Customer success portfolio · fictional company

Threadwell

Teams that grow together stay together

Threadwell is a year round team connection platform for remote and hybrid companies. It plans the annual offsite and a monthly rhythm of in person and virtual experiences, matches each team with the right facilitator, and measures whether people actually feel more connected.

Buyer
Head of People, remote and hybrid companies of 100 to 500
Model
Annual subscription, priced per employee
Mission
End loneliness and burnout at work through real connection
Point of view
Drinks don't build loyalty. Growing together does.

Why I built this

I built a customer success department from scratch in 2019. This is how I'd build it today.

At On the Map Marketing I hired and trained a team of 7, designed the onboarding process, and created a formal Sales to Customer Success handoff. We managed 200+ subscription accounts, and our retention strategy extended average customer lifespan by 3 months. Before that, at Vibes, I onboarded national retail brands onto an enterprise mobile platform. Since 2021 I've led 700+ people through workshops and 1:1 coaching. Threadwell is my answer to one question: what does that department look like with AI agents in the loop?

2019 · built by hand

  • Onboarding decks, email templates and CRM docs written one by one
  • A formal handoff with standardized workflows
  • A retention strategy built from account reviews

2026 · built with AI agents

  • Agents draft the onboarding plan, emails and CRM notes from the discovery call
  • The handoff brief is drafted from the sales conversation
  • A weekly health score flags risk long before renewal

The moment we're built for

Two strong people resign in one quarter.

Exit interviews say the same thing. They felt unsupported and disconnected. Pay never came up. Underneath it:

  • Teams work in silos and rarely help each other.
  • Leaders struggle to relate to younger employees and to people at different life stages.
  • Happy hours and one big offsite a year never built loyalty.

What changes

The old way

  • Happy hours and drinks
  • One offsite a year
  • Success means people showed up

The Threadwell way

  • Monthly experiences that make teams work better together
  • The offsite as the peak of a year long arc
  • Success means people feel connected and stay

Experiences invite reflection. They never require anyone to share. Employers see team level trends, never individual answers.

The customer success AI loop

A loop, not a funnel.

Customers move around the outer ring for as long as they stay. At the center, a learning loop turns everything that happens on the ring into better playbooks. AI does the noticing. People do the deciding.

Outer ring of six stages flowing clockwise back to the start. Inner learning loop: Signal, AI insight, Human decision, Action, Outcome, Learn. 01 Discovery 02 Onboarding 03 Adoption 04 Health 05 Renewal 06 Expansion Signal AI insight Human decision Action Outcome Learn Learning loop every outcome sharpens the playbooks

One turn of the loop · illustrative

  1. Signal. The agent tracks manager attendance at every session, across every account.
  2. AI insight. It spots a pattern: accounts where managers skip sessions are the ones whose health scores fall before renewal.
  3. Human decision. The Head of CS reviews the evidence and decides managers must be in the first session.
  4. Action. AI rewrites the onboarding plan template. A CSM approves it.
  5. Outcome. The agent compares health scores for new accounts against the old pattern for one quarter.
  6. Learn. If it holds, the playbook changes for good. If not, the team tries the next idea.

Around the ring

Six stages. Three kinds of work.

Every task on the ring sits in one of three tiers. Tap a tier to see it across the whole journey.

  1. Discovery

    Understand why they're looking now and whether Threadwell fits.

    Signal: a clear trigger and a named executive sponsorClaude skill · Discovery call

    Agent runs it

    • Research the company before the call: size, growth, remote setup, recent news, open roles
    • Log call notes and update the CRM
    • Send the recap within an hour

    AI drafts, human approves

    • A call brief with three guesses about their pain
    • The follow up email with next steps
    • A fit score with its reasoning

    Human only

    • Run the call and listen for the real trigger
    • Decide whether to move forward
    • Identify the executive sponsor

  2. Onboarding

    Deliver the first experience within 30 days of signing.

    Signal: days to first experienceClaude skill · Onboarding kickoff

    Agent runs it

    • Create the workspace and invite admins
    • Send the welcome sequence and schedule the kickoff
    • Track setup tasks and nudge owners

    AI drafts, human approves

    • A 90 day connection plan built from discovery notes
    • Facilitator matches for each team
    • The kickoff agenda

    Human only

    • Lead the kickoff
    • Agree on what success means, in the customer's words
    • Build the relationship with the sponsor

  3. Adoption

    Get every team into a monthly rhythm.

