Our Opportunity:
Chewy is seeking a proactive and detail-oriented Transportation Execution Manager II to support transportation operations. This role plays a key part in ensuring service reliability by executing dispatch plans, supporting carrier communication, and assisting with issue resolution. You will help monitor cost and service performance for third-party dedicated fleets and one-way truckload carriers, escalating risks and disruptions as needed. In this role, you will support the transportation function by driving adherence to plans, maintaining operational continuity, and assisting with real-time decision-making. You will work closely with Fulfillment Center Operations, Field Transportation, and third-party carrier partners to ensure consistent execution and service outcomes. Strong communication skills, the ability to react quickly to changing conditions, and a collaborative mindset are essential to success in this role.
This position offers the opportunity to gain exposure to transportation network operations while developing leadership and operational execution skills in a fast-paced environment.
This role covers a weekend shift, working 7:30 AM-4:30 PM EST. The daily schedule will be either Thursday-Monday or Saturday-Wednesday and occasionally will require an overnight shift.
What You'll Do:
- Execute transportation operations across multiple fulfillment centers. Ensure driver coverage and on-time dispatch performance through direct engagement and oversight of third-party carriers.
- Carrier Engagement & Communication: Lead calls with carriers to confirm driver assignments and readiness. Build carrier accountability through consistent communication and proactive troubleshooting.
- Load Planning & Operational Oversight: Manage load planning and execution. Ensure alignment with the transportation schedule, resolve exceptions, and maintain real-time accuracy in OTM.
- Real-Time Escalation & Problem Solving: Serve as the decision-maker for real-time operational disruptions. Identify risks, implement short-term solutions, and drive toward long-term corrective actions.
- Root Cause Analysis & Corrective Actions: Use SQL and Excel to analyze operational failures or inefficiencies and implement data-driven corrective action plans to drive performance improvements.
- Cross-Functional Alignment: Collaborate with fulfillment center operations, internal transportation teams, and carrier partners to drive service excellence and ensure alignment on goals and execution.
What You'll Need:
- 2+ years of experience in transportation, supply chain, or logistics
- Demonstrated ability to manage overnight or shift-based transportation operations.
- Proficiency in Oracle Transportation Management (OTM) or similar TMS platforms.
- Strong leadership, communication, and conflict resolution skills.
- Analytical proficiency, including basic SQL skills and Excel-based data analysis.
- Proven experience managing third-party carrier performance and accountability.
- Bachelor's degree in supply chain, logistics, business, or a related field.
Bonus (if applicable):
- Hands-on experience in transload and yard management operations.
- Background in e-commerce or retail transportation environments.
- Familiarity with Lean/Six Sigma methodologies is a plus.
- SQL, Tableau or data visualization experience is a bonus.
Position Details
- This role requires occasional overnight coverage, covering evening and early morning hours.
- Travel may be required depending on business needs.
- Full-time role with competitive compensation and benefits.
Join us in delivering excellence overnight and shaping the future of our transportation network!
Chewy is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, ancestry, national origin, gender, citizenship, marital status, religion, age, disability, gender identity, results of genetic testing, veteran status, as well as any other legally-protected characteristic. If you have a disability under the Americans with Disabilities Act or similar law, and you need an accommodation during the application process or to perform these job requirements, or if you need a religious accommodation, please contact [email protected].
To access Chewy's California CPRA Job Applicant Privacy Policy, please click here.
Skills Required
- 2+ years experience in transportation, supply chain, or logistics
- Experience managing overnight or shift-based transportation operations
- Proficiency in Oracle Transportation Management (OTM) or similar TMS platforms
- Strong leadership, communication, and conflict resolution skills
- Analytical proficiency, including basic SQL skills and Excel-based data analysis
- Proven experience managing third-party carrier performance and accountability
- Bachelor's degree in supply chain, logistics, business, or a related field
- Hands-on experience in transload and yard management operations
- Background in e-commerce or retail transportation environments
- Familiarity with Lean/Six Sigma methodologies
- Tableau or data visualization experience
What the Team is Saying
Chewy Compensation & Benefits Highlights
How does Chewy ensure its pay and bonus plans are competitive?
