Director of Customer Experience

(Remote)

About This Role

Title: Director of Customer Experience

Reports to: CRO

Location: Remote (Canada, US; must be EST or CST)

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 8–12 years of experience, with demonstrated ownership of multiple customer-facing functions in a B2B SaaS environment
• Prior experience scaling Customer Success at a $5–20M 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 benefits—dental and vision included—so 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 Policy—an 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 Stipend—perfect 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.