Stack Timekeeper vs Toggl Track
Stack Timekeeper vs Toggl Track — which one is right for you?
Toggl Track is the most polished pure time-tracker on the market. The timer, the autotracking, the browser-extension activity detection, the reporting — all of it is the work of a team that has been refining one product for over a decade, and it shows. Stack Timekeeper does not try to out-Toggl Toggl on pure time-tracking depth. What Timekeeper does is collapse the freelancer’s entire money-loop — track time, generate invoice, accept payment via Stripe Checkout — into one Mac menu-bar app plus a small web surface for invoicing. If you are a freelancer or a small consultancy, the question between these two tools is not "which timer is better" but "do I want one tool that closes the loop, or two tools stitched together?" This page lays out the honest tradeoffs.
Pick Stack Timekeeper if…
Pick Stack Timekeeper if you bill clients and want one tool, not three.
Timekeeper is built around a simple premise: the time you track is only valuable when it turns into money in your bank account. So the menu-bar tray timer feeds directly into per-project rates, recurring invoices, and a "Pay" button on every invoice that points to Stripe Checkout against your own Stripe account. Your client clicks the button, pays the card, and Stripe deposits to you the next day. There is no QuickBooks integration to maintain, no Bill.com seat to pay for, no Stripe Invoice template to set up separately. If your tracking-to-paid-invoice loop today involves more than one tool, Timekeeper is built for you. As a bonus, it is part of the $20/month Stack bundle — for less than what Toggl Starter costs for a single seat, you get Timekeeper plus seven other apps.
Pick Toggl Track if…
Pick Toggl Track if pure time-tracking depth is the whole job.
Toggl wins, decisively, when the entire job is "track time accurately and report on it." The browser extension auto-detects what you are working on across 100+ apps (Google Docs, Figma, GitHub, Linear, Asana, Trello, the works), the desktop app does idle detection and Pomodoro and autotracking with a maturity Timekeeper does not match, the mobile apps are first-class on both iOS and Android, and Premium-tier reporting is genuinely powerful for team leads who need utilization rates, billable percentages, and project profitability. If you do not invoice (you are an employee, or your employer handles billing), or if you already have an invoicing system you are happy with, Toggl is probably the better timer.
Feature-by-feature breakdown
| Feature | Stack Timekeeper | Toggl Track | Winner |
|---|---|---|---|
| Mac menu-bar tray timer | Yes — primary surface | Yes (desktop app + tray) | Tie |
| Autotracking / browser activity detection | Basic — manual start/stop with project picker | Yes — auto-detects 100+ apps | Toggl Track |
| Pomodoro + idle detection | Idle detection only | Both, mature | Toggl Track |
| Native invoicing | Yes — generate, send, recurring schedules | No — bring your own (QuickBooks, Bill, Stripe Invoice) | Stack |
| Stripe Checkout pay button on invoice | Yes — one click, your Stripe account | No (not an invoicing tool) | Stack |
| Per-project billable rates | Yes — rate per project, override per entry | Yes (Starter+) | Tie |
| Recurring invoices (retainers) | Yes — set monthly schedule, auto-send | No | Stack |
| Weekly timesheet export | Yes — CSV / PDF | Yes — CSV / PDF / Excel | Tie |
| Mobile apps | iOS PWA only — no native Android | Native iOS + Android, polished | Toggl Track |
| Reporting depth (utilization, profitability) | Basic project / client / week views | Deep at Premium tier | Toggl Track |
| Native integrations | Stripe (deep), Slate task links | 100+ via browser extension + Zapier | Toggl Track |
| Pricing (1 seat / yr) | $144 standalone, $240 bundled | $0 free, or $120 Starter annual | Toggl Track |
| Pricing (5 seats / yr) | $240 flat (whole bundle) | $600 Starter (still no invoicing) | Stack |
| End-to-end freelance loop in one tool | Yes — track → invoice → paid | No — needs invoicing tool alongside | Stack |
Pricing
Stack Timekeeper
$20/mo flat for the whole Stack bundle (Timekeeper + 7 other apps), or $12/mo standalone
Toggl Track
Free (5 users, basic); Starter $10/user/mo annual; Premium $20/user/mo annual; Enterprise custom
At five seats on annual billing, Toggl Starter is $50/month or $600/year — and that still does not include invoicing, so you are paying another $20–$50/month on top for QuickBooks or Bill. Stack is $20/month or $240/year flat, including Timekeeper plus seven other apps and the Stripe Checkout invoicing flow. Even at one seat the math favors Stack once invoicing matters: Timekeeper standalone is $144/year vs Toggl Starter at $120/year plus whatever your invoicing tool costs. Toggl's free tier is genuinely generous for solos who do not need invoicing — if that is you, stay free.
UX differences worth knowing
Starting a timer
Stack Timekeeper: Click the menu-bar tray icon → pick project → typing project name filters in real time → ⌘↵
Toggl Track: Click the tray icon, or rely on autotracker to detect what you are doing
Logging time you forgot to track
Stack Timekeeper: Web app weekly grid — click an empty cell, type hours, tab to next day
Toggl Track: Calendar view in the web app — drag to create a block, similar feel
Generating an invoice
Stack Timekeeper: Click "Invoice this week" on the project → preview → send. PDF + Stripe pay link in one email.
