Reply.io vs Yesware
Which one do AI engines recommend, and how do they differ on price, fit and features?
The short answer
Reply.io is the stronger AI pick in Sales Engagement: it has a visibility score of 14.4 versus 1.8 for Yesware, and ranks ahead in 100% of the answers that name both.
Choose Reply.io if…
- You want the brand AI engines rank higher (14.4 vs 1.8)
- AI answers describe it more positively (42% vs 33% positive)
- You need SOC 2 or GDPR coverage
- Flat tiers pricing suits your budget better than per seat
Choose Yesware if…
- You want a free plan to start
- You need SOC 2 Type II coverage
- Per seat pricing suits your budget better than flat tiers
- Basic email tracking, templates, and campaigns inside Gmail or Outlook
AI visibility side by side
Latest weekly run · Nov 3
| Metric | Reply.io | Yesware |
|---|---|---|
| Visibility score | 14.4% | 1.8% |
| Change vs last week | down−3.3% | down−0.6% |
| Rank in Sales Engagement | #6 | #33 |
| Share of voice | 3.5% | 0.5% |
| Mentions this run | 23 | 4 |
| Positive in AI answers | 42% | 33% |
The stronger value in each row is marked with a ✓.
Visibility score trend
Weekly runs over the last 60 days
Reply.io −3.299999999999999pp · Yesware −0.5999999999999999pp over 1 weekly runs.
Engine by engine
Reply.io leads on 3 of 3 engines
Head to head in AI answers
1 engine answers name both brands
| Prompt | Engine | Reply.io | Yesware |
|---|---|---|---|
| Which sales engagement platform offers a free trial? | Perplexity | #4 | #11 |
Features, pricing & fit
| Dimension | Reply.io | Yesware |
|---|---|---|
| Pricing model | Flat tiers | Per seat |
| Entry price | $49 / mo | Free; paid from $19 per seat / mo |
| Free plan | No · 14-day trial | Yes |
| Deployment | — | Gmail Chrome extension and Outlook add-in, cloud-hosted on Amazon Web Services and Heroku |
| Compliance | SOC 2, GDPR | SOC 2 Type II |
| Support | Live chat, Email, CSM onboarding | Email support, Phone support on Pro and above, Help Center, Weekly webinar trainings |
| Founded | 2014 | 2010 |
| Headquarters | San Jose, California, US | Saskatoon, SK, Canada |
| Employees | 51–200 | 51–200 |
| Funding | Series A | Funding round · $48M raised |
| Best for | Founders, sales teams, and agencies who need results fast without juggling 5+ tools. | Individual sellers, sales teams and SMBs that sell through email and want simple tools without enterprise overhead |
Plans side by side
Reply.io
Yesware
Pros and cons
Themes from the AI answers that mention each brand
Reply.io
- Multichannel outreach and AI-assisted engagement across email, calls, LinkedIn and more
- 14-day free trial to test core sequencing and automation
- Transparent self-serve pricing with annual discounts
- Affordable, lower-cost option
- Strong choice for smaller and mid-market sales teams
Yesware
- Basic email tracking, templates, and campaigns inside Gmail or Outlook
- Free-forever tier
- Offers a free tier
- Suited to individual reps or very small teams
- Likely cheaper for solo operators
Data collected ·ChatGPT, Perplexity, Google AI Mode·coverage 98.8%·next run
Cite as: SlateIndex, “Reply.io vs Yesware”, https://slateindex.ai/compare/reply-io-vs-yesware, data of Nov 3, 2026. Licence: CC BY 4.0.