Senior Enterprise Sales Director

Lakeside Software is seeking a strategic Enterprise Sales Director to drive new business development, manage large enterprise sales cycles, and build relationships with large organizations. This is not a post-sale Sales or Customer Success role, focusing instead on a hunter mentality and a proven ability to expand within complex enterprise sales cycles. The role involves achieving revenue targets and aligning solutions with customer needs.

Requirements

• Minimum 8 years of experience selling cloud-based SaaS solutions to large enterprise organizations.
• Experience in Digital Employee Experience (DEX), digital monitoring, or End User Computing (EUC) is highly preferred.
• Proven success in selling to enterprise verticals such as Financial Services, Healthcare, and the Public Sector.
• Demonstrated experience partnering with large, strategic Channel Partners and GSIs to drive joint success.
• Expertise in value-based selling, with the ability to articulate financial impact and business outcomes.
• Strong track record of quota achievement, pipeline development, and accurate forecasting.
• Exceptional collaboration and relationship-building skills.

Benefits

• Medical, Dental & Vision Insurance
• Flexible Spending
• Short & Long Term Disability Insurance
• Company Paid Life & Voluntary Life & AD&D Insurance
• 401(k) matching
• Paid Time Off
• Sick Time
• Career Development
• Collaborative and supportive team culture