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Forward Deployed Engineer (Chicago)

FleetWorks is a vertical AI agent for the outdated freight brokerage industry. To book just a single truckload of Coca-Cola from Atlanta to Chicago, a freight broker has to send and receive up to 50 phone calls, emails, and text messages. This can take hours out of their day. FleetWorks automates this human labor with an omni-channel AI.

Our product is already used by many of the top 100 brokers in the U.S. This role is a good fit if you are excited to learn about logistics and are passionate about AI, owning product decisions, and great design.

Our AI solution is actively deployed with many of the top 100 freight brokers in the U.S. This Forward Deployment Engineer role is perfect if you thrive on bridging technology and customer success, enjoy being close to product deployments, and are excited about bringing cutting-edge AI directly to clients.

About you:

  • You have 1+ years of engineering experience, ideally involving direct interaction with customers or on-site product deployments.

  • You enjoy working closely with customers, gathering feedback, troubleshooting real-time issues, and directly influencing product improvements.

  • You are based in Chicago or open to relocating.

  • You want to make outsized impact and thrive when surrounded by top performers.

  • You have a strong drive. Other people describe you as someone who takes their work seriously (maybe a little too seriously). It goes from just being a job to an obsession.

  • You have to like challenges. This is hard. We handle tens of thousands of phone calls/emails per day and coordinate complex agentic workflows to make them happen. 

  • You have to want to win.

Responsibilities:

  • Deploy, integrate, and optimize FleetWorks solutions directly at client locations or remotely.

  • Collaborate closely with clients to understand their unique operational needs, ensuring seamless integration and high customer satisfaction.

  • Diagnose, troubleshoot, and resolve technical issues swiftly to maintain customer trust.

  • Provide direct feedback to the engineering and product teams, advocating for enhancements based on field experiences.

  • Continuously improve documentation, deployment practices, and client onboarding processes.

About the interview:

If we interview you, you can expect the following process

  • A 30-min take-home technical challenge.

  • Two 1-hour live coding interviews with engineers.

  • A paid onsite work trial (number of days variable based on your availability).

  • We may speak with 1–2 references that you provide.

Average salary estimate

$75000 / YEARLY (est.)
min
max
$60000K
$90000K

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What You Should Know About Forward Deployed Engineer (Chicago), FleetWorks

FleetWorks is on the lookout for a dynamic Forward Deployed Engineer in Chicago to join our mission of transforming the freight brokerage industry with cutting-edge AI. Imagine cutting down the hours a broker spends on calls and messages to book a truckload of Coca-Cola from Atlanta to Chicago. That’s where our omni-channel AI solution comes into play, simplifying complex workflows and facilitating operations like never before! In this role, you’ll be at the intersection of technology and customer success, engaging with clients to ensure our solutions are pushed to their peak performance. You will have hands-on duties like deploying and optimizing FleetWorks solutions, diagnosing technical issues on the fly, and advocating for enhancements based on firsthand field experiences. We’re seeking someone who thrives on challenges and is excited to make a significant impact. With at least a year of engineering experience and a passion for logistics and AI, you’ll help us revolutionize the industry while ensuring seamless integration and high customer satisfaction. If you’re based in Chicago or are open to relocating and have a drive to own your work, this role is perfect for you. Get ready to bring your best self to a team that values dedication and success. Join FleetWorks and be part of something extraordinary!

Frequently Asked Questions (FAQs) for Forward Deployed Engineer (Chicago) Role at FleetWorks
What are the responsibilities of a Forward Deployed Engineer at FleetWorks?

As a Forward Deployed Engineer at FleetWorks, your responsibilities include deploying, integrating, and optimizing our AI solutions directly at client locations or remotely. You will also collaborate closely with clients to assess their unique operational needs, swiftly troubleshoot technical issues, and provide valuable feedback to our engineering and product teams to advocate for necessary improvements.

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What qualifications do I need to apply for the Forward Deployed Engineer position at FleetWorks?

