HelloSign

Overview

HelloSign is e-signature software for legally binding electronic signatures on business documents (contracts, proposals, NDAs, order forms, HR documents).

Core capabilities:

• E-Signature: Legally binding electronic signatures (ESIGN Act, UETA, eIDAS compliant) → Recipients sign with mouse/trackpad or upload signature image → Tamper-proof audit trails
• Document Templates: Create reusable templates for recurring documents (standard NDA, MSA, offer letter) → Auto-populate fields with recipient data → Send in 2 minutes vs 10 minutes manual upload
• Multi-Party Signing: Sequential routing (A signs first → B signs second → C signs third) or parallel signing (A, B, C all sign at same time) → Automated workflows eliminate manual coordination
• Mobile App: iOS/Android app for creating signature requests, signing documents on-the-go → Real estate agents send docs from phone during property showings
• Audit Trails: Tamper-proof certificate of completion tracking who signed, when, from what IP address, authentication method used → Legal defensibility for disputes

Typical workflow: B2B sales rep sends $100K master services agreement (MSA) to client → Uploads MSA PDF to HelloSign → Drags signature field for client, date field, company name text field → Adds client email → Sends request → Client receives email → Clicks link → Reviews 5-page MSA → Signs with mouse → Submits → Rep receives "Document Signed" notification in 15 minutes → Signed MSA auto-saved to HelloSign account. vs Manual: Email unsigned MSA PDF → Wait 2-3 days for reply → Client prints 5 pages → Signs with pen → Scans → Emails back (or loses in email thread for 2 weeks).

vs DocuSign: HelloSign 10-minute setup (upload → drag fields → send) vs DocuSign 30-45 minute learning curve (create envelope → assign recipient roles → configure signing order → choose authentication method → set reminders → configure expiration). HelloSign prioritizes simplicity for straightforward workflows vs DocuSign offering advanced features (bulk send 1,000+ docs, notarization, conditional routing) for complex enterprise needs.

HelloSign offers 3 pricing tiers starting at $15/user/month (Essentials) up to $25/user/month (Standard) plus custom Premium pricing.

Essentials Tier: $15/user/month

What you get:

• ✅ Unlimited signature requests (no per-document fees)
• ✅ Unlimited templates (create reusable document templates)
• ✅ Mobile app (iOS/Android - send/sign docs on-the-go)
• ✅ Basic integrations (Salesforce, HubSpot, Slack, Google Drive, Dropbox)
• ✅ Audit trails (tamper-proof certificate tracking signatures, IP addresses, timestamps)
• ✅ Sequential signing (route documents through signing order: A → B → C)

Limitations:

• ❌ No team management (single user account, can't add team members with permissions)
• ❌ Limited custom branding (HelloSign logo appears on some templates)
• ❌ No bulk send (must send each document individually)
• ❌ No API access (can't build custom integrations)

Best for: Freelancers, solo consultants, small sales teams (1-5 users) needing affordable unlimited e-signatures with core integrations.

Cost comparison:

• HelloSign Essentials: $15/user = $900/year for 5-user team
• DocuSign Standard: $25/user = $1,500/year for 5-user team
• Savings: $600/year (40% cheaper) with HelloSign

Standard Tier: $25/user/month

What you get (everything in Essentials +):

• ✅ Team management (add users, set permissions, manage team signature requests)
• ✅ Custom branding (remove HelloSign logo, add company logo/colors to all templates)
• ✅ Bulk send (send same document to 50 recipients at once)
• ✅ In-person signing (use tablet/iPad for in-person signature capture at events, meetings)
• ✅ Advanced integrations (Zapier, API access for custom workflows)
• ✅ Advanced fields (checkboxes, radio buttons, dropdowns)

Best for: Small to mid-sized teams (5-20 users) needing team collaboration, bulk sending, custom branding, and API access.

Cost comparison:

• HelloSign Standard: $25/user = $1,500/year for 5-user team
• DocuSign Standard: $25/user = $1,500/year for 5-user team
• Pricing parity but HelloSign maintains simplicity advantage (complexity 1/5 vs DocuSign 3/5)

Premium Tier: Custom Pricing

What you get (everything in Standard +):

• ✅ Advanced authentication (SMS verification, knowledge-based authentication - KBA)
• ✅ Advanced fields (conditional logic, calculated fields, field validation)
• ✅ SSO (Single Sign-On) - SAML 2.0 for enterprise security
• ✅ Dedicated support (phone support, dedicated account manager)
• ✅ Salesforce CPQ integration (generate contracts from Salesforce with product catalog)
• ✅ Higher volume bulk send (500+ recipients vs Standard 50)

Best for: Mid-market to enterprise teams (20+ users) requiring advanced authentication, SSO, or Salesforce CPQ integration.

Typical pricing: $40-65/user/month based on volume (similar to DocuSign Premium $40-60/user/month).

When to Use HelloSign ($15-25/user)

✅ Use HelloSign if:

• You need simple e-signature workflows (upload doc → add fields → send)
• You prioritize ease-of-use (complexity 1/5, 10-minute setup, no training required)
• You're budget-conscious ($15/user Essentials = 40% cheaper than DocuSign $25/user Standard)
• You use Dropbox for file storage (HelloSign acquired by Dropbox, native integration)
• You're sending 10-50 documents/month (straightforward volume, no bulk operations)

Example: Real estate agent sending 20 purchase agreements/month → HelloSign Essentials at $15/user = $180/year provides unlimited signatures with 10-minute setup vs DocuSign $25/user = $300/year with 30-minute learning curve.

