Head of Sales Academy (AI)

TL;DR

Head of Sales Academy (AI): Revolutionizing and scaling sales training for a marketplace sales organization with an accent on designing and implementing an AI-enhanced training ecosystem. Focus on building scalable systems, leveraging technology, and driving sales excellence through comprehensive programs and data-driven performance improvement.

Location: Chicago, IL (Hybrid - 3 days/week in office)

Salary: $110,000–$155,000 + bonuses

Company

hirify.global is a marketplace connecting over 16 million customers with local businesses, focused on helping them succeed on a performance basis.

What you will do

• Design and implement a comprehensive AI-enhanced sales training framework.
• Create a train-the-trainer model to empower managers for consistent training delivery.
• Develop automated training workflows, AI-powered coaching, and data-driven improvement systems.
• Design programs for selection, onboarding, performance acceleration, and cross-functional sales effectiveness.
• Implement conversational intelligence platforms like SaltedCX and AI Co-Pilot.
• Build dashboards and analytics to measure training effectiveness and business impact.

Requirements

• 5+ years of sales training/enablement experience in marketplace, on-demand, or technology companies.
• Proven track record designing training programs that improved sales metrics (conversion rates, ACV, quota attainment).
• Experience with AI-powered sales tools (conversational intelligence, AI coaching platforms, LMS systems).
• Demonstrated ability to build scalable training systems with small teams by leveraging technology and distributed trainers.
• Strong understanding of marketplace/local commerce sales dynamics and challenges.
• Excellent instructional design skills with ability to create engaging, multimedia training content.

Nice to have

• Experience with SaltedCX, Gong, Chorus, or similar conversational intelligence platforms.
• Background in sales operations, revenue enablement, or sales leadership.
• Familiarity with adult learning theory, competency frameworks, and performance consulting.
• Experience managing training teams or cross-functional training initiatives.
• Data analysis skills (SQL, Tableau, or similar tools a plus).

Culture & Benefits

• Lead training innovation at a company serving millions of customers and thousands of local merchants.
• Opportunity to build from the ground up with cutting-edge AI tools.
• Collaborative culture that values experimentation and continuous improvement.
• Competitive compensation including base + bonus + equity.
• Comprehensive benefits including Medical, Dental, Vision, EAP, 401(k) Match, ESPP, Life and Disability Insurance, FSAs, and Flexible PTO.