Top Tech Jobs & Startup Jobs in Chicago, IL

Leads a portfolio of insurance SaaS implementations from kickoff through go-live, ensuring timeline, scope, quality, margin, financial, and client satisfaction objectives. Directly manages strategic customer implementations while coaching project managers and business analysts. Oversees governance, risks, dependencies, staffing, utilization, and stakeholder alignment; partners with engineering, product, QA, sales, and PMO teams. Drives AI adoption, standardized delivery practices, and improved implementation predictability and operational consistency.

Leads end-to-end execution of complex, concurrent SaaS transformation programs for insurance and financial services clients. Owns timelines, scope, quality, margins, risks, production readiness, go-live stability, and client outcomes. Partners with executive stakeholders, oversees financial governance, uses delivery tooling and AI capabilities, and coaches project and program leaders. Requires deep insurance technology expertise, particularly Life, Health, and Annuity platforms, along with strong delivery governance and financial control.

Lead presales discovery and solution consulting for Life, Annuity, and Health insurers. Translate insurance business challenges and requirements into solution narratives, demonstrations, presentations, and modernization recommendations. Partner with sales, product, and technical teams on strategic pursuits, RFI/RFP responses, core system transformation, AI adoption, and enterprise software evaluations. Serve as a functional insurance domain expert engaging business and executive stakeholders.

Leads portfolio-level product strategy across P&C insurance technology products, including policy, underwriting, billing, claims, and data/AI. Defines cross-product initiatives, builds data-driven business cases, tracks portfolio health and dependencies, manages a Senior Product Analyst, and presents product capabilities to executives, customers, and analysts. Requires strong financial modeling, analytical, communication, stakeholder management, and insurance technology expertise.

Owns the roadmap and backlog for P&C policy administration and commercial underwriting capabilities, including submissions, quoting, issuance, endorsements, renewals, risk evaluation, and AI-assisted decisioning. Partners with engineering, architecture, QA, customers, insurers, MGAs, and implementation teams to define workflows, integrations, configuration requirements, and Agentic AI use cases. Requires deep commercial underwriting and policy administration expertise, strong stakeholder management, and experience translating insurance processes into scalable platform capabilities.

Develop and execute a national sales strategy for Taft Hartley and multiemployer pension, health and welfare, and claims solutions. Build pipeline, manage complex enterprise sales cycles, cultivate relationships with trustees and fund executives, lead proposals and negotiations, and coordinate cross-functional pursuit teams. Translate customer needs into measurable value while maintaining forecasts, account plans, and sales targets in a specialized B2B market.

Own strategic enterprise insurance accounts across North America, driving account expansion, renewals, multi-million-dollar revenue growth, and client retention. Build C-level relationships, lead consultative solution selling and full sales cycles, manage RFPs and negotiations, and position SaaS, cloud, and digital transformation solutions. Partner cross-functionally with product, delivery, and marketing teams while conducting executive reviews, tracking success metrics, and representing customer needs internally.

Technical Account Manager serving premium support customers in the insurance industry. Builds customer relationships, provides technical guidance, manages incidents and escalations, coordinates issue resolution, develops support and upgrade plans, and drives product adoption and operational improvements. The role requires collaboration across technical and business stakeholders, software implementation experience, project management, insurance technology expertise, and bilingual English-Spanish communication. Candidates must reside in Puerto Rico and work remotely.

Own enterprise sales across the Life, Annuities & Health insurance market. Build territory strategy, generate new-logo pipeline, expand strategic accounts, develop executive relationships, lead consultative value-based sales, navigate complex buying groups, orchestrate internal resources, and close large software opportunities. The role requires direct L&AH insurance expertise, enterprise SaaS or complex software sales experience, disciplined forecasting, competitive strategy, and success exceeding quota.