Role Overview

We are seeking an experienced and inspirational Director, Enterprise Sales who will lead our rapidly growing enterprise segment. In this role, you will recruit, coach, and scale a high-performing team of Enterprise Account Executives who are transforming logistics and supply chain operations for leading carriers, shippers, and 3PLs.

You will drive strategy, elevate performance, and ensure your team consistently closes deals typically ranging from $50K to $1.5MM in ARR. Your leadership will shape our go-to-market motion, expand our presence across major enterprise accounts, and strengthen our position as the leader in AI-driven freight planning and decision automation.

This role is both strategic and hands-on, blending team leadership, deal coaching, GTM partnership, and executive engagement to generate meaningful revenue impact.

Key Responsibilities

Team Leadership and Development

• Recruit, develop, and coach AEs to consistently achieve and exceed monthly, quarterly, and annual revenue targets
• Build a high-performance culture that motivates, inspires, and empowers sellers to deliver exceptional results
• Lead weekly forecast reviews, deal strategy sessions, and team coaching rhythms

Strategic Sales Execution

• Guide the design and execution of sales plays that win new enterprise logos and expand existing accounts
• Act as executive sponsor on key strategic opportunities, supporting sellers throughout the full deal cycle
• Collaborate with Sales Engineers and Customer Success to deliver high-impact, value-driven solutions

GTM Alignment and Optimization

• Partner closely with GTM leadership to strengthen sales processes, systems, enablement, and operational rigor
• Provide real-time feedback on customer needs, industry trends, and competitive dynamics to influence product and GTM strategy
• Ensure accurate forecasting, pipeline management, and reporting to drive executive decision-making

Market Engagement and Relationship Building

• Foster and expand relationships with senior buyers across transportation and logistics organizations
• Represent Optimal Dynamics at industry events, customer meetings, and strategic engagements
• Travel up to 50 percent to support team development, customer interactions, and deal advancement

Non Negotiables

• Tenacious: You showcase initiative, hustle, and self-motivation in driving new business
• Experienced:
• 10+ years of experience in enterprise SaaS or technology sales
• 5+ years managing and scaling high-performing enterprise sales teams
• 3+ years of experience in logistics, transportation, or supply chain solutions
• Growth Mindset: You’ve obtained professional experience. You’re up-to-speed on the latest industry and technological advancements, and honing your craft.
• Servant Leadership and Collaborative:
• Exceptional ability to build trust, coach teams, and foster a collaborative, motivating culture
• Proven track record of collaborating across sales, customer success, and product teams.
• Consultative: Demonstrated capability of quickly building trust with all levels of leadership, specifically with executive-level decision makers.
• Communicative: Exceptional oral and written communication skills with polished presentation abilities.
• Independent & Flexible: Requires 30-50% travel.

Bonus Points

• Experience selling to or working with For-Hire Carriers
• Experience selling in a rapidly growing startup environment
• Established industry connections in logistics, transportation & supply chain

Pay Range

$180,000—$200,000 USD

Benefits

• Competitive compensation, including Series C level equity
• Health / Dental / Vision 100% covered for employee and 50% for dependents
• Life Insurance, with optional supplemental insurance
• Flexible Spending Account (FSA)
• Health Spending Account (HSA)
• 401(k) with match
• Unlimited PTO (vacation, personal days, sick days, jury duty, military leave, bereavement)
• 11 Holidays
• Paid Parental Leave for all employees
• Short-term and Long-term Disability Insurances, and AD&D Insurance
• Fitness membership reimbursement
• Commuter benefits

Optimal Dynamics is proud to be an equal opportunity employer that celebrates diversity and is committed to creating an inclusive workplace with equal opportunity for all applicants and employees. Our goal is to recruit the most talented people from a diverse candidate pool regardless of race, color, ancestry, national origin, religion, disability, sex (including pregnancy), age, gender, gender identity, sexual orientation, marital status, veteran status, or any other characteristic protected by law.

Optimal Dynamics is committed to working with and providing access and reasonable accommodation to applicants. If you require an accommodation, please reach out to careers@optimaldynamics.com once you've begun the interview process. All requests for accommodations are treated discreetly and confidentially, as practical and permitted by law.