Top Scheduling Apps When You Run Your Own Deliveries

Most lists of the top scheduling apps are written for someone who books meetings. If your day ends with a van going out, you need a different shortlist, and you need to know which of three jobs each app is doing.

Those three jobs are your hours, your people, and your drops. Almost every app on the market does one of them well and the other two badly, which is why owners end up paying for two subscriptions and still doing the third job in a notebook. Knowing which column an app sits in before you start a trial saves more money than any discount code.

This post compares the apps to consider, what they cost as of September 2026, and which combination makes sense at two vehicles versus ten. If you haven’t yet settled the plan the app is meant to hold (stops per hour, cutoff times, window widths), start with the hourly planner for dispatch and routing, because software will hold a bad plan just as faithfully as a good one.

The Bottom Line

• Scheduling apps split into three jobs: your own hours, your staff’s shifts, and your customers’ delivery slots. Buying the wrong category is the usual mistake.
• You can cover the shift side for nothing at small scale. Homebase Basic is free for one location and up to 10 employees, and Connecteam’s Small Business plan is free for up to 10 (Homebase, Connecteam, retrieved 2026-09-30).
• Day-planning apps are the expensive column per head: Sunsama is $22 a month billed monthly, Motion starts at $19 a seat (Sunsama, Motion, retrieved 2026-09-30).
• Shift apps price per user, day-planners price per seat, and delivery tools price per driver or per order. At ten people those three models diverge sharply.
• Two vans needs one free shift app and a calendar. Ten needs a paid shift app and a dedicated delivery tool, and the day-planner becomes optional.

The three things a scheduling app can schedule

Every app in this space schedules one of three resources, and the category tells you more than the feature list does.

Your own hours: day planners and time-blocking apps take your task list and lay it against your calendar, so the hour you meant to spend building tomorrow’s route is defended rather than swallowed. Motion, Sunsama and Reclaim live here. They schedule one person: you.

Your people: shift scheduling apps build the rota, publish it to phones, handle swaps and time-off requests, and usually track hours for payroll. Homebase, When I Work and Connecteam live here. They care about who is working, not where the van goes.

Your drops: delivery scheduling and route tools take orders with addresses and time windows and turn them into sequenced routes with departure times. Nothing in the first two categories does this, and no amount of calendar cleverness substitutes for it once you pass a few dozen stops a week.

The reason this matters commercially: the three categories have different pricing models. Day planners charge per seat and you only ever buy one or two. Shift apps charge per user or per location, so cost scales with headcount. Delivery tools usually charge per driver or per order, so cost scales with volume. An app that looks cheap in one model can be the most expensive line on the list in another.

Top scheduling apps compared, with current pricing

Prices below were taken from each vendor’s own pricing page on 30 September 2026. Vendors change tiers often, so treat the table as a starting point and confirm before you commit.

Sources: vendor pricing pages, retrieved 2026-09-30 (Sunsama, Motion, Reclaim, Homebase, When I Work, Connecteam).

Apps that schedule your own hours

Start here only if your problem is that dispatch admin keeps landing in whatever hour is left. If your problem is the rota or the routes, skip this section: these apps won’t touch either.

Google Calendar is the unglamorous default, and plenty of operations never need more. Blocking out “build tomorrow’s route, 4pm to 4:30” as a recurring event costs nothing and solves most of the problem. Its limitation is that it has no opinion: nothing moves the block when a delivery goes wrong, so the discipline has to come from you.

Sunsama is built around a daily planning ritual. You sit down once, pull tasks in from your other tools, and place them against the calendar. It suits an owner who wants a deliberate ten minutes each morning and evening rather than an algorithm. At $22 a month billed monthly, or $17 on annual billing, it’s the priciest per-person option on the list, and it’s aimed squarely at the one person who plans.

Motion is the automating end of the category. You tell it what has to be done and by when, and it builds and rebuilds the day around your calendar. Pro AI is $19 a seat monthly and Business AI is $29, with annual billing advertised at 33% less. There’s a trade-off: an auto-scheduler that keeps reshuffling can feel worse than a manual plan if your day is already interrupt-driven, which a delivery day usually is.

Reclaim takes the narrower job of protecting recurring blocks: focus time, habits, buffers between commitments. Its Lite plan is free indefinitely with a one-week scheduling range, and paid tiers start at $10 a seat per month. If the specific thing you keep losing is the same half-hour every day, the free tier may be enough.

A caution for this whole column: these tools assume your calendar is the system of record. If the real schedule lives in a notebook by the packing bench, a $22 planner won’t change anything.

Apps that schedule your drivers and packers

This is where the money is at any headcount above a couple of people, and where the free tiers are unusually generous.

Homebase prices per location rather than per person, which is the right shape for one site with a shift-working team. The Basic plan is free for a single location with up to 10 employees and covers basic scheduling and time tracking; Essentials is $30 per location per month, Plus $70, and All-in-One $120. New accounts get a 14-day trial of All-in-One and drop to Basic if no plan is chosen.

When I Work prices per user, starting at $2.50 a month on Essentials, $5 on Pro, and $8 on Premium, with a 14-day trial and no card required. Per-user pricing is easier to forecast when headcount moves around, and at a small crew it’s cheaper than a per-location plan.

