Check-In by Ascendvent

The Challenge

Coaches often reconstruct what happened between sessions from messages, notes and memory. Client updates and open commitments are scattered, leaving the coach to piece them together before the next conversation.

I found this problem while exploring a consumer AI confidence product for creators and PMs. Interviews and ad experiments kept surfacing practitioners’ follow-up and session-preparation work. Check-In focuses on that work for 1:1 coaches.

Key Decisions

• Stop when the unit economics fail

  Ads drew clicks and interviews validated the confidence problem. Customer acquisition looked expensive and the unit economics didn’t work, so I stopped the B2C product six months in. The early interest wasn’t enough to support the business.

• Build for the practitioner

  Coaches, tutors and mentors described practices held together by email, calendars and spreadsheets. I shifted toward their follow-up and session-preparation work. Consulting gave me direct access to those day-to-day operations before I wrote product code.

• Keep Check-In to one workflow for launch

  The first release connects the follow-up after a session to preparation for the next one. I can test B2B distribution and willingness to pay before expanding the platform.

• Require coach approval before sending

  Check-In drafts the email from the client’s goals and commitments. The coach reviews it, edits it if needed and approves it before the client receives it. Nothing goes out without the coach’s approval.

What I Delivered

• Check-in drafts and approval

  The coach adds the client’s current goals and commitments, then reviews the AI-drafted follow-up before sending it.

• Email-based client responses

  The client responds through the link in the approved check-in email.

• Pre-session briefs

  Check-In brings the client’s response and open commitments together for the coach to review before the next conversation.

Status

Example brief

The composite example on the product page illustrates how the brief handles uncertainty. A client moves quickly past a potentially important comment. The brief presents two possible readings: a disclosure the client moved away from, or a passing remark. It suggests asking the client to clarify before the coach changes the session’s direction.

This is an illustrative example, not a measured customer outcome.

Current status

Check-In is live and free for up to three clients. Pro costs $40/month for unlimited clients. Every plan includes check-in drafts, email-based client responses and pre-session briefs.