Overview of How to balance a two-sided marketplace, with Care.com CEO Brad Wilson
In this episode of Masters of Scale, Care.com CEO Brad Wilson explains how he’s reshaping the company’s two-sided marketplace to better serve both families and caregivers. The conversation covers the economics of care, why employer benefits matter, how AI is changing operations, and why care infrastructure needs both private-sector and public-policy solutions. Wilson also shares how his own family experience deepened his commitment to Care.com’s mission.
The core challenge of Care.com’s marketplace
Wilson frames Care.com as a marketplace with a built-in tension: families want high-quality care at the lowest possible cost, while caregivers need fairer pay and better working conditions.
What was broken when he joined
- Conversion rates were below typical marketplace benchmarks, with less than 2% of users paying after matching.
- Messaging responsiveness and overall match quality were weak.
- The company’s consumer and enterprise businesses were operating too separately.
- The backend technology was outdated and slowed innovation.
How he thinks about the fix
- One brand, one team instead of separate operating systems for different business lines.
- A “ubiquitous care platform” that merges supply across consumer and enterprise use cases.
- More efficient matching and fewer fragmented systems across the company.
Care as a growing economic and family issue
Wilson emphasizes that Care.com is not just a convenience service; it’s becoming essential infrastructure for modern families.
The scale of the problem
- Most families juggle about four care categories: child care, senior care, pet care, and home care.
- Care costs are consuming a large share of income:
- Around 20% of income for child-care-related expenses
- Up to 40% when senior care and other needs are included
- Burnout is widespread:
- 90% report losing sleep
- 89% report feeling burnt out
The business opportunity
- Employers increasingly use caregiving benefits to improve retention and loyalty.
- Care.com serves both sides:
- Families get support and flexibility
- Companies get happier, more stable employees
How Care.com makes money and serves employers
Wilson outlines three main enterprise offerings:
1. Backup care
- Employers offer employees a set number of backup care days when primary care falls through.
- It’s positioned as a well-being benefit that reduces stress and increases loyalty.
2. Care concierge
- A guided support service staffed by master’s-level social workers.
- Helps with complex situations like:
- Choosing senior care
- Understanding payment options
- Navigating legal or family-care questions
3. Digital membership
- A lower-cost option for smaller businesses.
- Gives employees access to Care.com’s marketplace without a full backup-care program.
AI and the transformation of work at Care.com
Wilson says AI is helping the company improve both internal efficiency and customer support.
Where AI is already useful
- Debugging code and handling mundane engineering tasks
- Sifting through customer notes and case history
- Helping support agents make faster, better recommendations
- Accelerating research for care plans from days to hours
What AI is not replacing
- Human judgment in complex care decisions
- The personal and emotional parts of caregiving support
- The need for trained social workers and experienced staff
Digital transformation and technical debt
A major theme of the conversation is that Care.com had to slow down before it could speed up.
What Wilson changed
- Rebuilt the backend infrastructure
- Replaced key systems for:
- Authentication
- Messaging
- Payments
- Trust and safety
- Removed a lot of legacy, federated architecture
Why it mattered
- The old system limited experimentation and product launches.
- The company needed a strong technical foundation before it could move faster.
- Wilson says the company is now entering a more agile “transformation era.”
Brand, go-to-market, and the future of search
With AI changing how people discover products, Wilson says Care.com must meet users where they are.
Current go-to-market strategy
- Publish more authoritative, educational, and entertaining content
- Distribute through social media, influencers, and owned channels
- Build trust outside of traditional search and TV advertising
Brand repositioning
- Care.com is moving from being seen as just childcare-focused to being a broader “emotional ally” for all types of care.
Product direction
- Build AI directly into the product
- Focus on the full journey:
- Before hiring
- During the care relationship
- After the hire
- Move toward an “always-on” platform over time
Public policy and the future of care
Wilson argues that solving the care crisis requires more than private enterprise.
His policy view
- Government should help subsidize care more effectively
- Enterprise should continue to play a major role
- Technology must simplify matching and care access
Why in-home care matters
- More than half the country lives in “child care deserts”
- In-home care is often the only viable option, especially outside dense urban centers
Examples and momentum
- New Mexico’s universal child care is cited as a promising model
- Wilson wants Care.com to engage more actively at the federal and state levels
Advice for families hiring caregivers
Wilson shares practical advice based on both data and personal experience.
Best practices
- Be clear about expectations upfront
- Set boundaries and terms early, even informally
- Clarify:
- Hours
- Pay
- Mileage or driving compensation
- Responsibilities
A cost-saving insight
Families often already pay for other forms of home care, such as:
- Housekeeping
- Pet care
- Additional household tasks
Wilson notes that caregivers may prefer to take on more of these duties in one household, which can:
- Reduce travel between jobs
- Simplify schedules
- Lower total family costs
- Increase caregiver earnings
Key takeaways
- Two-sided marketplaces require constant balancing of price, quality, and fairness.
- Caregiving is becoming a core work-and-life infrastructure problem, not a niche service.
- Enterprise benefits are a major lever for helping families afford care.
- Care.com’s future depends on technical modernization, AI adoption, and clearer product value.
- Public policy and private enterprise both need to be part of the solution.
- Clear agreements and broader household planning can improve outcomes for both families and caregivers.
Notable insight
“We want to make sure that they get the best and most fair pay.”
Wilson’s central point is that care works best when families, caregivers, employers, and policymakers all share the load rather than forcing any one party to absorb the full burden.