Chili Piper vs Help Scout
A side-by-side look at 2 CRM & Sales tools for 2026 — the verdict, pricing, ratings, features, and what readers think.
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chilipiper.com
Best for B2B revenue teams that need inbound lead routing and instant meeting booking tied to their CRM
Turn website traffic into pipeline: instant form-to-meeting booking, lead routing and AI agents that qualify and book buyers around the clock.
Visit Chili Piper
helpscout.com
Best for small and mid-sized support teams that want a simple shared inbox with AI help
Shared inbox and help desk with AI drafts, an AI support agent and a free plan for up to 5 users.
Visit Help ScoutPricing compared
Chili Piper
$1,250/mo (billed yearly)
Help Scout
$25/user/mo
Head to head
| Chili Piper | Help Scout | |
|---|---|---|
| Starting price | $1,250/mo (billed yearly) | $25/user/mo |
| Free tier | No | Yes |
| Free trial | Demo only; no free plan | Free plan; Envoy AI add-on has a 3-month free trial |
| Platforms | Web · API | Web · iOS · Android |
| Founded | 2016 | — |
Pros & cons
Chili Piper
Pros
- Books meetings instantly from web forms, with routing to the right rep.
- Deep native Salesforce and HubSpot integration.
- SOC 2 Type 2, ISO 27001, GDPR and CCPA compliance.
- Pricing is published, with a calculator.
Cons
- High entry price: Growth starts at USD 15,000 per year.
- Annual billing only, with no monthly option.
- No free plan; standalone ChiliCal needs at least 200 seats.
Help Scout
Pros
- A permanent Free plan covers up to 5 users, 1 Inbox and 1 Docs site.
- Email, chat, SMS, social and voice land in one shared Inbox.
- AI Drafts and Copilot help agents reply faster while a human stays in control.
- Envoy AI is billed per resolution at USD 0.75, so cost follows results.
- SSO/SAML and HIPAA compliance are listed on the Pro plan.
Cons
- Pro plan pricing and many advanced limits push larger teams to a sales conversation.
- Extra inboxes cost USD 10 per month each on Standard, Plus and Pro.
- The Free plan is capped at 100 contacts per month.
- Fewer marketplace integrations than the largest help desks (the vendor lists 100+).