Workspace369 Pricing 2026: Which Plan to Pick and What You Will Pay

Workspace369 costs $29 a month for one person on Cadet, $74 for two on Voyager, $149 for ten on Specialist, $299 for twenty on Commander and $699 for fifty on Enterprise, billed monthly in US dollars. Yearly billing saves 20%. Unless you need full accounting, three questions settle the choice between Cadet, Voyager and Specialist: do you bill by the hour, do clients text you, and do clients book themselves or pay a deposit?

Prices checked October 7, 2026 on the Workspace369 pricing page and on each other vendor’s own pricing page. This is an assessment of published plans, not a hands-on test of every product. For what Workspace369 is and how it works, start with our Workspace369 overview.

Jump to plans and prices, which plan to pick, cost per user or when another tool fits better.

Workspace369 plans and prices in 2026

Our #1 pick is Workspace369, and we make it. That is why this guide sticks to published plan rules and arithmetic, and names the cases where another tool costs less.

Workspace369 prices by plan, not per user. Each plan includes a set number of seats and everything in the plans before it.

USD list prices from Workspace369 pricing, checked October 7, 2026. Teams over 100 seats talk to sales.

Cadet already covers the core client job for one person: proposals from your service catalog that clients accept and sign through a link, invoices paid online by card through Stripe, retainers and payment schedules, recurring invoices, a client portal, up to five projects, one email inbox, two-way Google Calendar sync and a connection to Claude and ChatGPT through MCP. Higher plans add channels, seats and finance tools.

Which Workspace369 plan should you pick?

Work through these questions in order. Each “yes” sets a minimum plan, and your plan is the highest minimum you reach.

1. Do you bill by the hour? Time tracking starts on Voyager ($74): timers, timesheets and billable time that becomes invoice line items. That holds even if you work alone.
2. Do clients text you? Texting also starts on Voyager, with a shared inbox, two-way SMS and missed-call text back. Voice calls and voicemail start on Specialist ($149).
3. Do clients need to book themselves or pay a deposit on acceptance? Client self-booking pages with appointment reminders, a deposit collected when a proposal is accepted, and payment plans in installments all start on Specialist. A coach who sells sessions may need Specialist with a team of one.
4. How many people need a login? One person fits Cadet. Two to nine people fit Voyager plus $10 a month for each person after the first two. From ten people, Specialist costs less than Voyager with extra seats.
5. Do you need full accounting? Expense tracking with receipt capture and basic accounting start on Specialist. Full accounting is on Commander ($299).

Two smaller limits also move solo users off Cadet. It holds up to five projects, and up to three active workflows with email steps only. Voyager makes projects unlimited and allows ten active workflows with SMS steps.

If every answer is no, Cadet at $29 is enough. Enterprise ($699) is for organizations that need 50 seats or two additional workspaces, each with Commander-tier AI tokens.

Workspace369 cost per user, from 1 to 20 people

Our overview lists the cheapest plan for each team size; here are per-person and yearly figures at list prices.

How the totals work: Voyager’s $74 covers two people, so five people add three seats at $10 each, for $104. At ten people, Voyager plus eight seats would be $154, so Specialist at $149 is cheaper and adds booking, deposits and basic accounting. Fifteen people is $149 plus five seats, or $199. Twenty is Specialist plus ten seats at $249, against Commander at $299, so choose Commander for full accounting or unlimited workflows, not for seats.

Billed yearly, a ten-person team on Specialist pays $1,430.99 instead of $1,788, which is $357.01 less. Extra seats are listed at $10 a seat a month, so check at checkout how they bill on a yearly plan.

Features can raise the floor: a five-person team that needs client booking pays $149 for Specialist, not $104. To price a whole stack, try our software stack calculator.

Extra costs you can predict

Four items can add to the plan price:

• Extra seats: $10 a seat a month on Voyager and above. Cadet holds one seat only, so a second person means Voyager at $74, not $39.
• Extra storage: $15 a month per 100 GB, from Voyager, on top of the storage in the table above.
• Dedicated numbers: claiming dedicated SMS or voice numbers adds a one-time $50 carrier compliance setup, on Voyager and above.
• A feature one plan up: moving from Cadet to Voyager for time tracking or texting adds $45 a month, and moving from Voyager to Specialist for booking or deposits adds $75.

Each plan also includes a monthly allowance of AI tokens for Workspace AI, from 10,000 on Cadet to 300,000 on Enterprise.

