Handyman Scheduling Software: One Calendar From Booking Request to Dispatch
Handyman scheduling is five or six short visits a day, a few repeat customers on a cycle, and sometimes a helper who needs to know where to be. Pocket Boss puts those on one calendar: a day, week and month view, recurring visit series, booking requests you approve, a live dispatch board, reminders and On My Way messages, and a timer on each visit.
The calendar, recurring visits and the timer are on every plan, from $19.99/month (Solo, one user). The dispatch board and online booking start on Essentials. This is the scheduling piece of the full handyman business software; the CRM holds the customers and invoicing bills the visits.
The Month view, as it looks today
Day, Week and Month toggle, the Everyone crew filter, Hide cancelled, and the Sync to Google Calendar button. Each visit is tinted by its category.
Example: a handyman week, Monday to Friday
An illustrative week for an owner on Essentials with one part-time helper. It is not a customer story; it is what each feature does on the day you need it.
Monday
On the calendar: Three visits you booked on Friday: 8:30 lock change (Repair), 10:30 TV mount (Installation), 1:30 gutter clean (Maintenance). Each color on the calendar is the visit category.
What the app does: Reminders went out on their own at 24 hours and 1 hour before, by email on every plan and by text when your plan includes text segments. At 8:05 you tap On My Way on the first visit; the customer gets the message once and the visit shows On my way sent 8:05. You start the timer when you arrive and stop it when you leave.
Tuesday
On the calendar: A rental turnover punch list booked as an Anytime visit: the owner sees the date only, and one reminder goes out at 8 AM that morning.
What the app does: At 9 PM Monday a customer used your booking page to request Wednesday 9:00 for a drywall patch plus a door adjustment (two services in one cart). It did not land on the calendar. It is waiting under Pending Booking Requests, where you approve it Tuesday morning and it becomes a Scheduled visit.
Wednesday
On the calendar: The approved drywall visit at 9:00. At 1:00, a quarterly gutter visit for a customer on a recurring series. You did not book it; the series generates visits about five weeks ahead.
What the app does: The customer asks you to come back in two weeks for the fascia. You tap Schedule a visit from their record so the new visit sits under the same job history as the gutters.
Thursday
On the calendar: Your part-time helper's first day. You open the Dispatch Board, drag two visits from Waiting for a tech onto her row, and leave Notify tech on assign checked so she gets a text and an email with the job, time and address.
What the app does: You take a two-day deck repair as one job with two visits. The board shows her On the clock and you On the way, and refreshes every 30 seconds while you are both out.
Friday
On the calendar: Deck visit two. Rain.
What the app does: You open the visit, choose Delay/Reschedule and move it to next Tuesday, then call the customer. Monday's three completed visits still show Create Invoice in the Appointments tab; you bill them from there, and the hours you timed appear under Invoiced Labor.
Deciding whether Friday's rain day could have taken one more visit is a capacity question, not a software one. The can one more job fit today worksheet is the honest way to answer it, and the cancellations article covers what to record when a visit falls through.
Phone calendar or scheduling software?
Each row names the plan the feature starts on, so you are not paying for dispatch before you have a crew.
| Your situation | What breaks | Use |
|---|---|---|
| You alone, two to four visits a day, no repeat plans | Nothing. A phone calendar is fine. | Keep the phone calendar. Come back when one of the rows below starts happening. |
| Customers want to book at night or ask "what times do you have?" | Phone tag, and the slot you quoted is gone by the time they answer. | The booking page: they pick a 15-minute slot inside your hours, you approve it from Bookings. Essentials and up. |
| Quarterly gutters, monthly rental checks, spring and fall tune-ups | You remember in May. | A recurring visit series (weekly to yearly) or a service plan. Every plan, Solo included. |
| A helper, even part time | They do not know where to be; you text screenshots. | The Dispatch Board with Notify tech on assign, and their own My Jobs view. Essentials and up. |
| Multi-day jobs with hours to bill | Time is on a notepad in the truck. | A job with several visits and the timer on each one. Every plan. |
| Six or more stops a day across town | The order you drive is the order you booked. | Smart Routing orders up to 25 stops. Pro and up. |
The calendar itself
What the Scheduling page does and does not do, so the screenshot is not doing the talking.
Day, Week, Month
Month is the grid in the screenshot. Week is seven columns on a desktop and a stacked list on a phone. Day is an hourly agenda with an All day row for Anytime visits and a line for the current time. The view you pick is remembered.
Color is the visit category
Maintenance, Repair, Consultation, Installation, Service, Remodeling and Projects each get a tint. Completed and cancelled visits turn grey, with a dashed edge for cancelled, and a Hide cancelled checkbox clears them.
Whose work
A filter for Everyone, No crew yet, or one crew member. Crew initials sit on each chip in the week and day views.
