Account Executive Player Coach (SaaS)

TL;DR

Account Executive Player Coach (SaaS): Driving regional sales strategy and managing a team of Account Executives while maintaining an individual revenue target with an accent on coaching, pipeline health, and complex deal closure. Focus on leveraging AI-powered sales tools to optimize performance and setting the standard for high-impact sales execution.

Location: Must be based within commuting distance of Chicago, IL

Salary: $100,000 – $118,000 + commission + equity

Company

hirify.global is an intelligent platform for travel and spend management, automating manual processes to help businesses reclaim lost productivity.

What you will do

• Manage a personal revenue target while closing net-new SMB and MM deals.
• Line-manage, coach, and develop a team of 3–5 Account Executives.
• Conduct weekly 1:1s focused on performance, pipeline health, and individual growth.
• Drive regional strategy in collaboration with Senior Sales Management.
• Design and facilitate training programs using gamification, role-play, and AI-enabled workflows.
• Act as a visible role model and point of contact for the broader sales team.

Requirements

• Must be based within commuting distance of Chicago, IL
• English: C1+ required
• 4–6 years of active B2B sales experience, preferably in SaaS or travel tech.
• Proven track record of managing complex deals across multiple segments.
• Experience with coaching, role-play facilitation, or sales training.
• Comfort with AI-powered sales tools and a curiosity for technology-driven performance.

Nice to have

• Experience in the North American corporate travel industry.
• Hands-on experience building sales enablement materials like decks and playbooks.

Culture & Benefits

• Competitive compensation with equity ownership and commission.
• Comprehensive medical, dental, and vision plans with HSA options.
• 401(k) plan with company matching.
• 20 vacation days and 12 public holidays.
• 12–16 weeks of paid parental leave.
• Wellbeing support via Spring Health, including therapy and coaching sessions.
• Relocation support available for eligible roles.