Help the user with Yesware platform questions — from email tracking and campaign setup through templates, Prospector, Meeting Scheduler, Salesforce integration, and reporting.
Step 1 — Gather context
If references/learnings.md exists, read it first for accumulated knowledge.
Ask the user:
What area of Yesware do you need help with?
A) Email Tracking — open, click, and attachment tracking notifications
B) Campaigns — creating and managing multi-channel sequences (for strategy, hand off: /sales-cadence {your question})
C) Templates — creating, sharing, and personalizing email templates
D) Prospector — finding B2B contacts from the built-in database
J) Admin — billing, plan features, account settings
K) Something else — describe it
What's your role?
A) Sales rep / AE / BDR
B) Sales manager / team lead
C) RevOps / Sales Ops
D) Admin / IT
E) Founder / solo seller
F) Other
What are you trying to accomplish? (describe your specific goal or question)
If the user's request already provides most of this context, skip directly to the relevant step. Lead with your best-effort answer using reasonable assumptions (stated explicitly), then ask only the most critical 1-2 clarifying questions at the end — don't gate your response behind gathering complete context.
Note: If the user needs a specialized skill, route them there with a brief explanation of why that skill is a better fit.
Step 2 — Route or answer directly
If the request maps to a specialized skill, route:
List building / prospecting strategy → /sales-prospect-list
Otherwise, answer directly from platform knowledge using the reference below.
Step 3 — Yesware platform reference
Provide module-by-module guidance based on the user's area:
Email Tracking
What it is: Real-time notifications when recipients open emails, click links, or view attachments — powered by an invisible tracking pixel
Key features: Per-email open/click tracking, real-time desktop notifications, engagement history per contact, attachment tracking (know when and how long they viewed)
How it works: Yesware inserts an invisible pixel into outgoing emails. When the recipient's email client loads images, the pixel fires and Yesware records the open. Link clicks are tracked via redirect URLs.
Limitations: Tracking pixels are blocked by privacy tools (Apple Mail Privacy Protection, Hey, corporate proxies). Open tracking is increasingly unreliable — use click tracking and reply tracking as more reliable engagement signals.
Best practices: Don't over-rely on open data. Use tracking to prioritize follow-ups — if a prospect clicks a link or opens 3+ times, follow up quickly.
Campaigns
What it is: A campaign in Yesware is a multi-channel automated sequence — email steps plus phone call reminders, LinkedIn InMail tasks, and custom tasks (called "touches")
Key concepts: Campaign = multi-channel sequence, Touch = a step in the campaign (email, phone, LinkedIn, or custom task), Recipient = a contact enrolled in a campaign
Campaign recipient limits by plan: Free = 10 recipients/month, Pro = 20 recipients/month, Premium = unlimited, Enterprise = unlimited
Best practices: Start with 3-5 email touches and 1-2 phone touches. Space touches 2-3 business days apart. Personalize the first and last touches. Use merge fields for dynamic content.
Templates
What it is: Reusable email templates with dynamic personalization fields — available as personal or shared (team) templates
Template types: Personal templates (visible only to you), Shared templates (visible to the team, requires Premium+)
Personalization: Merge fields for dynamic content — {{first_name}}, {{company}}, {{title}}, and custom fields
Best practices: Create templates for common scenarios (intro, follow-up, meeting request, breakup). Track template performance in reporting to identify top performers. Keep templates under 125 words for best engagement.
Prospector
What it is: Built-in B2B contact database with 100M+ contacts for finding new leads directly from within Yesware
Key features: Search by company, title, industry, location, and other filters. Export contacts directly into Yesware campaigns.
How to use: Access Prospector from the Yesware sidebar. Search by company name or domain, filter by title/seniority/department, and add matching contacts to a campaign or your contact list.
Data quality: As with any B2B database, verify email addresses before high-volume outreach. Contact data can be stale — cross-reference with LinkedIn.
