Sales Enablement Lead - 12 month contract

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 company,  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.

Key Responsibilities:

• Own the sales asset library - Maintain and organize pitch decks, one-sheets, case studies, and external-facing sales pages across the full 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 Use AI tools to automate updates, flag outdated content, and speed up production.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.

This is a temporary 12 month contract position

Experience (Required)

• 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

Experience (Nice to Have)

• 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

Skills:

• 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

We are committed to providing an inclusive and barrier-free recruitment process ensuring equal access to employment opportunities for candidates, including persons with disabilities. In compliance with Accessibility for Ontarians with Disabilities Act and Ontario Human Rights Code we will endeavour to provide accommodation to persons with disabilities in the recruitment process upon request. If you are selected for an interview and you require accommodation due to a disability during the recruitment process, please notify the hiring manager upon scheduling the interview of your requirements.

This posting is for an existing vacancy. Our Applicant Tracking System (ATS) uses AI for initial screening and assessment; however, all final selection decisions are made by our Hiring Managers.