Director of Product Development

ESSENTIAL DUTIES

Product Vision & AMMI Platform Leadership

• Own the product vision, strategy, and multi-year roadmap for AMMI, ensuring it evolves into an industry-leading, AI-enabled logistics toolkit.
• Define and prioritize the product backlog based on SPEED impact, business value, customer need, and technical feasibility.
• Serve as the internal champion for AMMI—articulating the platform’s value to internal stakeholders, leadership, and external partners.
• Establish product governance and sprint cadence frameworks that align development velocity with enterprise priorities.
• Translate the EASE growth strategy into a phased, deliverable-driven product roadmap with measurable outcomes tied to SPEED, customer retention, and operational leverage.
• Drive product discovery and user research processes to ensure AMMI capabilities are built in response to real operational needs and market opportunities.

AI Strategy & Innovation

• Co-own EASE’s enterprise AI strategy alongside the CSO, establishing a clear framework for how AI capabilities are identified, evaluated, integrated, and measured.
• Lead the identification, evaluation, and management of AI vendors and technology partners, ensuring EASE maintains access to cutting-edge capabilities.
• Build AMMI as a genuinely AI-native platform—embedding machine learning, predictive analytics, intelligent automation, and decision-support capabilities throughout the product stack.
• Champion an experimental mindset across the product and development organization: hypothesis-driven development, rapid prototyping, structured pilots, and data-informed iteration.
• Stay ahead of emerging AI trends in logistics and adjacent industries, translating market signals into actionable product investments.
• Establish EASE’s internal AI governance framework, including model performance standards, responsible AI practices, and adoption measurement.

Build, Buy, & Partner Decisions

• Own the build/buy/partner decision framework for new product capabilities, working closely with the CSO to evaluate the optimal path to each new capability.
• Lead structured assessments of third-party solutions, open-source tooling, and partner integrations as alternatives or complements to internal development.
• Evaluate and manage AI and technology vendor relationships, including capability assessments, commercial negotiation, performance accountability, and integration roadmaps.
• Ensure all vendor and partner engagements are governed with clear SLAs, ROI expectations, and strategic alignment criteria.
• Maintain a living technology partnership roadmap that reflects current integration priorities, partner performance, and evolving strategic fit.

Resource Strategy & Team Leadership

• Lead and develop a high-performing internal product and engineering team, setting clear expectations, fostering a culture of accountability, and enabling team members to grow.
• Design and implement a blended development resource model that strategically combines in-house talent with external development capacity to accelerate delivery and manage cost.
• Manage external product development relationships, including performance oversight, scope management, and quality assurance, ensuring external teams operate as seamless extensions of the internal team.
• Define onboarding standards, development norms, and collaboration practices that unify internal and external contributors under a shared operating model.
• Partner with Finance and the CSO to manage the product development budget, forecasting capacity needs and balancing investment across internal headcount and external resources.

Data Science & Analytics

• Own EASE’s data science capability, building internal expertise and platform infrastructure that transforms raw logistics data into predictive insight and autonomous action.
• Lead the design and development of ML models, intelligent pricing tools, operational forecasting capabilities, and other data-driven product features within AMMI.
• Establish a data product strategy that treats EASE’s proprietary data as a strategic asset—defining how it is captured, structured, surfaced, and operationalized.
• Champion the use of data and experimentation in product decision-making, embedding A/B testing, analytics instrumentation, and model performance monitoring into the development lifecycle.
• Ensure data science work is tightly connected to operational outcomes, with a clear line from model or feature to SPEED impact.

Pricing Science & Predictive Cost Modeling

• Own the design, development, and continuous improvement of EASE's pricing science systems, including predictive cost models, dynamic rate engines, and margin optimization tools embedded within AMMI.
• Lead the development of carrier cost prediction and lane-level pricing models that enable EASE to price with speed, accuracy, and confidence across all freight modes and markets.
• Build and maintain a feedback loop between operational outcomes and pricing models—continuously retraining and improving model accuracy using real shipment, cost, and margin data.
• Partner with Sales, Operations, and Finance to ensure pricing science capabilities are integrated into quoting workflows, sales tools, and executive reporting.
• Build product capabilities that support and accelerate the RFP response process—enabling cost estimates to be generated faster, with greater accuracy, and with reduced manual processing effort.
• Establish model performance standards, drift monitoring, and governance practices that ensure pricing models remain accurate, explainable, and aligned with business objectives.

SPEED Ownership & Product Performance

• Treat SPEED (Shipments Per Ease Employee Daily) as the defining product KPI—ensuring every feature, release, and investment decision is evaluated against its anticipated contribution to SPEED.
• Define product OKRs and delivery metrics that create a clear feedback loop between product development activity and measurable business outcomes.
• Establish release cadence and product performance review processes that drive continuous improvement and hold the roadmap accountable to quarterly targets.
• Partner with Operations and Sales to validate that new capabilities are adopted effectively and delivering intended value in the field.
• Report to the CSO and executive leadership on product performance, roadmap progress, development velocity, and SPEED contributions.
• Develop and maintain win/loss analytics capabilities within AMMI that give Sales and leadership accurate, timely insight into bid outcomes, pricing competitiveness, and revenue conversion patterns.

