Regional Sales Manager - Mid-Market

Regional Sales Manager-Mid-Market

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.