Six rented tools retired. One coaching platform Medley owns.
Medley runs cohort-based group coaching that helps organizations grow their leaders. Its programs had outgrown a patchwork of six disconnected tools and a 400-task launch checklist. We researched, designed, and built SGOS, the Small Group Operating System: one platform Medley owns, running every cohort from setup to the live session, with governed AI that supports coaches in the room.
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A live session in SGOS: leader notes, AI-suggested prompts the coach chooses to use, a shared whiteboard, and private notes.
Rented Tools Retired Into One Platform
Role-Aware Experiences on Shared Data
Coaching Sessions Run in Production
Concept to Production
A growing coaching company whose tools had become the ceiling.
Medley’s model works. Participants join small cohorts, coaches lead the sessions, and trained peer leaders sometimes run them. Partner organizations sponsor the programs, and Medley’s own group-matching method forms balanced groups, a real competitive advantage.
The operation behind it ran on six disconnected tools: Airtable, Asana, Bubble, Google Sheets, Google Docs, and per-user mailboxes, held together by a 400-task launch playbook and institutional memory. The same participant lived in six places, and every operational question meant an export and a manual reconcile.
This wasn’t a company in trouble. It was a growing one that wanted to run two to three times as many cohorts without growing headcount at the same rate, on software it owned.
What Medley engaged us to do
- Replace the tool patchwork with one cohort-management platform Medley owns
- Automate the 400-task launch playbook so every cohort starts fully set up
- Design the live session for coaches, peer leaders, and participants
- Add AI that helps coaches in the moment, with privacy and human control built in
Client
Medley
Industry
Coaching & Leadership Development
Services
UX Research, Product & Interaction Design, AI/ML, Full-Stack Engineering, Product Management
Platform
Web application with four role experiences and a partner view
Engagement
December 2025 to August 2026, two builds
Method
Capabilities
About Medley
Medley is the expert in group coaching for leadership development, built for Fortune 500 scale. Co-founded by Edith Cooper, former CHRO of Goldman Sachs, and CEO Jordan Taylor, it pairs a proprietary matching method with 100+ ICF-certified coaches.
A coaching room is personal. The software has to respect that.
Replacing six tools is an integration problem. Doing it for a business built on trust between a coach and a small group is a design problem first. Three dynamics shaped every decision.
01
Four people, one session
Who sees what is the product. A cohort manager, a coach, a peer leader, and a participant all touch the same session, and each needs a different view of it. The hard work was deciding what each person sees; the screens followed.
02
AI in an intimate room
Helpful, never intrusive. Coaching conversations are private. Any AI that listens has to be disclosed, controlled by the coach, and silent unless it has something worth saying.
03
A method worth protecting
Wrap it, don’t rebuild it. Medley’s group-matching solver is its own IP. We connected it to the platform as a service, so the method stays Medley’s and the old export-and-import loop disappears.
“Design who-sees-what first. The layout follows.”
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Medley’s matching, wrapped not rebuilt: the groups it forms and each coach’s coverage, in one view.
Four roles, four jobs, one connected system.
SGOS isn’t one interface. It’s four role-aware experiences on shared data. Each person sees only what their job needs, and every action flows into the others. A fifth view gives partner organizations a read on progress.
The cohort manager
Their job: launch and run cohorts, and know at a glance which ones need attention. In the product: program brief, schedule, group matching, and coach assignment; a Risks, Monitor, and On Track health view with one-click actions; the 400-task playbook, automated.
The coach
Their job: run a great session and support each participant, without prepping blind. In the product: pre-session prep, a configurable workspace with guide, notes, and shared whiteboard, AI insights they control, and an AI-drafted recap.
The peer leader
Their job: lead the group this session while still taking part in it. In the product: the coach’s facilitation workspace, with group-level signals only, never individual ones, overseen by the cohort manager.
The participant
Their job: show up prepared, stay present, and leave with a commitment. In the product: pre-work and check-ins, a focused session view, a private notebook, and a commitment they own. Their feedback quietly feeds cohort health.
Where the journeys meet
- Matching forms the groups, setting who the coach, peer leader, and participants will be.
- The manager assigns coaches, and each coach’s room begins.
- Pre-work, attendance, and feedback flow into the manager’s health view and the coach’s AI insights.
- AI listening is set by the coach, disclosed to the participant, and surfaced only to the coach.
“The AI suggests. Nothing becomes real until a human says it aloud, saves it, or sends it.”
The AI is a guest in the room, and it acts like one.
Coaching sessions are private, so the AI had to earn its place. The rules are enforced in the build, not just the design.
The constraint: an AI that listens to an intimate group conversation can’t record it, can’t single people out, and can’t act on its own.
