Regional Sales Manager – Mid-Market

Overview

Regional Sales Manager – Mid-Market. Remote, United States.

Position Overview

We are seeking a driven Mid-Market / Lower Enterprise Account Executive to manage a high-opportunity territory focused on organizations up to 5,000 employees. This role involves a mix of new business development and customer expansion, requiring strong sales execution, solution positioning, and the ability to build trusted relationships across multiple levels of an organization from C-level leaders down through HR, Talent, L&D, and functional teams.

The ideal candidate is a consultative seller with experience navigating multi-stakeholder buying groups and managing a fast-moving, high-volume sales motion.

• Develop and execute a territory plan for accounts up to 5,000 employees.
• Prospect and qualify net-new opportunities across the full sales cycle.
• Manage and expand existing customer relationships through cross-sell and upsell opportunities.
• Establish and nurture relationships from C-level executives to operational leaders and end users.
• Lead discovery, solution positioning, and product demonstrations with support from Solution Consultants.
• Build compelling proposals and business cases that articulate Cornerstone’s value.
• Maintain accurate forecasting and pipeline management within CRM.
• Collaborate effectively with Customer Success, Marketing, and Product teams to support deal progression and long-term growth.

• 3–5+ years of SaaS or technology sales experience, ideally within mid-market or lower enterprise accounts.
• Proven track record of consistent quota achievement.
• Ability to manage high-velocity sales cycles while engaging strategically at all organizational levels.
• Demonstrated success building relationships from C-suite executives down to functional leaders and influencers.
• Strong communication, presentation, and negotiation skills.
• Excellent pipeline discipline, territory management, and organizational skills.
• Self-starter with strong business acumen and a competitive, solution-oriented mindset.

• Experience in HCM, HR tech, Talent, or Learning technology.
• Familiarity with multi-stakeholder buying processes in mid-size organizations.
• Ability to articulate complex value propositions in a clear, outcomes-oriented way.

Spark Greatness. Shatter Boundaries. Share Success. Are you ready? Because here, right now – is where the future of work is happening. Where curious disruptors and change innovators like you are helping communities and customers enable everyone – anywhere – to learn, grow and advance. To be better tomorrow than they are today.

Cornerstone powers the potential of organizations and their people to thrive in a changing world. Cornerstone Galaxy, the complete AI-powered workforce agility platform, meets organizations where they are. With Galaxy, organizations can identify skills gaps and development opportunities, retain and engage top talent, and provide multimodal learning experiences to meet the diverse needs of the modern workforce. More than 7,000 organizations and 100 million+ users in 180+ countries and in nearly 50 languages use Cornerstone Galaxy to build high-performing, future-ready organizations and people today.

At Cornerstone, we are dedicated to inspiring excellence and pushing boundaries in everything we do. Our compensation strategy is based on three fundamental principles: equitable pay, market-driven research, and skill-based appraisals. As part of our mission to share success and empower individuals to thrive in an ever-changing world, the listed salary range is just one element of Cornerstone’s comprehensive compensation package.

This compensation package may also include annual bonuses, short- and program-specific awards depending on the role, and a comprehensive benefit offering. The disclosed salary range reflects the geographic differential based on the location of the position if applicable. The starting salary for the successful applicant will depend on several job-related factors, including education, training, experience, certifications, location, business needs, and…