Trial, upgrades, downgrades and cancellation

Every plan has a 14-day free trial. The pricing page lists no free plan.

• Upgrades apply immediately, so you can move up on the day you need a feature or a seat.
• Downgrades take effect at the next billing cycle. On a yearly plan that is your renewal date, so start yearly billing on a plan you are sure about.
• Cancelling keeps your access through the end of the billing period, and workspace data is kept for 90 days afterwards.

Start on the smallest plan that runs your week, and consider yearly billing once it has stayed the same for a few months.

When another tool fits better or costs less

Workspace369 is built to run the whole client relationship, from inquiry to paid invoice. If your job is narrower, a cheaper tool may cover it. Prices below were checked October 7, 2026, billed monthly unless noted.

Working alone on the basics. Moxie Starter is $12 a month ($10 billed yearly) and includes proposals and contracts, invoicing and payments, time tracking, meeting schedulers and basic accounting; team members come in on its Teams plan at $40. Moxie pricing Plutio Core is $19 a month (about $15 billed annually) for one person with up to nine active clients and no additional contributors. Plutio pricing If you need neither texting nor a team, either costs less than Cadet, and Moxie Starter costs far less than Voyager for hourly billing.

A ten-person team that fits HoneyBook’s workflow. HoneyBook Premium is $129 a month billed monthly, or $109 a month billed yearly, and Premium removes the team-member limit, so the price stays flat as you hire. At ten people that is $20 a month less than Specialist ($10.25 less billed yearly), and at twenty it is $120 less than Specialist plus ten seats. It fits teams whose work already runs through proposals, contracts, a scheduler and automations the HoneyBook way. HoneyBook pricing

An invoicing-first team. FreshBooks Plus is $43 a month billed monthly, or $464.40 a year billed yearly, at its regular price, plus $11 a month for each team member, and bills up to 50 clients. For ten people billed monthly that is $43 for the plan plus nine team members at $11, or $142 a month ($1,704 a year), against Specialist at $149 ($1,788 a year). Billed yearly, Specialist is $1,430.99 and FreshBooks Plus is $464.40 before team members, so compare the same billing period. FreshBooks pricing Our FreshBooks review covers its client limits.

For the wider field, our Bonsai vs Moxie vs 17hats vs Plutio comparison and the client software pricing tracker set the main tools side by side.

How to check your real cost in the 14-day trial

1. List everyone who needs a login and what each person does.
2. Answer the five plan questions above and write down the plan they point to.
3. Start the trial on that plan, not the cheapest one, so you test the features you would pay for.
4. Import your client list from a CSV and run one real client from proposal to paid invoice.
5. Test the feature that set your plan: a week of timers on Voyager, or a booking page and a deposit on acceptance on Specialist.
6. Price the year both ways: twelve monthly payments against the yearly total, plus extra seats, extra storage and the one-time $50 setup if you will claim a dedicated number, then compare one alternative on the same billing period.

Our printable trial checklist works for any tool you compare.

Frequently asked questions

How much does Workspace369 cost?

Billed monthly in US dollars, Cadet is $29 (1 seat), Voyager $74 (2 seats), Specialist $149 (10 seats), Commander $299 (20 seats) and Enterprise $699 (50 seats). Billed yearly, the same plans work out to $23.25, $59.25, $119.25, $239.25 and $559.25 a month. Prices checked October 7, 2026. Workspace369 pricing

Is there a free Workspace369 plan?

No. The pricing page lists no free plan; every plan has a 14-day free trial, after which the plan price applies. The lowest plan is Cadet at $29 a month for one person.

Is Workspace369 cheaper billed yearly?

Yes. Yearly billing saves 20%: Cadet is $278.99 a year instead of $348 billed monthly, Voyager $710.99 instead of $888, and Specialist $1,430.99 instead of $1,788. Downgrades wait for the next billing cycle, so on a yearly plan choose the plan carefully.

How much does an extra seat cost in Workspace369?

Extra seats are $10 a seat a month on Voyager and above. Cadet holds one seat only, so adding a second person means moving to Voyager, which includes two seats for $74. At ten people, Specialist ($149) costs less than Voyager with eight extra seats ($154).

Which Workspace369 plan has time tracking, texting and booking?

Time tracking and texting, through a shared inbox with two-way SMS, start on Voyager at $74 a month. Client self-booking pages, deposits on proposal acceptance and voice calls start on Specialist at $149. Each higher plan includes everything in the plans below it.