About Company Company is a fast-growing SaaS company with under 50 employees. We help organizations simplify and scale their expense management processes with an intuitive,

powerful platform. As we continue to scale, we are looking for a business builder who can step into executive leadership, own key commercial functions, and help us grow from startup to scale-up.

The Role

We are seeking a VP of Revenue & Customer Experience (with a explicit pathway to COO) who will partner directly with the CEO to work on the business, not in the business. This leader will independently run two of our core commercial functions (spanning Sales & Support, Sales & Success, or Support & Success) while maintaining broad familiarity with the third.

This role is ideal for a high-performing Director ready for their next step, someone with 8–12

years of experience combining strong analytical capabilities, operational rigor, and hands-on team leadership. You thrive in fast-moving, ambiguous environments, possess a heavy bias for action, and want to leave your mark building a business from the ground up.

Key Responsibilities

● Dual-Function Commercial Leadership: Directly own, lead, and scale two primary customer-facing functions (Sales, Customer Support, or Customer Success) while driving unified alignment across the broader commercial umbrella.

● Operational Strategy Execution: Design long-term strategy, operational roadmaps,

and cross-functional OKRs, utilizing frameworks from business operations, revenue operations, or professional services to drive execution excellence.

● AI Workflow Innovation: Bring a builder mindset to evaluate and implement AI tooling leveraging experience having built or prototyped with LLMs to automate operations and elevate team output.

● Build Scale Teams: Hire, coach, and grow hungry, smart people; foster an empowering culture rooted in ownership, accountability, bottom-up innovation, and our core company values.

● Metrics Accountability: Carry accountability for commercial results (managing quotas,



or operational targets) and build rigorous metrics, reporting, and analytics systems.

● Product Executive Partnership: Surface front-line customer and operational insights to influence product roadmap, onboarding, and GTM strategy, partnering directly with the CEO to scale the business.

Core Qualifications:

● 8–12 Years of Experience: Background in an operations role (RevOps, Sales Ops,

Support Ops) or strategic role (BizOps or Management Consulting / Professional

Services).

● Functional Management: Proven track record directly managing a team in one core area (Sales, Support, or Success) with broad familiarity and operational execution across a second.

● Small-Company Agility: Experience working in early-stage, fast-moving environments with a strong bias for action, high energy, and comfort navigating ambiguity.

● AI & Technical Capability: Hands-on experience building something using an LLM

(ideally a working prototype or internal product tool). Tech sector background is welcome, but non-tech backgrounds are also considered.

● Analytical + Leadership Balance: Unique combination of structured, data-driven analytical problem-solving skills and proven team leadership abilities.

● Value & Target Alignment: Track record carrying quotas, or equivalent operational targets, with strong alignment to cross-functional culture building.

Preferred Experience (Nice-to-Haves)

● Experience with finance/accounting/payment SaaS or products selling into the CFOs office.

● Experience with partnership models (banks, channels, etc.).

● Worked with $5-10K ACV products with complex onboarding.

● Experience pivoting horizontal SaaS to verticals.

● HubSpot fluency.

● Background in companies still iterating toward ICP.

● Leading remote/distributed teams.

Why Join Us?

● Impact: Step into a true builders role with high visibility to the CEO and Board.

● Growth: Clear pathway to step into the COO scope as the company scales.

● Culture: Entrepreneurial, ownership-driven environment with a heavy bias for action.

📌 Director, Revenue & Customer Experience (Winnipeg)
🏢 Gaia
📍 Winnipeg