mayuri Jaltare

Company Secretary, Qapita

Read case study

Pricing: HelloSign vs Docusign

When comparing eSignature tools, pricing is a major deciding factor, especially for small businesses choosing between a free plan and an enterprise plan. While HelloSign’s lower tiers are ideal for freelancers, Docusign offers a more robust enterprise plan with advanced routing and phone support. However, unlike Docusign, Dropbox Sign may be more accessible to budget-conscious teams.

Which one’s more cost-efficient from HelloSign vs. Docusign?

• For basic signing needs with a simple document signing process, HelloSign is more budget-friendly if you don’t need complex routing or CRM integrations.
• For businesses needing enterprise-level tools, bulk sending, or legal workflows, Docusign justifies the higher cost with its robust feature set.

And if you’re looking beyond just signatures to manage contracts from draft to renewal, HyperStart CLM is a contract signing software that offers a pricing model based on workflow volume, not users. That means you don’t pay more just because your team is growing.

HelloSign vs Docusign: Strengths vs Weaknesses

To help you wrap things up, here’s a straightforward comparison of the key pros and cons for both HelloSign and Docusign.

Pros and cons of HelloSign (Dropbox Sign)

Pros	Cons
Clean, minimal interface that’s easy to use.	Limited advanced features like payment collection or conditional workflows.
Quick setup and easy onboarding—ideal for small teams.	Fewer third-party integrations compared to Docusign.
Affordable pricing plans for startups and solo users.	Basic audit trail—may not meet compliance needs for regulated industries.
Seamless integrations with Dropbox, Google Workspace, and Slack.	No support for payment fields or offline/in-person signing.
Custom branding and reusable templates are available on mid-tier plans.

Pros and cons of Docusign

Pros	Cons
Enterprise-grade features like conditional workflows and role-based routing.	Higher pricing for full feature access on larger teams.
Integrates with 400+ tools, including Salesforce, SAP, and Microsoft.	Steeper learning curve due to the number of configuration options.
Built-in support for payment collection and advanced signer authentication.	Many advanced features are only available on Business Pro or Enterprise plans.
Supports in-person and offline signing with dedicated mobile apps.	Can overwhelm smaller teams with basic signing needs.
Strong security and compliance standards (HIPAA, FedRAMP, ISO 27001, etc.).	Longer implementation time for enterprise-level teams.

Pros and cons of HyperStart CLM

Pros	Cons
94% accurate AI for complete contract automation.	Fewer third-party integrations compared to enterprise-level CLM tools.
Budget-friendly pricing for startups and growing businesses.	It may not be the best option for enterprises.
Intuitive dashboard that’s easy to navigate.
Quick implementation—get started in days, not weeks.

In-depth feature comparison of HelloSign and Docusign

Let’s take a closer look at how HelloSign (Dropbox Sign) and Docusign stack up across core features. From template creation and audit trails to integrations and signer verification, each platform offers unique features that cater to different business needs. This comparison will help you determine which one fits your workflow best.

Questions to ask when choosing between HelloSign and Docusign

Here’s a helpful checklist of questions to guide your decision.

Pricing

• Does the pricing fit our current budget and team size?
• Are we billed per user or signature request?
• Do we need features locked behind higher-tier or enterprise plans?
• Is there a free trial or free plan available to test?

Features

• Do we need only basic features or more advanced options like workflow automation and payment collection?
• Do we need to automate eSign and/or other parts of the contract lifecycle?
• Does it support simple workflow configuration, audit trails, and commenting?
• Can multiple users collaborate on the same document with version control?
• Is in-person signing or mobile signing supported?

Collaboration

• Is the interface intuitive for all stakeholders?
• Will it fit smoothly into our CRM, HR, or procurement workflows?
• Does it integrate with our existing tools (Google Workspace, Salesforce, Dropbox, SAP)?

Setup

• Are onboarding, setup, and support effective and affordable?
• Can this scale as we grow?

Why is HyperStart the more intelligent choice for end-to-end contract management?

While e-signature tools like HelloSign and Docusign only handle signing, HyperStart CLM offers a complete, end-to-end solution. It goes beyond just signatures to streamline every contract stage: drafting, approvals, execution, tracking, and renewals.

Unlike disconnected tools that slow you down and increase risk, HyperStart integrates everything, saving time, reducing risk, and ensuring compliance. Plus, it’s built-in AI assistant instantly summarizes contracts, finds key terms, and offers smart suggestions for all users.

And when it comes to cost, HyperStart’s pricing scales by workflow, not per user like Docusign, so your costs stay predictable.

Book a demo and see how HyperStart can simplify and scale your contract processes.