Head of Ocean Operations

| Chicago
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Head of Ocean Operations, NA

The opportunity:

The role of the Head of Ocean Operations, NA is a critical part of making Flexport’s mission to make global trade easy for everyone a reality. Flexport today connects almost 10,000 clients and suppliers across 109 countries. In this role, your direct customers are the partners within your region: our account management and customs teams, subcontractors, carriers, terminals and trucking providers. Your work directly supports Flexport’s end customers in achieving their logistics goals. Most importantly, you will play a pivotal role in building the next operational model at Flexport: allowing us to effectively scale to achieve our mission of making global trade easier for everyone.

This role is designed to be the senior operations leader for Flexport’s largest market and product line, North American Ocean Operations: designing and building the new model of operations at Flexport while strategically leading the region team through the complex world of logistics. You will work cross-functionally to navigate ambiguous challenges and establish a world-class operating team designed to catapult Flexport to realizing its mission. At this stage in Flexport's journey, we understand that great leadership is what will help us achieve our goal. We are looking for best-in-class leadership that can articulate a clear vision and excite teams to execute it day in and day out.

Tactical Responsibilities:

As an operations executive, you are a seasoned operator experienced in scaling, running and continuously improving high volume logistics service operations.  You have a sustained track record of high performance leadership across these dimensions: people, process, technology and data with a passion for empowered front line operators synonymous to the toyota production system environment. Your passion is to build teams and grow operations talent with a track record of implementing logistics management technology.

  • You will set and drive the operations strategy and operating cadence to deliver on Quality, Cost, Delivery, Safety and Compliance commitments to Flexport.
  • You will design and implement standardized and repeatable operational processes, mistake proofing and technology automation to ensure profitable Flexport value delivery to customers.
  • You will build a vibrant organization with modern talent development principles, with an emphasis on learning and competency development. 
  • You will set the strategy and roadmap for regional operations development to deliver new service offerings, perfect existing service offerings and continuously evolve the team and footprint to scale operations in line with growth and future strategies.
  • You will empower the front line teams to achieve the highest standard of Flexport quality: designing the right expectations on individual performance, talent management, process excellence and technology adoption. You will be responsible for communicating and sustaining achievement of key performance indicators and service performance.
  • You will lead the development and execution of OKRs, business plans and budgets for the North America operations region.

Adaptive Responsibilities:

  • You will provide leadership and direction to a high-performance team across US and Canada including an extended team in Manila Philippines.
  • You will run a high total-motivation (TOMO) culture blending structure, autonomy and velocity by driving play, purpose and potential into the fabric of the team.
  • You will contribute to the expansion and positive growth of Flexport unit economics and profitability.
  • You will contribute to technology product and engineering teams to develop and implement technology features and functions.
  • You will design and implement execution standards and procedures to deliver differentiated logistics services to market.
  • You will act as a strategic expert and leader to your global counterparts in EU and Asia, product & engineering, operational excellence, sales and account management to deliver customer and business results. 

What you will need:


  • 15+ years of operations leadership including 5+ in a senior or executive role leading multi-site, technology enabled, high volume ocean freight operations.  
  • Verifiable track record of developing operations talent from operational excellence principles
  • Experience working at the logistics and technology intersection


We’re looking for a leader that has:

  • Intellectual horsepower and energy to integrate Talent, Process, and Technology into a 10x scale ready system.
  • Demonstrated ability to lead large multi-site operations teams in day-to-day execution and process improvement, including leading manager of managers.
  • Passion to serve customers in freight or logistics services and experiencing working with commercial teams to translate customer needs into standardized and repeatable operations procedures. 
  • Process and Systems end to end thinking able to continuously map and connect the dots
  • Strategic vision and ground floor execution
  • World class communicator, written and verbal
  • Client service mindset - obsessed with repeatable and scalable customer success
  • A deep passion for technology, process and scaling operations
  • The pedigree and chops to attract, train, develop and prepare the next generation of Flexport operations leaders.

About Flexport: 

We believe global trade can move the human race forward. That’s why it’s our mission to make global trade easier for everyone. We aim to do this by building the Operating System for Global trade - a strategic model combining advanced technology and data analytics, logistics infrastructure, and supply chain expertise. Flexport today connects almost 10,000 clients and suppliers across 109 countries, including established global brands like Georgia-Pacific as well as emerging innovators like Sonos. Started in 2013, we've raised over $1.3B in funding from SoftBank Vision Fund, Founders Fund, GV, First Round Capital and Y Combinator. We’re excited about the three big ways we’re moving forward after our recent $1B investment from SoftBank Vision Fund in February 2019.

