Field Sales Enablement Coach, Quill

Quill is a valuable part of the Staples family of brands. Since 1956, Quill has held its position as a leader in office supplies.

Acquired by Staples in 1998, Quill delivers the essential services, solutions, and award-winning customer support to help our customers – and our people – thrive. When you partner with Quill, as a customer or as an associate, every workday is more rewarding.

From paper, ink & toner, to technology and custom print, we deliver the right products at the right value, plus an unmatched assortment of over 900 instant rewards available with every order.

Quill is seeking a passionate and experienced Field Sales Coach to join and enable our Field Sales team! You will play a crucial part in driving mid-market and key account growth by designing and delivering impactful onboarding, training, and coaching programs for our internal and third-party field sales teams. You will partner closely with Sales Leadership and cross-functional teams, along with influencing product development including AI powered resources.

This position is ideal for someone who thrives on empowering others, fostering collaboration, and bringing innovative ideas to life. If you are skilled in upskilling sellers, driving their performance and aligning training with business goals, we want to hear from you!

This position will require travel 1 time per month (may be for several days) and ability to work onsite at our Lincolnshire, IL location at least 4 days / week if not traveling.

What you’ll be doing:

• 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.
  
  

What you bring to the table:

• 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.
  
  

What’s Needed- Basic Qualifications

• 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.
  
  

What’s needed - Preferred Qualifications:

• Demonstrated experience dealing with adversity and showing a result-oriented mindset while having the ability to have crucial conversations.
  
  

We Offer:

• 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!
  
  

The salary range represents the expected compensation for this role at the time of posting. The specific base pay may be influenced by a variety of factors to include the candidate's experience, skill set, education, geography, business considerations, and internal equity. In addition to base pay, this role may be eligible for bonuses, or other forms of variable compensation.