Strategic Enterprise Regional Sales Director

As our Enterprise Sales Director, you will embody Pluralsight's values, lead a team of highly skilled sales professionals, and foster a collaborative and hardworking environment across the NA region. We are looking for someone with a proven track record of exceptional performance, a deep commitment to our mission, and a passion for building a great team culture.

Who you’re committed to being:

• Passionate about Pluralsight's mission: To Advance the World’s Technology Workforce.

• A strong and conscientious leader with the vision and instinct to inspire outstanding results.

• Creative and entrepreneurial in your approach.

• Possess influential interpersonal and communication skills, tackling complex business challenges with humility and a growth mindset.

• A collaborative team player, adept at navigating ambiguity and adapting to a constantly evolving environment.

• Consistently demonstrate the ability to accurately forecast and exceed revenue goals as a sales leader.

• A natural listener who thinks logically, strategically, and tactically to solve complex problems.

• Highly self-motivated with a dedication to taking responsibility and working autonomously.

What you’ll do:

• Partner with Sales Director peer(s) to establish, shape, and execute strategies for recurring revenue growth to achieve booking targets.

• Provide operational rigor and ensure forecasts and metrics are up-to-date and correct

• Oversee the entire sales process, setting appropriate metrics for sales funnel management and reporting on all business aspects.

• Collaborate with senior leaders and relevant stakeholders to develop, implement, and manage policies and procedures that effectively support the business.

• Support your team by participating in client and prospect meetings and engaging other corporate resources as needed.

• Provide coaching to sellers in alignment with the MEDDPICC framework

• Conduct weekly forecast meetings and 1:1 reviews with your team, ensuring sales tracking and forecasts are readily available to senior leadership and the ELT.

• Maintain key customer relationships and develop and implement strategies for expanding the company’s footprint within key Enterprise accounts.

• Support Business Development and Marketing efforts by attending industry conferences and marketing events.

• Occasional travel will be required (~30%).

Experience you’ll bring:

• A successful history of quota attainment with 5+ years of proven experience in Enterprise software sales, including leadership position.

• Expertise in the MEDDPICC framework (ideally both as a seller and a leader/coach)

Requirements:

• This is a remote role; however, applicants located within 45 miles of our Westlake/Dallas, TX office should expect to work on-site Tuesday through Thursday, with remote flexibility on Mondays and Fridays. This approach enables more effective collaboration, quicker decision-making, and a stronger culture, while still providing flexibility.

• Travel: Travel expectations differ by role. Some quota-bearing sales positions involve limited travel, while others may involve travel of up to 40%, depending on business needs.

Why you’ll love working here:

• We work in a blended environment that supports collaboration, flexibility, and connection across teams.

• We are mission-driven, shaping the future of tech upskillling and delivering impact that matters.

• We foster a culture of inclusion and belonging, where everyone can contribute and thrive.

• We are always learning, creating an environment where you can take on new challenges, expand your skills, and grow with purpose.

• Benefits include competitive compensation, bonus eligibility, comprehensive medical coverage, unlimited PTO, wellness reimbursement, professional development funds, and more.

About us:

Pluralsight provides the only learning platform dedicated to accelerating the technology skills and capabilities of today’s tech workforce. Thousands of companies, government organizations and individuals around the world rely on Pluralsight to support critical technology skill development in areas that are crucial to innovation including artificial intelligence, cloud computing, cybersecurity, software development, and machine learning. We offer highly curated content developed by vetted technology experts, industry leading skill assessments, and hands on, immersive learning experiences designed to help individuals skill-up faster.

Physical Requirements:

This role is primarily performed in an office or home office setting and involves standard computer-based work.

EEOC Statement & Accommodations Statement:

Bring yourself. Pluralsight is an equal opportunity employer. We evaluate qualified applicants without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, age, or veteran status. We also consider qualified applicants with criminal histories, consistent with EEOC guidelines and local laws.

If you need an accommodation to apply, interview, or perform essential job functions, please visit the bottom of our website to learn how to request an accommodation. Learn more about our commitment to diversity, equity, inclusion, and belonging in our DEIB Report.

Pay Transparency:

The annual US base + variable range for this role is $173,000-$432,000 USD. Actual compensation will depend on location, skills, experience, and other factors. Additional benefits and bonuses may apply.

Recruiting Scam Notice:

Please be aware of recruiting scams. We’ll only contact you from an @pluralsight.com email or verified channels. We never ask for sensitive personal info or payments as part of the hiring process. All openings are posted on our Careers page.

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