Keep customers happy, active, and growing, before they ever reach the “I’m canceling” point. In this role, you’ll proactively reach out to at-risk accounts, run retention and reactivation plays, and uncover upsell opportunities while supporting payments and product issues when needed.
About Booksy
Booksy is a global platform that helps service businesses and entrepreneurs run and grow, while helping customers easily book their “me time.” They’re remote-first, fast-moving, and scaling, which means you’ll have real room to make impact if you’re the kind of person who thrives in change.
Schedule
• Full-time, remote (United States)
• Remote-first with flexible work schedules (office access may vary by market)
• Non-exempt role
• Outbound-heavy role focused on churn prevention and reactivation
What You’ll Do
⦁ Proactively engage customers showing churn risk through outbound communication to prevent cancellations and drive retention.
⦁ Run reactivation efforts for inactive customers, resolving blockers and getting accounts back on track.
⦁ Identify upsell and cross-sell opportunities and collaborate with internal teams to build migration or expansion plans.
⦁ Manage ongoing customer relationships, track sentiment, and conduct satisfaction surveys to spot improvement areas.
⦁ Provide product support as needed, including basic technical troubleshooting and guidance.
⦁ Handle payment-related issues and help customers navigate solutions that keep them active and successful.
⦁ Document activity and outcomes in CRM tools (Salesforce, Zowie, Google Suite, or similar).
What You Need
⦁ Hands-on experience in customer success, retention/reactivation, sales, or similar customer-facing roles.
⦁ Strong persuasion and negotiation skills with the ability to build long-term B2B relationships.
⦁ Proven organization and time management in a fast-moving, high-touch environment.
⦁ Comfort using CRM and support tools (Salesforce, Zowie, and Google Workspace or similar).
⦁ Strong problem-solving mindset, proactive attitude, and team-player energy.
⦁ Fluency or native-level Spanish (required).
⦁ Industry experience is a plus.
Benefits
⦁ $40,000 to $50,000 base salary plus bonus.
⦁ Comprehensive health, dental, and vision coverage.
⦁ Company-paid short-term disability and $25,000 basic life insurance.
⦁ 401(k) with 50% match up to 6% (annual contribution, 3-year vesting).
⦁ PTO: 160 hours per year for non-exempt employees (does not roll over).
⦁ 12 weeks paid parental leave.
⦁ EAP plus voluntary pet insurance through Fetch.
⦁ $50/month Booksy credit for services booked through the app.
⦁ Discounts via SmartSpend.
If you’re bilingual, persuasive, and you get a weird satisfaction from saving accounts that are halfway out the door, this is a strong fit. Apply while it’s open.
You’ll be the reason businesses stick around and keep winning.
Happy Hunting,
~Two Chicks…