Meeting Scheduler
What it is: Booking link tool that lets prospects schedule meetings directly — integrates with your calendar and Zoom
Best practices: Include your booking link in email signatures and campaign emails. Offer multiple durations (15-min and 30-min). Set buffer times to avoid back-to-back calls.
Contacts
What it is: Integrated contact management within Yesware — view engagement history, enrichment data, and campaign activity per contact
Key features: Contact profiles with full engagement timeline (opens, clicks, replies), enrichment data (title, company, phone), notes and tags
Contact enrichment: Yesware can enrich contacts with additional data points (title, company, social profiles). For deeper enrichment, use /sales-enrich.
Reporting & Analytics
What it is: Personal and team-level engagement reports — track email performance, campaign results, and recipient engagement
Report types: Personal Activity Report (your sends, opens, replies), Team Activity Report (compare team members, Premium+), Recipient Engagement Report (per-contact engagement), Campaign Report (campaign-level metrics)
Team reports: Require Premium or Enterprise plan. Compare performance across reps, identify top templates, and track team-wide engagement trends.
Best practices: Review reports weekly. Focus on reply rate and meetings booked — these are the metrics that correlate with pipeline. Use template reports to identify and scale what works.
Salesforce Integration
What it is: Bi-directional activity sync between Yesware and Salesforce — Enterprise plan only ($65/mo)
Key features: Auto-log emails to Salesforce records (contacts, leads, opportunities), sync calendar events, Salesforce inbox sidebar (view CRM data from Gmail/Outlook), activity reporting in Salesforce
Salesforce inbox sidebar: View Salesforce contact/lead/opportunity data directly in your inbox without switching tabs. Update fields, log notes, and create tasks from the sidebar.
Sync behavior: Bi-directional — emails sent from Yesware log to Salesforce, and Salesforce data surfaces in Yesware's inbox sidebar
Setup: Requires Enterprise plan. Connect via Settings > Integrations > Salesforce. Admin must authorize the Salesforce OAuth connection. Map Yesware fields to Salesforce fields.
Data model, pricing, integrations & the no-API constraint
Yesware has NO public API — no REST endpoints, no developer docs, no programmatic access. Everything runs through the Gmail Chrome extension / Outlook add-in, the native Salesforce connector (Enterprise only), and Zapier (limited triggers/actions); if the user needs API-level automation, point them to platforms with public APIs (Mailshake, Apollo, Salesloft) or Zapier as a workaround. See references/platform-guide.md for the full data model (Campaign → Touch → Recipient, Template, Contact, Meeting Type, Report), pricing tiers (Free/Pro $15/Premium $35/Enterprise $65, annual — verify at yesware.com), and integration list (Gmail, Outlook, Salesforce, LinkedIn, Zoom, Zapier, DocSend, Clari).
Step 4 — Actionable guidance
Based on the user's specific question:
Step-by-step instructions — numbered steps to accomplish their goal in Yesware
Configuration recommendations — specific settings to change, with navigation paths (typically via the Yesware sidebar in Gmail/Outlook)
Common pitfalls — what can go wrong and how to avoid it
Verification — how to confirm the change worked
Plan check — flag any features that require a specific plan tier before recommending them
Gotchas
Best-effort from research — review these, especially items about plan-gated features and integration gotchas that may be outdated.
No public API — don't suggest API solutions. Yesware has no REST API, no developer docs, and no programmatic access. Don't recommend building integrations or scripts against Yesware. The only automation path is Zapier (limited) or the native Salesforce connector (Enterprise only).
Salesforce integration is Enterprise-only ($65/mo). Don't recommend Salesforce sync features to users on Free, Pro, or Premium plans. Always ask about the user's plan before suggesting Salesforce-related workflows.
Campaign recipient limits are strict and plan-gated. Free = 10 recipients/month, Pro = 20/month. Users on lower plans hit this wall fast. Unlimited recipients require Premium ($35/mo) or Enterprise ($65/mo). Always surface these limits when discussing campaigns.
Yesware is inbox-native — there is no standalone web app for campaigns. All campaign creation and management happens inside the Gmail or Outlook extension. There is no separate yesware.com dashboard for building campaigns. Users expecting a standalone UI (like Mailshake or Apollo) will be confused.
