SECTION I · THE BRIEF
Brief #59723Updated 24 JUL 2026SASKATOON, SKBamboohrGV
Employbl Company Profile

Senior Product Manager

Yesware, Inc. develops and distributes sales and communications software. The Company's software enables sales people to track emails, create custom templates, prospect, and communicate with customers using email or…

Location
Saskatoon, SK
Company size
50–100
Posted
1mo ago
Via
Bamboohr
Section II · Full ProfileFree with an account
  • 01Comp band & equity packageLocked
  • 02Seniority & experience requirementsLocked
  • 03Interview process & rubricLocked
  • 04Hiring manager & team contextLocked
  • 05Growth trajectory in this roleLocked
  • 06Offer & decision timelineLocked

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Senior Product Manager

Yesware· Saskatoon, Saskatchewan, CanadaView company profile


Job title
Senior Product Manager
Job location
Saskatoon, Saskatchewan, Canada
Job description

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 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

  • Define, present, and execute a 12–24 month comprehensive product strategy 
  • 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.
  • Prototype hands-on with AI. Build high-fidelity, working prototypes of AI-powered experiences 
  • Own evaluation and quality frameworks for AI features to prove reliability at scale 
  • Own product decisions across billing and ordering & inventory 
  • Uphold a correctness-critical mindset in domains where defects directly affect revenue and customer trust
  • Maintain awareness of relevant financial, payment, tax, and data-security obligations 
  • Drive quarterly strategic planning across both development teams


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 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.
  • 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.

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Yesware headquarters

Boston, MA

Company size

50100 employees

Founded

2010

Total raised

$47,050,000

View company profile ↗

Funding rounds