At Flexport, our ability to fulfill our mission of making global trade easy for everyone relies on having a diverse, dedicated and engaged workforce. That is why Flexport is committed to creating and nurturing an environment where anyone can be their authentic self. All qualified applicants will receive consideration for employment regardless of race, color, religion, sex, national origin, age, physical and mental disability, health status, marital and family status, sexual orientation, gender identity and expression, military and veteran status, and any other characteristic protected by applicable law.

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Technology we use

  • Engineering
  • Product
  • Sales & Marketing
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    • AsanaManagement
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Come be a part of the founding team in our newest U.S. office! We're located near tons of restaurants and only a 10-minute walk from 3 parks!

An Insider's view of Flexport

What’s the vibe like in the office?

The people in this office are the cream of the crop. They’re down to earth and razor-sharp. You could go up to anyone in the office, ask them a question, and they will stop whatever they were doing and help you out every time.


Sales Development Representative

What's the biggest problem your team is solving?

We are solving the extreme complexity and opacity of trucking coordination and execution in international supply chains. We bring visibility and control to our customers while also reducing operational overhead.


Senior Engineering Manager

What makes someone successful on your team?

Ownership. Our company is growing quickly and the surface area of our product is growing quickly as well. The strongest contributors identify important projects and see them through completely. They are proactive from the initial research and design phases to the post-launch productive monitoring. As Flexport grows, they emerge as natural leaders.


Senior Staff Engineer

How does your team reward individual success?

The squad model makes every team member's accomplishments integral to his/her peers success which, in turn, stimulates each us to celebrate each others wins through shoutouts on slack, nominations for projects and applause at team meetings.


Global Operations Associate

What are Flexport Perks + Benefits

Flexport Benefits Overview

Flexport is an employee forward company. We know that life comes first and want you to take the time you need with our flexible paid time off program. We offer 100% covered health, vision, and dental insurance, 401K, performance bonuses, stock with a 10-year tax option, commuter benefits, a generous maternity (18 weeks with a phase back program that offers reduced hours and flexible schedule during their first month back) and paternity leave (8 weeks), free lunch and snacks, dog-friendly offices, pay equity, career advancement, and more.

Volunteer in local community
Partners with Nonprofits
Friends outside of work
Eat lunch together
Intracompany committees
Team owned deliverables
Team based strategic planning
Group brainstorming sessions
Open office floor plan
Dedicated Diversity/Inclusion Staff
Unconscious bias training
Diversity manifesto
Health Insurance & Wellness Benefits
Flexible Spending Account (FSA)
Disability Insurance
Dental Benefits
Vision Benefits
Health Insurance Benefits
Life Insurance
Wellness Programs
Team workouts
Retirement & Stock Options Benefits
Company Equity
Performance Bonus
Child Care & Parental Leave Benefits
Generous Parental Leave
Flexible Work Schedule
Family Medical Leave
Adoption Assistance
Vacation & Time Off Benefits
Unlimited Vacation Policy
Flexport's flexible PTO policy allows employees to take as many days off as they need, providing they get manager approval.
Paid Volunteer Time
Flexport encourages employees to give back with paid volunteer time off up to 10 hours per year.
Paid Holidays
Flexport gives all full-time employees paid time off to observe all major holidays.
Paid Sick Days
Perks & Discounts
Casual Dress
Commuter Benefits
Flexport offers pre-tax commuter benefits for all full-time employees.
Company Outings
Free Daily Meals
Flexport provides catered lunches Monday - Friday and stocks our kitchen with breakfast foods for employees to enjoy in the morning.
Stocked Kitchen
Happy Hours
Pet Friendly
Recreational Clubs
Relocation Assistance
Professional Development Benefits
Job Training & Conferences
Diversity Program
Lunch and learns
Cross functional training encouraged
Promote from within
Mentorship program

Additional Perks + Benefits

We're proud that we collectively speak over 40 languages and live on 3 continents. We strive to create a workplace where candidates, employees, and all community members within Flexport’s ecosystem of connected organizations are encouraged to share their stories, celebrate their cultures, and learn from one another. Joining Flexport means joining a truly global community.

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