Product Owner / Project Manager

ClearConnect Solutions•Chicago, IL

About The Position

The Product Owner / Project Manager serves a dual-purpose role, driving product vision, backlog, and requirements while keeping the software development team aligned, unblocked, and on schedule. The role owns the product lifecycle from concept through deployment for data and risk-management platforms, leads agile ceremonies, develops precise user stories, and partners with engineering, QA, and business stakeholders to deliver scalable features for the fleet and insurance sectors. The position bridges business strategy and agile execution at ClearConnect Solutions, an Acrisure company. Its products support fleet insurers, underwriters, and policyholders through data-driven technology for risk monitoring, MVR services, screening, telematics, and route optimization.

Requirements

  • 3+ years of experience as a Product Owner, Technical Project Manager, or Scrum Master in an Agile software development environment.
  • Strong familiarity with software development life cycles (SDLC), API integrations, and data-heavy platforms.
  • Exceptional written and verbal communication skills, including the ability to translate technical concepts into business language and business needs into technical requirements.
  • Analytical mindset and comfort working with complex data systems, risk models, and compliance workflows to define logical product solutions.
  • Proficiency with agile project management and documentation tools such as Jira, Confluence, or Azure DevOps.

Nice To Haves

  • Certified Scrum Master (CSM), Professional Scrum Product Owner (PSPO), or an equivalent agile certification.
  • Experience with SaaS, InsurTech, FinTech, fleet-management technology, or related data-driven platforms.
  • Experience supporting products involving MVR automation, telematics, risk scoring, screening, compliance, or route optimization.

Responsibilities

  • Own, prioritize, and groom the product backlog, ensuring user stories align with strategic business goals and product roadmaps.
  • Collaborate with internal stakeholders, data analysts, and industry experts to translate complex data workflows into actionable technical requirements.
  • Write detailed user stories, acceptance criteria, and technical specifications for software developers and QA teams.
  • Assist leadership in defining release scopes, tracking milestones, and aligning software releases with company growth objectives.
  • Lead agile ceremonies, including daily stand-ups, sprint planning, backlog refinement, sprint reviews, and retrospectives.
  • Manage sprint velocity, remove blockers, and help the engineering team deliver high-quality code on schedule.
  • Serve as the primary communication conduit between technical teams and business stakeholders, manage expectations, and provide project-status updates.
  • Continuously optimize agile workflows, tools, and documentation practices to improve team efficiency.

Benefits

  • Competitive salary and comprehensive benefits package.
  • Comprehensive medical insurance, dental insurance, and vision insurance.
  • Life and disability insurance.
  • Fertility benefits and wellness resources.
  • Paid sick time.
  • Paid time off and holidays.
  • Employee Assistance Program (EAP) and complimentary Calm app subscription.
  • Immediate vesting in a 401(k) plan.
  • Health Savings Account (HSA) and Flexible Spending Account (FSA) options.
  • Commuter benefits and employee discount programs.
  • Paid maternity leave and paid paternity leave, including for adoptive parents.
  • Legal plan options and pet insurance coverage.
  • Opportunities for professional growth and continuous learning.
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