Aimed at mid-level customer success leaders who thrive in high-growth SaaS environments and have experience scaling CSM functions with AI-driven workflows.
Derived from job-description analysis by Serendipath's career intelligence engine.
Original posting from Owner via Ashby
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 → https://www.owner.com/c
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 http://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!
Why we are looking for you
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.
The impact you will have
- 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
Who you’ll work with
- 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
- CSMs + CSM Managers - your team!
What we’re looking for
Experience & Leadership
- 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
Customer & Commercial Acumen
- 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
Operational & Analytical Strength
- 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
AI Fluency
- 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
People Leadership
- 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
Technical Fluency
- Familiarity with SaaS platforms, restaurant tech, online ordering, or POS solutions is a plus
Pay and benefits
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!
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.
Source: Owner careers (Ashby)