This is a save-the-account, grow-the-relationship role. You’ll proactively reach customers showing churn signals, bring them back from the edge, and help them get more value from Booksy through retention, reactivation, and smart upsell conversations.
About Booksy
Booksy is a global platform helping service professionals and small business owners grow, manage bookings, and deliver great client experiences. Their mission is simple: help people feel great and help entrepreneurs build thriving businesses. Booksy moves fast, scales globally, and rewards self-starters who like ownership.
Schedule
• Fully remote (United States)
• Full time, non-exempt role
• Remote-first culture with flexible schedules (market dependent)
• Outbound-heavy work focused on proactive retention and reactivation
What You’ll Do
• Proactively contact customers showing churn risk and implement retention strategies to keep them engaged
• Manage account reactivations through outbound communication and relationship rebuilding
• Identify upsell and cross-sell opportunities and collaborate with internal teams on migration or improvement plans
• Run satisfaction surveys, capture feedback, and surface trends to improve customer experience
• Provide product support and assist with payment-related issues to remove friction and reduce churn
• Track activity, outcomes, and customer health using CRM and support tools
What You Need
• Hands-on experience in customer success, retention/reactivation, sales, or a similar customer-facing role
• Fluent or native Spanish (required)
• Experience using CRM tools such as Salesforce, plus comfort with tools like Zowie and Google Workspace
• Strong communication, persuasion, and negotiation skills with B2B relationship confidence
• Organized, consistent follow-through, and strong time management across a high-volume book of business
• Problem-solving mindset with a proactive, team-first approach
Benefits
• Base salary $40,000–$50,000 plus bonus
• Comprehensive medical, dental, and vision coverage
• Company paid short-term disability and $25,000 basic life insurance
• Optional long-term disability
• 401(k) with 50% match up to 6% (paid annually, 3-year vesting)
• PTO: 160 hours per year for non-exempt employees (does not roll over)
• 12 weeks paid parental leave
• Employee Assistance Program (EAP)
• Voluntary pet insurance
• $50 per month Booksy credit for services in the app
• Discounts through SmartSpend
If you’re bilingual, persuasive, and you actually enjoy turning “I’m thinking of leaving” into “Glad I stayed,” apply now.
This is where relationship skills meet real revenue impact.
Happy Hunting,
~Two Chicks…