/
© 2026 RiffOn. All rights reserved.

Get your free personalized podcast brief

We scan new podcasts and send you the top 5 insights daily.

  1. Masters of Scale
  2. How to balance a two-sided marketplace, with Care.com CEO Brad Wilson
How to balance a two-sided marketplace, with Care.com CEO Brad Wilson

How to balance a two-sided marketplace, with Care.com CEO Brad Wilson

Masters of Scale · Jun 25, 2026

Care.com's CEO on balancing a two-sided marketplace by leveraging enterprise clients, overhauling tech debt, and advocating for policy change.

Unify Separate B2B and B2C Supply Pools into a Single Marketplace Platform

Care.com's enterprise and consumer businesses previously operated with separate pools of caregivers. A core part of their turnaround was merging this supply into a single "ubiquitous care platform." This eliminated redundancy, improved efficiency, and created a more robust network for all users.

How to balance a two-sided marketplace, with Care.com CEO Brad Wilson thumbnail

How to balance a two-sided marketplace, with Care.com CEO Brad Wilson

Masters of Scale·3 days ago

Increase Caregiver Wages by Bundling Household Tasks, Not Just Raising Hourly Rates

Care.com addresses wage/cost tension by encouraging families to consolidate tasks like pet care and housekeeping with one caregiver. This boosts the caregiver's total earnings from a single home, while reducing the family's aggregate spending on separate services.

How to balance a two-sided marketplace, with Care.com CEO Brad Wilson thumbnail

How to balance a two-sided marketplace, with Care.com CEO Brad Wilson

Masters of Scale·3 days ago

New CEOs Must Pause Feature Development to Pay Down Foundational Tech Debt

Care.com's new CEO paused new feature rollouts for 18-24 months to address a "very outdated" tech stack. This "infrastructure era" focused on replacing the entire backend—from authentication to payments—to enable future speed and innovation, despite the painful short-term slowdown.

How to balance a two-sided marketplace, with Care.com CEO Brad Wilson thumbnail

How to balance a two-sided marketplace, with Care.com CEO Brad Wilson

Masters of Scale·3 days ago

Motivate Engineers During Long Rebuilds With a Single, "Bold Swing" Product Launch

To keep teams engaged during a two-year backend overhaul, Care.com's leadership launched a "very bold" new go-to-market strategy mid-project. This challenging, tangible goal motivated engineers and product teams more effectively than abstract promises of future capabilities.

How to balance a two-sided marketplace, with Care.com CEO Brad Wilson thumbnail

How to balance a two-sided marketplace, with Care.com CEO Brad Wilson

Masters of Scale·3 days ago

Enterprise Sales Cycles for Employee Benefits Can Take 24 Months, Not 12

Care.com's CEO found that selling care benefits to enterprises takes longer than expected—often 18-24 months. This is because rising healthcare costs consume HR budgets, pushing care, considered a "one B benefit," to subsequent budget years and elongating the sales cycle.

How to balance a two-sided marketplace, with Care.com CEO Brad Wilson thumbnail

How to balance a two-sided marketplace, with Care.com CEO Brad Wilson

Masters of Scale·3 days ago

Care.com's Sub-2% Conversion Rate Highlights Critical Marketplace Health Metrics

CEO Brad Wilson reveals that upon joining, Care.com's conversion rate was below 2%, far from the 26% marketplace benchmark. This, along with low caregiver responsiveness, provided clear, quantifiable signals of a broken user experience that directed the new management's focus.

How to balance a two-sided marketplace, with Care.com CEO Brad Wilson thumbnail

How to balance a two-sided marketplace, with Care.com CEO Brad Wilson

Masters of Scale·3 days ago

Use AI to Augment High-Touch Experts, Not Replace Them

Care.com's concierge service uses AI to assist master's level social workers. The AI handles initial research for complex cases (e.g., finding senior care), reducing days of manual work to hours. This allows human experts to focus on creating high-value, personalized plans for customers.

How to balance a two-sided marketplace, with Care.com CEO Brad Wilson thumbnail

How to balance a two-sided marketplace, with Care.com CEO Brad Wilson

Masters of Scale·3 days ago