About This Role Title: Director of Customer Success Reports to: CRO Location: Remote Hybrid, Remote (Canada, US) Employment Type: Full-time About Bettermode Bettermode is a fast-growing B2B SaaS platform that helps mid-market and enterprise companies build modern customer communities that drive engagement, advocacy, and retention. Backed by investors such as CRV and Bessemer, we''re scaling from $5M ARR toward $20M+ with a small, high-impact team of 30+. We''re hiring a Director of Customer Success to own and scale our entire post-sale motion as we enter our next growth phase. The Opportunity This is a senior operating leadership role for someone who has built and scaled Customer Success before and is intentionally choosing to do it again at an earlier-stage company. As Director of Customer Success, you will own retention, expansion, time-to-value, and long-term customer trust. You''ll lead Customer Success, Onboarding, Support, and Solutions / Professional Services, and turn CX into a repeatable, scalable system. This is a hands-on role. You''ll design the systems, coach the leaders, handle escalations when needed, and make the hard trade-offs required to scale CX without bloating the team. This role reports to the Chief Revenue Officer (CRO) and works in close partnership with Product, Sales, and Marketing leadership. What You''ll Do Customer Outcomes & Revenue Protection Own Gross and Net Revenue Retention, including renewals and expansion motion design Drive customer adoption, value realization, and long-term trust Build predictable customer health, renewal forecasting, and expansion visibility Partner closely with the CRO on revenue forecasting and account strategy Post-Sale Organization & Systems Lead and scale Customer Success, Onboarding & Adoption, Support & Enablement, and Solutions / Professional Services Design clear role boundaries, handoffs, and escalation paths across the post-sale lifecycle Define customer segmentation and coverage models across Enterprise, Mid-Market, and PLG Ensure CX scales through systems, not headcount alone Onboarding, Support & Operational Excellence Reduce time-to-value and onboarding friction Improve support efficiency and CSAT without over-hiring Establish scalable playbooks, processes, and performance metrics Turn fragmented workflows into a cohesive CX operating system Cross-Functional Leadership Partner with Sales on deal quality, handoffs, renewals, and expansions Partner with Product to translate customer insights into roadmap input Partner with Marketing on advocacy, references, and customer proof points Act as the executive escalation owner for key customer relationships Serve as a strong internal leader and voice of the customer Team Leadership & Development Hire, coach, and develop CX leaders and individual contributors Set clear performance standards, expectations, and growth paths Build a culture of accountability, ownership, and customer empathy Create clarity, focus, and momentum across the CX organization What You Bring Typically 812 years of experience, with demonstrated ownership of multiple customer-facing functions in a B2B SaaS environment Prior experience scaling Customer Success at a $520M ARR company Experience managing cross-functional CX teams (CS, Onboarding, Support, Services) Strong operational, analytical, and systems-thinking mindset Comfortable operating in ambiguity and building from imperfect foundations Proven ability to influence Sales, Product, and Revenue leaders Hands-on operator who thrives in fast-moving startup environments Bonus Experience with PLG and Enterprise hybrid revenue models Exposure to professional services or complex implementations Background in SaaS platforms, communities, or configurable products Cultural Values We''re looking for someone who lives our core values: Focus: Eliminate noise, drive meaningful results. Bold: Take smart risks and challenge the status quo. Grit: Stay resilient through challenges and push through discomfort. Accountability: Take ownership, deliver, and support your teammates. Ambition: Set audacious goals and pursue them relentlessly. Benefits At Bettermode, we''re dedicated to empowering our team to thrive both professionally and personally. We offer location-based,competitive compensation that reflects your expertise and impact, with annual reviews so you can grow with us. Our culture is built on ownership and trust, giving you real influence over how we scale and succeed. From your very first day, you and your family are covered by comprehensive Canadian health benefitsdental and vision includedso you can focus on what matters most. Enjoy unlimited paid vacation days, paid parental leave to support your family, and bereavement leave should you need it. You''ll have all the equipment you need provided, or you can bring your own device and access our Device Upgrade Policyan interest-free hardware stipend repayable via payroll deductions, allowing you to upgrade when you need. We want you to thrive in your work: every team member receives a monthly Tech & Appreciation Stipendperfect for testing new tools and improving your workflows as you see fit. Additional Information Headcount: This is a vacancy at Bettermode. Compensation Range: CA$180-220k / US$180-220k AI Use: Large language models (LLM) might be used in the hiring process for this position to screen, assess or select job applicants.
Job Title
Director of Customer Success