About the Role
We're looking for a hands-on Manager of Customer Success to lead our growing post-sales team. This is a true player-coach position - you'll own the team's performance and culture while remaining deeply involved in the day-to-day: taking tickets when required, jumping on escalations, and maintaining direct relationships with our most complex customers.
You'll be joining a well-funded, small startup founded in 2020 with clear product-market fit in the accounts receivable space. At this stage, you won't inherit a finished playbook - you'll help continue to write it. That means continuing to work with the team to build the processes and customer journey rhythms, and customer engagement motions that will carry us through our next phase of growth.
Our customers rely on our platform to manage critical financial workflows, so your team is the front line for issues that directly impact their operations. You'll be expected to drive real commercial outcomes - retention, expansion, and adoption - not just keep the queue clear. You'll need the technical depth to understand how our system integrates with customer ERPs and financial stacks, and the interpersonal skill to navigate difficult conversations when things go wrong.
What You'll Do
Lead the team
- Manage a team across onboarding, Tier 1 and 2 support and customer success - own performance, morale, and growth through 1:1s, goal-setting, and hard conversations when needed.
- Define and enforce team KPIs (CSAT, response time, resolution time, onboarding completion), and stay hands-on by taking tickets and leading tough customer conversations yourself.
- Be the final escalation point internally and externally; hire and ramp new team members as the company grows.
- Own support workflows, escalation paths, playbooks, and tooling (ticketing, CRM, knowledge base); continuously improving them as we scale.
Drive customer outcomes
- Support and be accountable for the full post-sale journey and team - onboarding through renewal - with a relentless focus on time-to-value and long-term retention.
- Monitor account health and feature adoption via embedded tools; track usage patterns to proactively identify churn risks, measure time-to-value, and re-engage accounts that aren't getting full value from the product.
- Partner with Sales on renewals and expansion, leveraging deep feature-adoption metrics and customer insight to identify expansion opportunities and bring data to every conversation.
- Be the voice of the customer internally. Surface friction patterns to Product and Engineering, and start building a segmented engagement model for high-value accounts.
- Build training materials, self-serve resources, and onboarding sessions for partners and integrators - proactively closing knowledge gaps that drive unnecessary support volume.
- Report on team and customer health metrics to leadership; use data to identify what's working and where to focus next.
What You Bring
- 4-6 years in customer support, customer success, or technical account management - with at least 2 years managing a team directly.
- Proven player-coach: equally comfortable running a team and jumping into tickets, calls, and escalations yourself.
- Comfortable with hard conversations - performance issues with direct reports and tense escalations with unhappy customers.
- Solid understanding of how SaaS products connect to customer systems via APIs and integrations - you can troubleshoot without writing code.
- Experience with B2B SaaS and support/CRM tooling (Zendesk, Intercom, HubSpot, Salesforce, or similar).
- Strong communicator - clear and calm under pressure, with high emotional intelligence.
- Self-starter who thrives in ambiguity and builds structure where there isn't any yet.
- Familiarity with financial workflows (AR, invoicing, ERP systems) is a strong plus.
Nice to Have
- Background in fintech, accounting software, payments, or AR/AP platforms.
- Experience building partner or reseller enablement programs.
- Experience scaling a CS or Support function from an early stage.
Compensation range: $125,000 - $135,000 base salary CAD + up to 15% annual bonus.
Why Join Benji Pays
- A true startup experience with well-funded backing with a strong runway and clear growth trajectory.
- A product customers genuinely depend on and have impact. Your work directly impacts their financial operations.
- Collaborative, low-ego team that values people who 'get stuff done'.
- Health Care Spending Account assisting you and your family with your most important health needs.
- Opportunity to grow further in your role as the company scales.
- Our office is right in the heart of downtown Vancouver with stunning ocean and mountain views from one of the city's most exclusive business neighbourhoods.
- Easy commute with close access by SkyTrain, West Coast Express, or car.
- We support a hybrid lifestyle with a focus on work-life balance out of our Vancouver office.
- Stocked kitchen with local coffee and snacks.
- Mac laptops so you can do your best work.
Exceptional Opportunities Are Rare
Benji Pays is not your typical software company. When we hire you, we are not just offering you a job; we are committing to investing in you and your long-term career. You'll help shape how this innovative company operates and make a genuine impact on the future of our people, product, and clients.
