Sales Enablement Lead

Job Title: Sales Enablement Lead

Office-first: Boca Raton, FL or Saskatoon, CA

Business owners buy when a rep really gets their problem. This job makes every rep that ready, on every call.

What You’ll Do

You’ll work with Direct and Channel sales managers, Product Marketing, Product and RevOps

• Build the sales tools for every launch: talk tracks, objection handling, discovery guides
• Give every rep the current pitch, demo and answers before launch
• Turn what top performers do into one pitch and demo standard
• Send managers a weekly brief on where to focus 1:1s
• Run the training calendar and certify reps before live calls
• Spot where deals stall and drive each fix to an owner
• Build AI agents that review calls and keep answers current
• Work on the Boca sales floor and support other teams virtually

What You’ll Bring

• Three or more years on a high-performing SaaS sales team serving small businesses, in sales or enablement
• A degree in Business, Marketing, Communications or a related field is an asset
• AI agents or automations you built that replaced manual work, and can show us
• Experience working closely with sales managers, or leading a team
• A playbook or talk track from top-performer calls that lifted results
• You read CRM and pipeline data yourself

Nice to have: channel or partner enablement, or APIs and scripting.

Why Vendasta

Our purpose is simple: make technology easy, accessible and affordable. We’re building the AI workforce for business owners, so the people who run local businesses can spend less time on busywork and more time on their customers. Everything we do starts with those customers. If it doesn’t help a business owner win, we don’t build it.

How We Work
We’re accountable (Drive), we’re radically candid (Respect), we keep learning (Agility) and we find creative ways to solve problems (Innovation). We work hard, celebrate each other’s wins, and keep it fun. It’s part of why we were named one of Canada’s Most Admired Corporate Cultures for 2025 and 2026.

And the coolest part?
We don’t just talk about AI. We build it. Whatever your role, we’ll train you to use it like a power user, with tools that are cutting edge. Add coaching, mentorship, hands-on learning opportunities that move your career forward, and you’ll grow faster here than anywhere else. Plus, you’ll get health and wellness benefits, flex days and paid volunteer time, because doing your best work means having time for what matters outside of it.