SECTION I · THE BRIEF
Brief #27908Updated 01 SEP 2026SASKATOON, SASKATCHEWAN, CANADABamboohrGV
Employbl Company Profile

AI Activation Strategist

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, Saskatchewan, Canada
Company size
50–100
Posted
4d 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

Free account · no card · 2 minutes

Yesware logo

AI Activation Strategist · Yesware

View company profile
Job title
AI Activation Strategist
Job location
Saskatoon, Saskatchewan, Canada
Job description

Job Title: AI Activation Strategist 

Location: Office-first


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!


About the Job

The mission of the AI Activation Strategist is to act as the primary architect and partner for clients, transforming business needs into functional AI-driven solutions within the Vendasta ecosystem. The incumbent of this role demonstrates a full-stack service mindset, deep AI fluency, and consultative communication skills, and will be responsible for end-to-end client scoping, workflow validation and setup, and post-delivery AI optimization. The successful candidate will also leverage AI technologies to streamline execution, identify insights, and drive innovation across their responsibilities.


Your Impact

As a AI Activation Strategist, you'll work with clients, Senior Specialists, and AI Workflow Architects to:

  • Consult with clients to deeply understand their business objectives and identify opportunities for AI integration
  • Design tailored AI solutions based on available Vendasta AI technologies (e.g., Rep AI, Content AI)
  • Act as the single point of contact, eliminating internal hand-offs between departments
  • Build, configure, and validate AI workflows and "AI Employees" within the Vendasta platform
  • Ensure technical integrity of the setup, troubleshooting issues before delivery and automating repetitive tasks using AI where applicable
  • Partner with Senior Specialists or AI Workflow Architects only for high-complexity customizations
  • Demo and showcase the validated AI solution to the client for final approval
  • Train clients on the solution to ensure self-sufficiency and long-term adoption, embedding AI in cross-functional processes
  • Monitor AI performance metrics, auditing and adjusting the AI to improve accuracy and success rates


What You Bring to the Table

Candidates should bring 2+ years of experience in Client Success, Implementation, Technical Consulting, or a related field, preferably within a SaaS or technology environment, along with a Bachelor's degree (preferably in Business, Communications, Information Technology, or a related field). You must possess strong AI fluency—including an understanding of LLM capabilities, prompt engineering, and customizing AI workflows within a SaaS environment—as well as analytical auditing skills to monitor AI outputs for errors and make iterative adjustments. Clear written and verbal communication and consultative communication skills to translate complex AI concepts into business value for SMBs are required.


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 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.

View job listing ↗
The Saturday Briefing

Get the Saturday tech briefing

New company profiles, funding moves, and who’s hiring across the market — every Saturday morning.

Yesware headquarters

Boston, MA

Company size

50100 employees

Founded

2010

Total raised

$47,050,000

View company profile ↗

Funding rounds