To apply for the Forward Deployed Engineer role at FleetWorks, you need a minimum of 1+ years of engineering experience, ideally with direct interaction with customers or involvement in on-site product deployments. A strong interest in logistics and AI, combined with a drive to make meaningful impacts, is essential for this role.

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How does FleetWorks integrate AI into the freight brokerage process?

FleetWorks leverages omni-channel AI to automate and streamline the freight brokerage process. This technology drastically reduces the manual labor involved in booking truckloads, enabling brokers to operate more efficiently and effectively by handling tens of thousands of communications effortlessly.

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What type of work environment can I expect as a Forward Deployed Engineer at FleetWorks?

At FleetWorks, you can expect a fast-paced and collaborative work environment where innovation thrives. Our team consists of top performers who are driven by challenges and focused on delivering high-quality solutions, making collaboration and camaraderie key components of our workplace culture.

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What is the interview process for the Forward Deployed Engineer position at FleetWorks?

The interview process for the Forward Deployed Engineer position at FleetWorks includes a 30-minute take-home technical challenge, followed by two 1-hour live coding interviews with our engineers. Candidates will also participate in a paid onsite work trial to ensure a good fit, and we may reach out to 1-2 references provided by the candidate.

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Common Interview Questions for Forward Deployed Engineer (Chicago)
Can you explain a technical issue you resolved and how you handled it?

When answering this question, start with a brief overview of the issue, detailing your thought process as you approached it. Highlight your problem-solving skills, the steps you took to diagnose the issue, how you communicated with the client, and the eventual resolution to demonstrate both technical prowess and client management abilities.

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How do you prioritize customer feedback in your engineering projects?

In your response, outline the significance of client feedback in shaping product improvements. Share your methodology for collecting and analyzing feedback, collaborating with the engineering team to integrate this input effectively, and ensuring that customer needs are adequately addressed in your solutions.

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What strategies do you use to learn about new technologies in the logistics sector?

Discuss methods like attending industry-related webinars, reading industry publications, engaging with online courses, participating in relevant forums, and networking with professionals in the field as proactive strategies for staying updated on new technologies in logistics and AI.

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Describe a scenario where you had to work under pressure. How did you manage it?

Share a specific scenario, focusing on your emotional response, prioritization of tasks, and communication with the team. Emphasize your ability to remain calm, draw on technical knowledge, and employ effective problem-solving skills to navigate challenges efficiently under pressure.

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How do you ensure customer satisfaction during product deployments?

Explain your systematic approach to client engagement, which includes thorough preparation for rollouts, clear communication about expectations, addressing queries promptly during deployment, and providing aftercare support. This responsiveness reinforces customer trust and satisfaction.

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What tools and technologies have you used for deployment and troubleshooting?

Reflect on your experience with specific tools related to your previous roles, such as API tools, monitoring systems, or data analytics software. Elaborate on how you've utilized these technologies to facilitate smooth deployments and troubleshoot issues, integrating specific examples when possible.

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Can you give an example of a successful client relationship you've built?

Choose a scenario illustrating the duration and evolution of the relationship, highlighting actions you took to build trust, enhance communication, and solve client issues effectively. Demonstrating your interpersonal skills showcases your ability to foster and maintain fruitful partnerships.

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What role does teamwork play in your work as an engineer?

Emphasize the importance of collaboration in engineering roles, particularly how sharing ideas and knowledge with colleagues, seeking feedback, and ensuring open lines of communication are crucial for project success and personal and team growth.

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How do you handle situations where a project does not go as planned?

Discuss your proactive approach to recognizing issues early, analyzing the factors contributing to the problem, re-evaluating objectives, and maintaining open communication with stakeholders to address concerns. This adaptability demonstrates your maturity and professionalism.

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What excites you most about working in AI and logistics?

Express your passion for technology, particularly how AI offers revolutionary potential for efficiency and innovation in logistics. Highlight any specific projects or trends that inspire you and explain how you aspire to contribute to this evolving field in your role at FleetWorks.

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Full-time, on-site
DATE POSTED
April 19, 2025

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