Head of Operations

About Benji Pays

At Benji Pays, we're on a mission to revolutionize how businesses get paid. We build automated accounts receivables solutions that help businesses streamline their financial operations, reduce manual errors, and improve cash flow — and we're growing fast.

Our success is driven by a commitment to innovation, excellence, and delivering an amazing customer experience from sales to support and all through the customer journey. You'll work on real problems that have a real impact, and you'll see exactly how your contributions help take this company to the next level.

If you thrive in an environment where great work is valued over titles, and you want to be part of something that genuinely moves the needle for our customers, you might be the perfect fit.

Our Core Values

At Benji Pays, our core values shape everything we do:

• Integrity - We believe in doing the right thing, always.


• Consultative - We listen and provide expert guidance. 


• Solve Real Problems - We are dedicated to finding effective solutions.


• Get Stuff Done (GSD) - We are proactive and results-oriented. 

About the Role

We’re looking for a hands-on operational leader to own and drive the day-to-day running of our business. We have foundational structure in place and are looking for someone to build on that momentum — formalizing processes, closing gaps, and establishing the operational backbone that will carry us through our next stage of growth.

This isn’t a pure strategy role. We are looking for someone who has done this before. We need a player-coach who has thrived in fast-moving startup environments, can balance strategic thinking with day-to-day execution, and is confident managing experienced stakeholders — including founders — without waiting for direction. You’ll have broad oversight across every function, serving as the connective tissue between our CEO’s vision and the team executing it, with a clear path to COO for the right person who can demonstrate impact as we continue to grow.

What You’ll Do

Full Organizational Oversight

• Coordinate and align all functions across the business — Revenue (Marketing, Sales, Customer Success, RevOps), Finance, People & Culture, and Product & Engineering.


• Serve as the primary escalation point for cross-functional issues, blockers, and coordination gaps.


• Ensure every function is moving in alignment with company priorities and operating efficiently.


• Act as a key decision-maker empowered to drive changes quickly across the organization.

Operating Rhythm (Entrepreneurial Operating System (EOS) Framework)

• Own and manage the full EOS cadence — weekly leadership and team meetings, monthly scorecard and rock reviews, and quarterly planning sessions.


• Define and track quarterly rocks (short-term objectives) across the leadership team.


• Maintain and evolve the organizational accountability chart.


• Build and manage a KPI framework that gives the leadership team clear, consistent visibility into performance.


• Drive annual operating plan development in partnership with the CEO.

Process & Capability Building

• Lead the annual improvement plan and own initiatives that build organizational scalability.


• Assess existing processes, identify gaps, and systematically close them across all functions.


• Strengthen revenue function workflows across Marketing, Sales, and Customer Success.


• Design and embed process improvements alongside the team — you’re in it with them, not just recommending them.


• Drive change initiatives from end to end, including stakeholder alignment and execution.

Strategic Coordination & CEO Leverage

• Translate CEO priorities into clear organizational direction across all departments.


• Facilitate cross-functional alignment and surface blockers or problems before they escalate and bring a point of view on how to solve them.


• Maintain a clear line of sight between day-to-day execution and longer-term company goals.


• Manage and influence senior stakeholders, including founders and experienced executives, with professionalism and conviction.

What You Bring

• 8+ years in operations, with meaningful time in high-growth startups (SaaS experience a plus). You know what that chaos feels like and you know how to bring order to it.


• Proven experience thriving in fast-moving, ambiguous environments where structure needs to be built, not inherited.


• Hands-on EOS experience — you’ve run the system, not just been exposed to it.


• A track record of building and improving processes that scale across multiple functions.


• Demonstrated ability to manage and influence senior stakeholders, including founders and executives.


• Broad cross-functional fluency across Revenue, Finance, People, and Product.


• Strong independent judgment — you solve problems and drive decisions without waiting for all the answers.


• A player-coach mentality: you lead, and you do.

Compensation range: $155,000 - $175,000 base salary CAD + up to 20% 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.

We invite all qualified candidates to apply. Please note, you must be eligible to work in Canada to be considered for this role. We thank you for your interest; however, only successful applicants will be contacted.

Please, no recruiters or phone calls.