Staples Canada · 2 months ago
Field Sales Enablement Coach, Quill
Lincolnshire, IL, United States
Full-time
Onsite
Mid, Senior Level
4+ years expStaples Canada is a leader in office supplies through its brand Quill, which has been operational since 1956. They are seeking a passionate Field Sales Enablement Coach to design and deliver impactful onboarding and training programs for their field sales teams, driving growth in mid-market and key accounts.
E-CommerceInformation TechnologyOffice Supplies
Responsibilities
Design and deliver structured onboarding programs for third-party “feet on the street” (FOTS) sales representatives
Lead onboarding and ongoing training for internal field sales reps, focusing on acquiring mid-market and key accounts
Train field sales teams on CRM, quoting tools, digital platforms, and other essential technologies
Facilitate call coaching sessions with actionable feedback to improve conversion, upselling, and closing skills
Partner with Sales Leadership to define success benchmarks and equip reps to meet their KPIs
Develop field-ready playbooks, pitch decks, and objection-handling guides tailored to customer segments
Drive alignment between training content and real-world field execution through continuous feedback loops
Collaborate with Merchandising, Marketing, and Sales Operations to ensure messaging, tools, and systems are integrated into training
Analyze performance data to identify knowledge gaps and deliver targeted refresher or upskilling sessions
Support territory ramp-up plans by tailoring onboarding journeys based on market and representative experience
Actively participate in ride-alongs, shadowing, and sales calls to observe and enhance seller performance
Provide sales rep feedback to improve UX related to digital tool enhancements and usability
Host regular workshops, virtual sessions, and field huddles to drive continuous learning and collaboration
Support wider Coaching and L&D for Business-wide training or program rollouts
Travel required: 1 visit per month to a Field Sales territory for FOTS campaign launch and onboarding, with flexibility for additional travel as business needs dictate
Qualification
Required
4+ years of sales experience, including demonstrated, deep understanding of field sales processes, routines, and incentives
2+ years of experience in coaching, training or adult learning / education
Experience and proficiency with Salesforce.com
Ability to work onsite at our Lincolnshire, IL location at least 4 days / week and travel once per month
Demonstrated experience using key tools, systems, and reporting effectively while meeting requested deadlines and deliverables
Deep understanding of field sales dynamics and channel selling
Ability to articulate and leverage sales coaching methodology and apply within various team focuses
Strong facilitation and public speaking skills for both live and virtual audiences
Empathetic listener with the ability to coach reps of varying skill levels and backgrounds
Data-driven mindset and use of performance metrics to guide coaching decisions
Curious and adaptable, comfortable navigating fast-changing tech and business environments
High emotional intelligence, allowing you to quickly build trust across internal and external teams
Proactive communicator, delivering clear and actionable feedback
Demonstrated, deep understanding of field sales processes, routines, and incentives — and how to maximize team performance within that framework
Skilled in simplifying complex systems and processes for a range of learner audiences
Organized and resourceful, able to manage multiple training rollouts across different regions or teams
Collaborate cross-functionally with Sales, Operations, Marketing, and Product stakeholders
Think creatively, using real-world examples and storytelling to make training come alive
Possess strong written and visual communication skills to aid in developing engaging training materials
Preferred
Demonstrated experience dealing with adversity and showing a result-oriented mindset while having the ability to have crucial conversations
Benefits
Inclusive culture with associate-led Business Resource Groups.
Flexible PTO (22 days) and Holiday Schedule (7 observed paid holidays).
Online and Retail Discounts, Company Match 401(k), Physical and Mental Health Wellness programs, and more!
Company
Staples Canada
STAPLES Canada is a company that sells office supplies, technology and equipments.
10001+ employees
Funding
Current Stage
Late StageLeadership Team
Brian McDougall
Chief Retail Officer
Recent News
Ottawa Business Journal
2025-12-13
Canada NewsWire
2025-12-02
Company data provided by crunchbase