Associate Director, Direct Field Sales

What You’ll Do (The Player/Coach Breakdown)

• The Coaching (Management) Side:
  • Lead & Mentor: Directly manage and motivate a team of Field Sales Professionals, providing coaching, guidance, and strategic direction to help them achieve their sales targets.
  • Sales Enablement: Conduct regular 1:1s, ride-alongs, and team training sessions on sales process, product knowledge, and consultative selling techniques.
  • Performance Management: Monitor team activity and pipeline health, providing constructive feedback and implementing strategies to improve performance.
  • Recruiting: Assist in the interview and onboarding process for new members of your growing team.
• The Player (Selling) Side:
  • Full Sales Cycle Ownership: Put together your ultimate playlist of local businesses and guide them through the entire sales cycle—first call to final high-five.
  • Bonus points if you’re a lead-generation wizard.
  • Network Building: Forge rock-solid partnerships with local POS dealers, web designers, and BNI folks to build an unstoppable referral network.
  • Consultative Demos: Perform demos so dazzling, prospects will feel like they’re front-row at a magic show.
  • Cross-Functional Collaboration: Team up with our awesome colleagues across North to make sure your promises turn into real results.

Requirements

Proven Sales Performance: Demonstrated success in a high-volume, full-cycle sales role, preferably with experience in SaaS, Software, or Payment Processing.

Emerging Leadership: A strong desire to step into a leadership role, with a natural ability to coach, mentor, and motivate others.

Operational Excellence: Strong organizational, presentation, and communication skills, with experience using CRM.

Agile & Resourceful: Thrives in a fast-paced, startup vibe. A self-starter who can pivot on a dime and still shine brighter than the Vegas strip.

Territory Experience: Cold-calling and local canvassing experience is a significant plus. You’re at least 18, have a valid driver’s license, and must live in the area of your remote field sales territory.

Benefits

We offer the most lucrative compensation in the SaaS & Payments space – we call it North ’25. Top earning potential: Sky-high weekly commissions, residuals for the life of your accounts, and a slice of portfolio equity.

First-year pros in the top 25% can expect $120,000–$150,000 with uncapped weekly commissions, lifetime residuals, and portfolio equity.

Compensation includes an additional component for the coaching/team leadership responsibilities.

W2 Status with medical, dental, life, and disability insurance. Comprehensive benefits package.

Career Growth: This role is the formal pathway into Sales Leadership, with opportunities to grow into Director and beyond within Sales Leadership, Business Development, or Revenue Operations.