Customer Success Manager - Retention (US/Canada)

About Owner Owner is the AI-native system local business owners use to succeed, starting with restaurants. We’re building the system that replaces the many tools owners use to run their business. It powers everything from the restaurant’s website, online ordering, CRM, POS, and more. Product philosophy Most small business software makes owners do the work to get what they want: sales growth and profit growth. Owner does the work for them agentically. Our system drives demand, converts it, and helps operators run their business day to day. As it improves, the business improves with it. Using Owner should feel like having a team of great operators, engineers, and marketers working for you. Our vision We’re starting by helping independent restaurants succeed online. But it’s not just restaurants that need our help. Most local businesses are struggling with these same problems. Huge technology corporations are taking their customers, bleeding their profits, and making it hard for them to survive. Once we nail the solution for restaurants – we’ll scale it into every other local business type. In the future we envision, tens of millions of local business owners will use our technology to succeed in the digital age. Read our Series C memo here → Our traction Since 2020, we've generated tens of millions in revenue and processed over a billion dollars of online orders. 1 in 5 Americans have used an Owner.com website. More importantly, we’ve helped over 20,000 restaurant owners, and saved them nearly $200 million in fees. Our team Our team is now in the low hundreds. We’ve got top talent from the most successful companies in SMB software, including: Shopify, HubSpot, DoorDash, ServiceTitan, Rappi, Faire and Stripe. We’ll be scaling even faster in 2026 to keep pace with our customer growth. Where we work Owner is a remote-first, global company headquartered in San Francisco, with a sales hub in Toronto. For a few of our roles we prioritize in-person collaboration at one of our office locations. Most of our teammates are distributed throughout the globe. Please review the role description and discuss with your recruiter for more details on location! 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: We are seeking candidates who bring a solution-focused mindset and strong interpersonal skills to thrive in a fast-paced environment. Specifically, we value individuals who have: 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. The Impact You Will Have: Deliver a world-class customer experience in collaboration with our Operational teams. Own a dual-track book of business: approximately 50 accounts in a proactive capacity focused on optimization and value realization, and approximately 15 accounts in a reactive retention capacity focused on saving at-risk customers. You'll manage both simultaneously and know when to shift focus. Drive customer retention with a target save rate of 60%+, reducing churn through a combination of relationship management, data-informed storytelling, and genuine problem-solving. Help customers improve ROI through strategic, personalized advice and solutions. Play an integral role in refining health metrics and identifying what it takes to scale success across our entire customer base. Influence Owner.com's product roadmap by uncovering product opportunities. Set the stage for strategic follow-up with CSMs and surface actionable insights for Product, Sales, and Marketing. ✅ Minimum requirements To be considered for this role, you should meet the following qualifications: 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! Notice - Employment Scams Communication from our team regarding job opportunities will only be made by an Owner team member with an @owner.com email address. We do not conduct interviews over email or chat platforms, and we will never ask you to provide personal or financial information such as your mailing address, social security number, credit card numbers or banking information. If you believe you are being contacted by a scammer, please mark the communication as "phishing" or “spam” and do not respond.