Head of Solutions Delivery

About Our Company

Built on over four decades of pioneering research at Princeton University, our platform represents the leading edge of innovation in freight and transportation planning. We help customers unlock double-digit revenue gains and drive smarter, data-driven operations at scale.With the recent close of our Series C funding round led by Koch Disruptive Technologies, we’re entering an exciting new phase of growth. Today, Optimal Dynamics is a high-growth company of ~70 employees, backed by top-tier investors including Bessemer Venture Partners, The Westly Group, Activate Capital, and Koch.

We're on a mission to redefine the way logistics decisions are made—and we’re just getting started.

About Our Team

We are a team of bright, kind, and solution-oriented people focused on creating value for our customers. We can solve problems individually, but understand that the best solutions are found when the team brainstorms ideas together. We are excited about balancing the need to deploy new solutions quickly and designing solutions that are secured, reliable, maintainable, and scalable for the long run.

As the Head of Solutions Delivery at Optimal Dynamics, you will lead the successful execution of customer projects from kick-off through go-live. This role is critical to ensuring our AI platform is deployed efficiently and effectively, aligned with each customer’s business objectives. You will lead a team driving implementation excellence, accelerate time-to-value, and establish scalable delivery frameworks that enable repeatable, high-quality deployments.

You will also oversee cross-functional coordination among the Sales, Deployment, and Customer Success teams, ensuring seamless handoffs, clear accountability, and a consistent customer experience throughout the deployment lifecycle.

• Oversee and direct the full deployment lifecycle of Optimal Dynamics solutions, from project kick-off through go-live, ensuring alignment with customer goals and operational needs.
• Set the strategic direction for deployment and lead a team of implementation specialists to deliver high-quality, timely, and cost-effective solutions.
• Champion the integration of change management principles to support customer teams in adapting to new workflows, systems, and technologies.

• Continuously assess and refine deployment workflows to accelerate time-to-value and maximize delivery efficiency.
• Implement scalable best practices and methodologies that enhance resource utilization, streamline execution, and leverage data to inform process improvements.

• Build strong, trust-based relationships with customers to understand their business drivers, success metrics, and expectations.
• Collaborate with customers to define clear implementation goals, monitor progress through data-backed insights, and ensure those goals are met and exceeded.
• Support customers in navigating operational change by aligning deployment plans with internal readiness and user adoption strategies.

• Manage seamless coordination between Sales, Deployment, and Customer Success teams, ensuring full transparency and alignment throughout the deployment journey.
• Partner closely with Sales to facilitate smooth transitions for new customers, providing key insights into customer needs and operational requirements.
• Ensure cross-functional teams are aligned in supporting change adoption, from technical onboarding to process transformation.

• Lead, mentor, and grow a high-performing deployment team, providing training, feedback, and development opportunities to build expertise and accountability.
• Foster a team culture centered on collaboration, ownership, and continuous improvement, with a focus on using data to identify performance trends and coaching opportunities.

• Define and track KPIs related to deployment success, project timelines, customer satisfaction, and retention.
• Use performance data and trend analysis to inform tactical decisions, identify gaps, and drive strategic adjustments.
• Provide regular updates and insights to senior leadership on deployment progress, risks, and improvement opportunities.

• Proactively identify and mitigate risks that could impact project delivery, scope, or customer satisfaction.
• Leverage data to surface early warning signs, guide resolution strategies, and ensure structured, responsive problem-solving.
• Plan for organizational change risks and support stakeholder readiness during transitions.

• Set the stage for long-term customer success by ensuring effective handoff to post-go-live teams and equipping customers with the tools and knowledge they need.
• Partner with Customer Success to use data from the deployment phase to inform retention strategies and reinforce value realization from OD solutions.
• Align deployment outcomes with customer adoption plans to drive continuous value and minimize resistance to change.

Key Requirements

• 10+ years of experience in customer-facing implementation, deployment, or professional services roles within enterprise SaaS, freight tech, transportation, or a related industry. 5+ years in a senior leadership capacity, with a proven track record of building, leading, and scaling high-performing delivery or deployment teams.
• Demonstrated success overseeing complex, enterprise-grade deployments, including multi-stakeholder engagements, change enablement, and technology adoption.
• Strong grounding in project and program management methodologies (e.g., Agile, Scrum, PMP), with the ability to lead structured execution while navigating ambiguity.
• Proven ability to embed and lead change management practices—guiding customers and internal teams through process, platform, or operational transitions.
• Deep experience designing and refining scalable delivery processes that drive time-to-value while ensuring a consistent customer experience.
• Analytical and data-driven, with a strong command of performance metrics, KPIs, and data-informed decision-making.
• Excellent communicator with strong executive presence; skilled at managing stakeholder expectations and influencing outcomes across all levels.
• Comfortable working cross-functionally with Sales, Product, Engineering, and Customer Success to ensure seamless delivery and handoffs.
• Direct experience or deep familiarity with the freight tech space is strongly preferred; exposure to optimization, AI, or advanced planning systems is a plus.
• Bachelor’s degree in Logistics, Industrial Engineering, or Business Administration required; advanced degree or equivalent relevant experience is a plus.