Director of Sales

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
Sales Team Leadership & Development
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
Innovation & Product Development
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 effectiveness
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
Bachelor's degree required
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)
Compensation & Benefits
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
Comprehensive vacation and sick package
Travel & entertainment budget for networking, prospecting and client meetings
Work Environment
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 out

Work arrangement
Yes