Cross-Functional Collaboration

• Partner closely with the VP, Technology to ensure seamless alignment between new product development and the underlying systems, infrastructure, and internal tools that support them.
• Collaborate with Sales, Customer Operations, and Marketing to ensure AMMI capabilities are understood, positioned, and adopted effectively.
• Serve as a bridge between the technical and business domains—translating complex product and AI concepts into clear commercial and operational narratives for non-technical stakeholders.
• Contribute to EASE’s go-to-market strategy by providing technical and product depth for sales enablement, RFP responses, and customer engagements where AMMI is a differentiator.
• Partner with Sales and Operations to embed RFP response tooling into AMMI workflows, reducing the time and manual effort required to produce competitive, data-backed bids.

KPIs, Performance & Measurement

• Define, monitor, and enforce accountability for KPIs related to system performance, uptime, project delivery, security, and deliverable outcomes.
• Responsible for tracking product budget, forecasting, and spend.
• Use data-driven insights to guide decision-making and continuous improvement.

Leadership and Supervisory Responsibilities

• Lead and mentor the Product Development function, including internal engineers, product managers, data scientists, and external development resources.
• Establish a high-accountability team culture grounded in EASE’s manifesto: execution is necessary, results are mandatory.
• Create and maintain clear performance expectations, sprint cadences, and delivery commitments for all product development resources.
• Partner with the executive team to ensure product strategy is tightly integrated with corporate strategy, commercial priorities, and operational goals.
• Submit monthly leadership reports no later than the 7th calendar day of the following month.
• Provide regular reporting to the CSO and executive leadership on product roadmap status, development velocity, resource utilization, and SPEED impact.
• Build organizational capability by developing internal talent and structuring the team for scale as EASE grows.

• Responsible for tracking product budget, forecasting, and spend.
• Establish KPI’s for each individual on the product development team, establish AI adoption KPI’s to ensure and track ROI on projects and deliverables.

Qualifications:

Education

• Bachelor’s degree in computer science, data science, software engineering, information technology, or related technical field required.
• Master’s degree in computer science, data science, artificial intelligence, or related technical field is strongly preferred.
• Relevant product management, AI/ML, or cloud certifications are a plus.

Experience

• 10+ years of progressive experience in product management, product development, or software engineering, with at least 3–5 years in a senior leadership role.
• Demonstrated success building and scaling modern software products in production environments, ideally in logistics, supply chain, transportation technology, SaaS, or adjacent industries.
• Proven experience developing and deploying AI/ML-powered products, including hands-on familiarity with model development workflows, ML Ops practices, and AI integration patterns.
• Experience leading blended development teams that include both in-house engineers and external product development resources or offshore/nearshore vendors.
• Track record of managing and delivering complex, multi-workstream product roadmaps in a high-growth, fast-paced operating environment.
• Experience with cloud-native product development (AWS, Azure, or GCP) and modern software architecture patterns (microservices, APIs, event-driven systems).
• Experience with data science team leadership, including ML model development, data pipeline management, and analytics product delivery.
• Demonstrated ability to translate business strategy into product requirements and measurable outcomes.
• Experience managing AI and technology vendor budgets and relationships, including commercial negotiation, SLA accountability, and integration oversight.

Knowledge, Skills, & Abilities

• Deep understanding of modern software development practices, including agile/scrum methodologies, CI/CD pipelines, and product-led development frameworks.
• Strong command of AI/ML technologies, including large language models, predictive analytics, automation tooling, and data science platforms.
• Familiarity with logistics technology ecosystems, including TMS, WMS, EDI, and digital freight platforms, is highly preferred. McLeod TMS experience preferred.
• Ability to architect and manage a blended internal/external development model, with strong vendor and contractor management skills.
• Strong analytical, problem-solving, and data-driven decision-making capabilities, with experience establishing product KPIs and measurement frameworks.
• Excellent leadership, communication, and cross-functional stakeholder management skills.
• Entrepreneurial mindset with a bias for action, comfort with ambiguity, and the ability to operate effectively in a high-accountability environment.
• Strong ability to translate complex technical concepts into clear, commercially-oriented narratives for non-technical audiences.
• Mindset of continuous improvement and a genuine passion for building products that deliver
• Ability to translate complex technical information into actionable business strategies.
• Excellent leadership, communication, and stakeholder management skills.
• Strong communication and interpersonal skills, with the ability to work effectively in a team environment.
• Ability to prioritize tasks and manage time effectively in a fast-paced environment.