• Job Description

  Req#: REQ6878

  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 a strategic and empathetic trainer and coach with a proven track record of driving performance in high-volume sales environments. The ideal candidate will be deeply invested in the growth of others, fluent in sales enablement best practices, and energized by helping both new and tenured reps achieve their full potential. Specifically, we’re looking for someone with:

  • 5–7 years of experience in sales coaching, sales enablement, or sales leadership (preferably with inside sales or SaaS experience)

  • Demonstrated success building coaching frameworks, call review scorecards, or training programs

  • Familiarity with sales engagement platforms (e.g., Outreach, Salesforce), LMS tools, and communication channels like Confluence or Slack

  • Strong interpersonal and communication skills, with an ability to build trust across varying skill levels

  • A data-informed mindset with comfort tracking performance trends and coaching outcomes

  • Experience partnering across functions to ensure training programs are aligned with process and product evolution

  What you’ll do:

  • Deliver consistent, hands-on training and coaching to Account Executives (all levels), Inbound Sales reps, and other sales partners across the acquisition teams

  • Own the strategy of training execution across disparate acquisition teams: both internal and external

  • Build and iterate a structured coaching framework and scorecard in partnership with enablement, curriculum leads, and other trainers

  • Lead personalized coaching sessions with a regular cadence—focusing on reinforcement, roleplay, call reviews, and accountability tracking

  • Provide increased coaching frequency and targeted support to lower-performing team members; partner with sales leaders on development plans and performance strategies

  • Collaborate with curriculum partners on training content, assessments, and formats (in-person, virtual, asynchronous) to ensure learning sticks

  • Incorporate key learnings, coaching tips, and rep highlights into the sales communications plan, celebrating wins and reinforcing culture

  • Ensure “hunter” teams have the tools and workflows needed to succeed and that those processes are reinforced in coaching

  • Deliver performance reports and coaching insights to sales leaders to support pipeline, ramp, and retention initiatives

  How you’ll be measured:

  • Improvements in rep performance metrics (e.g., conversion, call quality, ramp time) tied to coaching engagement

  • Uptake and adoption of coaching frameworks and tools across sales leadership

  • Feedback from reps and sales managers on the value of coaching and training support

  • Visibility and integration of coaching insights in broader enablement and leadership strategies

  • Success of coaching interventions for underperforming reps (measured by PIP outcomes, retention, or improvement)

  How you’ll make a difference:

  As a Senior Sales Trainer & Coach, you’ll elevate Custom Ink’s sales performance through expert coaching, structured development, and thoughtful collaboration. Your support will empower reps and leaders across the acquisition function to grow their skills, improve their results, and feel seen and supported in their development. With your guidance, our sales team will not only meet goals but also build confidence and connection in how they achieve them.

  
  Compensation:

  We are committed to providing pay transparency and equitable compensation.

  • For this salaried exempt position, the OTE range is $85,000 - $110,000. 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.

• About the company

  Custom Ink is an American online retail company headquartered in Fairfax, Virginia that makes custom clothing and other items such as T-shirts, sweatshirts, bags, and tech accessories.

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