Commercial sales manager Jobs in Richmond Hill, ON

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About the Opportunity

Our EHS & ESG business unit sells complex, high-value solutions to Fortune 500 companies navigating environmental reporting mandates, process safety, and operational risk. We are executing a commercial transformation, rebuilding our go-to-market engine with a clear mandate and executive sponsorship. A critical enabler of that transformation is this role.

A Divisional Enablement function exists and is beginning to mobilize, but its output has had minimal impact at the business unit level to date. This role is the last mile: taking what the Divisional team provides, delivering it with context and relevance to our Sales and BDR teams, and building the BU-specific enablement layer that the Division cannot. Our product and GTM strategy will evolve significantly over the next three years. The person in this role must build an enablement framework that can travel that journey with the business, flexible enough to absorb change, durable enough to drive consistently. If you are energized by building in motion and owning the enablement function end-to-end, this role is for you.

What You Will Own

Onboarding & Ramp

• Design and own a structured, role-specific onboarding curriculum for Sales and BDR hires, building on Divisional resources where available and developing BU-specific content where gaps exist.
• Define onboarding milestones and readiness criteria tied to measurable competencies; continuously refine based on performance data to shorten time-to-productivity as the GTM motion matures.

Playbooks, Sales Plays & GTM Content

• Build the BU’s sales play capability from the ground up, this is a muscle the organization has never developed and must build quickly. Design, deploy, and iterate on plays tied to specific accounts, segments, use cases, and campaign moments.
• Develop and maintain Sales and BDR playbooks covering ICP, personas, discovery, objection handling, competitive positioning, and deal progression, translating GTM strategy into practical, executable field guidance.
• Design an enablement framework built for change: as product offerings evolve from point solutions toward an integrated platform with AI orchestration, the framework must absorb that evolution with minimal friction and maximum field continuity.
• Partner with Marketing and Product to ensure messaging stays current and differentiated; govern content quality and relevance within Highspot so materials are findable, up to date, and actively used.

Ongoing Training, Tactical Programs & Skill Development

• Design and deliver a continuous learning program, skills training, product and messaging updates, GTM motion reinforcement and build coaching frameworks that equip Sales managers to sustain it in the field.
• Support tactical enablement programs including call blitzes, targeted sales campaign tests, and grassroots initiatives, acting as a nimble resource that keeps the field moving while broader product, marketing, and GTM strategy continues to develop.
• Partner with the RevOps Manager (Top of Funnel) to align BDR enablement to the account-based operating model; partner with the RevOps Manager (Pipeline to Bookings) to ensure Sales teams execute quoting and forecasting processes with accuracy.

Cross-Functional Collaboration & Divisional Partnership

• Serve as the key BU stakeholder and point of contact for the Divisional Enablement team, influencing their roadmap, representing BU needs, and acting as an extension of that central resource at the business unit level.
• Work cross-functionally with Marketing, Product, and GTM leadership to stay ahead of strategic shifts and translate them into enablement programs before the field feels the gap.
• Leverage AI tools to scale enablement output, content creation, personalization, training delivery, and reinforcement, with a hands-on, curious approach to emerging tools and a focus on making the team more efficient and effective.

Measurement

• Define and track enablement KPIs, onboarding ramp time, content utilization, training completion, and correlation to pipeline and win rate, using data to continuously optimize programs and demonstrate impact.

What We’re Looking For

Required

• 5+ years in Sales Enablement, Revenue Enablement, or a closely related B2B function with direct ownership of onboarding, playbook development, and training programs.
• Demonstrated experience building sales plays and deploying them in the field, not just content creation, but the full cycle of design, launch, adoption, and iteration.
• Strong content development skills: able to translate complex value propositions, evolving GTM strategies, and sales methodologies into clear, practical, field-ready materials.
• Experience managing a sales content platform (Highspot, Seismic, Showpad, or equivalent) including governance, content architecture, and adoption.
• Comfortable operating as a BU-level resource within a matrixed organization that includes a central enablement function, able to influence upward, fill gaps independently, and deliver last-mile execution.
• Able to build enablement frameworks designed for change, experience enabling teams through significant GTM, messaging, or product strategy shifts.
• Appetite and aptitude for AI tools: experience leveraging AI to create, personalize, or scale enablement content and delivery, or a clear track record of rapidly adopting emerging tools.
• Thrives in fast-moving environments where strategy and execution are happening simultaneously.

Preferred

• Experience enabling teams executing account-based GTM motion, including BDR-specific enablement aligned to account prioritization and multi-stakeholder outreach.
• Familiarity with Highspot specifically, including content scoring, analytics, and Salesforce integration.
• Exposure to complex enterprise B2B with long sales cycles, technical buyers, and multi-stakeholder buying committees.
• Exposure to EHS, ESG, sustainability, or industrial/process safety software markets.

Why This Role, Why Now

Enablement is not a support function in this transformation; it is a core driver of whether investment in people and process translates into results in the field. The person who takes this role will own a domain that didn’t previously exist at the BU level, with the latitude to build it right and the cross-functional relationships to make it stick. Four Revenue Operations and Enablement roles are being hired concurrently, this is a team being built, with executive sponsorship and a clear mandate.

Our Interview Practices

Compensation:

$98,500.00 - $172,700.00 USDThis role is eligible for Bonus.

Additional Information:

Wolters Kluwer offers a wide variety of competitive benefits and programs to help meet your needs and balance your work and personal life, including but not limited to: Medical, Dental, & Vision Plans, 401(k), FSA/HSA, Commuter Benefits, Tuition Assistance Plan, Vacation and Sick Time, and Paid Parental Leave. Full details of our benefits are available upon request.