Top Tech Jobs & Startup Jobs in Chicago, IL

Design, build, and maintain scalable batch and streaming data pipelines, cloud infrastructure, and the Enterprise Data Hub. Partner with stakeholders to productionize ingestions, ensure data quality, implement metadata/catalog solutions, mentor junior engineers, and support analytics and ML workloads using cloud and big-data tooling.

Leads Hagerty’s APEX technology transformation EPMO, overseeing program governance, budgeting, financial reporting, vendor contracts, risks, dependencies, status reporting, change control, benefits realization, and executive communications. The role manages Accenture, builds Hagerty’s permanent EPMO capability, establishes an enterprise program and project management Center of Excellence, supports audit-ready governance, and leads EPMO staff across business, technology, finance, risk, and vendor stakeholders.

Develops concepts and integrated campaigns across digital, print, video, and event marketing. Creates compositionally strong designs using Adobe Creative Suite and Figma, builds presentation decks, applies brand guidelines, supports photo shoots and print production, and collaborates with creative leaders, clients, writers, strategists, and cross-functional teams. The role requires conceptual thinking, art direction, graphic design, attention to detail, and effective incorporation of feedback.

Lead product vision and roadmap for data and analytics products (ML, generative AI, data pipelines, BI). Translate business needs into developer-ready features, maintain backlog, collaborate with engineering and stakeholders, track KPIs, and drive adoption and continuous improvement.

Owns end-to-end delivery of integrated marketing projects across multiple business-unit pods. Responsibilities include managing timelines, milestones, stakeholder communications, cross-functional coordination, project plans, dependencies, risks, capacity, and delivery reporting. The role partners with marketing, creative, production, and channel teams while maintaining visibility into portfolio health and adapting processes as the organization scales.

Owns the business controls framework for Hagerty’s insurance technology platform. Responsibilities include designing and documenting controls, conducting risk and control assessments, managing remediation, supporting audits and regulatory examinations, evaluating change impacts, and partnering with IT, compliance, finance, and insurance operations. The role requires insurance operations governance expertise, familiarity with platforms such as Guidewire, Duck Creek, or Majesco, knowledge of SOX and insurance regulations, and experience with GRC tools and audit readiness.

Develops concepts, campaign platforms, headlines, copy, scripts, and integrated creative executions for Hagerty’s brand and marketing initiatives. Collaborates with creative, strategy, marketing, and production teams; presents work to stakeholders; researches audiences and automotive trends; maintains brand voice standards; and mentors other creatives. The role owns projects from brief through execution and may require quarterly event travel.

Leads Hagerty’s Private Client experience standards across insurance, claims, brokers, events, underwriting, marketing, auctions, and trusted advisors. Defines service protocols, SLAs, communication playbooks, training curricula, escalation processes, segmentation models, member journeys, and multi-year improvement roadmaps. The role integrates Hagerty’s broader ecosystem into a differentiated high-net-worth client experience while influencing cross-functional teams without direct authority.

Analyzes underwriting performance, pricing, production trends, competitive dynamics, risk segmentation, and predictive model results for specialty vehicle insurance. Develops recommendations for underwriting guidelines, risk appetite, process improvements, and compliance changes. Builds business cases, presents insights to leadership, defines data and system requirements, supports user acceptance testing, and leads cross-functional projects with underwriting, claims, technology, and analytics teams.

Lead execution of Hagerty’s enterprise insurance platform transformation across policy, billing, claims, distribution, data, integrations, and forms. Own the integrated master schedule, critical path, dependencies, capacity planning, risk management, forecasting, and delivery buffers. Integrate multiple project managers and align business, IT, engineering, and vendor efforts. Drive readiness, identify constraints, enforce trade-offs, and provide executives with data-backed delivery recommendations.