Click a day to book
Clicking an empty day in Month, or an empty half-hour in Day, starts a new visit at that time. Rescheduling is a Delay/Reschedule dialog on the visit, not drag-and-drop; drag-and-drop lives on the dispatch board.
Appointments and Invoiced Labor tabs
Appointments is the searchable list with a status filter (Scheduled, Confirmed, Completed, Cancelled, No Show). Invoiced Labor lists the timed hours already pulled onto an invoice and lets you un-invoice them.
Visit statuses are Pending, Scheduled, Confirmed, Completed, Cancelled and No-Show. Working, paused, on the way and late are not statuses you set; the dispatch board and the Jobs Today view work them out from the timer, the On My Way stamp and the clock.
Around the calendar: booking, recurring work, dispatch, reminders, timer
Each one with the plan it starts on.
Online booking requests
Your public page at /b/your-name lets a customer put one or more services in a cart, see 15-minute slots inside your business hours (slots that collide with an existing visit are not offered), and submit. It arrives as a pending request; you approve, decline or reschedule it on the Bookings page, and only then does it reach the calendar and the dispatch board. Deposits and card-on-file need Stripe connected; bookings without payment work without it.
Essentials and up.
Recurring visits and service plans
A series runs weekly, bi-weekly, semi-monthly, monthly, quarterly or yearly, on the weekdays you choose, open-ended or to an end date, and the app generates the visits about five weeks ahead every hour. Service plan visits are different on purpose: by default you pick the date and time for each member, and the Service Plans page keeps a count of plan visits still needing a slot. Flip Auto-schedule visits on and they land on the first of their month at your default time.
Every plan, Solo included.
Dispatch Board
Day view is one row per crew member on an hour timeline with a Waiting for a tech lane; Week view is crew by seven days. Drag a visit onto a person to assign it, onto someone else to move it, or back to the lane to unassign; in Week view you can drag it to another day. Tiles count On the clock, On the way, Not started, Waiting for a tech and Done today, and the board refreshes every 30 seconds. If you assign someone who is already booked at that time, the board says so and marks the row Double-booked; it warns, it does not refuse.
Essentials and up (adding employees needs it).
Reminders and confirmations
Defaults are 24 hours and 1 hour before, by email, with text as a second channel. Add more timings up to 72 hours or 14 days before. Each visit has its own Send automatic reminders switch and can carry its own timing. A confirmation when the visit is booked is a separate switch, off by default.
Every plan by email. Text reminders use plan text segments, which start on Essentials (300 a month).
On My Way
One button on the visit. It opens your template (Hi {name}, I'm on my way to your {time} appointment) with Email and SMS checkboxes, you can edit the message, and it sends once per visit. The time it was sent shows on the visit and on the dispatch board.
Every plan by email; text needs plan text segments (Essentials and up).
Job timer
Start, pause, resume and stop on any visit, from the Job Timer page, the visit, or the Jobs Today view. Each person on a job has their own clock, so you and a helper can both be timing the same deck. A Quick Timer runs with no job attached. The hours feed the invoice under From Time Tracked.
Every plan, Solo included.
Your Google, Apple or Outlook calendar
Sync to Google Calendar on the Scheduling page gives you a private subscription link: Add to Google Calendar, Add to Apple or Outlook Calendar, or copy the link. It is one-way and read-only. Visits from the last 90 days forward appear in your own calendar; editing them there changes nothing in Pocket Boss, and nothing is read back from Google. Anyone with the link can see your schedule, so you can rotate it.
Every plan.
Smart Routing
Pick the day's customers and any extra addresses, up to 25 stops, set a start and end, and get a driving order with arrival estimates. It plans the route; it does not track where your truck is.
Pro and up.
The booking page has its own walkthrough on the online booking page, and route planning on the Smart Routing page. For scheduling across other trades, see contractor scheduling software.
What each plan adds to scheduling
Prices are the current monthly catalog. The 14-day trial applies to every plan.
| Plan | Monthly / users | Scheduling capabilities |
|---|---|---|
| Solo | $19.99 One user | Day, Week and Month calendar, Anytime visits, email reminders and confirmations, On My Way by email, recurring visit series and service plans, jobs with several visits, the job timer, Jobs Today, Create Invoice from a completed visit, the Google, Apple or Outlook subscription. |
| Essentials | $29.99 Up to 5 users | Adds the Dispatch Board and employees, Notify tech on assign, the online booking page and Bookings approval queue, text reminders, confirmations and On My Way texts (300 segments a month), two-way texting with customers. |
| Pro | $49.99 Up to 10 users | Adds Smart Routing (up to 25 stops) and SMS campaigns (600 segments a month). |
| Boss | $99.99 Up to 25 users | Adds the AI Receptionist on a dedicated local number with 100 minutes a month; its calls arrive as requests you turn into visits. |
Text overages, online card and ACH processing and AI Receptionist minutes beyond the allowance are priced separately; the pricing page has the allowances and the current terms.
