Calendly · Go-to-market · Entry · 60 to 90 minutes

GTM plan for team routing to existing Calendly users

Calendly is a scheduling platform that lets people share booking links and automate meeting setup. Answer this product management case and get it graded line by line against a weighted rubric.

User segmentation
Go-to-market strategy
Metric design
Prioritisation
User empathy

The situation

The GM for self serve growth has asked you for a launch plan to help existing individual Calendly users adopt team scheduling workflows that route meetings across more than one person. Calendly already offers team focused scheduling features on some plans, but many users start with a single personal link and only later grow into a two to ten person workflow. In recent user interviews, some customers said they were manually forwarding meetings, sharing one teammate's link, or rotating ownership outside the product when more than one person could take a meeting. Assume the following numbers: among monthly active individual users, 24 percent host more than 30 meetings a month, 11 percent have invited at least one coworker to their account or workflow, and fewer than 4 percent try a team scheduling setup within 60 days of those signals. Leadership wants to improve expansion from existing users because it is cheaper than acquiring new teams. The tension is that most users are still truly solo, so heavy team messaging could hurt clarity and activation, and giving away too much could reduce the reason to upgrade.

What to produce

A 1 to 2 page go-to-market proposal.

Your answer must

Identify 1 to 2 target user segments within existing individual users, and name the product or behavioral signals you would use to find them.
Describe the main user problem and a clear value proposition for team scheduling that routes meetings to the right person.
Recommend a launch approach across specific channels, for example in product prompts, lifecycle email, trial or packaging, and explain why those channels fit the target segment.
Define 3 to 5 success metrics for the first 90 days, including at least one adoption metric, one conversion or revenue metric, and one guardrail metric.
Call out the biggest risks or tradeoffs, and propose one simple experiment or phased rollout to reduce uncertainty before a broad launch.

Constraints

You have one quarter for the initial launch, with one PM, one designer, four engineers, one lifecycle marketer, and shared analytics support.
Assume the motion must stay mostly product led and self serve, with no new sales team or large paid campaign.
You may change messaging, onboarding, packaging, or trial design, but you cannot rebuild core calendar integrations in this quarter.
Any sharing of scheduling data or teammate availability must follow existing account permissions and privacy rules.

Format

Use short sections with headings. A simple table for target segments, channels, and metrics is welcome if it keeps the plan clear.