Director of Field Sales

caddi

Chicago, United States

November 17, 2025

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Share this job SVGs not supported by this browser. Description CADDi is currently searching for a Director of Field Sales to manage, develop, and enhance the performance of our Account Executive team. This position entails a blend of strategic leadership and active sales engagement, ensuring that the team achieves and surpasses sales targets while fostering relationships with senior stakeholders within the manufacturing sector. The ideal candidate will display a proven track record in field sales leadership, the ability to operate independently in a sales capacity, a strong growth-oriented mindset, and a willingness to travel extensively to guide their team and interact directly with clients. Key Responsibilities: Lead and Develop the Sales Team: Manage, mentor, and inspire a team of Enterprise Account Executives, establishing clear performance expectations, KPIs, and growth plans. Drive Strategic Sales Initiatives: Lead the creation and execution of account strategies, guiding the team in targeting, deal structuring, and closing high-value opportunities to expand market share. Hands-On Field Sales Leadership: Actively sell alongside the team and lead by example in the field, demonstrating best practices, building strong customer relationships, and ensuring successful deal outcomes. Executive Engagement: Lead interactions with C-suite executives, directors, and key decision-makers, aligning sales initiatives with client objectives and company priorities. Pipeline and Forecast Management: Lead the management of sales pipelines, forecasting, and performance metrics to drive predictable revenue growth. Cross-Functional Leadership: Collaborate with marketing, product, and operations teams to identify opportunities, optimize sales processes, and ensure customer success. Requirements Experience: 8–13 years of experience in enterprise or complex B2B sales, ideally within the manufacturing, industrial, or technology sectors. Leadership: Proven experience leading high-performing sales teams (5–15 direct reports) with a track record of coaching and developing talent. Hands-On Sales: Demonstrated ability to actively sell complex deals independently, with a strong mindset for personally contributing to revenue while managing a team. Executive Selling: Experience selling to director-level and C-suite executives, navigating complex decision-making processes. Sales Acumen: Consistent record of meeting or exceeding revenue targets in enterprise sales environments. Communication & Negotiation: Exceptional verbal and written communication skills, with the ability to influence and engage senior stakeholders. Field Sales & Travel: Comfortable leading the team in the field, traveling frequently to drive results and maintain customer relationships. Strategic Thinking: Ability to develop and lead sales strategies, analyze data, and implement actionable plans to drive growth. Self-Motivation: Results-driven, independent, and capable of fostering a high-performance, collaborative team culture. Benefits At CADDi, we're committed to creating a work environment that fosters your well-being and professional development. Here are some of the benefits you'll enjoy as part of our team: Comprehensive Health Benefits: We provide 100% company-covered employee comprehensive health insurance, including medical (UnitedHealth), dental (Principal), and vision (VSP) to keep you and your family healthy. On Target Earnings: $200,000-$300,000 with uncapped commission, based on experience. Ownership & Rewards: Be a part of our success story with a competitive stock options plan. Financial Security: Start saving for your future with our 401k plan, featuring a generous 4% company match starting on day one. Generous Time Off: Maintain a healthy work-life balance with 15 days of paid time off, five dedicated sick days, and ten company holidays to celebrate throughout the year. Thriving Culture: We foster a vibrant work environment with delicious company lunches, engaging events, and healthy drinks and snacks to keep you fueled. Celebrate your achievements with us at quarterly events and holiday gatherings. Learning & Development: We invest in your growth by providing opportunities to join professional organizations, attend industry conferences, and participate in various learning initiatives. Financial Incentives: Benefit from commuter and parking benefits to simplify your daily commute. We also offer referral bonuses to help you spread the word about exciting opportunities at CADDi. We are a diverse and inclusive workplace that values your unique talents and perspectives. We are committed to building a team that reflects the communities we serve. Ready to join a passionate team and make a real difference in the future of Manufacturing in the US? Apply today, and let’s talk! Apply for this job
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