For coaches who want to coach — not run an agency.

Pipeline of warm leads, recurring program billing, calendar with deal-linked sessions, time tracking, books, and an AI agent that handles the back office while you handle the actual coaching. Built for business, executive, and sales coaches running 1–10 person practices. Multi-currency for clients across borders.

Recurring program billing · Multi-currency · Calendar sync · No card

Four wedges that matter to coaches.

Recurring program billing without a separate tool.

Each client engagement (12-week program, 6-month executive coaching block, monthly group cohort) is a deal with a payment plan. Otto drafts and sends the next round of invoices in batch — right amount, right currency, right reference per client. Books ledger captures it as recurring revenue.

Calendar that knows who you're seeing and why.

Sessions linked to deals and contacts. Day / week / month views. Recurring events for weekly coaching slots. Google Calendar two-way sync. When you open Tuesday at 10am, you see who, what engagement, what stage they're at, and what was discussed last time.

Notes and follow-ups that don't live in five places.

Each contact has a notes field; each deal can have linked tasks. Otto can draft follow-up emails, schedule the next session, log the post-session homework — by voice or chat. The session is over; the admin around it is done before you stand up.

An AI for the work that isn't coaching.

35 tool-calling actions across pipeline, invoicing, time, books, and calendar. Voice or chat. Editable confirmation card before every write. 30-day undo. The agent handles the boring parts so the calendar opens up for actual coaching hours.

The coaching stack you stop paying for.

CRM (HubSpot Free / Pipedrive / spreadsheet)
Pipeline + deals + contacts
Invoicing (Stripe Invoicing / Bonsai / FreshBooks)
Recurring program invoicing in any currency
Scheduling (Calendly + Google Cal)
Calendar with deal/contact linking
Books (QuickBooks SE / Wave / spreadsheet)
Revenue + expense ledger + bank import
Time tracker (Toggl / Clockify)
Time on engagements with daily recap
AI helper (ChatGPT Plus / Claude Pro)
35-action AI agent — voice + chat

Things coaches ask.

Is Hey Otto a coaching-specific tool like Practice or Paperbell?

No — and that is on purpose. Coaching-specific tools (Practice, Paperbell, CoachAccountable) are great if your single biggest need is a packaged client portal with session notes, intake forms, and program templates baked in. Hey Otto is a more general operations platform: pipeline, recurring program billing, calendar, time tracking, books, and an AI agent. Coaches who want one app for the *whole business* (not just the coaching workflow) tend to prefer us.

How does recurring program billing work?

Each client engagement is a deal with a payment plan — for a 12-week program, you can set up the payment schedule once (deposit + 3 monthly installments, or whatever). Otto can draft and send the next round of program invoices in batch with the right amount, currency, and reference per client. Books ledger captures it as recurring revenue.

Calendar — is it as good as Calendly?

Calendly is a scheduling specialist; we have a full calendar with Google sync, day/week/month views, recurring events, and deal/contact linking. We do not have Calendly's public booking-link flow today (that is on the roadmap). Most coaches use us for the operational calendar and keep Calendly for public booking pages until we ship that.

Can I take session notes inside Hey Otto?

Yes — every contact has a notes field, and every deal/event can have linked notes. We do not yet ship a coaching-specific session-template (e.g. "wins / blockers / next steps") format. If you want that structure, use a Notion page per client and link it from the contact record. Native session templates are on the roadmap.

Multi-currency for international clients?

Native. USD, EUR, GBP, ILS, AUD, CAD, plus per-deal override and live FX rates. A coach in Tel Aviv with US, UK, and Australian clients handles all three currencies in the same dashboard with PDF invoices in either currency.

Can I run a coaching cohort or group program?

Each cohort participant becomes a contact with their own deal (linked to a shared 'Cohort 12 — Q3 2026' company record, if you want). Send invoices in batch, track payment status across the cohort, schedule shared events on the calendar. Not a perfect fit if you need cohort-specific gamification or community features — pair with Circle/Slack for those.

Is there a free plan to try it?

Yes. 1 user, unlimited contacts, light agent use, USD only. Multi-currency unlocks at the Solo plan ($29/mo). No card to start.

Otto

More coaching.
Less back office.