Sales Enablement Lead - 12 month contract

Torstar•Toronto, ON

About The Position

We're looking for a detail-obsessed, media-savvy Sales Enablement Lead to keep our advertising sales teams running efficiently. You'll be supporting advertising sales teams across the full Torstar portfolio - including the Toronto Star, Metroland Media Group, and specialty brands like The Kit, Canadian Immigrant, TravelAlerts, Save.ca, and more. That means managing sales materials and go-to-market execution across diverse audiences, advertising products, and content categories - from community news to lifestyle, sports, travel, and beyond. Your job is to make sure every seller has the right materials at the right time to walk into a pitch confidently. This role is also a meaningful opportunity to shape how we work. We expect the right candidate to actively use AI tools to streamline workflows, accelerate content production, and reduce manual effort - not occasionally, but as a regular part of how they get things done. This is not a strategy role. It's the role for someone who gets genuine satisfaction from a perfectly organized asset library, a polished pitch deck, and a sales team that can find what they need in under 60 seconds.

Requirements

2–4 years of experience in advertising sales support, marketing coordination, or sales operations — ideally within a media, publishing, or digital advertising environment
Demonstrated experience building and formatting client-ready PowerPoint/Google Slides decks
Familiarity with digital advertising sales cycles (display, programmatic, branded content, or similar)
Hands-on, regular use of AI tools (e.g., ChatGPT, Copilot, Gemini, or similar) to improve personal productivity or team workflows
Exceptional organizational skills - you manage competing deadlines and multiple brand priorities without dropping details
Strong written communication - clear, concise, and professional for internal audiences
Advanced PowerPoint and Excel proficiency (formatting, templates, basic data analysis)
AI fluency - you don't wait to be told to try an AI tool; you experiment, evaluate, and implement
Comfortable with ambiguity and fast-changing priorities in a deadline-driven, multi-brand environment

Nice To Haves

Exposure to CRM platforms (e.g., Salesforce) or sales enablement tools (e.g., Seismic, Highspot, Showpad)
Experience with project tracking methodology
Experience supporting multiple brands or business units simultaneously
Experience building AI-assisted workflows or prompts in a professional setting

Responsibilities

Own the sales asset library - Maintain and organize pitch decks, one-sheets, case studies, and external-facing sales pages across the full Torstar brand portfolio. Keep everything brand-compliant, current, and findable. Use AI tools to automate updates, flag outdated content, and speed up production.
Coordinate go-to-market launches - Manage the GTM process alongside product leads to ensure sales teams are fully equipped before any product rollout.
Run internal sales communications - Draft and distribute internal updates, coordinate department-wide meeting logistics, and keep sellers aligned. Use AI to improve turnaround time and consistency of communications.
Support sales reporting - Track rep engagement by product, brand, or initiative to help identify training gaps and inform enablement priorities.
Champion smarter ways of working - Proactively identify where AI tools can replace manual, repetitive tasks within the enablement function and implement those improvements. Share what's working with the broader team.