Director of Sales

Principal Consultant · Twin Cities/ Midwest · Remote-Flexible, Full Time

Position Summary

The Director of Sales is a critical member of The Bailey Group’s leadership team, owning the firm’s sales and marketing function. They develop and lead an integrated sales and marketing strategy, build and coach a team of salespeople and marketing resources, and ensure the firm hits its revenue targets. In this player-coach (not pure management) role, the Director also carries a personal production goal of ~$350k, growing to ~$500k+ over three years. The right candidate genuinely wants to carry a personal book of business while growing firm revenue.

For 35+ years, The Bailey Group has earned the trust of senior leaders and organizations navigating their most important leadership challenges. Our experienced coaches and consultants deliver executive coaching, assessments, leadership cohorts, team development and strategic consulting with a 96% client satisfaction rate. TBG’s next chapter needs a Director of Sales who can win meaningful new work, deepen key client relationships, and build a team and sales approach that grow its impact and revenue.

A unique opportunity to build a sales and marketing function at a pivotal moment for the firm: the Director steps into a planned succession from a retiring Sales Director. Rather than inheriting a fully built-out operation, they will shape the function from the ground up — an exciting challenge for someone wanting real ownership of how sales and marketing grow at TBG.

What You’ll Do

Individual Production (60–80% of time)

• Maintains and grows a personal book of key client accounts
• Manages the website lead pipeline — monitoring, qualifying, and distributing inbound leads while personally owning a portfolio of assigned leads
• As the firm’s rainmaker, generates leads and feeds them to other salespeople and consultants
• Keeps CRM and sales admin tools current, supported by sales support and Operations

Strategic Leadership

• Serves on the leadership team, owning Sales and Marketing and giving strategic input toward organizational goals
• Owns a new organizational priority (rock) and a personal rock each quarter
• Develops and leads an integrated sales and marketing strategy, scanning the external environment to inform sales and drive differentiation
• With the leadership team, builds an updated annual sales and marketing plan using data on what did/didn’t work the prior year
• Builds relationships with, influences, and inspires people of diverse backgrounds to drive strong communication, teamwork, and collaboration
• Owns the firm’s total annual revenue goal, plus a personal booked-business goal
• Coaches, supports, and holds salespeople accountable for sales plans and revenue targets via regular 1:1s
• Acts as sales manager for those engaged in selling, advising on prospecting strategy and coaching sales skills
• Creates and/or facilitates team sales training, delivering it personally or via outside resources
• Conducts ride-alongs/listen-alongs with salespeople, especially early in tenure, to build closeness and keep deals moving
• Maintains and continually enhances a sales operating system for everyone engaged in selling, holding individuals accountable for its use
• Is the firm’s go-to sales process expert, educating, training and supporting non-sales colleagues
• Oversees sales meeting agendas and keeps stakeholders updated regularly
• Maintains a cohesive, collaborative sales effort, staying neutral and supportive when performance issues arise

Team Building & Hiring

• Evaluates sales team structure and capacity as the organization grows
• Develops and coordinates a hiring program and tools for new salespeople, including defining expectations, screening candidates, and coordinating assessments
• Creates or refines sales job profiles and postings
• Stays attuned to client needs, the target market, and competitors’ offerings
• Identifies new product opportunities and provides market knowledge for product development

Marketing Leadership (5–10% of time)

• Sets strategy and content direction for the outside marketing vendor (e.g., Digital Park), which executes day-to-day
• Leads relationships with the content marketing firm and other vendors, including regular strategy meetings and content approval
• Monitors marketing KPIs to assure ROI on marketing investment
• Ensures a strong TBG digital brand presence across social media and the website
• Builds data systems and reports to continually evolve marketing strategy and effectivenes

Why Join TBG

• A respected 35+ year brand serving CEOs, executive teams, and organizations across industries.
• A collaborative team of experienced consultants, coaches, and advisors who genuinely support one another and believe teamwork drives the best client outcomes.
• Operational and marketing support so you can spend more time building relationships.
• Opportunities to grow your visibility and influence via strategic partnerships and networking.
• A meaningful voice in shaping TBG’s future – as we grow, you’ll influence strategy, contribute new ideas, and help define what’s next.

