Senior Sales Trainer and Coach

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.