Toggl Track: Export hours as CSV → import to QuickBooks/Bill → build invoice there → send through that tool
Getting paid
Stack Timekeeper: Client clicks "Pay invoice" in the email → Stripe Checkout → card processed → next-day deposit to your account
Toggl Track: Depends entirely on which invoicing tool you stitched in alongside
Reporting for a team lead
Stack Timekeeper: Per-project hours, billable totals, week-over-week trend
Toggl Track: Utilization %, billable %, profitability by project, custom dashboards (Premium tier)
Capturing time on the phone
Stack Timekeeper: iOS PWA — works but slower to open than a native app
Toggl Track: Native iOS / Android — first-class, fast launch
Switching from Toggl Track
Migrating from Toggl Track to Stack Timekeeper is straightforward for the time-entry side and a separate decision for the invoicing side. For time entries, export from Toggl (Reports → Detailed → Download CSV) and drop the CSV into Timekeeper's importer. Projects, clients, descriptions, durations, and billable flags all carry over; tags map to tags. The harder migration is on invoicing: if you have been billing clients through QuickBooks or Bill.com, you will want to issue a final invoice in the old tool, then start a clean ledger in Timekeeper next month rather than back-filling history. Recurring invoice schedules need to be re-created by hand — there is no programmatic import for those across tools. Most freelancers complete the switch over a single billing cycle (one month) and never look back, but the cutover does require a deliberate mental commitment to "this month is the last time I generate an invoice in the old tool."
FAQ
Is Stack Timekeeper a Toggl alternative?+
Yes, with a specific lens: Timekeeper is the right alternative for freelancers and small consultancies who want time-tracking and invoicing in a single tool. It is not aimed at large teams who need autotracking and deep utilization reporting — that audience is better served by Toggl Premium.
Does Stack Timekeeper have a browser extension that auto-detects activity like Toggl?+
No. Timekeeper is a manual-start tray timer. We made that tradeoff deliberately — autotracking is genuinely Toggl's strongest feature, and we are not going to ship a worse version of it. If autotracking is your top requirement, Toggl is the better tool.
How does invoicing work in Timekeeper?+
You set per-project hourly rates in the web app. At any point — end of week, end of month, end of project — you click "Invoice this period" on a project or client, preview the line items (one per day or one per task, your choice), edit if needed, and send. The recipient gets an email with a PDF attachment and a "Pay invoice" button that opens Stripe Checkout. Payment lands in your Stripe account, and Stripe deposits to your bank the next business day.
Do I need a Stripe account?+
Yes for the pay button to work. Connecting Stripe takes about 90 seconds via Stripe Connect — Timekeeper never holds your funds. You can still issue invoices without Stripe (PDF only, no pay button) if you prefer to be paid by ACH or check.
Can I import my Toggl history?+
Yes. Toggl → Reports → Detailed → Download CSV. Drop the CSV into Timekeeper's importer. Projects, clients, durations, descriptions, tags, and billable flags all carry over. Recurring invoice schedules from any prior invoicing tool have to be re-created by hand.
How does pricing compare for a 5-person consultancy?+
Toggl Starter is $10/user/month annual = $600/year for 5 seats — and that still has no invoicing, so add another $20–$50/month for QuickBooks or Bill. Stack is $20/month flat = $240/year for the whole bundle including Timekeeper, with the Stripe Checkout invoicing flow built in. The break-even is below 1 seat once invoicing matters.
Will Timekeeper add autotracking and a browser extension?+
Eventually, yes — but only when we can match Toggl's quality, not before. The roadmap priority right now is depth on the invoicing side (line-item editing, multi-currency, Stripe ACH support, late-payment reminders). If autotracking is your day-one requirement, use Toggl.
Verdict
Toggl Track is the better pure timer. The autotracking, the browser extension, the native mobile apps, the Premium-tier reporting — these are real, substantive advantages built up over more than a decade of focused product work, and we are not going to pretend otherwise. If you only need to track time and somebody else handles billing, Toggl is probably the right answer, especially given the genuinely usable free tier. Stack Timekeeper wins when invoicing is part of the job. The whole product is shaped around the freelancer or small consultancy who needs to track hours, send invoices on a schedule, and actually get paid for them — and the Stripe Checkout pay button on every invoice is the part that closes the loop in a way Toggl does not even attempt. Choosing Toggl + a separate invoicing tool is a legitimate path; it just costs more money, more attention, and more glue work, and at five seats the difference is roughly $360/year just for Toggl Starter on top of whatever you spend for QuickBooks. The honest framing: if your time tracking ends in a CSV export and somebody else's spreadsheet, pick Toggl. If your time tracking ends in a wire transfer to your bank account, pick Timekeeper. Most readers of this page are in the second category.
Try Stack — $20/mo flat for all 8 apps.
Stack Timekeeper comes bundled with seven other work tools. One subscription, no per-seat surprise.