Yesware
Sales engagement that lives in your inbox — tracking, templates and campaigns inside Gmail and Outlook
By Yesware (Vendasta) · HQ Saskatoon, Canada · 4.5/5 Value-Position score (estimate)
Positioning guardrails
Best for
- Sales teams of any size whose pipeline depends on 1:1 email outreach and follow-up
- SMBs and start-ups that want sales engagement with no IT involvement or long implementation
- Sales managers who need shared templates, campaign reporting and team-level visibility
- Teams on Salesforce that need bi-directional activity sync and an inbox sidebar (Enterprise plan)
- Individual sellers and founders who want a free or low-cost tool that works where they already sell
Ideal size: 5–200 seats people · SMB or scaling sales team with an email-led motion
Not for
- Enterprise revenue operations teams needing deeply configurable, admin-heavy sequencing and governance
- Buyers who want a full CRM or marketing automation suite rather than an inbox layer
- Teams whose core requirement is AI-native capability such as autonomous agents or predictive scoring
- Organizations that require FedRAMP, HIPAA or ISO 27001 attestations before purchase
- Non-email-centric motions such as high-volume dialer-led or field-sales-only teams
Value metrics scorecard
Time-to-Value
Same day (60-second install)
~1 days to first production value
Total Cost of Ownership
$420/yr
Starts at $180 · Per seat, per month, billed monthly or annually (annual saves up to 23%): Free $0; Pro $15; Premium $35; Enterprise $65 per user/month on annual billing.
Implementation Friction
1/5
Engineering + admin effort required
Value-Position score
out of 5 · model estimate
Full cost breakdown
Mandatory implementation fee
None
Seat tiers
Free plan caps at 5 users; Pro, Premium and Enterprise are billed per user with unlimited seats.
Add-on costs
- Prospector lead credits: Starter 600 credits/year at $37.50/month billed annually; Growth 3,000 credits/year at $125/month billed annually
Company & support
Who is behind Yesware, and how your team gets help once it is live.
Company
- Founded
- 2010 · 16 yrs in business
- Headquarters
- Saskatoon, Canada
How you get support
- PhonePaid plans
- EmailAll plans
- Live chatNot listed
- Support portal / ticketsNot listed
- Community forumNot listed
- Help centre / docsAll plans
- Dedicated account managerPlan not stated
- In person / on-siteNot listed
- Hours
- Not recorded
- Response time
- Not stated
Pricing feature matrix lists email support (including Free), phone support from Pro up, Help Center access via docs.yesware.com, and a dedicated customer success manager at higher tiers. No support hours or SLA are published.
“Not listed” means the vendor’s public pages don’t mention that channel, not that it is unavailable. Ask about it during evaluation.
Market position
Where Yesware sits against its closest alternatives. Pick any two of cost, speed, friction and buyer score, and up to 9 companies to compare.
Quadrant view
Typical annual cost × Time-to-value
The lines cross at the median of the solutions shown, so about half sit on each side of each line. A dashed ring marks an outlier pinned to the edge; hover for its value.
Companies on the chart 6 / 10
- Yesware
- RB2B
- Instantly
- Mutiny
- Demio
- Outplay
Add or change companies
Up to 10 companies including Yesware. Listed closest first.
Stack fit signal
Compatibility with standard B2B ecosystems.
No supported MCP path today, so it cannot be driven from an AI client.
AI & MCP readiness
What Yesware ships in AI, and what it asks of your ecosystem.
Compliance attestations
* IAPP AIGP certifies individuals, not products. It means named staff hold the credential — not that the platform does.
Bottom line
Yesware is an inbox-based sales engagement product from Vendasta that adds email and attachment tracking, templates, multi-touch campaigns, meeting scheduling and CRM sync inside Gmail and Outlook. It installs in about 60 seconds with no IT work, offers a Free Forever tier plus Pro ($15), Premium ($35) and Enterprise ($65, Salesforce features) plans per user/month billed annually, and cites 6,000+ sales teams and 1.4M+ installs. Strong fit for SMB and mid-market email-led selling; lighter on enterprise governance and documented AI features.
Frequently asked questions
What does Yesware cost per user?
Yesware publishes a Free Forever plan and paid per-user plans: Pro from $15/user/month, Premium from $35, and Enterprise from $65 — all on annual billing, with monthly rates higher (Pro $19, Premium $45, Enterprise $85). Salesforce-specific features require Enterprise. Prospector lead credits are an optional add-on starting at $37.50/month billed annually.
How long does implementation take?
Yesware installs as a Gmail Chrome extension or Outlook add-in in about 60 seconds and requires no IT setup. The vendor reports teams with tracking live within an hour and fully trained within days, and offers free assisted setup, training and white-glove onboarding.
Do we need Salesforce or another CRM to use Yesware?
No. Yesware runs standalone inside Gmail or Outlook on the Free, Pro and Premium plans. Salesforce bi-directional sync, inbox sidebar, calendar sync and SSO are Enterprise-only, and Vendasta CRM and other CRMs can receive automatically logged activity.
What security and compliance credentials does Yesware hold?
Yesware's security page states it maintains a current SOC 2 Type II report (available under NDA), uses OAuth and OpenID for authentication, TLS for data in transit, and hosts on AWS, Heroku, MongoDB Atlas and Redis Labs. No ISO 27001, HIPAA, FedRAMP or ISO 42001 attestation is claimed on that page.
Does Yesware offer AI features?
No specific AI features are documented. Yesware's product, pricing, documentation and security pages do not describe copilots, agentic workflows, AI search or predictive scoring. Parent company Vendasta markets 'AI-powered engagement', but that is not evidenced as a Yesware capability.
Which plan do most sales teams choose?
Yesware says most sales teams choose Premium ($35/user/month annually), which adds unlimited campaigns and teams, shared templates and campaigns, team reporting and centralized billing. Solo sellers typically start on Pro.