If you’re quick on the keys, calm under pressure, and you actually like solving messy user issues, this role puts you on the front line of a fast-growing sports platform. You’ll support Sleeper Picks, help users win (and chill), and keep fraud and compliance issues from slipping through.
About Sleeper
Sleeper is a sports games platform built around messaging and community, designed to bring friends together around sports. They keep teams intentionally small so individual contributors can make real impact, and Customer Success is the heartbeat that funnels user feedback directly into product improvement.
Schedule
Remote within the United States
Full-time, 40 hours per week
5 days on, 2 days off schedule
Must be available for weeknights and weekends, plus holidays and major game days
What You’ll Do
• Support users across email, chat, and social media with timely, professional communication
• Resolve complaints and inquiries using solid conflict resolution and problem-solving
• Help onboard users and troubleshoot bugs and usability issues for Sleeper Picks
• Gather the voice of the customer and clearly communicate product/feature feedback to internal teams
• Support Regulatory Ops, Compliance, and internal partners with ad hoc requests and fraud reviews
• Review deposits and withdrawals for fraud signals to help protect users and the platform
• Support Operations and Fraud needs tied to user interactions and DFS gameplay
What You Need
• 1+ year of customer support or customer success experience (required)
• Strong written and verbal communication skills across multiple channels
• Strong troubleshooting instincts and the ability to ask the right questions to isolate root cause
• High empathy and customer-first mindset, even when users are heated
• Comfort collaborating across teams (Ops, Fraud, Compliance)
• Availability for a rotating schedule including nights, weekends, holidays, and big game days
Benefits
• Competitive salary (range not listed in the posting)
• Medical, dental, and vision insurance
• 401(k)
• PTO
• Remote work options and flexible working hours
• Opportunities for career advancement
Quick reality check: the schedule is the trade-off. If nights/weekends and big game days are a “no,” this won’t fit. If you can flex on timing and you like sports culture, this is a cool niche that can level up your support + ops + fraud muscles fast.
If you want, paste your current resume bullets and I’ll tailor them to hit the three big triggers here: multi-channel support, technical troubleshooting, and fraud/compliance collaboration.
Happy Hunting,
~Two Chicks…