Top Tech Jobs & Startup Jobs in Chicago, IL

Supports and enhances a pension administration system by gathering requirements, documenting processes, analyzing issues, coordinating with stakeholders and vendors, and conducting functional, integration, regression, and user acceptance testing. Performs data validation, reconciliation, reporting, process improvement, change management, and implementation support. The role also tracks defects, risks, decisions, dependencies, and project activities while ensuring system changes meet business and operational needs.

The Managing Consultant leads cybersecurity engagement scoping, proposal development, technical project coordination, client communication, report review, and delivery oversight. The role supports Directors and business development teams, troubleshoots technical execution issues, manages client relationships, mentors Security Consultants, and may perform limited hands-on consulting. Candidates need offensive security experience, strong client-facing communication, technical scoping and estimation skills, and the ability to translate complex findings into actionable recommendations.

Lead end-to-end enterprise sales cycles from prospecting through close across mid-market and enterprise accounts. Build relationships with OEM executives, engineering teams, and supply chain leaders; translate technical workflows into business value and ROI; maintain pipeline quality and forecasting accuracy; and collaborate with product, engineering, and leadership teams to shape product direction, messaging, and sales strategy.

The Assistant Project Manager will support project onboarding within the Community Solar portfolio, oversee contractors, manage stakeholders, track budgets, and ensure regulatory compliance while maintaining organized documentation.

Leads enterprise new-logo sales for strategic financial institution accounts, from prospecting through negotiation and close. Builds pipelines, manages complex multi-stakeholder sales cycles, forecasts in Salesforce, exceeds quotas, and closes large multi-year contracts. Partners with solutions engineering, product, partnerships, and executives to develop customized solutions and go-to-market strategies. Provides market insights, mentors junior sales professionals, and advises leadership on account strategy, pricing, and competitive positioning.

Own global payroll processing through Rippling, including audits, reconciliation, discrepancy resolution, documentation, and compliance support. Administer employee benefits, enrollments, qualifying life events, open enrollment, and vendor coordination. Support employee lifecycle processes, HR records, reporting, leave administration, recruiting coordination, and onboarding. Provide responsive employee support while maintaining confidentiality, accuracy, and adherence to recurring deadlines.

Leads institutional fundraising through foundation grant proposals, reports, stewardship communications, and grant-management systems. Translates organizational programs and impact into compelling funder narratives, coordinates cross-functional inputs, manages deadlines and documentation, oversees donor communications, supervises the Donor Communications Manager, and manages a small foundation portfolio. The role requires exceptional writing, project management, relationship-building, staff leadership, and experience with nonprofit development and CRM systems.

Manage a portfolio of B2B SaaS accounts throughout the customer lifecycle, building executive relationships, conducting business reviews, monitoring health and churn risk, and supporting renewals. Identify expansion opportunities with Account Executives, synthesize customer feedback for Product and Engineering, and advocate for customer needs. The role requires strong communication, analytical ability, attention to detail, resourcefulness, and cross-functional collaboration. Remote work is available across US time zones.

Leads vCISO and cybersecurity compliance engagements for multiple clients, including CMMC and NIST assessments, SSP and POA&M development, risk assessments, framework mapping, audit and assessor support, incident response, and remediation coordination. Advises clients on regulatory obligations, security tooling, and compliance strategies while managing client relationships, engagement health, reporting, and delivery quality across a large portfolio.

Lead enterprise payer and MSO sales from prospecting through signed agreements. Sell AI value propositions to health plans and value-based care organizations, manage complex 9–18 month procurement cycles, conduct proof-of-performance deployments, and convert pilots into paid engagements. Own territory strategy, pipeline accuracy, executive relationships, and commercial feedback to product and clinical teams.