Yesware vs Chili Piper Pricing (2026)
How do these two stack up on price? Here's what each one costs, what you get, and where the value sits.
| Yesware | Chili Piper | |
|---|---|---|
| Starts at | $19/mo | $1250/mo |
| Number of plans | 4 | 3 |
| Free plan | — | |
| Free trial | — | |
| Pricing model | per-seat | hybrid |
Free
- Basic Email Open Tracking
- Basic Attachment Tracking
- 10 Campaign Recipients/Month
- Meeting Scheduler
- Weekly Webinar Trainings
- Email Support
Pro
- Unlimited Email Open Tracking
- Unlimited Email Link Tracking
- Unlimited Attachment Tracking
- 20 Campaign Recipients/Month
- Personal Activity Report
- Recipient Engagement Report
- Email and Phone Support
Premium
Popular- Hide Yesware Branding
- Unlimited Campaigns
- Unlimited Teams
- Shared Templates & Campaigns
- Team Reporting
- Centralized Team Billing
- Customer Success On-Demand
Enterprise
- Salesforce Inbox Sidebar
- Salesforce Email Sent Sync
- Salesforce Email Reply Sync
- Salesforce Calendar Sync
- Salesforce Background Sync
- Bi-Directional Activity Sync
- Add Contacts to Campaigns
- Import List Views to Campaigns
- Salesforce Single Sign-On
- Trusted IP Ranges
Routing & Scheduling
- Instantly qualify, route and schedule leads from any web form
- Automated chat journeys that qualify and route visitors
- Inbound lead distribution and round-robin assignment
- Route and assign any Salesforce object
- SDR-to-AE handoff, without the dropped balls
- Funnel analytics
- Smart scheduling links for every rep
- SSO/SAML
- Access to Spam Checker and Meeting Prep Agents
- Re-engagement flows for visitors who didn't convert
Experiences
Popular- All that qualifies, routes, and converts 24/7
- Live calling from forms and handoffs, no waiting
- Account identification and ABM targeting based on account signals in Chat
- User provisioning and admin controls
- Access to new agents as they ship
Chili Data Platform
- Upcoming magic. Book a demo to learn more.
Yesware vs Chili Piper FAQ
- Which one is cheaper?
- Yesware starts lower at $19/mo, compared to $1250/mo for Chili Piper.
- Can I use either one for free?
- Yesware has a free plan. Chili Piper doesn't — you'll need to pay from day one.
- How do they charge?
- Different approach here. Yesware uses per-seat pricing, while Chili Piper goes with hybrid. That changes the math depending on your team size and usage.
- Which one is a better deal?
- Depends on what you need. Yesware: Yesware sits mid-market — pricier than bare-bones email tracking tools but cheaper than full sales engagement platforms like Outreach or Salesloft that often run $100+/seat. They're clearly going after SMB and mid-market sales teams who want engagement features without an enterprise-platform price tag or implementation lift. Chili Piper: Chili Piper plants itself firmly in premium territory — a $1,250/mo floor with no free trial or free plan filters out anyone testing the waters, which tells you they're chasing mid-market and enterprise RevOps teams with real budget, not SMBs or solo SDRs. This isn't a self-serve land-and-expand play; it's a sales-assisted, contract-first sell.
Still deciding? See the best Yesware alternatives or the best Chili Piper alternatives, ranked with verified pricing.
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