Email tracking pixels are increasingly unreliable. Apple Mail Privacy Protection (iOS 15+), Hey.com, and corporate email proxies pre-load or block tracking pixels. Open rates from these recipients are either inflated (Apple pre-loads all images) or zero (blocked). Advise users to treat open tracking as directional, not definitive, and rely more on click and reply metrics.
Self-improving: If you discover something not covered here, append it to references/learnings.md with today's date.
Step 5 — Related skills
/sales-meeting-scheduler — Meeting scheduling strategy and best practices (platform-agnostic)
/sales-email-tracking — Email tracking strategy and best practices (platform-agnostic)
/sales-cadence — Design outbound cadence strategy (platform-agnostic, works with Yesware campaigns)
/sales-prospect-list — Build prospect lists to import into Yesware
/sales-enrich — Enrich contacts with emails/phones before outreach
/sales-integration — Connect Yesware to other tools via Zapier or native integrations
/sales-do — Not sure which skill to use? The router matches any sales objective to the right skill.
Examples
Example 1: Multi-channel campaign setup
User says: "How do I set up a multi-channel campaign in Yesware?"
Skill does:
Explains Yesware campaigns as multi-channel sequences with email, phone, LinkedIn, and custom touches
Walks through creating a campaign from the Gmail/Outlook sidebar — name, touches, timing
Explains how to add recipients individually or via bulk import
Notes campaign recipient limits by plan (10 free, 20 Pro, unlimited Premium+)
Result: User has a campaign created with multiple touch types and understands recipient limits
Example 2: Salesforce integration
User says: "How do I connect Yesware to Salesforce?"
Skill does:
States upfront that Salesforce integration requires Enterprise plan ($65/mo)
Walks through the connection flow: Settings > Integrations > Salesforce > OAuth
Explains bi-directional sync — emails, calendar events, and tasks sync to Salesforce records
Highlights the Salesforce inbox sidebar for viewing CRM data from email
Result: User understands plan requirements and can set up the Salesforce connection
Example 3: Prospector for finding leads
User says: "I want to use Yesware's Prospector to find leads — how does it work?"
Skill does:
Explains the 100M+ B2B contact database accessible from the Yesware sidebar
Walks through search filters — company, title, industry, location, seniority
Shows how to export found contacts into a campaign or contact list
Points to /sales-prospect-list for broader list-building strategy beyond Yesware
Result: User knows how to search, filter, and export contacts from Prospector
Troubleshooting
Email tracking not showing opens
Symptom: Emails show as sent but no open notifications appear
Cause: Recipient's email client blocks tracking pixels (Apple Mail Privacy Protection, corporate proxies), or tracking is not enabled for the email
Solution: Verify tracking is enabled in the Yesware sidebar before sending. Note that Apple Mail (iOS 15+) pre-loads images, which may inflate or block accurate tracking. For critical prospects, rely on click tracking (include a link) and reply tracking instead of open tracking. See /sales-email-tracking for a full tracking strategy.
Campaign recipients not receiving emails
Symptom: Recipients added to a campaign but emails are not being sent
Cause: Campaign recipient limit reached for plan tier, campaign is paused/draft, or sender account disconnected
Solution: Check your plan's recipient limit (Free = 10/mo, Pro = 20/mo). Verify the campaign status is "active." Check Settings > Senders to confirm your email account is connected and authorized. If the limit is the issue, upgrade to Premium ($35/mo) for unlimited recipients.
Salesforce sync not logging activities
Symptom: Emails sent from Yesware don't appear in Salesforce
Cause: Not on Enterprise plan, Salesforce connection expired, or sync mapping misconfigured
Solution: Confirm you are on the Enterprise plan ($65/mo) — Salesforce sync is not available on lower plans. Re-authorize the Salesforce connection in Settings > Integrations. Check field mapping to ensure Yesware activities are mapped to the correct Salesforce objects (Contact, Lead, or Opportunity).
