Headspace · Go-to-market · Mid · 60 to 90 minutes

Grow Headspace sales to employers

Headspace is a mental health company best known for its meditation and sleep app, and it also sells workplace mental health benefits to employers. Answer this product management case and get it graded line by line against a weighted rubric.

Segmentation
GTM strategy
Buyer understanding
Prioritisation
Metric design

The situation

The GM of Headspace's employer business and the VP of Sales are asking for a go-to-market plan for the next planning cycle. Headspace has strong consumer brand awareness, but employer growth has slowed as HR teams face tighter budgets, more scrutiny from CFOs, and a crowded set of mental health and wellbeing vendors. Assume the following numbers are illustrative: inbound employer leads grew 18 percent year over year, but win rate fell from 26 percent to 18 percent, average sales cycle increased from 78 to 109 days, and only 32 percent of eligible employees at new accounts activate Headspace in the first 90 days. Feedback from recent deals says buyers like the brand, but ask who the true economic buyer is, how Headspace fits next to an EAP or other mental health benefits, what privacy protections exist, and what proof shows business impact beyond app downloads. Your job is to recommend which employer segment Headspace should focus on first, who the buying committee is, what sales motion and proof points to use, and where product support is needed without turning this into a large platform rebuild.

What to produce

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

Your answer must

Identify one primary employer segment to target first, using clear size, industry, or readiness criteria, and explain why it should be first.
Name the buying committee, including the economic buyer, likely champion, influencers, and common blockers in the deal.
Lay out the end to end motion from lead generation through signed contract and the first 90 days of employee activation, showing where sales, marketing, customer success, and product each contribute.
State the core value proposition and three proof points tailored to the chosen buyer, including how you would address ROI and privacy concerns.
Prioritise three initiatives for the next two quarters, with expected impact, dependencies, and what you are explicitly not doing.
Define success metrics with baselines, targets, and a measurement plan that covers both sales outcomes and post sale adoption.

Constraints

Use Headspace's current employer offering and brand assets, you may repackage or reposition them, but you cannot propose a net new clinical service.
Any employer reporting must be aggregated and privacy safe, no individual employee mental health data can be shared with employers.
You have two quarters, the existing employer sales team, one PMM partner, and engineering capacity for only small product changes such as onboarding, reporting, or admin tooling.
Assume there is limited incremental budget, enough for targeted campaigns and pilots, but not for a broad national brand campaign or major sales headcount expansion.

Format

Use sections for segment choice, buyer map, motion, proof, prioritised bets, and metrics. A simple table for funnel stages or initiatives is welcome.