Regional Sales Director, Mid Market

Summary

Join PagerDuty as a Regional Sales Director to lead and mentor a team of Mid-Market Account Executives. You will develop and execute sales strategies, coach AEs on prospecting and closing techniques, and drive revenue growth within the $50-500 million revenue segment. This role requires 5+ years of quota-carrying field experience in mid-market software/SaaS sales and 1+ year leading sales teams focused on new logo acquisition. PagerDuty offers a competitive salary, comprehensive benefits, flexible work arrangements, and generous paid time off. The ideal candidate will have experience with modern sales tools and a proven track record of success in a high-velocity sales environment. This is a hybrid, flexible role with opportunities for in-person and virtual connection.

Requirements

• 5+ years of quota-carrying field experience in mid-market software/SaaS sales
• 1+ years of leading sales teams focused on new logo acquisition
• Proven ability to coach AEs on prospecting techniques and opportunity management
• Experience with modern sales tools (SFDC, Outreach/SalesLoft, DemandBase/6Sense)
• Track record of accurately forecasting in a high-velocity sales environment

Responsibilities

• Lead and mentor a team of Mid-Market AEs focused on new logo acquisition and initial account expansion within the $50-500M revenue segment
• Coach AEs on effective prospecting techniques, including leveraging tools like Outreach/SalesLoft, DemandBase/6Sense, and other modern sales technologies
• Support AEs in developing efficient sales processes that balance prospecting activities with opportunity management
• Develop comprehensive sales strategies aligned with mid-market segment dynamics and buyer behaviors
• Guide AEs in building effective prospecting and qualification approaches using the MEDDICC framework
• Establish frameworks for AEs to manage their territories while maintaining high levels of prospecting activity and opportunity progression
• Drive adoption of PagerDuty's Command of the Message (COM) selling model and solution selling methodologies
• Implement structured pipeline management approaches that emphasize new logo acquisition and initial expansion opportunities
• Create systems for tracking and optimizing AE performance across prospecting, closing, and early expansion metrics

Preferred Qualifications

• Experience leading teams using solution-selling methodologies in the mid-market segment
• Demonstrated success in building teams that consistently exceed both prospecting and closing targets
• Strong background in developing efficient territory management strategies
• Experience coaching teams on leveraging sales technology and automation tools

Benefits

• Competitive salary
• Comprehensive benefits package from day one
• Flexible work arrangements
• Generous paid vacation time
• Paid holidays and sick leave
• Dutonian Wellness Days - scheduled company-wide paid days off in addition to PTO
• Company equity*
• ESPP (Employee Stock Purchase Program)*
• Retirement or pension plan*
• Paid parental leave - up to 22 weeks for pregnant parent, up to 12 weeks for non-pregnant parent (some countries have longer leave standards and we comply with local laws)*
• HibernationDuty - an annual company paid week off when everyone at PagerDuty, with the exception of a small, coverage crew, is asked to take a much needed break to truly disconnect and recharge
• Paid volunteer time off - 20 hours per year
• Company-wide hack weeks
• Mental wellness programs