From Chaos to Clarity: How We Set Up PTO for a 12-Person Agency in 5 Minutes

Brightside Creative is a 12-person digital marketing agency. Like most agencies, they started tracking PTO in a Google Sheet. Like most agencies, it eventually became a mess.

This is the story of how they went from spreadsheet chaos to organized PTO management in under 5 minutes, and what changed in the 3 months after.

The Before: Spreadsheet Chaos

What They Had

A Google Sheet with tabs for each year. Columns for employee names, PTO types, dates, and running balances. In theory, simple. In practice, a nightmare.

The Problems

Problem 1: Nobody could find the sheet

"Where's the PTO tracker?" was asked at least twice a week. It lived in someone's Google Drive, shared with everyone, but impossible to locate when you actually needed it.

Problem 2: Balance calculations were wrong

The formulas worked... until someone added a row in the wrong place. Or deleted a column. Or copy-pasted over a formula. By September, three employees had different balances than the sheet showed.

Problem 3: Approval happened in Slack

Requests came in via DM. Sometimes the founder saw them immediately. Sometimes they sat unread for days. There was no record of what was approved, denied, or pending.

Problem 4: No visibility into who was off

"Wait, Sarah's out this week?" happened at least once a month. The sheet existed, but nobody checked it before scheduling client calls or deadlines.

Problem 5: Year-end was chaos

Calculating carryover for 12 people with different remaining balances, some prorated for start dates, took the operations manager an entire afternoon. And she wasn't confident the numbers were right.

The Trigger

The breaking point: Two account managers approved themselves for the same week during a major client launch. Nobody caught it until the Monday of that week. Client calls were missed. The founder decided enough was enough.

The Setup: 5 Minutes, Really

Here's exactly what the operations manager did to set up Symple Team:

Minute 1: Create Account

• Went to sympleteam.com
• Clicked "Start Free"
• Entered email and created password
• Named the company "Brightside Creative"

Minute 2: Set Up PTO Types

Created three PTO types:

• Vacation: 15 days per year
• Sick Leave: 5 days per year
• Personal Days: 3 days per year

Each type with simple settings: annual allowance, no complex accrual rules.

Minutes 3-4: Add the Team

Two options: send email invites or add manually. She chose email invites.

• Uploaded a CSV with employee names and emails
• Each person got an invite link
• They'd set their own passwords on first login

Minute 5: Set Starting Balances

For mid-year migration:

• Entered each person's remaining balance from the spreadsheet
• Noted: "This was the only tedious part, but still just 12 entries"

Done

Total time: 4 minutes 47 seconds. She timed it.

No configuration wizards. No required fields for things they didn't need. No sales call to unlock basic features.

The First Week

Employee Adoption

All 12 employees had logged in within 48 hours. Most figured it out without instructions, the mobile app took about 30 seconds to understand.

First Requests

Seven PTO requests came in the first week. The founder approved them from his phone in about 2 minutes total.

Immediate Value

The team calendar showed everyone's upcoming time off in one place. For the first time, you could see at a glance who was out when.

Month 1: Building Habits

What Changed

Requests became formal

Instead of DMs and forgotten conversations, requests went through the system. Both the requester and the approver had a record.

Balances were trusted

Employees could check their own balances anytime. No more "hey, how many days do I have left?" messages.

The calendar became the source of truth

Before scheduling anything important, people checked the team calendar. The "wait, who's out?" moments dropped to almost zero.

Minor Friction

A few employees forgot to use the system and requested via Slack out of habit. The ops manager just replied "submit it in Symple Team" and within two weeks, everyone had adjusted.

Month 3: The Results

By the Numbers

Qualitative Changes

Founder: "I used to dread approving PTO because it meant digging through Slack history to figure out context. Now I approve requests from my phone while waiting for coffee. Takes 10 seconds."

Operations Manager: "The mental load is gone. I don't have to remember who requested what, whether I responded, or calculate balances manually. It just works."

Employees: "I actually know how many days I have. Before, I had to ask HR and wait for them to check the spreadsheet. Now I just open the app."

Unexpected Benefits

Better planning: When everyone can see the team calendar, people naturally spread out their time off. The December rush was much lighter than previous years.

Reduced guilt: Having a formal system made employees more comfortable requesting time off. Usage actually went up, which is good, because burned-out agency employees don't do great creative work.

New hire onboarding: The new designer who started in month 2 was added to Symple Team in 30 seconds. She understood how to request PTO immediately.

What They'd Do Differently

Start with software earlier

"We should have done this at 5 people, not 12. The spreadsheet was already causing problems by employee 8."

Migrate balances more carefully

"I trusted the spreadsheet balances when migrating, but two were wrong. Should have verified each one individually before entering."

Set clearer approval expectations

"We didn't establish how quickly managers should respond to requests. Adding a 48-hour guideline would help."

The Cost Analysis

Spreadsheet "Cost"

• Direct cost: $0
• Time cost: ~4 hours/month ops manager time = ~$120/month at $30/hour
• Error cost: At least one major incident per quarter
• Stress cost: Unquantifiable but real

Symple Team Cost

• 12 employees on Pro plan: $60/month ($5/user)
• Time cost: ~20 minutes/month
• Error cost: $0
• Stress cost: Basically none

Net Savings

Monthly: $60 saved in time, minus $60 software cost = Roughly breakeven on direct costs

Real value: Zero double-bookings, zero balance errors, zero year-end calculation headaches, and ops manager can focus on actual operations.

Would They Recommend It?

Direct quote from the founder:

"For $60 a month, I never have to think about PTO tracking. I never have to debug spreadsheet formulas or dig through Slack to see if I approved something. That's worth way more than $60."

The Takeaway for Other Small Teams

Brightside Creative isn't special. They're a normal small agency with normal PTO needs. What made the difference:

1. Recognizing the spreadsheet had limits - They didn't wait until disaster struck
2. Choosing simple over complex - They didn't need enterprise HR software
3. Getting the team on board - Email invites made adoption easy
4. Giving it a few weeks - Habits take time to form

If a 12-person agency can go from spreadsheet chaos to organized PTO in 5 minutes, so can you.

Try It Yourself

Ready to leave spreadsheet PTO behind? Symple Team is free for up to 5 users, and setup takes about as long as reading this case study.

Start your free trial - no credit card required.