VP, AI Customer Delivery

Job Title: VP, AI Customer Delivery

Location: Office-first (Saskatoon, SK)

Why this Role Matters

The mission of the VP, AI Customer Delivery is to turn Vendasta’s AI product capabilities into highly repeatable, scalable customer outcomes across our partner network and SMB end clients . This role exists to eliminate deployment friction, accelerate time-to-value, and dramatically reduce customer churn caused by poor activation . Success requires world-class technical customer operations leadership, deep AI system fluency, cross-functional authority, and an owner mindset, enabling the delivery of standardized AI deployment playbooks, high-margin professional services, and automated cross-functional workflows

What You’ll Own

AI Deployment Excellence & Playbook Standardization

• Define standard deployment playbooks for AI employees and AI-powered workflows to achieve a scalable configuration model across large partners.


• Reduce implementation cycle times and shorten the time-to-value window for complex partner and SMB installations.


• Establish crisp handoff mechanics, entry/exit readiness criteria, quality assurance, and automated setup processes for all deployment pipelines.


• Translate custom implementation learnings systematically back into Product and Engineering teams to transform custom services into productized features.

Cross-Functional Operations & Governance

• Coordinate and drive operating cadences across Vendasta Services, Professional Services, Customer Delivery, Project Management, and Technical Project Management.


• Implement escalation governance and clear accountability interfaces matching Product, CS, Revenue, Finance, and RevOps.


• Define the lines of demarcation between standard onboarding frameworks, high-margin paid custom services, and standard product roadmap handoffs.


• Champion the "Think 10x" and "Build Trust" leadership principles by defining an ethical, secure, and hyper-scalable AI rollout vision company-wide.

Organizational Scaling & Capacity Strategy

• Design and architect the organizational structure covering technical project management, applied AI deployment capabilities, solutions architecture, and support.


• Hire, develop, and mentor leaders capable of operating at the intersection of technical AI deployment and commercial customer outcomes.


• Manage professional services margins, resource capacity planning, and rigorous delivery standards across all regional teams.

What You Bring to the Table

• Strategic AI Vision & Execution: Proven ability to define a multi-year AI delivery vision, develop complex automation workflows, and establish an ethical rollout framework across high-volume environments 


• SaaS & Deep Technical Fluency: 10+ years operating within SaaS, enterprise cloud, automation, or data platforms, showing rich mastery over APIs, integration architectures, and workflow configurations.


• Scale Leadership: 5+ years heading technical delivery, solutions architecture, professional services, or forward-deployed customer engineering teams.


• Cross-functional Catalyst: A track record of collaborating closely with Product and Engineering leaders to build scalable systems out of bespoke processes.


• Baseline Requirement: Ability to communicate clearly and effectively in written and verbal formats.


• Experience deploying software solutions through multi-location business models, channels, or high-volume SMB networks.


• Background as a forward-deployed AI leader, top-tier transformation consultant, or highly technical Customer Operations executive.


• Bachelor’s degree in Computer Science, Engineering, Business Operations, or a highly relevant equivalent field.

About Vendasta

We help businesses get more customers. And keep them. We’re on a mission to build the most trusted AI-powered platform for small businesses and the partners who support them. At Vendasta, you’ll be part of something ambitious: helping bring AI transformation to local businesses at scale. As a team member, you’ll enjoy:

• Competitive health benefits, flex time, and annual work-from-anywhere options


• Equity opportunities and a chance to directly shape our AI future


• A vibrant workplace culture that embraces experimentation, thought leadership, and continuous learning


• A place where building AI isn’t just a buzzword, it’s the core of everything we do

Perks

Join the Vendasta team, where your well-being and growth come first. Step into a workplace that blends competitive health benefits with true flexibility, including flex time and an annual work-from-anywhere policy. Take ownership of your future with our Employee Options Program, and enjoy the little things, like daily snacks, a vibrant cafeteria, and catered Friday lunches at our offices.Invest in your growth through education reimbursement, in-house learning opportunities, and a suite of leadership development programs. We’re driven by our values; Drive, Innovation, Respect, and Agility, and it shows in everything we do. Give back through community initiatives and volunteer opportunities, and build more than just a career, build a life you love. At Vendasta, you’ll find the support, the challenge, and the culture to thrive. Discover your potential. Make an impact. Grow with us.

Discover your potential. Build something that matters.

Help us lead the AI revolution from right here in Saskatoon