Second Nature
secondnature.ai
AI sales coaching and roleplay platform.
Quick Information
- Category:
- Sales & Revenue
- Pricing:
- Contact Sales
- Platforms:
- Web
- Free Plan:
- No
- Last Verified:
- October 2026
What Is Second Nature?
Second Nature is an AI sales coaching and roleplay platform. Its earlier launch featured Jenny, a conversational AI coach that can roleplay as a potential customer so a salesperson can practise, though the search did not confirm whether Jenny is still the product name in 2026. Gartner describes a subscription pricing model with tiers that depend on features and user count and custom quotes for larger teams, and Capterra shows a free trial available.
Second Nature does not publish prices. One review site says quote-only with no public pricing page and lists unconfirmed third-party estimates of roughly $30 to $40 per seat per month and a $20,000 annual minimum. The most recent funding found is a $22 million Series B announced October 16, 2025, led by Sienna VC with Bright Pixel, StageOne Ventures, Cardumen, Signals VC and Zoom, preceded by a $12.5 million Series A led by Signals Venture Capital. Caplight lists $37.5 million total raised. No 2026 funding news turned up.
Second Nature suits sales and service teams that want scalable, scenario-based coaching. Compare Hyperbound, Quantified and Mindtickle. Browse the Sales & Revenue tools directory for more.
What Can You Use Second Nature For?
Sales roleplay
Practice with an AI customer.
Service training
Support team coaching.
Second Nature Features
- AI coach — Conversational roleplay.
- Free trial — Listed on Capterra.
- Series B — $22M led by Sienna VC in October 2025.
Who Is Second Nature For?
- Sales and service teams — Scalable coaching.
- Enablement leaders — Standardise practice.
Second Nature Pros & Limitations
What We Like
- Established AI coaching vendor
- Free trial listed
- Recent funding including Zoom
Limitations
- No public pricing
- Price estimates are unconfirmed
- Current product naming not confirmed
Second Nature Pricing
| Plan | Price | Main Features |
|---|---|---|
| Subscription | Quote only; unconfirmed estimates $30-$40/seat/month and ~$20,000 annual minimum | AI roleplay coaching |
Pricing was last verified October 2026. Check the official website for the latest pricing.
AI Listing Jungle Ranking
- Global Rank:
- #705
- Overall Score:
- 57.4/100
- Monthly Users:
- –
- Rank Change:
- ▼ 179
This ranking reflects AI Listing Jungle's own independent scoring methodology and is not an endorsement by Second Nature or its company. How Our Rankings Work
Frequently Asked Questions
What does Second Nature do?
AI roleplay and coaching for sales and service teams.
How much has it raised?
A $22M Series B in October 2025; Caplight lists $37.5M total.
How much does it cost?
Quote only; unconfirmed estimates exist.
Is there a free trial?
Capterra shows one.
Our Take
Second Nature is a mature AI coaching option.
Get a quote and test the roleplay quality with your own scripts.
Second Nature Alternatives
Second Nature Comparisons
Ready to try Second Nature?
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