Startup Automation Playbook

Core Rule

Automate the repetitive. Protect your time for the irreplaceable. Every hour you spend on a task a computer can do is an hour stolen from customers, product, and strategy.

When to Automate

Do I do this more than 3 times per week?  → Automate it.
Does it follow the same steps every time?  → Automate it.
Does it require zero judgment?             → Automate it.
Does it require nuance or relationship?    → Keep it manual. Add a template.

Category 1: Sales Automation

Auto-Follow-Up Sequences

Manual process: After a demo or sales call, you manually write and send follow-up emails at day 1, day 3, and day 7. You forget half the time. Leads go cold.

Automated version: A trigger fires when a deal moves to "Demo Completed" in your CRM. A 3-email sequence sends automatically with personalized merge fields.

Sequence template:

Email 1 (Day 0, 1 hour after demo):
  Subject: Great meeting, [FIRST_NAME] — next steps
  Body: Recap key points. Attach any promised materials. Clear CTA.

Email 2 (Day 3):
  Subject: Quick follow-up on [COMPANY] + [YOUR PRODUCT]
  Body: Address common objection. Share relevant case study. Ask for reply.

Email 3 (Day 7):
  Subject: Still interested, [FIRST_NAME]?
  Body: Short. Direct. "Should I close this out or is there still interest?"

Lead Scoring Rules

Manual process: You scan your CRM and guess which leads are hot. You waste time on unqualified prospects.

Automated version: Assign points based on actions. Sort leads by score. Work top-down.

Scoring rules:

+10  Visited pricing page
+10  Opened 3+ emails
+15  Booked a demo
+20  Replied to outreach
+5   Downloaded resource
-10  No activity in 14 days
-20  Bounced email / invalid domain

Hot lead:    40+ points → Call today
Warm lead:   20-39 points → Email sequence
Cold lead:   Under 20 → Nurture or archive

CRM Auto-Updates

Manual process: After every call, you manually update the deal stage, add notes, and log the activity. You fall behind. Your CRM becomes unreliable.

Automated version: Connect your calendar and email to your CRM. Calls auto-log. Email threads sync. Deal stages update based on triggers.

Trigger rules:

Meeting completed        → Move to "Demo Done"
Proposal sent (email)    → Move to "Proposal Sent"
Contract opened          → Move to "Negotiation"
Invoice paid             → Move to "Closed Won"
No activity for 30 days  → Move to "Stale" + alert

Category 2: Operations Automation

Invoice Generation on Deal Close

Manual process: A deal closes. You open QuickBooks or Wave. You manually create an invoice, fill in the client details, line items, and payment terms. You send it. You forget to follow up.

Automated version: When a deal moves to "Closed Won" in your CRM, an invoice auto-generates with the deal amount and client info, sends to the customer, and schedules reminders for overdue payment.

Zapier recipe:

Trigger: HubSpot deal stage → "Closed Won"
Action 1: Create invoice in QuickBooks (pull company name, amount, email)
Action 2: Send invoice via email
Action 3: Schedule Slack reminder if unpaid after 7 days

Onboarding Email Sequences for New Customers

Manual process: New customer signs up. You personally send a welcome email, setup instructions, a check-in at day 3, and a feedback request at day 14. You lose track with more than 5 customers.

Automated version: A signup or payment trigger kicks off a timed email sequence that guides the customer through setup and checks in at key milestones.

Onboarding sequence:

Email 1 (Immediate):
  Subject: Welcome to [PRODUCT] — here's how to get started
  Body: Login link, 3-step quick start, link to docs, support contact.

Email 2 (Day 2):
  Subject: Did you complete setup?
  Body: Link to most-used feature. Quick video walkthrough.

Email 3 (Day 7):
  Subject: How's it going with [PRODUCT]?
  Body: Check-in. Link to book a call if stuck. Share a tip.

Email 4 (Day 14):
  Subject: Quick feedback — 2 questions
  Body: "What's working? What's confusing?" Simple reply-based survey.

Recurring Report Generation

Manual process: Every Monday morning, you open 4 tabs. You screenshot dashboards. You paste numbers into a Google Doc. You send it to your cofounder. This takes 45 minutes and you dread it.

Automated version: A scheduled workflow pulls data from Stripe, Google Analytics, and your CRM, formats it into a summary, and posts it to Slack or emails it every Monday at 8 AM.

Report template:

WEEKLY METRICS — Week of [DATE]

Revenue:     $[X] MRR  |  Change: [+/-]%
New customers: [X]     |  Churned: [X]
Pipeline:    $[X]      |  Demos booked: [X]
Website:     [X] visits |  Signups: [X]
Burn rate:   $[X]/mo   |  Runway: [X] months

Top win: [Auto-pulled or manual note]
Top risk: [Auto-pulled or manual note]

Category 3: Marketing Automation

Social Media Scheduling

Manual process: You write a post. You open LinkedIn. You post it. Then you remember you should also post on Twitter. You open Twitter. You rewrite it. Tomorrow you forget entirely.

Automated version: Batch-write 5-10 posts in one sitting. Schedule them across platforms for the week. Done in 1 hour instead of scattered across 7 days.

Batching process:

1. Block 1 hour on Friday afternoon.
2. Write 5 posts (one per weekday).
3. Schedule: Mon, Tue, Wed, Thu, Fri at 9 AM.
4. Repurpose: Each post gets a LinkedIn version and a Twitter version.
5. Done. Don't touch social media again until next Friday.

Newsletter Automation

Manual process: You decide to send a newsletter. You stare at a blank screen for 40 minutes. You finally send something mediocre on Wednesday instead of Tuesday. Your audience forgets you exist.

Automated version: Use a template. Fill in 3 sections. Schedule it to go out the same day and time every week.

Newsletter template:

Subject: [PRODUCT] Weekly — [ONE INTERESTING HOOK]

1. What we shipped this week: [1-2 sentences + link]
2. One useful insight: [Tip, stat, or lesson — 3-4 sentences]
3. One ask: [CTA — reply, share, sign up, book demo]

That's it. See you next [DAY].
— [YOUR NAME]

Review / Testimonial Collection

Manual process: You remember that you need testimonials. You manually email 5 customers. Two reply. You forget to follow up with the other three. You never actually put the testimonials on your website.

Automated version: After a positive interaction (NPS score > 8, support ticket resolved, 30 days post-purchase), auto-send a request for a review with a direct link to leave it.

Request template:

Subject: Quick favor — 30 seconds?

Hi [FIRST_NAME],

Glad [PRODUCT] is working well for you. Would you mind leaving a quick
review? It takes about 30 seconds and helps other [TARGET AUDIENCE]
find us.

[LINK TO REVIEW FORM]

Thanks — it means a lot.
— [YOUR NAME]

Admin automation, quick wins, automation stack by stage, the monthly audit template, and common traps continue in automation-advanced.md.

This playbook covers workflows, not strategy. Automation handles the repeatable so you can focus on the unrepeatable: customer relationships, product decisions, and creative problem-solving. Start with one Quick Win this week.