Connecteam bundles scheduling into an operations hub with a free Small Business plan for up to 10 employees. Paid Operations tiers start at $29 a month covering the first 30 users, with additional users from $0.80 each, and yearly billing saves 18%. It’s the strongest option if you also want checklists, forms and team messaging in the same place as the rota.

If you also run a shop floor or counter alongside the packing bench, the rota spans two very different kinds of shift, and the retail scheduling software options handle that mix more directly than a driver-focused tool will.

All three are free or nearly free while you have fewer than about ten people, and the decision only gets expensive later. That makes it a low-risk category to try properly rather than agonize over.

Apps that schedule your customers’ delivery slots

This is the category most people need when they search for scheduling apps, and it is the one none of the above covers.

A delivery scheduling tool takes orders with addresses and promised windows, sequences them into routes, assigns each route to a vehicle, and gives the driver a stop list with proof of delivery. The pricing model is per driver or per order rather than per seat, and the entry point is usually higher than a shift app.

Because it’s a different purchase with a different evaluation, the features and selection criteria are set out separately in what delivery scheduling software does rather than squeezed into a paragraph here. What matters for this comparison is the boundary: once you’re planning more than roughly thirty stops a week across multiple vehicles, no calendar or rota app will hold the plan, and the money is better spent in this column than on a second day-planner seat.

Which scheduling apps to run at two vans versus ten

The right stack changes shape twice as you grow.

One or two vehicles, under ten people. Run a free shift app and a calendar, and nothing else. Homebase Basic or Connecteam’s free Small Business plan handles the rota at no cost; Google Calendar holds your own blocks. Total spend: zero. Put the saved budget into a route tool before you put it into a planner.

Three to five vehicles. The rota is now the pain point, and free tiers start to bind at the ten-employee line. This is where a paid shift plan earns its keep, since per-user pricing is usually kinder here than per-location, and where a delivery scheduling tool stops being optional, because you are re-sequencing multiple vehicles daily.

Six to ten vehicles and beyond. Two things change. You probably have someone other than you doing dispatch, which means the plan has to be legible to a second person rather than living in your head. And the per-head cost of the shift app is now a line item to negotiate annually. The day-planner seat, ironically, becomes the least important purchase on the list at this size, because the scheduling work has moved from your hours to the operation’s.

What to check before you pay for a scheduling app

Trials are short and feature lists are long. Five checks separate the apps that survive a busy delivery week from the ones that don’t:

• Does a change reach the phone? Push notification to the person affected, not an email nobody opens. Test it by moving a shift or a window on a Friday afternoon.
• Can someone else read the plan? If only you can interpret the schedule, you haven’t bought a system, you’ve bought a personal habit with a subscription.
• What happens offline? Basements, loading docks and rural runs lose signal. A driver-facing view that needs live connectivity to show the next stop will fail exactly when it matters.
• How does the pricing model behave at double your headcount? Per location, per user, per driver and per order diverge fast. Do the arithmetic at your likely size next year, not today’s.
• Does it export? If you can’t get your schedule out as a file, switching later costs you the history.

Run the trial on your busiest week rather than a quiet one. An app that handles a calm Tuesday tells you nothing about the Friday you need help with.

Frequently asked questions

What are the best scheduling apps for a business that does its own deliveries?

There isn’t one, because three different things need scheduling. For your own hours, Google Calendar free or Sunsama and Motion paid. For staff shifts, Homebase, When I Work or Connecteam, all of which have free or very cheap entry tiers. For customer delivery slots and routes, a dedicated delivery scheduling tool. No calendar or rota app covers it.

Is there a free scheduling app that works for a delivery operation?

Yes, on the shift side. Homebase’s Basic plan is free for one location with up to 10 employees, and Connecteam’s Small Business plan is free for up to 10 employees. Reclaim’s Lite plan is also free indefinitely for personal calendar blocking. The free tiers generally bind at around ten people.

How much should a small operation expect to spend on scheduling software?

At under ten people, plausibly nothing. Between three and ten vehicles, budget per-user shift pricing in the $2.50 to $8 range plus a delivery scheduling tool, which is usually the larger of the two. A day-planning seat at $17 to $29 a month is optional and only ever needed for one or two people.

Can one app schedule both staff shifts and delivery routes?

Some platforms advertise both, but the depth is rarely equal. A rota tool with a route add-on typically sequences poorly, and a route tool with a shift feature usually can’t handle swaps or time-off. Below about three vehicles the compromise is fine. Above that, two specialized tools tend to work better than one that does both.

Does an auto-scheduling app like Motion suit a delivery day?

Only sometimes. Auto-schedulers work best on days made of movable knowledge work. A delivery day has fixed anchors (cutoffs, load times, departures) that shouldn’t move, and an algorithm reshuffling them can create noise. A manual planner, or plain calendar blocks, often fits an operations day better.

Pick the column first, then the app

The decision that saves money here isn’t which brand, it’s which of the three jobs you’re actually buying for. Owners who skip that step tend to buy a day planner for a rota problem, or a rota app for a routing problem, and then conclude that scheduling software doesn’t work.

Name the job, use the free tier in that column for a full busy week, and only pay once it’s clear what the free version can’t do. Then check the pricing model against the size you expect to be next year, not the size you are now.