    Signal: share of teams with an experience in the last 30 days

    Agent runs it

    • Send reminders and post experience pulse surveys
    • Summarize feedback themes
    • Spot teams that haven't booked

    AI drafts, human approves

    • Next experience suggestions for each team
    • A tip sheet for managers before a session, such as leading across generations

    Human only

    • Coach hesitant managers
    • Adjust the plan when a team is in conflict

  4. Health monitoring

    See risk before the customer says it out loud.

    Signal: account health score

    Agent runs it

    • Score each account weekly on participation, repeat attendance, cross team pairing, manager involvement and the connection pulse
    • Alert the CSM when a score drops two weeks in a row

    AI drafts, human approves

    • A risk summary with likely causes
    • A suggested save plan

    Human only

    • Call the customer
    • Choose the save plan
    • Escalate internally when needed

  5. Renewal

    Renew on value the customer can see for themselves.

    Signal: renewal rate and contract value keptClaude skill · Renewal prep

    Agent runs it

    • Start renewal prep 120 days out
    • Pull usage and outcome data
    • Build the renewal timeline

    AI drafts, human approves

    • The value review, told in the customer's own success terms
    • The renewal proposal
    • Answers to likely objections

    Human only

    • Run the value review with the sponsor
    • Negotiate
    • Handle budget cuts with care

  6. Expansion

    Grow where the value is already proven.

    Signal: revenue added from existing customers

    Agent runs it

    • Flag teams and offices not yet using Threadwell
    • Watch for hiring growth

    AI drafts, human approves

    • An expansion case using results from existing teams
    • A proposal for the year's offsite

    Human only

    • Raise the idea with the sponsor
    • Build relationships with new department leaders

By role

How AI changes the week

Customer Success Manager

Less time on

  • Call notes and CRM updates
  • Recap emails
  • Building decks by hand

More time on

  • Real conversations with sponsors and managers
  • Save plans for accounts at risk
  • Coaching managers

Onboarding Specialist

Less time on

  • Chasing setup tasks
  • Scheduling
  • Writing the same welcome emails

More time on

  • Designing a first experience that lands
  • Building trust with new admins

Head of Customer Success

Less time on

  • Assembling reports
  • Hunting for at risk accounts

More time on

  • Patterns across accounts
  • Coaching the team
  • Feeding customer insight into the product

Guardrails

Where AI stops

Employee data stays at team level.No one's personal reflections ever reach their employer or the CS team.

Promises come from people.A human sends anything that commits Threadwell to price, scope or an outcome.

Every agent action is logged.The CSM can see what the agent did and why, and undo it.

Upset customers get a call.When a customer is unhappy, a person reaches out. Never an automated email.

Before and after · renewal prep skill

Eight months of data in. A renewal plan out.

The CSM hands the renewal prep skill one account file, 120 days before renewal. Here is part of what went in, and part of what came back.

What the CSM handed over

  • Renewal November 2, 2027 · 240 seats · 275 people now
  • Participation by month: 34%, 47%, 58%, 61%, 63%, 66%, 68%, 71%
  • Portugal at 41% in month 3, 57% in month 8
  • Month 8 call: finance wants every vendor to justify its renewal
  • Priya starts parental leave on August 16
  • Not on file: finance contact, engagement survey

What the skill returned

  • Risk: medium, because the sponsor is away during the renewal window
  • All three success measures met, each in Priya's own words
  • Recommendation: renew and expand to 275 seats
  • An honest answer ready for "Can't we run this ourselves now?"
  • Value review set for August 4, before Priya's leave
  • Gaps flagged, not guessed: finance contact, engagement survey

What AI didRead the data, scored each measure, spotted the risk hiding in a calendar date, and drafted the timeline, review outline and invitation email.

What the CSM decidesWhether the risk rating is right, how to talk budget with Tom, the price, and whether anything gets sent.

Case study

How I built this, and what it taught me.

What I built

What I learned

  • Check fit first. My first test account was bigger than Threadwell's 100 to 500 person range. The skill flagged it, and the range held.
  • Lead with work, not growth. Not everyone wants self growth from their employer. Value is framed as teams working better together, and onboarding plans for skeptics from day one.
  • AI is fast. Consistency is the human job. Four decks and three examples share one set of numbers. AI drafted them in minutes. Making sure every one still said 58% at month 3 was mine.
  • Draw the lines before building. Privacy and promises were settled before a single agent was designed.

What I'd do at your company

Days 1 to 30 · Listen

Join sales calls, read every churn note, shadow the team. Map where the hours go.

Days 31 to 60 · Pick one stage

Build one skill or agent for the most repetitive work, with a person approving every output.

Days 61 to 90 · Measure and teach

Hours saved, response times, customer sentiment. Keep what works, cut what doesn't, and teach the team to build their own.

AI does the noticing. People do the deciding.