About The Role

The Director of Sales is a critical leadership role responsible for driving Breakout Learning’s next phase of growth. You will refine and execute a scalable sales strategy, lead a high-performing team, and help shape the future of AI-powered learning in higher education.

This role sits at the intersection of revenue, product, and customer success. You will be responsible for creating repeatable sales processes, coaching and developing talent, refining our go-to-market strategy, and ensuring Breakout continues to meet the evolving needs of educators and institutions.

Experience matters, and so does your education, but what matters most is your character. “Rhinos,” as we call ourselves, are hard-charging, fiercely intelligent, customer obsessed, active listeners who are fearless of difficult conversations. Is that you?

Revenue Leadership & Growth Strategy

• Own revenue targets and sales performance across the organization.
• Refine and execute a scalable sales strategy aligned with Breakout’s growth objectives and go-to-market plans.
• Build and maintain a healthy sales pipeline while creating predictable revenue growth.
• Partner with executive leadership to identify new market opportunities and expansion strategies.
• Leverage data, analytics, and customer insights to improve forecasting, conversion rates, and sales effectiveness.

Sales Process & Execution

• Design, implement, and continuously improve Breakout’s sales playbook.
• Create scalable sales processes that support rapid company growth while maintaining a high-quality customer experience.
• Optimize CRM workflows, reporting systems, and sales enablement resources.
• Develop repeatable frameworks for prospecting, pipeline management, forecasting, and account expansion.
• Ensure the team consistently executes against key performance metrics and revenue objectives.

Team Leadership & Development

• Grow, lead, and inspire a high-performing, relationship-driven sales organization.
• Recruit, onboard, and develop top sales talent.
• Coach and mentor Sales Managers and Account Executives to maximize performance and career growth.
• Foster a culture of accountability, collaboration, and continuous improvement.
• Conduct regular performance reviews, pipeline reviews, and professional development conversations.

Customer Focus & Market Insight

• Form strong relationships with institutional leaders, faculty, and higher education stakeholders.
• Ensure customer feedback informs sales strategy and product direction.
• Act as a voice of the customer internally, helping shape product enhancements and future offerings.
• Partner closely with Customer Success to drive adoption, retention, and expansion opportunities.
• Stay informed on higher education trends, competitive dynamics, and emerging opportunities in AI and EdTech.

Cross-Functional Collaboration

• Collaborate closely with Product, Marketing, and Customer Success teams to align growth initiatives.
• Help shape Breakout’s positioning, messaging, and go-to-market strategy.
• Support strategic partnerships and institutional relationships that accelerate company growth.
• Provide leadership with actionable insights from the market, customers, and sales team

Startup Mindset

• Operate with urgency, adaptability, and a strong bias toward action.
• Thrive in ambiguity and embrace the challenges of a fast-growing startup.
• Roll up your sleeves and lead from the front when needed.
• Identify opportunities to improve systems, processes, and organizational effectiveness.
• Contribute beyond your functional responsibilities to help the company succeed.

What You Bring to the Table

• Sales Leadership Experience: 7+ years of experience in sales, with multiple years leading and developing high-performing teams.
• Higher Education Expertise: Experience selling into colleges, universities, or educational institutions preferred.
• Revenue Ownership: Demonstrated success carrying and exceeding significant revenue targets.
• Strategic Thinking: Ability to develop and execute long-term growth strategies while remaining highly operational.
• Coaching & Development: Proven ability to recruit, mentor, and scale successful sales organizations.
• Process Orientation: Strong experience building sales infrastructure, forecasting processes, and performance management systems.
• Communication Skills: Exceptional written, verbal, and presentation skills.
• Startup Mindset: Comfortable operating in a high-growth environment where priorities evolve quickly.
• Customer Obsession: Deep commitment to understanding customer needs and delivering meaningful solutions.

Why Join Breakout Learning?

Be part of a mission-driven team transforming education with cutting-edge AI solutions.

We are building what many believe will become the category-defining AI learning platform. This is an opportunity to join at a pivotal stage, help shape the company’s growth trajectory, and directly influence the future of education.

• Opportunity to lead a young and hungry sales team at a cutting edge AI start-up in the EdTech.
• Meaningful equity participation in a high-growth company.
• Collaborative and supportive team culture focused on innovation and continuous learning.
• Flexible remote work environment with the ability to make an outsized impact.

Compensation: $150,000–$175,000 base salary (depending on experience) + performance-based incentives, equity, company benefits, and unlimited PTO.

If you're a proven sales leader who is excited about transforming education through AI and building a category-defining company, we'd love to hear from you.