Customer Support Retention Specialist

Hallow • Chicago, IL

20h • Remote

About The Position

We're looking for a warm, tenacious communicator to join us as a contract Retention Specialist - someone who can meet a subscriber in a moment of doubt, listen well, and help them find a reason to stay. This work is incredibly humbling. Every day we hear amazing stories and we get the pleasure of working on something that's impacting lives. 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. 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.

Requirements

• 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.
• Native or near-native proficiency in spoken English is required.

Nice To Haves

• Experience specifically handling inbound cancellation calls, retention or "save" programs is a strong plus.
• Experience with tools such as Intercom, Slack, and ClickUp
• Foreign language skills in Spanish, French, Italian, Portuguese, Polish, or German are also a plus.

Responsibilities

• 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.

Benefits

• 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.
• 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 This Job Offers

• Career Level: Mid Level
• Education Level: No Education Listed