Customer Success Manager - Retention (US/Canada)

The Opportunity & You

Owner.com is growing quickly, and we are looking for a strategic and results-driven Customer Retention Manager to join our team. In this role, you will play a critical part in ensuring our customers continue to find value in Owner's offerings. This role operates across two tracks: proactively engaging a book of accounts to drive optimization and long-term value realization, and managing incoming cancellation requests with a focus on exceeding a 60%+ retention target.

• By leveraging strong communication, discovery, and objection-handling skills, the Customer Retention Manager will de-escalate concerns, translate customer data into compelling value narratives, and leave customers more bought-in by the close of the conversation.

The ideal candidate thrives in a fast-paced environment, excels at creative problem-solving, and knows how to independently shift focus between competing priorities as the day demands. They are equally comfortable building long-term customer relationships as they are navigating a high-stakes cancellation call, and they use data to do both.

👀 What We Look For

• A customer-centric approach, handling conversations with empathy, professionalism, and a solutions-first mindset.
• Strong communication and negotiation skills with an expertise in uncovering pain points, objection handling, and de-escalation techniques to retain customers and address concerns effectively. This includes a consultative approach to problem-solving — you know how to guide a customer toward the right solution without it ever feeling like a pitch.
• The ability to translate customer usage data and ROI metrics into compelling, real-time narratives that shift customer sentiment.
• Proficiency in interpreting and analyzing customer data to identify trends, wins, and opportunities for growth.
• Quick thinking and creative problem-solving skills to manage challenging situations and customer objections in real time.
• The ability to self-prioritize and context-switch fluidly — this role manages both scheduled reactive retention calls and proactive optimization outreach, and you'll need to independently assess which queue needs your attention most at any given moment.
• Mastery of time management and prioritization in a fast-paced, dynamic environment. Daily outreach runs 20–25 dials/contacts per day across both reactive and proactive work streams.
• Strong collaboration skills to work with Customer Success Managers and cross-functional teams.
• Process-oriented, with the ability to identify inefficiencies and optimize workflows for better results.

Minimum Requirements

• 2+ years of experience in a Customer Success, Account Management, or Retention role, ideally in a SaaS or subscription-based environment.
• Demonstrated track record of hitting retention, save-rate, or account health targets. You can point to specific metrics, not just outcomes.
• Experience managing a high-volume, call-based workflow and comfortable owning outbound and inbound outreach simultaneously and self-directing your prioritization throughout the day.
• Ability to interpret customer data and usage trends and communicate them clearly and persuasively to customers in real time.
• Experience with Customer Success tools, including (but not limited to) Salesforce, SalesLoft, TalkDesk, Gong, Loom, and Metabase.
• A background in B2B2C, ideally within the food/hospitality and technology space. You are familiar with industry trends and competitive dynamics and eager to share that knowledge with your team.
• A commitment to personal growth and continuous development.
• Bonus: Experience working in a restaurant, bringing additional perspective to the role.

Pay and benefits

• The estimated base salary for this role is $90,000 - $100,000 USD, / $125,500-$139,500 CAD
• Other benefits include comprehensive health coverage, work from anywhere (100% remote workplace), unlimited PTO - plus extra fun perks!