Role Overview
Lead and coach a team of Outside Sales Representatives (OSRs) through the complete B2B sales cycle, from pipeline generation to closing and account development. The role requires a leader who has personally carried a quota, built pipeline, and closed deals, with a strong consultative selling mindset and excellent coaching skills.
What You Will Do
Own the entire sales motion, including prospecting, pipeline generation, qualification, discovery, solution presentations, objection handling, negotiation, closing, and account nurturing. Develop, refine, and document scalable sales processes, and leverage AI tools to improve coaching, sales execution, and operational efficiency.
Why It Might Be a Fit
Proven full-cycle B2B sales leader with a strong consultative selling mindset, excellent coaching skills, and a high ownership, accountability, and continuous improvement mindset. Comfortable balancing live coaching with asynchronous development, and enthusiastic about AI.
Requirements
- Proven experience managing full-cycle B2B sales teams
- Demonstrated success leading Outside Sales Representatives
- Personal experience carrying a sales quota and closing complex B2B deals
- Experience generating your own pipeline, running discovery calls, presenting solutions, negotiating, and closing business
- Strong background in Managed Service Providers (MSP) or IT Services
- Solid understanding of consultative technology sales processes
- Hands-on experience using AI tools within daily sales operations
- Comfortable working with Claude Projects, Claude Code, and Claude Cowork
- Strong coaching, mentoring, and leadership abilities
- Excellent verbal and written English communication skills
- Native or near-native English proficiency strongly preferred
Benefits
- Fully remote work environment
- High ownership over sales performance and coaching
- Opportunity to shape sales processes using modern AI tools
- Clear growth path into Director of Sales, Head of Sales, VP of Sales, Revenue Leadership
To apply for this job please visit jobs.workable.com.

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