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Regional Sales Director, Strategic

liETtVLaARqgmMEbYzHNNLIzUPcdfPrwhYtVK7Qa.png Fast Facts

Pluralsight is seeking a Regional Sales Director to lead its sales strategy in the Northeast region, focusing on enterprise account expansion and sales process management in a remote capacity.

liETtVLaARqgmMEbYzHNNLIzUPcdfPrwhYtVK7Qa.png Responsibilities: Develop and implement sales plans for business growth, lead the sales team in achieving quotas, mentor team members, and maintain key customer relationships within assigned regions.

liETtVLaARqgmMEbYzHNNLIzUPcdfPrwhYtVK7Qa.png Skills: Proven experience in SaaS sales management, familiarity with Salesforce CRM, and expertise in sales training methodologies such as Solution-Selling and Value Selling.

liETtVLaARqgmMEbYzHNNLIzUPcdfPrwhYtVK7Qa.png Qualifications: Strong understanding of Meddpicc framework, excellent forecasting and collaboration skills, and experience in managing sales cycles up to the C-Suite level.

liETtVLaARqgmMEbYzHNNLIzUPcdfPrwhYtVK7Qa.png Location: This is a remote role for candidates in the USA, with optional in-office work in Westlake/Dallas, TX, on selected days.

liETtVLaARqgmMEbYzHNNLIzUPcdfPrwhYtVK7Qa.png Compensation: $227000 - $302000 / Annually




Job Description:

Pluralsight is the leading technology workforce development company. Over the last decade, we have transformed the tech skills development market, forever changing the way individuals and companies approach the never-ending need to learn tomorrow's tech skills. Through tech skill development, we help companies build better products and we empower individuals to grow their skills and their careers. Join us and help individuals and companies develop the tech skills of tomorrow.

The Regional Sales Director is responsible for the successful execution of the sales strategy in the Northeast region. This position will drive the sales team based on Pluralsight's sales methodology including account penetration, prospect qualification, supervision of sales activity, sales process planning, negotiation, and closing all sales opportunities.

Who you are:

  • You have proven sales experience in identifying market size and focus, developing sales pipelines, penetrating new accounts, and driving the sales process within a relationship selling environment.
  • You have experience using sales analytics and funnel management techniques to drive productivity, and have ensured appropriate sales activity with visibility of the pipeline to senior management for forecasting and business planning.
  • You have successfully managed the sales cycle from business champion to the SVP of Engineering/CEO/CTO level. Positioning the value proposition and selling to the “C”-suite is a must.
  • You have demonstrated leadership characteristics within a team setting through times of growth, change and ambiguity.
  • Consistently achieves quota with demonstrated success in accurately forecasting quarterly and annual targets, and achieving those sales commits.
  • You’re passionate when it comes sales training (i.e. Solution-Selling, Customer-centric Selling, Strategic Selling and/or Value Selling).

What you’ll own:

  • Develop and implement a business plan to expand business within our enterprise customer base.
  • Lead daily and weekly activities, pipelines, forecasts and closed deals to ensure above quota results based on successful pipeline management as well as mentoring the team with various prospecting techniques.
  • Attract, hire, onboard and retain top sales talent
  • Display a detailed understanding of business needs and revenue potential for accounts in the assigned region
  • Work with team members individually as needed while always promoting a balanced team environment through ongoing mentoring and development of the sales team
  • Work directly with the leadership team to craft strategies for driving balanced business growth
  • Maintain key customer relationships, develop and implement strategies for growing Pluralsight’s products with the customer base.
  • Provide detailed and accurate sales forecasting and reporting on all aspects of of the business to Sales leadership
  • Collaborate with leaders and other relevant team members to build, implement and lead policies and procedures to optimally support the business
  • Create and deliver effective presentation, including corporate and solution capabilities, prospective client proposals, bid defense and business reason.
  • Support business development efforts by attending industry conferences and events

Experience you'll bring:

  • Experience in SaaS sales / sales management experience with a track record of consistent annual sales goal achievement
  • Experience developing sales pipelines; penetrating new accounts and growing existing accounts within a relationship selling environment
  • Consistent record of meeting annual sales goals, pipeline generation, developing new opportunities and managing sales pipelines in a scale-up environment
  • Experience using Salesforce CRM, sales analytics and funnel management techniques to drive productivity
  • Expertise in sales training (i.e. Solution-Selling, Strategic Selling and/or Value Selling)

Preferred qualifications/skills

  •  Understanding of Meddpicc and the Three Whys Framework. Experience integrating the Three Whys into a team’s daily sales process, providing ongoing coaching.
  • Strong forecast hygiene with a “no surprises” approach. Look for evidence of proactive risk identification and the ability to articulate clear reasons for forecast change.
  • A commitment to customer-facing value possessing a track record of leading a team that consistently adds measurable value in customer interactions. 
  • Possesses strong cross-functional collaboration skills and has a history of successfully partnering with teams like Customer Success, Professional Services, and Product and Marketing to drive holistic business outcomes and improve the customer experience.   

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’re a blended workplace, where team members work remotely or in a hybrid setup depending on their role and location
  • We’re mission driven and guided by our culture pillars
  • We have a strong commitment to diversity and belonging
  • We cultivate a culture of trust, autonomy, and collaboration
  • We’re lifelong learners and champion team member growth and advancement
  • We’ve got you covered - team member benefits include competitive compensation packages, medical coverage, unlimited PTO, wellness reimbursements, Pluralsight subscription, 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. Pluralsight provides 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.

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.

The annual US base + variable range for this role is $227,000-302,000 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.

#LI-DF

Average salary estimate

$264500 / YEARLY (est.)
min
max
$227000K
$302000K

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Full-time, remote
DATE POSTED
October 24, 2025
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