SkipUp vs Blockit: Which AI Scheduler in 2026?
SkipUp is the better pick if your meetings start with outside people over email and the hard part is getting them to answer; Blockit is the better pick if you are back-to-back, work in Slack as much as email, and meet often with colleagues whose calendars it can read. Both are AI agents you loop into a conversation to book a meeting, but SkipUp is built around persistent follow-up and team routing at a low monthly price, while Blockit is built around a calendar network and an executive-grade assistant priced like one. For the wider field, see our SkipUp alternatives and Blockit alternatives roundups.
The One-Sentence Answer
Use SkipUp if you need a cheap email scheduler that keeps chasing prospects, candidates and customers until they book; use Blockit if you want an always-on scheduling agent across email and Slack that reads your team’s calendars and books instantly when the other side runs Blockit too.
Side-by-Side Comparison
| Dimension | SkipUp | Blockit |
|---|---|---|
| How you use it | CC skip@skipup.co on an email thread | CC it on email, or DM or @mention it in Slack |
| Calendars | Google and Microsoft, unlimited calendars | Google and Microsoft, as many as you want |
| Standout feature | Automatic follow-up on stalled threads, with adjustable frequency and tone | Instant booking when both sides run Blockit; reads colleagues’ shared calendars |
| Free option | 10 free meetings per person, no time limit, no card | Free plan, 15 meetings a month; every plan starts with a 30-day trial |
| Entry paid plan | Pro, $49/month for 30 meetings across the workspace | Lite, $145/month billed monthly or $83/month billed annually ($999/yr), 40 meetings a month |
| Top plans | Higher-volume tiers and custom company plans | Infinity (unlimited meetings), $495/month monthly or $395/month annually; Enterprise from $20k/yr |
| Team features | Round-robin team addresses, campaign addresses for attribution, workspace billing | Group scheduling with required and optional attendees; EA delegate access on Enterprise |
| Branded assistant | $199/month add-on for a custom name, email handle and signature | Custom domain on Enterprise |
| Security | SOC 2 Type 1 in progress | SOC 2 Type II |
| Beyond scheduling | No, by design | No, by design |
Prices checked on each vendor’s site on September 29, 2026. Both move often, so confirm before you buy.
When to Use SkipUp
- Your meetings come from outside: demo requests, candidates, renewals, investor intros. SkipUp is pitched at sales reps, customer success, recruiters and founders.
- The real problem is silence. SkipUp follows up on stalled threads on its own, and you can tune how often it nudges and in what tone, or tell it in a thread to back off.
- You run a team. A round-robin team gets its own address, so inbound prospects who email it are assigned to the next available rep. Campaigns get their own scheduling addresses too, so a conference booth or a newsletter can be tracked by booking rate.
- You want usage billing, not per-seat billing. Pro is $49/month for 30 meetings shared across the whole workspace, with bigger tiers as volume grows.
- You want hooks into your stack. SkipUp has an API, webhooks, and Zapier recipes for HubSpot, Salesforce and Pipedrive, such as starting a scheduling thread when a deal hits “Demo Requested.”
SkipUp is newer and narrower. Its own docs say the assistant is focused on scheduling and will decline requests like summarizing a thread.
When to Use Blockit
- Your calendar is packed and you want an assistant that thinks like an EA: it reads your saved meeting templates, remembers stated rules like “in-person meetings on Thursdays,” and moves low-priority internal meetings to fit important ones.
- You schedule in Slack. You can DM Blockit (“move my 3pm to Thursday”) or @mention it in a channel and it books right there.
- You schedule groups inside a company. It reads colleagues’ shared calendars directly, proposes times to outside guests, and treats required and optional attendees differently.
- The people you meet also run Blockit. When both sides do, the agents see both calendars and the meeting books in seconds with no email at all.
- You want control over autonomy. You choose anything from reviewing every invite to full autopilot, per person or meeting type.
Blockit announced a $5M seed round led by Sequoia in January 2026 and was reported at 200+ companies at the time, including a16z, Brex and Together.ai. Its pricing has changed since launch: the old $1,000-a-year individual price has become a free plan plus paid tiers, and the $83/month Lite price only applies if you pay annually.
