Director of Sales Coaching

StyleBlueprint • Nashville, TN

2d • Remote

About The Position

StyleBlueprint is seeking a Director of Sales Coaching to lead and develop its sales team as the company expands into new local markets and grows its existing publications. The role is the sales team’s primary leader and coach, responsible for developing current sellers, recruiting and onboarding new team members, and supporting the Market Leader program with sales development during participants’ first 6–12 months. The position reports to the CEO, and Sales Operations reports to this role.

The Director will make coaching a consistent part of the team’s work through weekly practice, one-on-ones, field coaching, thoughtful debriefs, and an actively used sales playbook. The role includes leading recruiting and hiring, establishing a structured 90-day onboarding plan, and addressing performance concerns with clear expectations and follow-through.

The Director is accountable for StyleBlueprint’s overall revenue goal and will lead weekly forecasting, maintain pipeline visibility, work with Sales Operations to keep CRM records useful and accurate, and use activity and revenue measures to identify where coaching or changes are needed. The role partners with the CEO on pricing, products, compensation plans, and sales strategy. By the end of month three, the Director is expected to have assumed primary responsibility for day-to-day sales management, with the CEO as a strategic partner.

This is a coaching and team-leadership role, rather than an individual sales or deal-closing position. Compensation is primarily base salary, with variable pay tied to company revenue. The position is virtual-first and requires periodic travel for quarterly planning, team gatherings, conferences, and market visits.

Requirements

• Experience coaching B2B salespeople in outside sales, with examples of people becoming more capable and successful under your guidance.
• Ability to understand individual development needs and provide specific, candid feedback warmly.
• Ability to balance encouragement with accountability.
• Structured and consistent approach to work.
• Experience leading regular sales practice and using team scorecards to guide decisions.
• Experience making thoughtful hiring decisions.
• Comfort using AI as a coaching and support tool.
• Ability to travel periodically for quarterly planning, team gatherings, conferences, and market visits.
• Experience developing and growing a sales team, with results achieved through the people you lead.
• Previous responsibility for sales coaching, recruiting, onboarding, and performance management.

Nice To Haves

• Formal sales-management training through Daly, Sandler, or a similar program, with experience applying it in day-to-day leadership.

Responsibilities

• Lead and develop the sales team, connecting individual development with company goals and clear expectations.
• Support expansion of the Market Leader program by providing sales development and leadership expertise, including a focused 6–12-month development program for new Market Leaders.
• Lead weekly sales practice sessions and provide additional roleplay as part of training for new sellers.
• Hold weekly one-on-ones with each salesperson to discuss opportunities, work through challenges, and follow up on commitments.
• Provide regular field coaching through joint meetings, demonstration training calls, and observation of salesperson-led coaching calls.
• Conduct thoughtful debriefs that help sellers identify what worked, what they missed, and what to try next.
• Maintain an evolving sales playbook covering client value, discovery, objection handling, proposals, and onboarding.
• Create an environment for questions, practice, direct feedback, and supportive accountability.
• Recruit and hire as the team expands, treating recruiting as an ongoing investment in candidate relationships.
• Lead a structured 90-day onboarding plan with clear milestones, regular feedback, and opportunities to demonstrate readiness.
• Address performance concerns promptly and respectfully, with clear expectations and follow-through.
• Be accountable for StyleBlueprint’s overall revenue goal and help the team understand the work that contributes to it.
• Lead weekly forecasting and maintain a clear view of pipeline health.
• Work with Sales Operations and the team to keep CRM records accurate and useful.
• Track revenue-driving activities and progress alongside closed business, and use results to identify coaching needs or changes in approach.
• Partner with the CEO on pricing, products, compensation plans, and sales strategy.
• Assume primary responsibility for day-to-day sales management by the end of month three.

Benefits

• Competitive base salary and a bonus tied to company revenue.
• Monthly profit sharing.
• 401(k) with company match.
• Four-and-a-half-day workweek, ending at 12:30 p.m. every Friday.
• Virtual-first work arrangement.
• Competitive medical insurance options.
• Access to dental and vision plans.
• Company-paid telehealth and short-term disability insurance.
• Unlimited PTO and sick days, with guidelines supporting time away and team coordination.
• Parental leave.
• Approximately 15 paid company holidays each year.
• $50 monthly cell phone stipend.
• Company-provided laptop that becomes the employee’s personal property after two years.
• Quarterly off-sites for planning sessions and team gatherings, typically in Nashville or within a three-hour drive.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed