Some of what you will do:
The B2B Sales Training Manager is responsible for the design, delivery, and continuous improvement of training programs that builds sales capability across systems, sales methodology, and product knowledge.
This role leads onboarding and ongoing development programs, ensuring sellers are equipped to effectively execute go-to-market strategies and leverage core tools such as, but not limited to, Salesforce.
As an initial individual contributor, this role directly delivers training while building scalable programs, content, and frameworks to support future team growth.
Specifically, You Will:
Owns the design and development of comprehensive training programs across sales methodology, systems, and product knowledge, ensuring alignment to B2B go-to-market priorities and enablement strategies.
Builds structured, role-based learning journeys that support both new hire onboarding and ongoing skill development across frontline sellers and sales leadership.
Partners with cross-functional stakeholders to identify capability gaps and translate business priorities into targeted training initiatives.
Leads training for Salesforce and related sales systems, ensuring sellers can effectively execute core workflows and fully leverage platform capabilities in their day-to-day selling activities.
Directly delivers instructor-led and virtual training sessions across onboarding and ongoing programs, engaging both frontline sellers and sales leaders.
Models strong facilitation practices and adapts delivery methods to meet diverse learning needs and business priorities.
Owns the end-to-end onboarding experience for new sales hires, including onboarding plans, training schedules, and readiness milestones.
Ensures new sellers achieve baseline proficiency across systems, tools, and sales motions prior to full productivity expectations.
Continuously evolves onboarding programs to improve ramp time, consistency, and overall seller experience.
Some of what you need:
Bachelor’s Degree in Business, Education, Communications, or related field (or equivalent combination of education and experience).
Certification in Training, Facilitation, or Learning & Development preferred.
Demonstrated expertise in designing and delivering sales training programs that build capability across systems, sales methodology, and product or program knowledge.
Strong understanding of B2B sales processes, with the ability to translate tools (e.g., Salesforce or similar CRM platforms) into practical workflows that support effective selling behaviors.
Proven ability to design structured onboarding programs and role-based learning journeys that improve seller readiness, consistency, and time to productivity.
Strong knowledge of adult learning principles, instructional design, and effective training delivery methods across both in-person and virtual environments.
5–7 years of experience in sales training, sales enablement, sales operations, or learning and development roles within a B2B environment.
Hands-on experience designing and delivering training programs across systems, sales processes, and onboarding, with demonstrated impact on adoption, capability, or performance outcomes.
Experience supporting CRM or sales enablement platforms (e.g., Salesforce), including training, user adoption, or workflow enablement.
Proven experience building and evolving onboarding programs, including defining ramp plans, readiness milestones, and certification or assessment frameworks.
Experience supporting go-to-market initiatives, system rollouts, or process changes through structured training and enablement programs.
Demonstrated ability to operate in a matrixed organization, partnering across multiple stakeholders to deliver coordinated outcomes.
Experience leading training delivery or informally coaching and mentoring others, with the ability to scale into a people leadership role over time.
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...
About Us
Skills Required
- Bachelor's Degree in Business, Education, Communications, or related field (or equivalent experience).
- Certification in Training, Facilitation, or Learning & Development.
- Demonstrated expertise designing and delivering sales training programs across systems, sales methodology, and product knowledge.
- Strong understanding of B2B sales processes and ability to translate CRM tools into practical workflows.
- Proven ability to design structured onboarding programs and role-based learning journeys that improve readiness and time to productivity.
- Strong knowledge of adult learning principles, instructional design, and effective in-person and virtual delivery methods.
- 5-7 years of experience in sales training, sales enablement, sales operations, or learning and development within a B2B environment.
- Hands-on experience delivering training across systems, sales processes, and onboarding with measurable impact on adoption or performance.
- Experience supporting CRM or sales enablement platforms (e.g., Salesforce) including training, user adoption, or workflow enablement.
- Proven experience building and evolving onboarding programs including ramp plans, readiness milestones, and assessment frameworks.
- Experience supporting go-to-market initiatives, system rollouts, or process changes through structured training and enablement.
- Ability to operate in a matrixed organization and partner across stakeholders to deliver coordinated outcomes.
- Experience leading training delivery or coaching others with potential to scale into a people leadership role.
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.
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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.
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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.
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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.







