The two axes that separate these five are workflow depth — signature-only, document automation, or full contract lifecycle — and what the bill scales with: per seat with an envelope allowance, per document, or quote-only. DocuSign is the compliance leader and the recognized brand: 14-day trial, no free tier, Personal $15/mo (or $10/mo billed $120/yr) capped at 5 envelopes a month, Standard $45/user/mo monthly or $25/user/mo annual ($300/yr, about 44% off), Business Pro $65/user/mo monthly or $40/user/mo annual; Standard and Business Pro each include 100 envelopes per user per year, and CLM, Identify, Payments and SMS are billed separately. PandaDoc is the proposals-plus-signature choice and the only one with a genuinely free tier worth using: Free eSign $0 with unlimited signatures at a 5-document/month cap, then Starter $35/user/mo monthly or $19/user/mo annual and Business $65/user/mo monthly or $49/user/mo annual (about 46% off annually); Enterprise is quote-only. Dropbox Sign is the simple, cheap signing path: Free $0 at 3 signature requests a month, Essentials $20/user/mo monthly or $15 annual, Standard $30/user/mo monthly or $25 annual with a 2-user minimum; API and embedded signing are a separate product from $75 per 50 requests/mo. airSlate is the compliance-per-dollar mid-market play: no free plan, 7-day trial, Business $20/user/mo monthly or $8 annual, Business Premium $30/$15, Enterprise $50/$30; every tier caps at about 100 signature invites per user per year with extras around $1.50 each, API is a separate product from about $146/mo, and HIPAA / 21 CFR Part 11 sit behind Site License. Juro is the contract-lifecycle outlier and the only quote-only entry — no published tiers, sized by contract volume and add-ons, but with unlimited users on all plans. So the choice resolves to: compliance breadth and brand (DocuSign), sales documents plus signature with a usable free tier (PandaDoc), cheap simple signing (Dropbox Sign), mid-market compliance depth per dollar (airSlate), or full CLM at negotiated pricing (Juro). All prices re-checked 2026-09-20 against official pricing pages, evidence=research.
The cluster's top rating (4.4/5): the e-signature market standard, legally binding in 180+ countries, the broadest enterprise integrations (1,000+ connectors) and the deepest compliance stack. From $10/mo annual (Personal) to $25/user/mo annual (Standard).
Free tier: No — trial only · 14-day free trial
Paid from: $10/mo (Personal, annual) (Per-seat billing with ~44% annual discount on Standard. Standard and Business Pro each include 100 envelopes per user per year; Personal is capped at 5 envelopes/month. Additional products (CLM, Identify, Payments, SMS) are billed separately.)
DocuSign is the e-signature market standard — legally binding in 180+ countries with the broadest enterprise integrations, compliance depth and agreement-lifecycle reach, priced per seat with annual-billing discounts.
The document-automation pick (4.2/5): proposal, quote and sales-doc builder with signing and payments in the same seat, the most generous free tier, and the strongest CRM integration. Starter $19/user/mo annual.
Free tier: Yes · 14-day free trial
Paid from: $0/mo (Free eSign) · $19/user/mo (Starter, annual) (Per-user billing; annual saves ~46%. Free eSign plan is unlimited signatures with a 5-document/month cap. Starter ($19/user/mo annual) adds unlimited documents; Business ($49/user/mo annual) unlocks CRM integrations, custom branding and payments. Enterprise is quote-only (SSO, API, CPQ).)
PandaDoc pairs document automation (proposals, quotes, sales docs) with built-in e-signature and payment collection, a genuinely free e-sign tier, and deep CRM integrations — priced per user with an annual-billing discount.
The simplicity and value pick (4.1/5): genuinely unlimited signatures on paid plans at a $15/user/mo annual entry, a free 3-requests/month tier, and signed docs filed straight into Dropbox.
Free tier: Yes · 30-day free trial
Paid from: $0/mo (Free, 3 requests/mo) · $15/user/mo (Essentials, annual) (Per-seat app plans with ~33% annual discount. Standard has a 2-user minimum. API and embedded signing are a separate product: from $75 per 50 requests/mo (embedded signing on Standard API ~$300/mo). SharePoint integration was discontinued March 2026.)
Dropbox Sign (formerly HelloSign) is the simple, affordable e-signature tool that saves signed docs straight into Dropbox: unlimited signatures on the paid plans, a free 3-requests/month tier, and a per-seat entry at $15/user/mo — with API and embedded signing billed on a separate track.
The value leader (4.0/5): SOC 2 Type II and HIPAA-grade compliance at roughly a third of DocuSign's bill, from $8/user/mo annual. Native Salesforce/NetSuite, 4-layer signer authentication. Watch the 100-invite/user/yr cap.
Free tier: No — trial only · 7-day free trial
Paid from: $8/user/mo (Business, annual) (Per-seat, no free plan. Every signNow tier caps at ~100 signature invites per user per year; extra invites billed ~$1.50 each. API access is a separate product (from ~$146/mo) and the WorkFlow automation platform bills on credits (Growth ~$399/mo). HIPAA/21 CFR Part 11 locked behind Site License.)
airSlate's signNow is the mid-market value play: SOC 2 Type II and HIPAA-grade compliance at about a third of DocuSign's price, per-seat plans from $8/user/mo on annual billing, with a 100-invites-per-user annual cap and separately priced API and WorkFlow automation.
The contract-automation pick (3.8/5): browser-native templates, repository and AI drafting with unlimited users on all plans. Quote-only pricing, so total cost is sized through a sales quote rather than a published tier.
Free tier: No — trial only · Demo-gated (20% off year-one for new customers)
Paid from: Quote-only (no published self-serve price) (No published tiers: Juro sells a single custom-priced plan sized by contract volume, type and add-ons (AI Draft/Extract/Review, premium integrations). Unlimited users on all plans. New customers signing the month of demo get 20% off year-one. No forever-free tier.)
Juro is a browser-native contract-lifecycle platform: no Word dependency, native e-signature, template library and a repository that tracks signed docs, with unlimited users on all plans — priced quote-only through a calculator, with no self-serve tiers.
Bottom line: DocuSign when compliance breadth and the recognized brand are the driver; PandaDoc when the workflow is proposals-plus-signature in a sales tool; Dropbox Sign when you want a simple, cheap signature flow with unlimited signatures; airSlate when mid-market compliance depth matters more than the bill; and Juro when the need is full contract lifecycle with unlimited users. Workflow depth and bill-scaling decide; price alone does not.
DocuSign at 4.4/5 — the cluster's top independent score, earned on compliance breadth (180+ countries), enterprise integrations and the deepest authentication stack. PandaDoc follows at 4.2/5 on document-automation depth, Dropbox Sign at 4.1/5 on simple value.
PandaDoc and Dropbox Sign have standing free tiers. The cheapest paid per-seat entry is airSlate signNow Business at $8/user/mo annual, then Dropbox Sign Essentials at $15/user/mo annual, then PandaDoc Starter at $19 and DocuSign Standard at $25. Juro is quote-only.
PandaDoc (unlimited e-signatures, 5 docs/month) and Dropbox Sign (3 signature requests/month) are free. airSlate and DocuSign offer paid-only plans with free trials; Juro is quote-only with no self-serve free tier.