VP of Customer Success

Vice President of Customer Success

About the Role

At Bucketlist Rewards, we help organizations make work more rewarding - and we're looking for a strategic, people-first VP of Customer Success to lead that mission. Reporting to the COO, you'll oversee our global Customer Success organization including Onboarding, Support, and Account Management, ensuring every customer achieves measurable value, retention, and growth through our platform maintaining our world-class NPS. You'll shape strategy, empower high-performing teams, and collaborate cross-functionally to drive adoption, expansion, and advocacy. This is an opportunity to build and scale a customer-centric function that directly fuels company growth and embodies our culture of recognition, innovation, and continuous improvement.

About Us: Bucketlist Rewards provides a leading B2B SaaS solution that allows organizations of all sizes to introduce effective rewards and recognition programs to its workforce. Our goal is to provide companies with an easy-to-use web platform that enables employers to reward team members in a meaningful way that matters to them, while achieving great business results and building better organizational cultures. When it comes to great company culture, the Bucketlist team walks the talk, and we are proud to be Great Place to Work certified

Key Responsibilities

Strategic Leadership

• Define and execute the customer success strategy aligned with company growth objectives
• Own success metrics, KPIs, and operational processes that drive predictable retention and expansion
• Partner with Sales, Product, and Marketing to bring the customer voice into strategic decisions and influence product direction
• Build financial models for the Customer Success organization including forecasting retention, expansion, and resource needs

Team Building & Management

• Recruit, develop, and lead a high-performing customer success team across Support, Onboarding, Account Management, fostering engagement, accountability, and growth
• Create a strong culture of customer advocacy, and a team culture unique to Customer Success
• Design and implement scalable customer success processes across onboarding, implementation, and account management to ensure consistency and efficiency as the organization grows
• Foster cross-functional collaboration and ensure Customer Success is the customer voice in our business strategy

Customer Experience & Outcomes

• Design and optimize customer lifecycle programs from onboarding through renewal and expansion, ensuring frictionless experiences and measurable outcomes
• Establish early warning systems for churn risks
• Create executive relationship programs for strategic accounts
• Improve systems and tooling that provide visibility into customer health, team performance, and operational effectiveness across the customer journey

Revenue & Growth

• Own retention and Net Revenue Retention (NRR) NPS and CSAT targets

• Build scalable customer enablement programs including training, certifications, and community engagement to deepen adoption and advocacy

• Partner with Product on roadmap prioritization based on customer insights

What You Bring

Required Experience & Skills

• 10+ years in Customer Success, Account Management, or related customer-facing roles
• 5+ years leading Customer Success teams, preferably in high-growth B2B SaaS environments
• Proven track record of building Customer Success functions from early stage through scale
• Experience managing teams of 10+ people across multiple customer segments

• Strong understanding of SaaS metrics including NRR, LTV, NPS and churn

• Strategic thinker who can balance long-term vision with execution excellence

• Data-driven decision maker with strong skills
• Excellent communicator who can influence at all levels including C-suite customers
• Ability to thrive in ambiguous, fast-paced startup environments
• Proven ability to design processes, systems, and teams that support rapid company growth at scale
• Experience using AI innovation to optimize Customer Success processes, uncover insights, and drive scalable growth

Nice to have:

• Experience in our industry vertical or with similar customer profiles
• Prior experience at a startup during hypergrowth phase (Series A-C)
• Experience running customer communities or advocacy program

The Perks:

• Growth Opportunities: Join a growing company where you'll be part of a high-performing team with lots of potential.
• Remote Work: We are a distributed workplace (100% remote). This position is open to anyone residing and able to work in Canada on a remote basis.
• Wellness Days: In addition to paid vacation days, we offer flexible paid time off to fit individual needs.
• Comprehensive Benefits Package: Includes health, dental, vision care, EFAP, and more.
• Annual Bucketlist Benefit: An additional paid day off and $$ to spend to help check items off your own bucket list
• Rewards and Recognition: We drink our own champagne We'll help you achieve not just your career goals but your personal goals as well

Compensation: The base salary range for this role is $150,000 to $180,000 CAD, plus quarterly performance bonuses. The final offer will consider factors such as your expertise and previous experience.

At Bucketlist Rewards, we are committed to fostering a diverse, equitable, and inclusive workplace. We believe that varied perspectives drive innovation and creativity, and we welcome applicants from all backgrounds and experiences. We encourage individuals from underrepresented groups to apply, as we strive to build a team that reflects the diverse communities we serve. We are dedicated to creating an environment where everyone feels valued, respected, and empowered to contribute their best work.