Highspot vs Chili Piper: Which Should You Choose in 2026?
Choosing between Highspot and Chili Piper comes down to understanding what each tool does best. This comparison breaks down the key differences so you can make an informed decision based on your specific needs, not marketing claims.
Short on time? Here's the quick answer
We've tested both tools. Here's who should pick what:
Highspot
The only agentic AI sales enablement platform for go-to-market teams.
Best for you if:
- • You want the higher-rated option (8.5/10 vs 8.4/10)
- • You need sales enablement features specifically
- • Unifies content, training, coaching, and buyer engagement for GTM teams.
- • Uses agentic AI (Nexus™) to turn GTM signals into actionable insights and guidance.
Chili Piper
Revenue acceleration through smart meeting scheduling
Best for you if:
- • You need workflow automation features specifically
- • Chili Piper is a scheduling and routing platform that helps sales teams convert more inbound leads
- • It instantly books meetings, routes leads to the right reps, and eliminates scheduling friction
| At a Glance |  Highspot |  Chili Piper |
|---|---|---|
Price | Paid | Paid |
Best For | Sales Enablement | Workflow Automation |
Rating | 85/100 | 84/100 |
| Feature | Highspot | Chili Piper |
|---|---|---|
| Pricing Model | Paid | Paid |
| Editorial Score | 85 | 84 |
| Community Rating | No ratings yet | No ratings yet |
| Total Reviews | 0 | 0 |
| Community Upvotes | 0 | 0 |
| Categories | Sales EnablementRevenue Intelligence | Workflow AutomationSales Enablement |
Understanding the Differences
Both Highspot and Chili Piper solve similar problems, but they approach them differently.Highspot positions itself as "the only agentic ai sales enablement platform for go-to-market teams." while Chili Piperfocuses on "revenue acceleration through smart meeting scheduling". These differences matter depending on what you're trying to accomplish.
When to Choose Highspot
Highspot makes sense if you're looking for a comprehensive paid solution. With a score of 85/100, it's our top pick in this comparison.
When to Choose Chili Piper
Chili Piper is worth considering if you need a professional-grade tool.
Who Should Use What?
Bootstrapped or small team?
Neither is free, but both have their value. Test them both and see which clicks.
We'd pick: Chili Piper
Growing fast?
Your team doubled last quarter and you need tools that won't break when you add 50 more people. Highspot handles scale better in our testing.
We'd pick: Highspot
Enterprise with complex needs?
You need SSO, compliance certifications, and a support team that picks up the phone. Highspot is built for organizations like yours.
We'd pick: Highspot
Still not sure? Answer these 3 questions
How much can you spend?
Both are paid tools. If money isn't the issue, go with Highspot—it scored higher.
Do you care what other users think?
Both have similar review counts. Read a few before you commit.
Expert opinion or crowd wisdom?
Our team rated Highspot higher (85/100). But the community has upvoted Chili Piper more (0 votes). Pick your source of truth.
Key Takeaways
What Highspot Does Better
- Higher overall score (85/100)
- Our recommendation for most use cases
Consider Chili Piper If
- Its specific features better match your workflow
- You prefer its interface or design approach
The Bottom Line
If we had to pick one, we'd go with Highspot (85/100). But the honest answer is that "better" depends on your situation. Highspot scores higher in our analysis, but Chili Piper might be the right choice if its specific strengths align with what you need most. Take advantage of free trials to test both before committing.
Frequently Asked Questions
Is Highspot or Chili Piper better?
Based on our analysis, Highspot scores higher with 85/100. Highspot ispaid while Chili Piper is paid. The best choice depends on your specific needs and budget. We recommend testing both with free trials if available.
Can I switch from Highspot to Chili Piper easily?
Migration difficulty varies. Check if both tools support data export/import in compatible formats. Some tools offer migration assistance or have integration partners who can help with the transition.
Do Highspot and Chili Piper offer free trials?
Most software in this category offers free trials or free tiers. Highspot is paid with potential trial.Chili Piper is paid with potential trial. Visit their websites for current trial offers.