Agentic onboarding teardown

Named by Nikhil · www.town.com

Town

Town: an AI work assistant (a 'Townie' with its own @town.com address) that connects to your email, calendar and tools, learns how you work, and runs inbox triage, scheduling, meeting briefings and custom routines; sold to individuals (Free → Power Plus) and teams (pooled credits).

Why it's here: Nikhil named town.com. Town is an AI work assistant ('Townies') with a 7-day Pro trial capped by credits, which is exactly Kite's AM-106 trial-credit territory.

Blocked17 steps
Where it stopped: Sign-up = OAuth with mailbox + calendar scopes (step 8). Google asks for gmail.modify, calendar.events, calendar.calendarlist.readonly, calendar.events.freebusy and cloud-identity.groups.readonly with offline access (step 10); Microsoft asks for Mail.ReadWrite, Mail.Send, MailboxSettings.ReadWrite, Calendars.ReadWrite and Contacts.ReadWrite (step 11). Creating an account means connecting a real inbox, which the safety rules forbid. Steps 12-17 are from Town's public docs.
What would unblock it: Use a dedicated empty test Google Workspace (or Microsoft 365) mailbox Nikhil controls, such as a fresh kite.ai test user with no real mail, so the inbox/calendar grant exposes nothing. Town promises 'never send an email... without your permission', but to be safe keep the test mailbox empty.

How they turn free users into paying ones

Town makes the data grant the sign-up itself (Google/Microsoft OAuth with mail and calendar scopes), so every account starts fully connected and the assistant can be useful immediately. Every user then gets a reverse trial: 7 days of Pro capped by a fixed batch of trial credits, whichever runs out first, after which they drop to a permanent Free tier (30 chats/month, weekly briefing). The routines and live triggers they got used to pause 'until you upgrade', and Pro is the cheapest tier that brings them back. Committing is made risk-free: a plan picked during the trial starts only when the trial ends. The pricing page steers to Pro (dark CTA, annual -20% preselected, calculator 'Best fit for you'), and usage-based upsell runs through opt-in overage ($0 cap by default), 80/90/100% emails, an in-app banner and the line 'steady overage is your upgrade signal'. A conversion-paid referral loop (friend gets 14 days, referrer gets 2,000 credits) adds growth.

Sharpest tactic

A reverse trial gated on automation, not chat: the 7-day/credit-capped Pro trial runs live email- and meeting-triggered routines, then Free keeps chat but pauses those routines 'until you upgrade', and Pro ($49) is the cheapest plan with event triggers.

The flow, step by step

Click any screenshot to enlarge; use ← → to page through. Viewport 1440×900; tall pages are full-page captures. Steps marked docs come from public help pages, not the live app.

Monetization mechanics

Trial / free offerReverse trial: every individual sign-up starts on a 7-day Pro trial with 'a batch of trial credits'. It ends when 7 days pass or the trial credits run out, whichever comes first, then drops to Free by default (no charge, nothing deleted). Picking Pro or lower during the trial charges only when the trial ends (or its credits run out); picking Power/Power Plus charges immediately and ends the trial. Referred friends get 14 days instead of 7. Extensions only by emailing support.
Card requiredNo (Free and the Pro trial need no card; a card is only needed to pick a paid plan)
What free actually allowsTrial: full Pro features with an unpublished trial-credit batch that doesn't refill. After the trial, Free = 30 chats/month, weekly briefing only, no custom routines, no triggers; paid-only routines 'pause until you upgrade'. Starter has schedule triggers only and no overage, so the live email/meeting automations from the trial need Pro ($49).
How usage is shownSettings → Plan & billing shows remaining credits and position in the cycle, a '% left' meter for plan credits with promo credits on a separate line, a daily usage chart by usage type, a per-routine credit table, and an 'Optimize credit usage' button that opens a cost-cutting chat with the Townie (step 17). Escalating emails at 80% ('You've used 80% of your Town Credits'), 90%, and 100% ('You're out of Town credits', or 'You've used all…' when PAYG is on), plus an in-app usage banner (step 14).
Discounts & annual nudgesAnnual billing preselected with 'Save 20%' (Starter is monthly-only, which pushes annual buyers to Pro). No countdowns or intro prices. Referral: friend gets a 14-day Pro trial; referrer gets 2,000 credits for every friend who starts a paid personal plan, uncapped (step 15). Occasional promotional/goodwill credits appear as a separate balance.
Sales assistLight: Enterprise and trial extensions go through support@corp.town.com ('handled case by case'); the 30-second plan-recommendation calculator stands in for a sales call. No 'Book a demo' on the captured pages.
Time to valueNot measured (blocked). Docs promise 'a few minutes': connect email and calendar in onboarding (one step for Gmail + Calendar + Drive), name your Townie (gets an @town.com address), review the profile it builds about you, then first prompt (step 12).
Aha momentPer docs: right after the inbox connect, the Townie shows a profile it built about you (role, top contacts, how you communicate) and gets its own email address. During the Pro trial, live email- and meeting-triggered routines (auto-inbox, meeting briefings) run on their own; those are exactly what Free and Starter take away.
Account usedNot created. Sign-up is SSO-only (Continue to Google / Continue with Microsoft); no email path, so no throwaway inbox could be used.
Geo notePrices shown in USD from the India IP; no redirect.

