Senior Manager - B2B Sales Enablement

Staples Inc.•Richmond Hill, ON

4d•Hybrid

About The Position

The Sr. Manager, B2B Sales Enablement is accountable for driving end-to-end Go-to-Market (GTM) readiness across Staples Canada’s B2B organization. This role leads to the development and execution of enablement strategies that ensure sellers are fully equipped with the tools, training, content, and knowledge required to successfully launch and scale strategic initiatives. This leader oversees core enablement functions including training, knowledge management, and seller-facing program execution, while partnering cross-functionally with Sales, Marketing, Merchandising, and Operations to deliver seamless GTM activation.

Requirements

Bachelor’s degree in Business, Marketing, or related field preferred.
Strong expertise in Sales Enablement, GTM execution, and change management.
Ability to operate in fast-paced, transformation-driven environments.
Experience building scalable processes, playbooks, and frameworks.
Proven track record of leading large-scale GTM launches or transformation initiatives.
5-7+ years of experience in Sales Enablement, Sales Operations, Strategy, or related roles.
3–5+ years of people leadership experience.
Experience in B2B sales environments (preferred; mid-market/SMB exposure is an asset).

Responsibilities

Lead end-to-end readiness planning and execution for all major B2B initiatives (e.g., product launches, pricing changes, platform enhancements, SMB programs).
Define and operationalize a standardized GTM readiness framework (playbooks, timelines, readiness checkpoints, success metrics).
Partner with cross-functional stakeholders to ensure alignment on launch priorities, dependencies, and execution plans.
Oversee development and governance of seller-facing content, ensuring accuracy, consistency, and accessibility.
Accountable for ensuring sellers are equipped to successfully execute B2B go-to-market priorities.
Oversee onboarding, training, and reinforcement programs delivered through the Sales Training Manager.
Develop and execute the B2B Sales Enablement roadmap aligned to strategic priorities (e.g., SMB growth, digital adoption, AI/Agentforce activation).
Establish scalable enablement models to improve seller productivity, adoption, and performance.
Define KPIs to measure enablement effectiveness (e.g., adoption rates, time-to-readiness, seller productivity).
Continuously assess gaps and optimize enablement strategies based on feedback and performance insights.