Senior Manager - B2B Sales Enablement

Richmond Hill, ON
Hybrid
Posted Jul 17, 2026
1 position

Opens an external site

Employment type: Full-time
Experience level: Senior · 7+ years
Minimum education: Bachelor’s degree
Posting language: English
Working hours: 40 hours per week
Office presence: 4 days per week

Job summary

Lead end-to-end Go-to-Market readiness and enablement strategies to equip B2B sellers with necessary tools, training, and content. Oversee core enablement functions including onboarding and knowledge management while partnering cross-functionally to scale strategic initiatives.

Job details

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... We value transparency in our hiring processes. Please note, artificial intelligence may be used in certain stages to screen, assess, or select applicants, however, a human reviewer makes all final decisions. This posting is for an existing vacancy. About the Team At Staples Canada we are dynamic, inspiring partners to our customers and the communities in which we live. As The Working and Learning Company, we inspire people to work smarter, learn more and grow every day. We’re looking for curious, approachable, and passionate individuals who love finding solutions. If that’s you, let’s work, learn, and grow together. We are building an inclusive and diverse team Staples Canada is continuously working towards creating an inclusive and diverse work environment. We welcome, value and thrive on perspectives and contributions from backgrounds that vary by race, gender, sexual orientation, gender identity or expression, lifestyle, age, educational background, national origin, religion or physical ability. If you have a disability or special need that requires accommodation, please let us know.

What you’ll do

Requirements

Requires 5-7+ years of experience in Sales Enablement or Operations and 3-5+ years of people leadership experience. A bachelor's degree in Business or Marketing is preferred, along with expertise in GTM execution and B2B environments.