If you’re built for saving accounts, calming fires, and turning “I’m about to cancel” into “okay, I’ll stay,” this is your lane. You’ll proactively reach out to customers who are at churn risk, fix what’s broken (product + payments), and keep businesses growing on Booksy.
About Booksy
Booksy is a global platform that helps service pros and small businesses (beauty, barbering, wellness, etc.) manage bookings and grow. Their whole mission is simple: help entrepreneurs thrive and help customers get their “me time” easily.
Schedule
• Full-time, remote (U.S.-based)
• Flexible work schedule (remote-first culture)
• Non-exempt role (hourly eligible for overtime rules, even though comp is stated as base + bonus)
What You’ll Do
⦁ Proactively contact customers showing churn risk and run retention plays through outbound outreach
⦁ Reactivate accounts and prevent cancellations by identifying root issues and driving solutions
⦁ Spot upsell/cross-sell opportunities and collaborate on migration plans when needed
⦁ Run satisfaction surveys and feed insights back to improve service and product experience
⦁ Provide product support, help troubleshoot issues, and coordinate across internal teams
⦁ Handle payment issues that may be blocking retention/reactivation
⦁ Manage your book of business with strong organization and time management
What You Need
⦁ Hands-on experience in customer success, retention/reactivation, sales, or a similar role
⦁ Comfortable using CRMs and support tools (Salesforce, Zowie, Google Suite)
⦁ Strong communication, persuasion, and negotiation skills (B2B relationships)
⦁ Problem-solver mindset, proactive, team-oriented
⦁ Consistent track record of staying organized and managing time well
⦁ Fluent or native Spanish (required)
Benefits
⦁ $40,000–$50,000 base salary + bonus
⦁ Medical, dental, vision
⦁ Company paid short-term disability + $25,000 basic life
⦁ Voluntary long-term disability
⦁ 401(k): 50% match up to 6% (paid annually, 3-year vesting)
⦁ PTO: 160 hours/year (non-exempt, does not roll over)
⦁ 12 weeks paid parental leave
⦁ EAP
⦁ Optional pet insurance (Fetch)
⦁ $50/month Booksy credit for services in-app
⦁ Discounts via SmartSpend
Quick real talk (backbone moment): this is not a “cozy support” job. It’s outbound, metrics-driven, and you’ll be talking people off the ledge daily. If you like the win of saving an account and you’re comfortable with “no” before “yes,” it’s a strong opportunity.
Happy Hunting,
~Two Chicks…