Sales Enablement Lead

SALES ENABLEMENT LEAD - TORONTO

Join Key Media and Shape the Future of Our Sales Excellence

Are you passionate about unlocking sales potential and driving team performance? We're looking for a dynamic Sales Enablement Lead to build and execute the strategies that transform our sales team into high-performing revenue generators.

THE ROLE

As our Sales Enablement Lead, you'll own the complete ecosystem that powers our sales success. From designing rigorous performance frameworks to creating world-class training programs and developing cutting-edge sales content, you'll be the architect behind our team's competitive advantage. You'll work at the intersection of data, people development, and strategic messaging – where impact is measurable and immediate.

WHAT YOU'LL OWN

Drive Performance Through Data & Accountability

You'll establish the KPIs and metrics that matter, then build the infrastructure to track them. Manage our CRM as a strategic asset, ensuring data quality that enables intelligent decision-making. Create compelling dashboards that keep managers and reps accountable, and partner with leadership to identify underperformance early and execute turnarounds.

Build World-Class Sales Talent

Design and deliver comprehensive onboarding programs that set new reps up for success from day one. Develop advanced training in solution selling, discovery, objection handling, and negotiation. Create vertical-specific knowledge sessions that give reps insider expertise on their target industries. Coach, mentor, and elevate the entire team through strategic feedback and resources.

Craft Compelling Messaging & Content

Develop the core sales narrative that guides everything we communicate. Build a library of high-impact sales assets – from value propositions and case studies to ROI calculators – all organized and searchable. Create vertical-specific content that demonstrates deep industry knowledge and clear product differentiation. Own every product launch with commercially-ready messaging and training.

WHAT WE'RE LOOKING FOR

Proven experience in sales enablement, training, or sales management

Experience and knowledge of media/advertising/B2B publishing 

Strong analytical mindset with ability to work confidently with data and CRM systems

Excellent training and coaching skills with the ability to communicate complex ideas clearly

Experience creating sales content, messaging frameworks, or marketing materials

Strategic thinker who can balance day-to-day execution with long-term capability building

Strong project management and organizational skills

Passionate about helping others succeed

WHY YOU'LL LOVE THIS ROLE

This isn't a back-office function – you'll have direct visibility into revenue impact. You'll work across all levels of the organization, from frontline reps to the C-suite. You'll combine creativity, strategic thinking, and data-driven decision making. And you'll build something meaningful: a competitive sales engine that delivers results.

WHAT WE OFFER

Competitive Compensation

A competitive base salary plus performance-related bonuses recognizing your impact.

Comprehensive Benefits - Health and dental coverage to support your wellbeing, plus 15 days annual leave that increases with each year of service through our loyalty scheme.

Work-Life Balance- Hybrid flexibility with 2 days per week in our downtown Toronto office on Adelaide Street and 3 days working remotely – giving you the best of both worlds.

Culture & Community

Work within a collaborative, supportive environment where people genuinely care about each other's success. We're a company that values innovation, quality, and creating amazing experiences. Plus, regular social events and team celebrations keep the energy high.

Global Opportunity- Be part of a thriving global organization with offices across Sydney, Toronto, and the Philippines. You'll work with talented professionals across time zones and build a truly international network.

Professional Growth - Meaningful opportunities to develop your skills, lead high-impact projects, and grow your career in a company that invests in its people.

Ready to transform sales performance? Apply now and let's talk about how you'll drive our next chapter of growth.

Compensation
The expected salary range for this position is $85,000–$125,000 per year (dependent on skills and experience levels) plus eligibility bonus/commissions and group benefits.

Vacancy status
This posting is for an existing vacancy that we are actively recruiting to fill.

Use of artificial intelligence in hiring
We use automated tools / artificial intelligence to help with note-taking during interviews. All decisions on candidate progression and hiring are made by human reviewers.

Inclusion, equity & accessibility
We are committed to employment equity and an inclusive, barrier‑free selection process. We welcome applications from all qualified candidates, including members of visible minorities, Indigenous peoples, persons with disabilities, women, and persons of any sexual orientation or gender identity/expression. If you require accommodation during any stage of the recruitment process, please contact us at [email protected].

Application updates
Candidates who interview for this role will receive an update on their application status no later than 45 days after their last interview, and in most cases much sooner.