Account Executive, Mid Market

About this role

Help Scout is hiring a mid-market Account Executive to build its outbound sales motion for companies with 100–1,000 employees. This is a full-cycle role focused on sourcing most of your own pipeline, closing higher-value deals, and developing the playbook for future upmarket sales.

About the company

Help Scout provides customer service software designed to help businesses deliver exceptional support experiences. The company focuses on building tools that enhance communication and collaboration between teams and their customers.

The team

Sales

What you'll do

• Source and own pipeline, with more than 75% of opportunities self-generated.
• Run full-cycle sales, from prospecting and tailored demos through business cases, negotiations, and closing.
• Develop the mid-market sales playbook with GTM leadership.
• Collaborate with Product, Marketing, and RevOps on customer needs, campaigns, and sales operations.
• Track and report pipeline coverage, forecast accuracy, and progress toward targets.

What we're looking for

• 8+ years of full-cycle B2B SaaS sales experience.
• Experience selling to mid-market accounts at companies with roughly 250–1,000 employees.
• Track record of sourcing at least 75% of your own pipeline.
• Experience closing $25K–$75K deals with 3–6 month sales cycles.
• Strong account-selection, prospecting, stakeholder-management, and solution-positioning skills.
• Comfort using modern GTM technology and AI tools for prospecting and sales execution.
• Able to build a sales motion from scratch.

Benefits

• Equity offered.
• Flexible time off.
• 12 weeks of fully paid parental leave.
• Home office stipend.
• Coworking stipend of up to $300 per month.
• $1,800 annual professional development stipend.
• Health insurance for employees and dependents in the U.S. or Canada.