Head of Sales
Choco
full-time
Posted on:
Location Type: Remote
Location: Illinois • United States
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Salary
💰 $380,000 - $400,000 per year
Job Level
About the role
- Leading, coaching, and developing a team of 6 Account Executives through regular 1:1s, hands on deal reviews, and tailored enablement support
- Creating a structured sales rhythm focused on skill development, collaboration, and data driven execution
- Modeling consultative selling excellence by helping reps diagnose customer challenges and connect Descartes solutions to measurable outcomes
- Building and managing a high quality pipeline grounded in customer value, not volume
- Recruiting and developing top talent who embody curiosity, commitment, and integrity
- Leveraging CRM and performance data to improve forecasting accuracy and pipeline discipline
- Consistently achieve pipeline, sales, and recruiting targets while celebrating wins, recognizing progress, and fostering a culture of growth and optimism
Requirements
- Frontline sales manager with individual contributor roots, leading mid-market teams to build, execute, and win through outbound-focused sales motions.
- Drive a consultative, value-based sales approach that builds trust and long-term customer relationships.
- Proven success selling to upper mid-market customers while consistently delivering predictable performance across both mid-market and upper mid-market segments
- Highly goal-driven and resilient, with a strong belief that disciplined work ethic fuels results
- Effectively balance strategic thinking with hands-on execution, taking a practical, solutions-first approach
- Leverage data to inform coaching, decision-making, and performance accountability
- Lead with curiosity, resilience, and emotional intelligence in every interaction
- View continuous recruiting and talent development as core, ongoing leadership responsibilities
- Develop and operationalize a repeatable sales playbook that drives consistent execution and results across multiple market segments.
Benefits
- Offers Equity
- Offers Commission
- Offers Bonus
Applicant Tracking System Keywords
Tip: use these terms in your resume and cover letter to boost ATS matches.
Hard Skills & Tools
consultative sellingsales forecastingpipeline managementsales playbook developmentdata analysisperformance accountabilityoutbound salesskill developmentcustomer relationship management
Soft Skills
leadershipcoachingcuriositycommitmentintegrityresilienceemotional intelligencestrategic thinkingcollaborationoptimism