twentyAI · 12 hours ago
Sales Director
twentyAI is seeking a Director of Sales for North America to lead regional revenue growth in the retail software space. This role focuses on executing sales strategies, managing enterprise sales cycles, and building a high-performing partner ecosystem to drive sustainable growth.
Responsibilities
Own and execute regional sales strategy across direct and partner-led motions
Manage complex enterprise sales cycles from prospecting through close and expansion
Build, enable, and expand a high-performing channel partner ecosystem
Develop account-based strategies for strategic retail prospects and customers
Forecast revenue accurately and manage pipeline health through CRM
Negotiate commercial terms, pricing, and contracts for software and services
Drive demand generation initiatives in partnership with marketing
Identify market trends, competitive positioning, and growth opportunities
Lead quarterly business reviews and executive-level customer engagements
Collaborate cross-functionally with product, services, and support teams to ensure customer success
Provide guidance and support to partners on commercial and solution positioning
Qualification
Required
15+ years of enterprise software sales experience with direct and channel models
Proven success selling retail or vertical-focused enterprise solutions
Strong background in partner/channel management
Track record of exceeding regional revenue targets
Excellent communication, negotiation, and executive presence
Comfortable operating in a matrixed, fast-paced environment
Bachelor's degree or equivalent experience
Based in the U.S. with ability to travel up to 30%
Preferred
Professional sales or business certifications preferred