Director of Customer Success Management

We're at an inflection point. As Owner scales, our biggest opportunity - and risk -is ensuring our restaurant customers consistently realize meaningful value from our platform. As Director of Customer Success, you will play a vital role in ensuring our customers are ultimately successful with our product, increasing their retention and growth with Owner.

We're looking for a Director to define the trajectory of the Customer Success Management function - building a proactive, lifecycle-driven CSM organization that drives retention, expansion, and customer advocacy at scale. You'll bring senior leadership experience, a builder's mindset, and a genuine passion for helping small business owners succeed.

You’ll collaborate closely with the SVP of Customer Success, alongside other cross-functional teams, to continuously improve the customer experience.

This role is 100% remote and can be based anywhere in the United States or Canada.

- Own and elevate retention outcomes: Drive measurable improvements in customer retention by operationalizing value realization, adoption, proactive account management, and risk mitigation across the entire customer portfolio

- Transform the CSM model: Continue to drive the team towards a proactive, lifecycle-driven engagement model - focused on driving customer outcomes; establishing clear operating cadences, resourcing/org design, health scoring, and playbooks that scale with the business

- Build a high-performing org: Recruit, coach, and develop a team of CSMs and managers with a high bar for accountability, intellectual curiosity, and customer obsession - across all customer segments / products

- Innovate with AI: Build AI-augmented workflows across the CS motion - from health scoring and predictive analytics to customer communication and just-in-time enablement. Champion AI fluency across the team and set the expectation that every CSM actively uses AI tools in their day-to-day work

- Strengthen the end-to-end customer journey: Partner across onboarding, support, product, and sales to deliver a seamless, consistent post-sale experience

- Turn customer insight into action: Serve as the voice of the customer to Product, Engineering, and Marketing - translating feedback into actionable insights that shape the roadmap and GTM strategy

- SVP of Customer Success - your direct manager and strategic partner

- Sales & Marketing - to align on segmentation, handoffs, and expansion strategy

- Product & Engineering - to influence roadmap based on customer needs and friction points; build feedback loops powered by data synthesis and pattern recognition

- Support & Launch - to reduce reactive volume and create a cohesive post-sale experience at-scale

- Data, Operations & Enablement - to build the systems, reporting, and forecasting needed to run the business effectively

- 8–12+ years in Customer Success, Account Management, or similar customer-facing roles in SaaS or technology; SMB and Enterprise experience ideal

- 3–5+ years leading high-performing CSM teams, including managers and/or senior ICs, with clear operating cadences, performance frameworks, and a culture of continuous improvement

- Proven track record of improving retention and driving expansion in a recurring revenue business

- Comfort operating in a high-growth, fast-moving environment where you'll be building the playbook as you go - not inheriting a fully mature operation

- Deep understanding of value realization, ROI articulation, and lifecycle management

- Strong instinct for identifying churn risk and building repeatable save motions

- Experience owning or influencing renewals and expansion targets

- Ability to engage and influence executive stakeholders at customer accounts

- Highly data-driven; experienced building and managing to KPI frameworks and metric trees

- Deep expertise in core CS metrics: product adoption, time-to-value, revenue retention, etc.

- Ability to translate data into clear actions and priorities

- Strong AI fluency - you actively use AI tools in your work, have a clear point of view on AI's role in customer success, and can drive adoption of AI-augmented workflows across a team

- Ability to develop a clear framework for where AI should handle, assist, or defer to human CSMs across the customer lifecycle

- Exceptional talent builder with a history of hiring, coaching, and retaining top performers

- Experience developing managers and building high-performance, accountable cultures

- Proven ability to transform teams from reactive to proactive through strong change management

- Familiarity with SaaS platforms, restaurant tech, online ordering, or POS solutions is a plus

The estimated base salary range for this role is $190-210K, plus a generous pre-IPO equity package

Other benefits include comprehensive health coverage, remote-first workplace, unlimited PTO - plus extra fun perks!