Chewy approaches compensation through a total rewards strategy that combines salary, bonuses, equity opportunities, healthcare benefits, employee discounts, and career growth opportunities. The company emphasizes supporting employees across ecommerce, healthcare, pharmacy, customer service, technology, and fulfillment operations while competing for talent in both retail and tech markets.
Competitive compensation and bonus opportunities: Chewy offers market-based compensation packages that may include salary, performance bonuses, commissions, and equity depending on role and level. Built In also notes benefits such as relocation assistance, employee discounts, and bonus opportunities across multiple teams and functions.
- Healthcare and wellness support: Benefits include medical, dental, vision, prescription coverage, HSA/FSA options, life insurance, disability coverage, telemedicine, mental health resources, and wellbeing programs. Chewy also offers wellness-focused resources designed to support employees physically, mentally, and financially.
- Retirement and financial wellbeing: Employees receive 401(k) plans with company matching along with financial wellness resources and broader support programs. Benefits are designed to support both short-term needs and long-term financial planning.
- Pet-focused and family-oriented benefits: Chewy offers pet insurance discounts, employee discounts on Chewy products, parental leave, fertility support, family-focused benefits, and caregiving resources. The company’s benefits package is closely aligned with its pet-focused identity and customer mission.
- Flexibility and workplace support: Corporate employees may have access to hybrid work arrangements, flexible scheduling, commuter benefits, PTO, paid holidays, and wellbeing initiatives. Employees also cite supportive managers and collaborative teams as important parts of the broader employee value proposition.
- Long-term career investment: Compensation is reinforced through career growth opportunities, mentorship, leadership development, cross-functional learning, and exposure to large-scale ecommerce, automation, healthcare, and logistics initiatives. Employees often describe growth opportunities as an important part of the overall company experience.
- External signals: Comparably reports that 70% of employee reviews are positive overall. Employees frequently highlight healthcare benefits, employee discounts, coworkers, and growth opportunities as strengths of the company experience. (Glassdoor; Comparably)
Chewy Insights
What We Do
Who We Are Chewy is where pet parents find everything they need for life with pets, from food to fun to pharmacy. We make pet care easier, more informed, and more joyful through fast, reliable delivery and award-winning 24/7 Customer Care, including access to pet health support when it’s needed. Founded in 2011, Chewy combines the convenience of online shopping with a high-touch, personalized experience built around the real moments of pet parenthood. Our Mission Chewy’s mission is to be the most trusted and convenient destination for pet parents and partners, everywhere. What We Do We support pet parents through the highs, lows, and everyday moments of the pet parenting journey with: • Pet food, treats, and daily essentials • Supplies for dogs, cats, fish, birds, reptiles, equine, and small pets • Pharmacy and veterinary services, including prescriptions and medications • Pet wellness and health products • Autoship for convenient recurring deliveries • Chewy+, our premium membership offering exclusive savings, faster delivery, and personalized pet care benefits • 24/7/365 customer support from knowledgeable, pet-loving experts What Makes Chewy Different Chewy is known for industry-leading service, deep personalization, and our customer-obsessed culture. We combine trust, convenience, and care, and pet parents come to us for: • Exceptional customer care • Human- and pet-centered product and experience design • Fast, dependable fulfillment across a nationwide operations network • A mission-driven culture built on empathy, trust, and passion for pets Our Culture Chewy’s culture is built for people who thrive on ownership, innovation, and impact. We value curiosity, creativity, and continuous improvement across all our teams. We empower Team Members—our Chewtopians—to learn, grow, and unleash their full potential in a collaborative, supportive, mission-driven environment. How We Work Chewy’s Operating Principles guide how we think, innovate, collaborate, and execute. These principles shape our character, decision-making, and approach to delivering results while connecting our people and culture in support of our mission. Where We Work Chewy headquarters: Plantation, FL, and Boston, MA Additional hubs: Bellevue, WA, and Minneapolis, MN
Why Work With Us
Why You Should Work at Chewy Chewy is a unique, fast-growing e-commerce and tech leader where builders, creators, and problem-solvers shape the future of pet care. Our teams drive innovation in a mission-driven culture that creates real impact for pets and the people who love them.
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Hybrid Workspace
Employees engage in a combination of remote and on-site work.
