Title: Senior Manager - B2B Sales Enablement
Some of what you will do:
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.
Specifically, You Will:
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.
Some of what you need:
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).
Physical demands/working conditions:
Office environment – Hybrid, with 4 days onsite in Richmond Hill, subject to the hybrid policy (for most positions).
Some of what you will get:
Associate discount
Health and Dental benefits
RRSP/DPSP
Performance bonuses
Learning & Development programs
And more...
#MakeAnImpact
About Us
Skills Required
- Bachelor's degree in Business, Marketing, or related field
- 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 (mid-market/SMB exposure an asset)
Staples Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Staples and has not been reviewed or approved by Staples.
-
Wellbeing & Lifestyle Benefits — Wellbeing offerings are described as broad, including wellness reimbursements, emotional support and coaching, legal services, identity theft protection, and pet insurance. Employee discounts and select on-site amenities are also positioned as meaningful add-ons beyond basic coverage.
-
Leave & Time Off Breadth — Time-off provisions are presented as relatively expansive, including paid time off, company-recognized holidays, and a personal or flexible holiday option. Vacation that grows with tenure and PTO flexibility are highlighted as valued elements.
-
Inclusive Benefits Coverage — Healthcare benefits explicitly include gender-affirming care alongside medical, dental, and vision coverage. Family and caregiver programs also include support that references LGBTQ+ considerations and broader life-stage needs.
Staples Insights
What We Do
For nearly 40 years, Staples has been a trusted leader in delivering end-to-end workplace solutions for consumers and businesses of all sizes across a broad range of industries. The company provides a comprehensive portfolio of products, strategic solutions, and services including print and marketing, shipping, technology, and travel. Its specialized assortment includes high-quality office supplies, janitorial products, technology, furniture, and breakroom essentials, all supported by best-in-class supply chain capabilities and a dedicated team of experts committed to making the workday easier. Headquartered near Boston, Massachusetts, Staples operates throughout North America via direct B2B sales, e-commerce, and more than 900 retail stores. To learn more, visit your local U.S. Staples store, download the Staples app, explore Staples.com or StaplesBusiness.com, or follow @Staples on social media.
.png)
