Howie vs Clara: Which AI Scheduling Assistant in 2026
Both of these tools do the same core thing: you CC an AI on an email thread and it books the meeting for you, handling the back-and-forth with the other party. Howie (howie.ai) is the newer, well-funded challenger — a “people’s secretary” that schedules over email or text, priced to be affordable for individuals but currently limited to Gmail and Google Calendar. Clara (Clara Labs) is the original — it helped invent the email-CC scheduling category around 2014, works natively with both Google and Outlook, and is priced and positioned for teams and enterprises. The one distinction that decides most choices is simple: which calendar you run on and how much you want to spend. Name that first and the pick gets easy.
The One-Sentence Answer
Use Howie if you’re on Google and want an affordable, modern scheduling assistant; use Clara if you need Outlook support or want the most established, enterprise-ready option — and are fine paying for it.
Side-by-Side Comparison
| Dimension | Howie | Clara |
|---|---|---|
| What it is | AI scheduling assistant you CC by email or text | AI scheduling assistant you CC by email |
| Origin | Launched publicly 2025; venture-backed ($6M seed) | Pioneered the category ~2014 (Clara Labs) |
| Core job | Books and reschedules meetings | Books and reschedules meetings |
| Calendars | Google Calendar / Gmail only (Outlook listed as coming) | Google Workspace and Outlook / Exchange |
| Automation model | Autonomous; applies your rules for times, buffers, VIPs | Fully autonomous; no human-in-the-loop review |
| Pricing (2026) | Free to start; ~$25/mo standard, ~$95/mo premium (white-label) | Free 14-day trial; $80/mo Standard (30 meetings); Enterprise custom |
| Best fit | Individuals and small teams on Google | Teams and enterprises, especially on Microsoft |
| Track record | 1,000+ paying customers, 5,000+ meetings/week | 1M+ meetings scheduled; used by large companies |
When to Use Howie
- You live in Gmail and Google Calendar and don’t need Outlook.
- You’re an individual or small team who wants scheduling without an enterprise price tag — the standard plan is roughly a quarter of Clara’s.
- You want to trigger scheduling by text as well as email, not just CC.
- You like the “delegation” framing: a secretary you hand a request to and forget about.
- You want a modern, actively developed tool and don’t mind that it’s younger.
Howie is the value pick for Google users. Its focus on doing scheduling well, and only scheduling, is also its ceiling.
When to Use Clara
- You or your team run on Microsoft 365 / Outlook / Exchange — Clara supports it natively today, Howie does not.
- You want the longest-running, most battle-tested option in the category.
- You’re scheduling at team or company scale and want admin controls, custom domains, and enterprise onboarding.
- You value that Clara is still fully operating in 2026 (the company was absorbed into what became Gem years ago, but the scheduling product runs and takes signups).
- Budget is less of a constraint than reliability and provider coverage.
Clara is the enterprise-and-Outlook pick. You pay more, but you get broader calendar support and a decade-plus track record.
The Difference That Actually Decides It
Strip away the marketing and the choice comes down to two variables: your calendar provider and your budget. If you’re on Google and cost-sensitive, Howie wins on both. If you’re on Outlook, Howie is off the table until its Microsoft support ships, and Clara is the obvious answer. If you’re somewhere in between — on Google but scheduling for a whole team — it’s a genuine toss-up between Howie’s price and Clara’s maturity.
But there’s a limit both share, and it’s worth naming before you commit to either: they only book meetings. Neither one triages the rest of your inbox, drafts a non-scheduling reply, chases a follow-up that isn’t about a calendar invite, or updates your CRM after the call. The moment your need is broader than “find a time,” you’re back at your keyboard. If you want that whole job handled, Carly is an AI assistant whose agents each get their own email address — you CC one to book a meeting exactly like Howie or Clara, and the same agent also replies to people, sends follow-ups, and updates your tools across 200+ integrations on Gmail or Outlook, set up by describing what you want in plain English. It’s a different category than a pure scheduler, but it’s the right frame if scheduling is only part of what you’re delegating.
Quick Reference
| Your situation | Pick |
|---|---|
| On Google, want the cheapest good option | Howie |
| On Outlook / Microsoft 365 | Clara |
| Scheduling for a large team or company | Clara |
| Individual who books a few meetings a week | Howie |
| Want to trigger scheduling by text | Howie |
| I want everything around the meeting handled too, not just the booking | Neither — see Carly |
FAQ
Is Clara still around in 2026? Yes. Clara Labs was folded into another company years ago, but the Clara scheduling product is still live, still takes signups, and still supports both Google and Outlook. Reports that it shut down are wrong.
Does Howie work with Outlook? Not yet. Howie is Gmail and Google Calendar only; Outlook is listed as coming but isn’t available. If you’re on Microsoft 365 today, Clara is the one that supports you.
Which is cheaper, Howie or Clara? Howie. Its standard plan runs around $25/month versus Clara’s $80/month Standard, and Clara moves to custom enterprise pricing above that. Howie’s premium tier (about $95/month) is where the two get closer, but that tier adds white-labeling rather than more scheduling.
What if I want the meeting-related work done, not just the booking? Both Howie and Clara stop once a time is on the calendar. If you also want the confirmation email personalized, the prep doc pulled together, the follow-up sent, and the CRM updated, that’s a broader AI assistant’s job, not a pure scheduler’s — plan for a second tool if that’s your real need.
Related: Howie alternatives · Clara alternatives · Best AI scheduling assistants
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