What You’ll Bring

• Willingness and ability to personally carry a book of business (~$350k, growing to ~$500k+ over three years) while leading sales and marketing — a player-coach role, not pure management
• Highly competent at building relationships and trust
• Experience motivating seasoned sales professionals and holding them accountable for revenue targets
• Strong written and verbal communication skills
• Experience building a quality client book and retaining, growing, and acquiring relationships
• Experience selling and closing complex, relationship-based professional services (not transactional products)
• Demonstrated thought leadership and ability to build credibility quickly with C-suite leaders
• Strong self-directed drive; comfortable with high autonomy and trust, without close oversight
• Mature, even-keeled approach to team performance — staying neutral and supportive rather than personally or emotionally absorbing team members’ performance issues
• Genuine curiosity and a non-judgmental, growth-oriented mindset toward self, team, and organization
• Ability to design and facilitate team sales training and development

Preferred Qualifications

• Background in leadership development, HR, organizational development, coaching, or human/adult development strongly preferred
• Formal coaching training or certification, or master’s-level education in a related field
• Experience with Traction (entrepreneurial operating system)
• Target first-year total compensation ~$150,000+, with meaningful upside as your book grows
• Market-competitive base salary plus uncapped commission

Benefits include:

• Medical and dental insurance
• HSA/FSA Options
• Simple IRA with company match
• Company-paid short/long-term disability and life insurance
• Travel & entertainment budget for networking, prospecting and client meetings

TBG sets clear expectations while fostering an inclusive workplace, welcoming qualified candidates of all abilities and committed to reasonable accommodations that enable individuals to perform the role’s essential functions.

Essential Functions & Physical Requirements

• Ability to travel regularly (locally and/or periodically overnight) to client, prospect, and event locations, ~50% of the time, with or without reasonable accommodation
• Ability to use a computer and standard office technology for extended periods
• Ability to navigate client sites, venues, airports, hotels, and other business locations as needed, with or without reasonable accommodation
• Ability to communicate effectively with clients, colleagues, and stakeholders in varied settings

Work Schedule & Availability

• Requires flexibility beyond standard business hours, possibly including early-morning meetings, evening events, and occasional weekend commitments for prospective client needs and networking events
• Timely, responsive service to current and prospective clients is essential, occasionally outside business hours
• Frequent travel to meet current and prospective clients is core to the role and may include some overnight or multi-day trips
• In this client-facing sales role, adapting to client schedules and needs is essential; hours are flexible, but client commitments take priority over a traditional 9-to-5

TBG is an equal opportunity employer committed to reasonable accommodations throughout hiring and employment. If you need one to apply or perform this role’s essential functions, please let us know.

By applying, candidates acknowledge reviewing the essential functions and work schedule expectations above.

About The Bailey Group

The Bailey Group (TBG) partners with CEOs, senior executives, and high-potential leaders to help individuals and their organizations realize their full potential. Our approach blends business acumen, humanistic psychology, neuroscience, and eclectic leadership insight — from academic theory to historical narrative.

For 35+ years, our success has been built on a commitment to excellence and shared values: contributing to a greater cause, collaboration, continuous learning, fully invested partnership, maximizing human potential, and authenticity. We celebrate each person’s unique experiences, perspectives, and strengths, and believe innovation and exceptional leadership emerge when people with different viewpoints engage with curiosity, respect, and shared purpose.

If you’re excited to build something meaningful with a team that values relationships, collaboration, and lasting impact, we’d love to hear from you. Send your resume and a brief overview of your professional network and business development experience to View email address on click.appcast.io; all conversations are strictly confidential.