Plans

PlanPriceBillingIncludes
Free$0 forever30 chat messages/month (no credits), weekly morning briefing only, all integrations, assistant via email/Slack/WhatsApp/Telegram, '7-day Pro trial on signup'; no custom routines or triggers
Starter$15/momonthly only1,250 credits/mo, daily briefing, auto-inbox triage/drafts/scheduling, 2 custom daily routines (schedule triggers only), 10 person-research lookups, 15 on-demand meeting briefings, email support; no overage
Pro (recommended, dark 'Try Pro')$49/mo billed annually (monthly 'slightly higher')annual preselected, 'Save 20%'5,000 credits/mo, unlimited custom routines, all trigger types (new-email, meeting-start), automatic meeting briefings, 50 person lookups, assistant-to-assistant, pay-as-you-go overage at $0.044/credit
Power$99/mo billed annuallyannual/monthly12,000 credits ('~2.4x the credits at lower per-credit cost'), 150 person lookups, priority model routing, higher concurrent routine limits; overage $0.038/credit
Power Plus$199/mo billed annuallyannual/monthly40,000 credits, unlimited person lookups, early access, email support with 2-business-day SLA; overage $0.032/credit
Team / Team Plus$59 / $149 per seat/moper seat6,000 / 18,000 credits per seat, pooled; overage $0.038 / $0.030. 'Team Free' exists for sharing integrations/routines but grants no credits and can't run background routines
EnterpriseCustomcustom contractvia support@corp.town.com

Paywall triggers

  • Trial ends at 7 days or when trial credits run out → drop to Free; custom routines and event triggers pause (steps 6, 13, 14)
  • Out of credits on Free/Starter → 'you'll be prompted to upgrade your plan'; both routines AND on-demand chats pause (steps 6, 14)
  • 80% / 90% / 100% credit emails and in-app usage banner (step 14)
  • Event triggers (new-email, meeting-start) gated to Pro+; Starter gets once-a-day schedule triggers only (steps 5, 16)
  • Free capped at 30 chats/month; assistant-to-assistant (Pro+) and priority model routing (Power+) locked (steps 3, 5)
  • Team Free can't run team background routines; an owner/admin must pick a paid team plan (docs, not shot)

Upgrade prompts & copy

  • Landing hero 'Meet your Townie' → /sign-up; 'Ask Bud anything' prompt box (step 1)
  • Pricing: 'Free to start, more when you're ready.' 'Pay Annually · Save 20%' preselected; Pro is the only dark button ('Try Pro'); 'Start free', 'Try Starter', 'Get started' (steps 2-3)
  • 'Still not sure? Get a recommendation in 30 seconds' → calculator that defaults to 3,000 credits/month, badges Pro 'Best fit for you' and marks Starter 'Doesn't fit' (steps 3, 7)
  • Overage section: 'When you hit your monthly limit, just keep going', 'steady overage is your upgrade signal' (step 4)
  • Settings → Plan & billing plan picker during the trial ('Switching to … on …', 'Keep current plan') and the 'Invite rewards' card (steps 13, 15)

Lifecycle emails

  • None arrived during the run.

What Kite could take from it

Caveats: No account was created, so onboarding, the in-app trial banner and plan picker come from Town's public docs (updated 2026-10-27), not observation. The size of the trial credit batch is not published anywhere public. Monthly-billing prices for Pro and above were not captured ('slightly higher' than annual). No emails were received; the 80/90/100% email subjects are quoted from the docs.

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