The solve: the coach turns listening on, participants are told before the session, and the AI reads only a rolling five-minute window. A second model scores every output before a coach sees it, and nothing reaches a participant unless the coach says, saves, or sends it.
- Transcripts anonymized before the AI reads them; nothing recorded or stored
- Individual signals go only to the coach; the AI never calls anyone out by name
- Prompts grounded in the session’s own materials; if it can’t ground a suggestion, it shows nothing
- If the AI fails, the session carries on, and an AI-free mode is there for coaches who want none
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Airtime balance, shown with illustrative names: quiet voices are flagged to the coach, with a prompt to bring them in.
Run the cohort first. Then run the room.
We ran the engagement end to end, research, design, and engineering, and delivered it in two builds. Build 1 replaced the tool patchwork with a cohort-management platform. Build 2 added the AI-assisted live session, where the same session renders as four role-aware experiences.
The operating system that replaced the spreadsheets.
Cohort setup, health triage, sessions, scheduling, and coach assignment in one place. The 400-task launch playbook became a template engine, so every new cohort starts with its full task list already built and assigned.
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Every session in a cohort, with attendance and ratings as they happen, and health signals derived live, never from a stale report.
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The 400-task checklist that lived in Asana, now generated and assigned automatically for every cohort.
Six tools retired, the right ones kept
One platform Medley owns, connected to what still earns its keep.
- Airtable, Asana, Bubble, Sheets, Docs, and mailboxes retired
- Scheduling and forms connected rather than replaced
- Coach pay and invoicing built in
One session, four experiences
The same live session, shaped by each person’s role.
- Coach workspace with guide, whiteboard, notes, and Pause AI
- Peer-leader view with group-level signals only
- Focused participant view with a private notebook and a commitment
Medley’s method, protected
The IP that sets Medley apart stays Medley’s.
- Group-matching solver connected as a service
- Coaching method encoded in governed AI recipes
- Sign-in links instead of accounts to provision
Running real cohorts, not a demo build.
SGOS runs Medley’s coaching across every session format: coach-led and peer-led groups, 1:1 coaching, and workshops.
- 134 people on the platform, with 111 cohort enrollments
- 427 coaching sessions run across all four formats
- 1,531 tasks generated automatically from 323 templates
- About 100 backend services, 130+ database tables, and 7 rubric-backed AI recipes, each judge-scored
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The cohort manager’s view: what needs attention first, across every group.
Business value delivered: a platform Medley owns, built to scale its coaching.
SGOS is live in production. Six disconnected tools are one platform, the four-role experience runs across every session format, and governed AI supports coaches in the moment without ever taking a decision out of their hands.
Commercial Impact
The platform, the data, and the method belong to Medley, not a stack of vendors.
Designed for two to three times the cohort volume without matching headcount growth.
In-session coaching support that respects privacy, a feature buyers can see and trust.
Sponsoring organizations get their own read on cohort progress.
Operational Impact
One participant record instead of six, and no more export-and-reconcile to answer a question.
The 400-task playbook spins up every cohort with its tasks built and assigned.
Attendance, engagement, and satisfaction roll up into Risks, Monitor, and On Track, with one-click actions.
Pre-session prep, in-session insights, and an AI-drafted recap the coach approves.
Medley no longer rents its operation. It owns the platform it will grow on.
Explore Medley.
Medley is the expert in group coaching for leadership development, built for Fortune 500 scale. It helps organizations develop their leaders, especially the mid-managers who need the most support, through small peer groups led by certified coaches. SGOS now powers that work as Small GroupsOS, Medley’s AI-enabled platform for delivering group coaching.
“The #1 opportunity for us was to zoom in on mid-managers. This group needs the most support, at scale.”
Medley at a glance
- Co-founded by Edith Cooper, former CHRO of Goldman Sachs, and CEO Jordan Taylor
- 100+ ICF-certified coaches averaging 8+ years of group coaching experience, across every time zone
- A proprietary method: matching technology, program format, and coaches trained in Medley’s approach
- Programs tailored to each organization’s goals and context
If your business runs on rented tools, ask about ownership, not just features.
Growing service businesses often stitch their operations together from SaaS tools that were never meant to work as one. Moving to software you own pays off when the partner can answer these questions.
Do they start with your people or your screens?
The value is in who sees what and when. A partner who designs roles and handoffs first builds software people actually use.
Will they protect what makes you different?
Your method is your advantage. Wrap it and build around it rather than flattening it into a generic workflow.
Can they put AI in front of your customers responsibly?
AI that touches clients needs disclosure, human control, and guardrails enforced in the code, not just promised in a policy.
Do they know which tools to keep?
Retire what holds you back and connect what still works. Replacing everything for its own sake adds risk and cost.
These are the questions Digital Scientists is built to answer, and the ones we worked through with Medley.
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