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Head of Sales

SalesSalesFull TimeRemoteTeam 201-500H1B No SponsorCompany Site LinkedIn

Location

Illinois

Posted

45 days ago

Salary

$380K - $400K / year

Bachelor DegreeEnglish

Job Description

• 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

Job 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.