Skylight Calendar — Customer Service Playbook (Practical, Professional)

Overview and purpose

Skylight Calendar customer service is responsible for delivering fast, accurate resolution for scheduling, sync, billing, and device support across consumer and small-business segments. The service model below assumes a SaaS product launched in 2018 with rapid growth (50% year-over-year for three consecutive years is typical in this category) and a mixed user base of individual accounts (70%) and team/paid accounts (30%). The objective: maintain a Net Promoter Score (NPS) ≥ 50 and first-contact resolution (FCR) ≥ 75% while scaling support headcount in line with ARR growth.

This guide synthesizes operational metrics, channel design, escalation, self-service, refund policy, and templates so a manager or team lead can implement or audit a Skylight Calendar customer service organization. Numbers and benchmarks are explicit and actionable; replace example contact points and SLAs with your live values when you operationalize.

Support channels, hours, and staffing

Offer omni-channel support: email, in-app chat, phone for paid tiers, and an always-on web knowledge base. Typical channel split for a mixed consumer/business calendar product is: email 45%, chat 30%, phone 15%, social 5%, knowledge base/self-service 5%. Peak hours will align with customer base—if 60% of customers are in North America, schedule primary coverage 08:00–20:00 ET and extend to 24/7 for paid enterprise contracts.

Staffing example: with 50k monthly active users and a 2% monthly ticket rate (1,000 tickets/month), staffed agents should number 8–12 full-time equivalents (FTEs) to maintain <12-hour average handle time and <1-hour median initial response on paid channels. For each 8 agents, assign 1 dedicated Tier 2 engineer for escalations and 0.25 QA/knowledge writers to keep content current.

Service level agreements (SLAs) and KPIs

• Priority SLAs (examples): P0 (outage: calendar sync down) — 15-minute response, 4-hour workaround, 24-hour full resolution; P1 (major feature broken) — 1-hour response, 24–72 hour fix; P2 (billing or account access) — 4-hour response, 72-hour resolution; P3 (how-to/support) — 12–48 hour response.
• Operational KPIs: First Contact Resolution ≥ 75%, Average Response Time (paid channels) ≤ 60 minutes, Average Resolution Time ≤ 48 hours, CSAT ≥ 4.3/5, NPS ≥ 50. Track ticket volume, backlog, agent utilization (target 70% occupancy), and repeat contact rate (target <12%).

Set automated routing rules in your ticketing system (Zendesk, Freshdesk, Intercom) to enforce SLAs and send alerts when breach probability exceeds 10%. Run monthly SLA reviews with engineering and product to convert common P1/P2 issues into bug fixes or UX changes — the single best lever to reduce ticket volume is product remediation.

Ticketing, triage, and escalation matrix

• Triage workflow: 1) Auto-classify incoming ticket (keywords: sync, 2FA, billing, duplicate events); 2) Assign priority (P0–P3); 3) Route to specialist queues (Onboarding, Integrations, Billing, Device); 4) Apply SLA timer and notify stakeholders for P0/P1.
• Escalation levels: Level 1 (Support Agent) — diagnostic steps and known fixes; Level 2 (Support Engineer) — logs, server-side checks, partial rollbacks; Level 3 (Product/Dev) — code fixes, schema migrations, production patches. Escalation SLAs: L1→L2 within 2 hours for P0/P1, L2→L3 within 8 hours for unresolved P0.

Maintain an on-call rota for Level 2 and Level 3 engineers with 24/7 coverage for P0 incidents. Record each escalation in a post-incident report within 48 hours: timeline, root cause, customer impact (number of users), remediation steps, and follow-up ticket references.

Knowledge base, self-service, and automation

Invest 60–80 articles covering setup, integrations (Google Calendar, Outlook, Apple Calendar), troubleshooting sync errors, two-factor authentication, and billing changes. Each article should include reproducible steps, screenshots, and recovery commands where relevant. Tag content by user persona (consumer, admin, integrator) and platform (iOS, Android, web) to reduce search friction.

Automate routine workflows: password resets via verified email, subscription upgrades/downgrades via in-app flows, and a webhook diagnostics exporter for device logs. Implement smart suggestions in chat using the knowledge base: a bot should resolve 20–30% of inbound chats automatically, escalating when confidence is below 80%.

Onboarding, training, and churn prevention

Create onboarding sequences for paid plan users: 7 emails over 30 days, one 15–30 minute live setup call for teams, and templated calendar migration tools. Measure activation rate (users hitting core event-create action) and aim for 60% activation within 7 days for paid cohorts. Track 30-day churn and intervene when a paid user has not created events or linked calendars within 10 days.

Use health scores combining login frequency, event creation rate, and error counts to trigger outreach: automated tips for low-engagement users, and personalized support for accounts trending toward churn. For accounts worth ≥$500 ARR, mandate a quarterly account review call with a CSM.

Refunds, billing, and compliance

Transparent billing policy: example pricing tiers $4.99/month (Basic), $9.99/month (Pro), $29/month (Team up to 10 users). For paid plans, offer a 14-day money-back guarantee and a documented refund SLA of 3–5 business days after approval. Maintain PCI-DSS compliance for payment processing via a certified gateway (Stripe, Braintree) and publish a clear privacy policy and terms of service on your site.

Keep a 90-day audit trail for all billing changes and chargebacks; this supports fraud investigations and appeals. Provide customers with a single view of invoices and payment history in-app and via exportable CSV for accounting needs.

Security, privacy, and data handling

Handle calendar data as sensitive personal information. Implement role-based access controls (RBAC), audit logs for admin actions, and encryption at rest and in transit (TLS 1.2+ and AES-256). For enterprise customers, offer SOC 2 Type II reports annually and respond to data subject access requests within 30 days as required by GDPR/CCPA.

When troubleshooting, collect the minimum required data (timestamps, calendar IDs, error codes) and delete diagnostic logs after 90 days unless retained for incident investigation. Communicate clearly to users what logs you collect and obtain consent when exporting or sharing data with third parties.

Operational contacts and templates (examples)

Example support contacts to put in your product footer: Support email: [email protected]; Phone (paid plans): +1-800-555-0100; Site: https://www.skylightcalendar.example/support. Use templated responses for common issues (sync failures, billing disputes) and keep a small library of 6–8 templates that agents personalize — templates reduce average handle time by 20–30% while maintaining tone and accuracy.