The Difference That Decides It: Who Is on the Other Side
If the person you are trying to meet is a prospect, a candidate or a customer who owes you nothing, the meeting dies when they stop replying. SkipUp is built for exactly that, with follow-up you can tune and team addresses that route new inbound to whoever is next. It is also far cheaper at modest volume: 30 meetings a month for $49 against Blockit Lite at $145 billed monthly, or $83 a month paid annually, for 40.
If that person is a colleague, a portfolio founder, or someone at a firm that already uses Blockit, speed and judgment matter more than persistence. Blockit reads calendars it has access to, protects the time you care about, and skips negotiation entirely when both agents are connected. Its demo even shows it stopping after three rounds of unanswered times, which fits an executive who does not want to look pushy, and is the opposite of what a sales rep wants.
Budget follows the same line. Blockit’s free plan (15 meetings a month) is more generous than SkipUp’s 10-meeting trial for a solo user, but once you pay, SkipUp’s workspace billing is the cheaper way to cover a team.
When the Meeting Is Only Half the Job
Both tools stop at the invite. After the meeting is booked, someone still has to answer the rest of the email, send the follow-up, and log the deal.
Carly handles that loop. Each Carly agent has its own email address, so you CC it the same way you would CC SkipUp or Blockit. The same agent that finds the time and sends the invite also replies to the other questions in the thread, sends the follow-up after the call, and updates your CRM. It can also run workflows that fire on a new email or a new calendar event, in the cloud, with no chat open, set up by describing what you want in plain English. Carly works over email and text and connects to thousands of apps, including Gmail, Outlook, HubSpot, Salesforce, Pipedrive and Slack. Pricing: free Zapier-style workflows; AI agents from $35/month.
Quick Reference
| Your situation | Pick |
|---|---|
| Prospects and candidates go quiet after the first email | SkipUp |
| I need round-robin scheduling for a sales team | SkipUp |
| I want the cheapest paid plan for a small team | SkipUp |
| I schedule in Slack as much as in email | Blockit |
| I’m back-to-back and want an EA-style agent that protects my time | Blockit |
| The people I meet often already run Blockit | Blockit |
| I want the meeting booked and the follow-up, reply and CRM update done too | Carly |
FAQ
Is Blockit still $1,000 a year? Not exactly. Blockit now has a free plan with 15 meetings a month. Lite is $83/month billed annually ($999/yr) or $145 billed monthly, Infinity is $395/month annually or $495 monthly, and Enterprise starts at $20k a year. Every plan starts with a 30-day trial, no card required.
How much does SkipUp cost? Every person gets 10 free meetings with no time limit. Pro is $49/month for 30 meetings shared across your workspace, with higher-volume tiers and custom company plans above it. A branded agent name and email handle is a $199/month add-on.
Do both work with Outlook? Yes. SkipUp connects Google Calendar and Microsoft calendars, and Blockit supports Google and Microsoft calendars plus Zoom, Meet and Teams links.
Which is better for a sales team? SkipUp, for most teams. Round-robin team addresses, campaign tracking, workspace-level billing and Zapier recipes for HubSpot, Salesforce and Pipedrive are all aimed at reps booking outside meetings. Blockit is aimed at individuals and executives with dense calendars.
Can either one handle the work after the meeting? No, both are scheduling specialists. If you want the same assistant to also reply, follow up and update your CRM, see our Carly vs Blockit breakdown.
Related: SkipUp vs Clara · SkipUp vs Howie · Blockit vs Skej · Reclaim vs Blockit · Best AI scheduling assistants
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"Before Carly, I relied on a Calendly link, but the whole process felt impersonal and not very professional. Carly changed that by handling all the back-and-forth, so I'm no longer stuck in endless email threads trying to line up schedules.
Now Carly reaches out to candidates, shares my real-time availability, lets them pick a slot, then sends a Zoom link and drops it straight into my calendar. She sends reminders to both of us before each call, which has significantly reduced no-shows and last-minute confusion.
On top of scheduling, Carly acts like a full executive assistant, sending me my schedule the night before so I can prepare for each call. It reminds me of the old x.ai assistant, but Carly is noticeably smarter, faster, and better suited to my healthcare recruitment business."
