Sales Trainer and Coach

Custom Ink; Pennsylvania; Remote; USD 65,000 - 86,000; Full time

Job summary

A leading online custom apparel company is seeking a Sales Trainer & Coach to enhance the capabilities of its Customer Success team. This remote role involves coaching, training development, and collaboration across teams to ensure high performance and customer satisfaction. Ideal candidates will have experience in sales training and a strong ability to communicate effectively. The position offers a competitive salary and comprehensive benefits.

Benefits

Generous Paid Time Off

Comprehensive Health Coverage

Employee Wellness Programs

Family-Friendly Benefits

Financial Wellness Resources

Professional Development Opportunities

Qualifications

• 2-4 years of experience in a sales training, coaching, or enablement role.
• Familiarity with coaching frameworks and adult learning principles.
• Strong facilitation and communication skills.

Responsibilities

• Provide training and 1:1 coaching support to Customer Success Managers.
• Collaborate with the training lead to develop learning experiences.
• Conduct recurring coaching sessions with reps to reinforce best practices.

Skills

Sales training

Coaching

Facilitation skills

Communication skills

Organizational skills

Tools

CRM platforms

LMS systems

Job description

Overview:

• Workstyle: Remote
• Reports to: Director, Sales Enablement
• Travel Expectations: Up to 10% for facilitation, team planning, or in-market training
• Physical Requirements/Demands: None.
  
  

What we’re looking for:

We’re seeking an energetic, compassionate, and collaborative trainer and coach to support the continued growth and success of our Customer Success team. This role is ideal for someone who’s passionate about developing others, skilled in facilitating learning, and thrives in a cross-functional environment. Ideal candidates will have:

• 2–4 years of experience in a sales training, coaching, or enablement role (customer success or account management experience preferred)
• Familiarity with coaching frameworks, adult learning principles, or sales training best practices
• Strong facilitation and communication skills, with the ability to coach across varying experience levels
• Experience with sales tools, CRM platforms, or LMS systems
• Organized and proactive mindset with an eye for surfacing opportunities for development
• A collaborative approach and eagerness to partner across training, operations, and revenue teams
  
  

What you’ll do:

• Provide training and 1:1 coaching support to Customer Success Managers and team leaders across the revenue organization
• Collaborate with the training lead to develop and deliver learning experiences across multiple formats (live sessions, asynchronous modules, roleplays, assessments)
• Integrate new tips, success stories, and coaching themes into the comms plan, celebrating rep wins and reinforcing strong habits
• Work closely with the Optimization lead for CSMs to ensure coaching aligns with team tools, systems, and processes
• Conduct recurring coaching sessions with reps to reinforce best practices and provide actionable feedback Build and maintain coaching documentation and scorecards in partnership with other enablement team members Share updates and coaching insights with Customer Success leadership, including performance trends, progress updates, and opportunities for support
• Offer increased coaching frequency and attention to underperforming team members; partner with sales leaders to support improvement plans as needed
  
  

How you’ll be measured:

• Training engagement, coaching session participation, and adoption of recommended practices
• Qualitative and quantitative improvements in rep performance (e.g., customer engagement, retention, upsell metrics)
• Uptake and consistent use of coaching tools and frameworks
• Feedback from reps and managers on coaching impact and support
• Results of targeted coaching interventions for underperforming team members
  
  

How you’ll make a difference:

As a Sales Trainer & Coach, Customer Success, you’ll play a key role in elevating the capabilities and confidence of our Customer Success team. Your work will directly shape how our reps show up for customers every day—through proactive coaching, skill development, and consistent reinforcement of high standards. By collaborating across functions and championing individual growth, you’ll help our CSMs deliver exceptional experiences and build lasting customer relationships.

Compensation:

We are committed to providing pay transparency and equitable compensation.

• For this salaried, exempt position, the range is $65,000 - $86,000. Placement within the range is determined by a variety of factors, including but not limited to: knowledge, skills, years & depth of experience, and equity with internal team members.
  
  

The perks!

• Generous Paid Time Off: Recharge with flexible paid time off policies and major paid holidays.
• Comprehensive Health Coverage: Complete Medical, Dental, and Vision coverage at a low cost through a PPO or HDHP plan to support your and your family’s well-being.
• Employee Wellness: Access to virtual medical consultations through MDLIVE, and mental health services through some of our preferred partners.
• Family-Friendly Benefits: Up to 12 weeks of fully paid parental leave for birthing parents and 6 weeks for non-birthing parents, plus adoption assistance and family-building benefits.
• Financial Wellness: Plan for the future with a 401(k) retirement plan with company matching, complimentary life & AD&D insurance coverage, and access to financial planning resources.
• Professional Development: Grow your career with access to training programs, certifications, and tuition assistance.
  
  

Cover letters are preferred (not required), Custom Ink values individuality, so use your judgment and write to us in your own voice.

CustomInk, LLC (""Custom Ink"") is an Equal Opportunity Employer. We celebrate diversity in all forms and are committed to maintaining a discrimination-free workplace that treats applicants and employees with dignity and respect. Our employment process is conducted without regard to race, color, religion, nationality or ethnic background, sex, pregnancy, sexual orientation, gender identity or expression, age, disability, protected veteran status, genetic information, or other attributes protected by state, federal, and local law.

Custom Ink uses E-Verify to confirm the employment eligibility of all new team members. To learn more about E-Verify, including your rights and responsibilities, please click here.

Custom Ink will only consider applicants who reside in states where it is registered to do business as an employer. We are currently not registered in the following states: AK, AR, CT, HI, ID, IA, KS, KY, LA, ME, MI, MS, MO, MT, NE, ND, NH, NM, OK, RI, SD, UT, VT, WV, WY.