Customer Support Retention Specialist

What You'll Do

• Conduct Retention Calls: You'll be on the front lines speaking with subscribers who have expressed intent to cancel, listening carefully and using good judgment to help them find a path forward.
• Make Tailored Offers: Work within an approved offer framework to present the right option for each subscriber - a discount, a pause, or sometimes just a good conversation.
• Handle Difficult Conversations: Approach every call with empathy and patience, including conversations where a subscriber ultimately decides to leave. Every interaction reflects Hallow's care for the person, not just the outcome.
• Track Outcomes & Surface Insights: Log every call and outcome accurately - what worked, what objections came up, and what would have changed the outcome. You'll be the person who knows best why subscribers leave, and the broader team will count on you to surface those patterns to improve the product and experience.
• Intercom Support & QA: In-between calls, you'll also answer live chat and email messages and support the needs of our community through our Intercom customer messaging platform, while helping ensure the quality of our automations and AI agent responses.

What You'll Love

• Mission: This work is incredibly humbling. Every day we hear amazing stories and we get the pleasure of working on something that's impacting lives. One of our favorite user quotes: "I hate quoting an old, overused cliche, but I've been very lost. And I think for the first time in a while I may be found."
• Ownership: You'll be directly responsible for keeping people connected to their prayer life. Every save is meaningful — not just for Hallow, but for the subscriber on the other end of the call.
• Growth: From day 1, you'll be a part of the startup journey. Over the next year, we'll build out the team significantly, and we'll need your help to build a world-class retention function.
• Flexibility: HQ is in Chicago (USA); this position is remote. We're flexible on location within the United States. This role is expected to be between 30-40 hours per week depending on volume.
• Comp: We will pay competitive market rates for this hourly contract position.

What We're Looking For

• Passion: First & foremost, we're looking for someone excited about our mission. It makes it a lot more fun :)
• Empathetic Communicator: You speak and write simply and warmly. You know how to meet someone where they are, you don't get flustered when someone's frustrated, and people feel heard when they talk to you.
• Good Judgment: You know when to offer a discount, when to push back gently, and when to let someone go gracefully — and you don't need a script to figure that out.
• Integrity: You care about the person on the other end of the call. You won't pressure someone into staying if it's not the right call. You're honest even when it means losing the save.
• Experience: 3+ years of experience in customer support, retention, customer success, or a related role — ideally handling phone calls for a subscription or consumer app environment. Experience specifically handling inbound cancellation calls, retention or "save" programs is a strong plus. Native or near-native proficiency in spoken English is required. Experience with tools such as Intercom, Slack, and ClickUp and foreign language skills in Spanish, French, Italian, Portuguese, Polish, or German are also a plus.