Who this scheduler is not for
- You want the calendar to refuse a double booking. It will not. The dispatch board flags a crew member booked twice and the booking page hides taken slots, but nothing stops you from putting two visits on yourself at 9:00.
- You want to drag visits around the main calendar. Rescheduling there is a dialog; drag-and-drop is on the dispatch board (and only Week view changes the day).
- You want two-way Google Calendar sync. The feed is a one-way, read-only subscription.
- You need a recurrence like every ten days or the second Tuesday. The cadences are weekly, bi-weekly, semi-monthly, monthly, quarterly and yearly, on chosen weekdays.
- You want online bookings confirmed without you. Every request waits on the Bookings page for your approval.
- You dispatch more than 25 people or route more than 25 stops a day.
Questions handymen ask about scheduling
Does handyman scheduling software stop double bookings?
Pocket Boss warns rather than blocks. On the dispatch board, assigning a crew member who is already booked at that time shows a Double-booked badge and a red ring on the clashing visit, and the assign menu shows Free all day or Busy with the time. On the public booking page, 15-minute slots that collide with an existing visit are simply not offered unless you turn on allow double bookings. On the main calendar you can still put two visits on yourself at the same time; the app does not reject it.
Do online bookings go straight onto my calendar?
No. A customer picks one or more services, a date and a 15-minute slot inside your business hours, and submits. The request sits under Pending Booking Requests on the Bookings page until you approve, decline or reschedule it. Approved requests become Scheduled visits on the calendar and the dispatch board. The booking page is on Essentials and above. Deposits and card-on-file require a connected Stripe account; bookings with no payment step work without one.
Does it send appointment reminders by text?
Yes, when your plan includes text segments. Reminders default to 24 hours and 1 hour before the visit, by email; SMS is a second channel you switch on. You can add more timings up to 72 hours or 14 days ahead, turn reminders off for one visit, or give one visit its own timing. Solo includes no text segments, so on Solo reminders go by email; Essentials includes 300 segments a month, Pro 600 and Boss 1,500. Customers who reply STOP are not texted.
Does it sync with Google Calendar?
One way. The Sync to Google Calendar button on the Scheduling page creates a private subscription link you can add to Google Calendar, Apple Calendar or Outlook, or copy. Visits from the last 90 days forward appear in your own calendar with the customer and booked lines in the description, and Anytime visits show as all-day events. Changes you make in Google do not come back, and the app never reads your Google events. Anyone with the link can see the schedule, so rotate it if it leaks.
How do recurring visits work for a quarterly gutter customer?
Create a recurring visit series on the customer with a quarterly cadence and a start date, open-ended or with an end date. The app generates the upcoming visits about five weeks ahead and keeps generating as dates approach, so the calendar is never empty months out. Weekly and bi-weekly series let you pick the weekdays. If the customer is on a service plan instead, plan visits are left for you to place by default, with a count of plan visits still needing a slot on the Service Plans page; an Auto-schedule visits switch puts them on the first of their month. Recurring visits and service plans are on every plan, Solo included.
Can my helper see only their own jobs on their phone?
Yes. A crew member without scheduling permission gets My Jobs: the visits assigned to them, today and the week ahead, scoped on the server so nobody else's work appears. When you assign a visit on the dispatch board with Notify tech on assign checked, they get a text and an email with the job, time, customer and address. Employees and the dispatch board start on Essentials (up to 5 users).
What runs from the truck: the timer, On My Way, the board?
All of it. Pocket Boss runs as an iPhone and Android app and on the web with the same calendar, so you start and stop the timer on the visit, send On My Way from the visit, and the dispatch board reads the same live state (on the clock, on the way, done) wherever you open it. The one thing that is desktop-shaped is the Week view, which becomes a stacked day list on a phone.
How much does handyman scheduling software cost?
The calendar, reminders by email, recurring visits, jobs and the timer are on every plan, from $19.99/month (Solo, one user). The dispatch board, employees, the booking page and texting start on Essentials at $29.99/month for up to 5 users. Smart Routing starts on Pro at $49.99/month. The top plan is Boss at $99.99/month for up to 25 users. Every plan has a 14-day trial.
Put next week on the calendar and subscribe your phone
Start the trial, book the visits you already have, set up one recurring customer, and add the calendar feed to the phone you carry. Turn on the booking page when customers start asking for it.
Related: handyman CRM software, handyman invoicing software, handyman estimating software, plans and pricing.
Plan names, allowances and prices on this page come from the current catalog (Solo, Essentials, Pro, Boss); the pricing page has the current terms. Online payments use Stripe; Stripe fees and approval apply. Google Calendar, Apple Calendar and Outlook are trademarks of their respective owners.