Director of Sales Coaching

If the most rewarding part of your career has become helping other people succeed, we’d like to meet you. StyleBlueprint is looking for a Director of Sales Coaching to help our sales team and local Market Leaders grow in skill, confidence, and results. This role also includes recruiting new, full-time members of our sales team as needed. Our team already brings strong relationships, thoughtful listening, and a willingness to practice and improve. We’re looking for a leader who recognizes those strengths and knows how to build on them through consistent coaching, clear expectations, and a consultative approach to sales. This is a full-time leadership and coaching role. You will have no personal book of business or individual sales quota, and you will not receive commissions on deals you help close. Your success will come through the people you develop and the team’s achievement of StyleBlueprint’s overall revenue goal.

The opportunity

As a trusted lifestyle media brand, we help businesses become familiar to an audience they want to reach. Our advertising partnerships span sponsored articles, social media, emails, display advertising, event marketing, and related offerings across our Travel & Lifestyle, Home, and Local editions.

We believe good sales conversations begin with curiosity: understanding a business, asking thoughtful questions, and helping someone make a sound decision about whether and how we can help.

As we expand into new local markets (led by Market Leaders) and grow our existing publications (sold by full-time members of our sales team), this role will help us bring that approach to more businesses while developing the people who represent us.

You will report to the CEO, with Sales Operations reporting to you. You will become the sales team’s primary leader and coach, giving the CEO room to focus on the company’s broader direction and growth.

Our core values

Be Kind. Do Good.

Treat people with care and respect—our colleagues, readers, clients, and the communities we serve. Kindness includes honest conversations, thoughtful feedback, and following through.

Take Ownership.

Care about the outcome. Bring ideas, address challenges, and follow through on your commitments. Understand how your work contributes to the team's success.

Better Every Day.

Stay curious, welcome feedback, and keep learning. Progress comes from the small improvements we make consistently and the willingness to help one another make them.

The job

Build a growing sales team and support our expanding local Market Leader program.

For our sales team, this means developing our current team, recruiting thoughtfully, and creating the structure and support people need to do their best work. You’ll connect individual development with company goals, making expectations clear and helping each person understand how to reach them.

For our Market Leader program, this means working with a focused sales development program over a Market Leader’s first 6-12 months to develop their sales confidence and skills to effectively sell in their local markets. This also includes working with the Market Leader program team as they lead the program's expansion and success.

You should enjoy both the human side of leadership and the discipline it requires: preparing for practice, observing conversations, giving useful feedback, reviewing results, and following up.

Coaching culture

Our team already sets aside an hour each week for sales practice. You’ll lead and build on that commitment, creating focused sessions that help people apply what they learn in real conversations. New sellers will need more roleplay as part of training.

You will:

• Hold weekly one-on-ones with each salesperson to discuss opportunities, work through challenges, and follow up on commitments.
• Market Leaders have their own leadership team and 1:1s, Your role here is to support that team with expertise and continued sales leadership training.
• Make field coaching a regular part of development through joint meetings, training calls where you demonstrate an approach, and coaching calls where the salesperson leads, and you observe.
• Use thoughtful debriefs to help people recognize what worked, what they missed, and what to try next. Exercise judgment about when to demonstrate, when to support, and when to give someone room to learn.
• Keep a practical, evolving sales playbook in active use, covering our value to clients, discovery, objection handling, proposals, and onboarding. Draw from real conversations so it stays useful.
• Create an environment where people can ask questions, practice unfamiliar skills, and receive direct feedback with confidence that you are invested in their success.

Talent and recruiting

Help us grow a team we’re proud to work alongside.

You will be responsible for team performance and development, as well as recruiting and hiring as we expand. We approach recruiting as an ongoing investment in relationships, giving us time to recognize strong candidates and make thoughtful decisions.

We hire for attitude and aptitude, then provide the training and support people need to learn our approach. You will lead a structured 90-day onboarding plan with clear milestones, regular feedback, and opportunities to demonstrate readiness.

You’ll also address performance concerns promptly and respectfully, with clear expectations and follow-through.

The number and the forecast

You will be accountable for StyleBlueprint’s overall revenue goal and for helping the team understand the work that moves us toward it.

You will:

• 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 the activities and progress that lead to revenue, alongside closed business.
• Use the numbers to identify where coaching, attention, or a change in approach is needed.
• Partner with the CEO on pricing, products, compensation plans, and sales strategy.

What success looks like in year one

We achieve our revenue goal: The team meets StyleBlueprint’s overall revenue target, supported by consistent pipeline management and reliable forecasting.

Coaching is part of how we work: Weekly practice, individual coaching, and field coaching happen consistently and provide clear value to the team.

People grow in skill and confidence: Improvements are visible in sales conversations, individual performance measures, and follow-through.

You lead the sales team day to day: By the end of month three, you have assumed primary responsibility for sales management, with the CEO serving as a strategic partner.

We are prepared to grow: Recruiting is ongoing, and new hires have a clear, supportive path to becoming effective contributors.

Who this is for

You have experience coaching B2B salespeople in outside sales, and you can point to people who became more capable and successful with your guidance.

You enjoy understanding what each person needs to improve. You can give specific, candid feedback with warmth, and you know that encouragement and accountability belong together.

You bring structure and consistency to your work. You have led regular practice, used team scorecards to guide decisions, and made thoughtful hiring choices.

You are comfortable using AI as a coaching and support tool. We already use an AI coach to review sales calls, and we welcome a leader who is curious about how technology can strengthen both their own coaching and the team’s development.

You can travel periodically for quarterly planning, team gatherings, conferences, and market visits.

A strong background includes

• Experience developing and growing a sales team, with results achieved through the people you lead.
• Formal sales-management training through Daly, Sandler, or a similar program, with experience applying it in day-to-day leadership.
• Previous responsibility for sales coaching, recruiting, onboarding, and performance management.

This is not a fit if

This role will be most rewarding for someone who wants coaching and team leadership to be their primary work.

If you want to maintain your own book of business, earn individual deal commissions, or spend most of your time personally closing sales, the role is unlikely to offer what you’re looking for.

You’ll also need to enjoy the consistency that development requires: regular practice, prepared one-on-ones, ongoing recruiting, clear expectations, and thoughtful attention to performance.

Compensation is primarily base salary, with variable pay tied to company revenue.

What we offer

We care about doing meaningful work together and making room for a full life outside it.

• Compensation: Competitive base salary, a bonus tied to company revenue, monthly profit sharing, and a 401(k) with company match.
• 4½-day workweek: Our workweek ends at 12:30 p.m. every Friday.
• Virtual-first work: Work remotely while staying connected through daily huddles and recurring weekly meetings.
• Health and wellness: Competitive medical insurance options, access to dental and vision plans, and company-paid telehealth and short-term disability insurance.
• Flexible paid time off: Unlimited PTO and sick days, with guidelines that support time away and thoughtful coordination with your team. Parental leave is also available.
• Company holidays: Approximately 15 paid company holidays each year.
• Technology: A $50 monthly cell phone stipend and a company-provided laptop that becomes your personal property after two years.
• Quarterly off-sites: Planning sessions and team gatherings that bring us together, typically in Nashville or within a three-hour drive.