At Vendasta, we’re leading the AI revolution from right here in Saskatoon—and beyond. We work together to empower our partners and customers through our AI-powered customer acquisition and engagement platform to help them get more customers—and keep them. We’re proud to share that Vendasta has officially been named one of Canada’s Most Admired Corporate Cultures for 2025!
The mission of the Senior Product Manager is to drive the success of the R&D Platform Division's billing and ordering product portfolio by leading the development and execution of product strategies that align with the overarching vision and goals. The incumbent of this role demonstrates Customer Obsession, Ownership, and Earn Trust, alongside strong technical depth and will be responsible for defining 12–24 month product roadmaps, leading customer discovery, and executing go-to-market strategies with cross-functional teams.
Your Impact
Product Strategy & Roadmap Ownership:
- Define, present, and execute a 12–24 month comprehensive product strategy and 3-year vision for the platform portfolio that aligns with business objectives.
- Take full ownership of the product roadmap, prioritizing features and enhancements while anchoring decisions in deep customer research and data analytics.
- Lead discovery sessions, facilitate solution hypotheses, and run active experiments to validate assumptions and solve core customer problems.
AI-First Product Development:
- Prototype hands-on with AI. Build high-fidelity, working prototypes of AI-powered experiences (assistants, copilots, smart forms, automated workflows) using modern tools (e.g., Claude Code, Cursor, v0) and test them with users before full engineering scoping.
- Own evaluation and quality. Define eval frameworks for AI features (test scenarios, accuracy and quality thresholds, scoring rubrics, edge-case coverage, and ongoing monitoring) to prove reliability at scale and catch model drift, hallucination, and bias.
- Elevate the team's AI practice. Refine AI prompts and workflows to accelerate discovery synthesis, quantitative usage analysis (PostHog/Looker), and competitive research, and share repeatable AI systems across product leadership to expose hidden assumptions and mitigate risk early.
Billing & Ordering Domain Ownership:
- Own product decisions across billing (invoicing, payments, subscriptions/metering, revenue flows, reconciliation) and ordering & inventory (order management, fulfillment, inventory state), managing the dependencies where an ordering event drives a downstream billing event.
- Uphold a correctness-critical mindset in domains where defects directly affect revenue and customer trust; partner with engineering on data integrity, auditability, and security.
- Maintain awareness of relevant financial, payment, tax, and data-security obligations and partner with the right stakeholders to keep the portfolio compliant.
Cross-Functional Collaboration & Delivery:
- Partner closely with Product Marketing, Sales, Engineering, and Design (TLG) to define GTM narratives, activation, pricing, and messaging for major releases.
- Drive quarterly strategic planning across both development teams, maintaining high shipping momentum while proactively managing quality risks, cross-team dependencies, and conflict resolution.
- Foster an inclusive team culture built on transparency and continuous feedback, providing structured mentorship to associate product managers.
What You Bring to the Table
- 5–8 years of experience in Product Management, Product Strategy, or a related field: Preferably within a SaaS or technology environment.
- Bachelor’s degree preferred in Computer Science, Business, Engineering, or a related field preferred.
- Experience in billing, payments, subscription/monetization, or a commerce/ordering & inventory domain preferred (fintech, financial infrastructure, or commerce platforms).
- Ability to communicate clearly and effectively in written and verbal formats
- High proficiency in product strategy, quantitative analytics (e.g., PostHog, Looker), and customer research synthesis
- Demonstrated ability to build AI prototypes, define and run evals for AI features, write AI-ready requirements, and apply sound judgment on when to trust and verify AI output, backed by real, repeatable systems rather than one-off prompting.
- Strong track record of driving cross-functional alignment, managing complex product roadmaps, and leading hypothesis-driven experiments
- Experience coordinating a roadmap across multiple engineering teams with shared dependencies.
About Vendasta
We help businesses get more customers. And keep them. Vendasta is an AI-powered customer acquisition and engagement platform for SMBs and the partners who support them, streamlining marketing, sales, and operations through intelligent AI employees, automation, and real-time actions and insights. From creating awareness to nurturing lasting customer relationships, Vendasta offers a suite of solutions with AI assistants that streamline every stage of the customer journey. By combining a business's unique data with AI and automation, Vendasta simplifies marketing, sales, and operations, eliminating the need for multiple disjointed systems.
Perks
Join the Vendasta team, where your professional mastery and intellectual growth drive our platform forward. Step into an AI-first organization built for elite problem solvers who thrive on tackling complex business challenges and scaling sophisticated, automation-driven solutions.
Accelerate your professional trajectory through rigorous learning tracks, continuous operational development, and exposure to cutting-edge AI methodologies designed to push the boundaries of the B2B SaaS industry. We are bound by a high-performance culture rooted in our core values—Drive, Innovation, Respect, and Agility—where the true reward is the complexity of the challenge and the scale of your global impact. At Vendasta, you will find the infrastructure to build, the ecosystem to innovate, and an elite peer group required to sharpen your expertise.
Master your craft. Solve the impossible. Build the future of SaaS with us.
Skills Required
- 5-8 years of experience in Product Management, Product Strategy, or related field
- Bachelor's degree in Computer Science, Business, Engineering, or related field
- Experience in billing, payments, subscriptions/monetization, ordering, inventory, or commerce domains
- High proficiency in product strategy, quantitative analytics (e.g., PostHog, Looker), and customer research synthesis
- Ability to communicate clearly and effectively in written and verbal formats
- Demonstrated ability to build AI prototypes, define and run evaluations for AI features, and write AI-ready requirements
- Strong track record of driving cross-functional alignment and managing complex product roadmaps
- Experience coordinating a roadmap across multiple engineering teams with shared dependencies
- Experience in a SaaS or technology environment
What We Do
Our core purpose is to democratize technology for small businesses by making technology easy, accessible and affordable. We are a technology ecosystem that connects business with the vendors of products and services and the trusted experts that implement them. Trusted experts use our platform and marketplace to build a catalog of white label solutions to market, sell, bill, fulfill, and deliver to their business customers. Their business customers are provided access to a tightly integrated operating system, with a single login, to access all of the technology products and services they need to operate their businesses. Vendors of products and services provided a platform to manage the orders and fulfillment needed to manage their sales through our channel distribution network of over 10,000 trusted experts serving 6 million businesses