When to Use DocuSign ($25-45/user)

✅ Use DocuSign if:

• You need advanced compliance (HIPAA for healthcare, 21 CFR Part 11 for FDA pharma, FedRAMP for government)
• You're high-volume sender (500+ documents/month, bulk send 1,000+ docs)
• You need notarization (DocuSign has notary network for notarized signatures)
• You need advanced authentication (SMS verification, knowledge-based authentication on Standard tier vs HelloSign Premium only)
• You're in highly regulated industry (healthcare, finance, legal, pharma)

Example: Healthcare provider sending HIPAA-compliant consent forms → DocuSign at $25-45/user offers HIPAA compliance on Standard tier vs HelloSign lacking HIPAA features at comparable price.

When to Use PandaDoc ($19-49/user)

✅ Use PandaDoc if:

• You need all-in-one document automation (proposals + contracts + e-signatures + payment collection)
• You're creating documents from scratch (not just signing existing PDFs)
• You need product catalogs (5-50 SKUs with dynamic pricing tables)
• You want payment collection (Stripe/PayPal embedded in documents)

Example: B2B SaaS company sending proposals with pricing tables → e-signing contracts → collecting payments → PandaDoc at $19-49/user provides full workflow vs HelloSign only handling signature step.

Important: HelloSign and Dropbox Sign are the same product after Dropbox's $230M acquisition in 2019 and October 2022 rebrand.

Timeline:

• 2011: HelloSign founded as standalone e-signature startup
• 2019: Dropbox acquires HelloSign for $230M
• 2019-2022: Product operates as "HelloSign" under Dropbox ownership
• October 2022: Dropbox rebrands HelloSign as "Dropbox Sign"
• 2025: Both names still in use - "HelloSign" brand recognition persists, Dropbox promoting "Dropbox Sign"

For users:

• Same product, same features, same pricing under both names
• Existing HelloSign accounts transition to Dropbox Sign accounts
• URLs: hellosign.com redirects to sign.dropbox.com
• Search behavior: Users still search "HelloSign" (legacy brand) → see profile for dropbox-sign.md for "Dropbox Sign" coverage

Native Dropbox integration: Store contracts in Dropbox folders → Send for signature via Dropbox Sign/HelloSign → Signed docs auto-save back to Dropbox → Unified file management without leaving Dropbox ecosystem.

HelloSign is a user-friendly e-signature software at $15-25/user/month offering unlimited signature requests with industry-leading simplicity (complexity 1/5, 10-minute setup). Acquired by Dropbox (2019, $230M) and rebranded as Dropbox Sign (October 2022) - both names remain in use.

Use HelloSign when:

• You need simple e-signature workflows (upload doc → add fields → send) without advanced features
• You prioritize ease-of-use (no training required, 10-minute setup) over feature depth
• You're budget-conscious ($15/user Essentials = 40% cheaper than DocuSign $25/user)
• You use Dropbox for file storage (native integration, signed docs auto-save to Dropbox folders)
• You're sending 10-50 documents/month (straightforward volume)

Use alternatives when:

• DocuSign ($25-45/user): You need advanced compliance (HIPAA, 21 CFR Part 11, notarization) or high-volume features (bulk send 1,000+ docs)
• PandaDoc ($19-49/user): You need all-in-one document automation (proposals + e-signatures + payment collection)
• Adobe Sign ($10-35/user): You heavily use Adobe/Microsoft tools and want native integration

Pricing sweet spot: Essentials tier at $15/user provides core e-signature needs (unlimited signatures, templates, CRM integrations, mobile app, audit trails) at 40% lower price than DocuSign Standard $25/user. Standard tier at $25/user adds team management, custom branding, bulk send (50 recipients), API access at pricing parity with DocuSign but maintains simplicity advantage (complexity 1/5 vs DocuSign 3/5).

Rating: 🥇 Gold - Best affordable e-signature alternative to DocuSign for SMBs prioritizing simplicity at $15-25/user (vs DocuSign $25-45/user = save $1,200-2,400/year per 10-user team). Industry-leading ease-of-use (complexity 1/5, 10-minute setup) vs DocuSign 30-45 min learning curve. Essentials $15/user provides unlimited signatures, CRM integrations, mobile app, audit trails (95% of SMB e-signature needs). Standard $25/user adds team management, custom branding, bulk send, API access at DocuSign pricing parity. Dropbox acquisition (2019, $230M) provides enterprise stability, native Dropbox integration (signed docs auto-save to Dropbox folders). Honest limitations: DocuSign ($25-45/user) offers deeper compliance (HIPAA, 21 CFR Part 11), higher volume bulk send (1,000+ vs 50), advanced authentication on Standard tier (vs HelloSign Premium only). Use HelloSign when simplicity and affordability matter more than advanced compliance. Target ICP: 5-20 reps at SMBs ($1-15M ARR) sending 10-50 documents/month for straightforward signature workflows.