Senior Technical Support Engineer

Chicago, IL
High Definition Vehicle Insurance – Engineering /
Full-Time Remote /
What we do
HDVI is modern insurance for today’s fleets driven by service, safety and savings. With real-time telematics data informing our risk models, we help lower premiums, mitigate risk, engage and reward drivers and simply put, offer uncomplicated protection for trucking fleets. Our customers are small to midsize truck fleet operators who benefit from dynamic and transparent pricing – automatically reducing their premiums for safer driving. Leveraging a best-in-class partner ecosystem, HDVI combines magnitude and stability with innovation to revolutionize commercial trucking insurance.

Why work here
HDVI is building the industry-defining commercial auto insurance company for the next 100 years. The $50 billion commercial auto industry hasn’t seen real innovation for decades and is broken in a number of ways, creating a significant opportunity for HDVI.

HDVI is co-founded by a former Esurance co-founder, and has a senior management team with experience building innovative insurance and logistics companies from zero to $1B+ enterprises and deep expertise in trucking insurance. HDVI is well-funded by leading logistics and mobility-focused venture capital firms and strategic investors, including 8VC, Munich Re, and Daimler Trucks.

The HDVI Team is values-driven, data-driven, ambitious, and collaboratively minded, with a diverse background of experiences and skills in the insurance and logistics industries. We like challenges and building solutions that improve the quality of life for our customers. We offer generous benefits, including employee stock options, health, dental, vision, 401k, flexible work environment, and unlimited PTO.

About the Role
You will be a technical support engineer (TSE) working closely with the engineering, product, and business teams, solving production-related issues. Primary responsibilities include triaging issues, answering complex questions on function and usage of the HDVI suite of web, mobile, core, and data products, while prioritizing issues with appropriate escalation. You will utilize deep product knowledge to work through data requirements and trace data issues. You will interface with our development and QA operations, product managers, integration teams, and business units to ensure quick issue remediation and to establish and maintain high product service and satisfaction levels.

What You'll Do

    • Receive, log, and triage customer support requests from different intake paths
    • Responding to technical support tickets
    • Assess severity level to the problem and initiate the case resolution workflow
    • Manage and develop a ticketing process to ensure focus on customer service and timeliness of resolution
    • Find solutions as Tier 2 to identify root cause and also work in priority order
    • Work cross systems to identify solutions that may require full stack knowledge of back-end, front-end, and various complex integration layers
    • Ability to efficiently troubleshoot, debug, and document issues thoroughly in a highly  integrated environment, and creatively recommend solutions or explore workarounds
    • Collaborating with developers to understand and manage an issue from start to finish
    • Report and help test product issues (and also fixes) by working with the development team to resolve customer issues with a sense of urgency
    • Awareness of SLA’s and ability to thoughtfully prioritize
    • Provide timely well documented status updates on critical identified issues and maintain records of the troubleshooting steps and timeline
    • Highly involved with cross team coordination to understand parallel release schedules, and continuously learning the product features for web, mobile, core systems, and data product nuances
    • Participate in learning about product enhancements and understand basic business rules & data practices
    • Keep skills current as the tech stack is evolving and the product suite utilizes several vendor solutions and technologies
    • Identifies recurring issues. Address root cause, mitigating recurrences
    • When possible, help to maintain and develop a sustainable knowledge base and library of resources for internal use
    • Optimization of the end-to-end (primarily internal) customer experience through continuous process improvement and streamlining for scalability
    • Help define and refine the onboarding and implementation process for new customers
    • Write complex SQL queries to investigate and resolve issues
    • Write complex MongoDB queries to investigate and resolve issues
    • Work with JSON data structures to identify and fix issues
    • Work with policy administration systems to identify and fix issues
    • Help write tools to automate support requests

What You Have

    • Minimum of 5 years of experience in technical support or a related field
    • Strong experience with both SQL and MongoDB queries, as well as database management
    • Experience with insurance industry and policy administration systems
    • Strong experience in writing automation tools and scripts
    • Proven ability to work with cloud-based infrastructure: AWS, Heroku, Azure with events processing architecture
    • Exposure to software testing and working with test data, following a variety of test scenarios is a big plus
    • Must be able to adapt and adjust to highly agile iterative software development, with changing priorities and large integration projects.A high degree of interaction and teamwork are required to be effective. Additionally, complex and exhaustive problem-solving abilities is a requirement
    • Experience as a customer service or customer support specialist within a SaaS company is a plus
    • Possess a strong  desire for helping clients and colleagues
    • Demonstrate excellent verbal and written communication skills, with poise and polish
    • Able to handle stressful situations, excellent time management skills and attention to detail; resourceful and independent
    • Able to embrace the importance of teamwork and able to operate comfortably in an innovative, fast-paced start-up environment
    • Customer skills desired: active listening, patient, empathy, assertiveness, problem-solving, inquisitive, and positive communication
    • Exhibit a positive product-centric (concerned about the product functioning properly) attitude and ability to handle various client communications in a professional manner
    • Comfortable with learning new technology, constantly
    • Ability and flexibility to pivot and think on your feet, depending on impacts from release schedule or business urgency or broad client exposure
    • Proficient in Microsoft Office and Google suite
    • Experience working with defect tracking software or customer support ticket software such as Jira.

Preferred Skills

    • Computer programming coursework or work experience
    • Experience with SQL, MongoDB, JSON, or query languages
    • Postman (API testing)
    • Javascript (node.js)


    • Competitive salary & stock options - we want our success to be yours too
    • Unlimited PTO with 11 paid holidays each year
    • Medical, Dental, Vision, Short/Long Term Disability, Basic Life, and AD&D to support you and your well-being
    • FSA / HSA programs
    • 401(k) retirement plan with company match contribution
    • Inclusive Parental Leave policy that supports all parents
    • Wednesdays are standing meeting-free, allowing you to focus on deep work without distractions
    • Birthday meal reimbursement, because celebrating our employees is part of our company culture
    • A remote-friendly environment with the opportunity to participate in periodic in-person team offsites
If you are interested in this position, please contact our Senior People Operations Specialist, Morgan Harrison. You can reach him at