Account Executive - Mid Market - U.S. Remote

Location: U.S. Remote

Who We Are: 

CYPHER Learning is the AI-native learning platform for organizations that need to train employees, customers, and partners at scale. While many platforms layer AI onto legacy systems, CYPHER was built differently. At the center of our platform is CYPHER Agent, a natural-language, agentic interface that connects content creation, administration, delivery, personalization, and analytics in one unified system. Organizations can create and launch training in minutes, not months, and deliver it seamlessly across distributed audiences. We help companies move faster and turn learning into measurable performance. As we continue to redefine the LMS industry, we are looking for builders who want to help scale the business to new levels.

The Role: 

We are seeking a driven and consultative Account Executive to join our growing sales team, focused on mid-market opportunities in the $50K to $500K ACV range within distributed organizations. In this role, you will run a high-velocity sales motion while engaging operators, Learning & Development leaders, and revenue teams looking to move faster but held back by slow, fragmented training systems. Success in this role means consistently closing ideal-customer opportunities, building strong pipeline momentum, running efficient sales cycles, and positioning CYPHER Learning as a faster, modern alternative to outdated learning systems. The ideal candidate will have a strong track record in B2B SaaS sales and the ability to manage opportunities from prospecting through close. This is not a traditional LMS sale. You will help customers replace outdated approaches with an AI-powered platform that delivers measurable business outcomes.

What you’ll do:

• Own and close mid-market opportunities ranging from $50K to $500K ACV across a full sales cycle. 
• Manage a fast-paced pipeline while balancing multiple active deals across 30–120 day sales cycles. 
• Build and grow a self-generated pipeline within distributed organizations training employees, customers, partners, and field teams. 
• Sell business outcomes by positioning CYPHER Learning around speed, scale, onboarding effectiveness, readiness, and productivity. 
• Lead consultative discovery conversations that uncover operational challenges and buying priorities. 
• Navigate multi-stakeholder deals with operators, L&D leaders, revenue teams, and procurement partners. 
• Create urgency by helping prospects understand the impact of outdated training systems and the value of moving faster. 
• Partner closely with Marketing, SDRs, Customer Success, and Product to improve conversion, adoption, and market feedback.
• Perform other related duties as assigned.

  
  

Your Skills & Experience:

• Bachelor’s degree or equivalent practical experience preferred. 
• 5–8 years of B2B SaaS sales experience, ideally within mid-market environments. 
• Proven track record of consistently closing opportunities in the $50K–$500K ACV range. 
• Strong pipeline generation skills with the ability to self-source opportunities, not rely solely on inbound demand. 
• Experience managing multiple active deals simultaneously while maintaining quality execution. 
• Strong understanding of the full sales cycle, from prospecting through close and expansion. 
• Confidence selling to Director, VP, and executive-level stakeholders. 
• Excellent verbal, written, presentation, and negotiation skills. 
• Ability to simplify complex solutions and communicate a clear, compelling value story. 
• Self-starter mindset with the ability to operate independently and collaborate effectively across teams. 
• Strong sense of urgency, consistent follow-through, and disciplined execution.

Our Values:

• Curiosity: Continues learning to stay agile and innovative.
• Connection: Embracing and celebrating our differences.
• Empowerment: Rewarding positive people-centric behaviors and decisions.
• Potential: Challenging status quo and pushing for what’s possible.
• Impact: Making a positive impact for our clients and communities around the world.

 Why Join CYPHER Learning?

• Be part of an innovative and global organization that is revolutionizing digital learning.
• Collaborate with a diverse, international team in a fast-paced and dynamic startup environment.
• Opportunity to drive customer success strategies that impact businesses and educational institutions worldwide.
• Competitive compensation package, professional development opportunities, and a supportive work culture.

This is an evergreen posting intended to build our pipeline for future opportunities. While we may not have an immediate opening today, we welcome applications from talented candidates interested in future consideration.

Equal Employment Opportunity

At CYPHER Learning, we believe diversity is essential to innovation and progress. We are committed to creating a workplace where individuals of all backgrounds, identities, and experiences are respected, included, and empowered to thrive. Our culture is built on connection, curiosity, empowerment, potential, and impact—and we know that these values are only fully realized when everyone has a seat at the table.

CYPHER Learning is proud to be an Equal Opportunity Employer. We make all employment decisions based on merit, qualifications, and business needs—without regard to race, color, religion, sex, sexual orientation, gender identity or expression, age, national origin, disability, veteran status, genetic information, or any other protected status under applicable law.

As a global, remote-first company, we embrace flexibility and accessibility in every aspect of how we work. If you require a reasonable accommodation during the application or interview process, please contact our People team at peopleteam@cypherlearning.com. We are committed to providing an inclusive and equitable experience for every candidate.