Senior Operations Lead

Chicago, Illinois, United States · Operations expand job description ↓



Fraight is an early stage, ambitious logistics AI technology company. We are working on challenging, real world problems that require unconventional interdisciplinary thinking. Our goal is to revolutionize the logistics industry through automation and AI to create a more positive experience for us, our customers, and the carriers with whom we work, to reduce the cost of transporting freight while providing top tier service every moment of every day, and to eliminate waste.

We have been recognized by Built-In Chicago as 50 Startups to Watch in 2018, and ChicagoInno, who says we’re one of the Coolest Companies to work for. We are a collaborative, hard working, intelligent, and friendly team and are excited at the thought of you joining us and adding to our unique culture!


About You

  • You are not only looking for an opportunity, but you’re looking for an adventure. This is an opportunity to tangibly shape the future of a company and of an industry. Like any adventure it takes a comfort with ambiguity and an incredible amount of hard work. Sometimes it may be scary or frustrating, but you get to do it with a team of people working in the same direction who enjoy working together.
  • Strong sense of ethics—you’ll always do right by your coworkers, customers, carriers
  • Scrappy - you’re a do-er, and a manager of things or people. You’re ready, able, and willing to dig in and get the job done. You hustle and find a way to get it done.
  • Resourceful - you’re not afraid to be wrong, and not afraid to ask for help. You know you’re a smart person, so you’re going to give it your all to figure it out; but you won’t let your pride get in the way.
  • Growth mindset - Just because a process exists, doesn't mean it should. You always consider an alternative explanation may exist. You aren’t afraid to speak your mind when it comes to suggesting ideas and processes for things that we could be doing better.
  • Insightful about your process and creative - You spend a lot of time thinking about how you work, how you can work better, and how your work fits into the bigger picture. You think a lot about how the tools you have help you, and how you have to workaround the edges.
  • Detail Oriented - You are extremely organized and meticulous. You have the experience and the foresight in your role to know what is required of you. You will ensure you always have all the details required to get the job done.


  • Your main focus is to own and manage customer relationships. With that said, you are comfortable stepping up to the plate and being in a hybrid role that focuses on both customer and carrier operations. You are willing to step in whenever and wherever an extra set of hands is needed on the team.
  • You will work closely with the carrier sales, operations, and product teams to make sure we’re delivering for our customers and building the right product for our team.
  • You will help shape our software product through your industry experience and your experience as the core user of Fraight’s platform, knowing what is working and not working for the process and pain points, so we can consistently improve our offering.
  • You will learn more deeply about the customers and carriers with whom we’re working and strategic initiatives which may be impactful to them.

That being said, in a startup we all do the dishes sometimes. No task is beneath any of us.



  • You have 4+ years in a brokerage environment, with an emphasis on OTR truckload.
  • We prefer you have experience in a leadership role, such as team lead
  • Your goal is not just to be in the top 1% of service providers, but to be The 1. Your customers call you because you shoot them straight, and you get done what you say you’re going to.
  • We prefer you have some experience with software, but its not required.
  • You MUST have an entrepreneurial spirit.
  • You have the ability to work flexible schedules, and perhaps travel from time to time (0-20% of the time).



  • Competitive base salary
  • Equity grant, so each person in the company is rewarded and feels a sense of ownership as the company grows
  • 401k plan available with a variety of investment options
    • Fraight AI currently does not match, but aims to do so in the future


  • Fraight AI covers 75% of team member’s medical premium and offers dental and vision insurance

Healthy Living:

  • Delicious snacks and beverages provided by Industrious
  • Company Divvy membership discount
  • Weekly team lunches sponsored by Fraight AI

Family & Vacation:

  • Paid family leave and flexible work from home upon returning from leave
  • Flexible work from home policy
  • 9 paid holidays per year
  • 5 weeks paid time off per year


  • Ventra pre-tax benefit program
  • Learning resources (books, subscriptions, etc)
  • Solid tools. Fast mac, big monitor, nice headphones
  • Monthly team events outside of the office
  • Weekly all hands meetings

Commitment to diversity

We get it. The demographics of tech companies don’t match up with America. We believe in changing that and we are actively looking for candidates from all backgrounds. We intend to challenge the status quo in tech demographics by introducing innovative recruiting and HR practices that seek out, support, and join individuals from diverse backgrounds

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