Revenue Operations (RevOps) Role

Overview

You'll build and maintain the revenue infrastructure for Headspace's B2B2C business model. That means managing Salesforce, creating reporting dashboards, documenting sales processes, and supporting multiple GTM teams (enterprise sales, partnerships, maybe consumer growth). You're the person who makes sure data flows correctly from lead capture through closed-won and into customer success handoffs.

Role Snapshot

Company Context

Stage: Late-stage private (1550 employees, established consumer brand)

Size: ~1550 employees

Growth: Mature consumer app pivoting harder into B2B wellness programs for employers and health plans

Market Position: Strong brand recognition in consumer meditation/mental health space. Competing in increasingly crowded corporate wellness market against Calm, Virgin Pulse, Lyra Health, and traditional EAP providers.

GTM Reality

Pipeline Sources:

• Consumer side: App store downloads, paid social, content marketing, free trials (high volume, low ACV)
• Enterprise side: Outbound to HR/benefits teams, broker partnerships, health plan integrations (low volume, high ACV)
• Likely some inbound from companies whose employees already use the consumer app

SDR/AE Structure: Likely separate teams for SMB vs enterprise, possibly dedicated SDRs for outbound enterprise prospecting

SE Support: Probably customer success or implementation specialists who join enterprise sales calls

Competitive Landscape

Main Competitors:

• Consumer: Calm, Insight Timer, Ten Percent Happier
• Enterprise wellness: Calm Business, Virgin Pulse, Lyra Health, Ginger, Spring Health, traditional EAPs

How They Differentiate: Strong consumer brand recognition ("my employees already know Headspace"), science-backed content library, Andy Puddicombe's voice/brand

Common Objections:

• "We already have an EAP"
• "Isn't this just meditation? We need clinical mental health support"
• "How do we measure ROI/utilization?"
• Pricing concerns vs free alternatives

Win Themes: Brand trust, ease of adoption, breadth of content (sleep, stress, focus—not just meditation), mobile-first experience

What You'll Actually Do

Time Breakdown

Salesforce Admin (30%) | Reporting/Analytics (25%) | Process Documentation (20%) | Cross-functional Projects (15%) | Troubleshooting (10%)

Key Activities

• Salesforce Administration: Building custom fields, objects, and workflows to track enterprise deals vs consumer subscriptions. Creating validation rules, managing integrations with marketing automation and customer success platforms. You'll spend hours in Setup clicking through menus.
• Dashboard Creation: Building reports for sales leadership on pipeline coverage, win rates, sales cycle length, rep productivity. You'll be asked to slice data 47 different ways and explain why the numbers changed from last week.
• Forecasting Support: Pulling together weekly/monthly forecast rollups from multiple sales teams. Hunting down reps who haven't updated their opportunities. Building models to predict revenue based on historical conversion rates.
• Process Documentation: Writing out the deal review process, documenting lead routing logic, creating training materials for new sales hires. Most of this will need to be updated within 3 months because the process changed.
• System Integrations: Managing connections between Salesforce, marketing automation (probably Marketo or HubSpot), customer success tools (Gainsight?), data warehouse, BI tools. When something breaks, you're the first call.
• Sales Tool Evaluation: Testing new prospecting tools, conversation intelligence platforms, sales engagement systems. Building business cases for why the team needs (or doesn't need) the latest shiny tool.
• Cross-functional Meetings: Lots of syncs with sales, marketing, finance, customer success, and product teams. Everyone has an opinion on how CRM should work.

The Honest Reality

What's Hard

• Dual-Motion Complexity: Supporting both high-volume consumer subscriptions and long-cycle enterprise deals means your systems need to handle very different sales motions. What works for one breaks the other.
• Data Quality Issues: Sales reps don't update Salesforce consistently. You'll spend a lot of time chasing people to fix their opportunities or cleaning up bad data that makes your reports useless.
• Constant Change: Sales process changes every quarter. Leadership wants new reports. Marketing changes lead routing. You're always rebuilding things.
• Being the Bottleneck: Everyone needs something from RevOps. You'll have 15 Slack threads going at once, all marked urgent.
• Reporting Whiplash: Finance wants forecast accuracy. Sales wants to look good. You're stuck in the middle trying to show the real numbers while managing political dynamics.
• Mental Health Industry Context: You're selling wellness products during a period of economic uncertainty. Enterprise budgets for "nice to have" benefits get scrutinized when layoffs are happening.

What Success Looks Like

• Forecast accuracy within 5-10% of actuals
• Sales team actually uses the dashboards you build (not just leadership)
• Clean data that doesn't require manual cleanup before board meetings
• New sales hires onboard to CRM within 2 weeks without hand-holding
• System uptime—no "Salesforce is broken" fires during quarter-end
• Cross-functional teams stop creating shadow spreadsheets because they trust the CRM data

Who You're Selling To

You're not selling—you're supporting teams who sell to:

Consumer Side:

• Individual consumers looking for meditation/sleep/mental health support
• App store browsers, people Googling "meditation app"

Enterprise Side:

• HR Directors and VPs of People at mid-market/enterprise companies
• Benefits consultants and brokers
• Health plan partnerships teams
• Wellness program managers

What They Care About:

• Employee utilization and engagement rates
• Mental health outcomes and ROI data
• Integration with existing benefits platforms
• Ease of rollout and administration
• Clinical efficacy and evidence base
• Privacy/HIPAA compliance for health plans

Requirements

• 3-5 years in revenue operations, sales operations, or similar GTM systems role
• Strong Salesforce administration skills (admin certification preferred)
• Experience building reports, dashboards, and forecasting models
• SQL or data warehouse experience helpful for pulling custom reports
• Comfortable with multiple GTM motions (PLG, enterprise sales, partnerships)
• Process documentation and project management skills
• Cross-functional communication—you'll work with every team
• Ability to say "no" diplomatically when requests don't make sense
• Bonus: Experience in consumer subscription businesses or health tech
• Bonus: Familiarity with mental health/wellness industry regulations