Top Tech Jobs & Startup Jobs in Chicago, IL

Manage strategic relationships with property management companies and multifamily property owners. Provide day-to-day client leadership, resolve escalations, coordinate reporting and service requests, lead business reviews, oversee implementations and integrations, monitor performance and revenue goals, and support renewals, retention, and growth. Collaborate with Sales, Product, Legal, Finance, Compliance, and leadership to resolve complex issues and maintain accurate client arrangements.

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 full-funnel Meta advertising campaigns for U.S. home service businesses. Responsibilities include campaign strategy, targeting, budgeting, creative testing, lead-quality optimization, tracking implementation, attribution analysis, CRM collaboration, reporting, and scaling campaigns while maintaining target CPLs. The role requires managing multiple accounts, coordinating with creative teams, troubleshooting tracking, and staying current with Meta advertising updates.

Create digital graphics and visual assets for marketing, social media, websites, advertisements, presentations, product content, and internal communications. Maintain CareerSwift’s visual identity and brand guidelines while adapting designs across platforms and formats. Collaborate with marketing and other teams, incorporate feedback, organize reusable design assets, and deliver multiple projects on deadline in a remote environment.

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.

Lead the vision, strategy, and execution of Oyster’s Employer of Record product across onboarding, payroll, benefits, compliance, and offboarding. Manage and develop a multi-layered product organization, prioritize complex initiatives, and partner with Engineering, Design, Legal, Finance, and Operations. Drive AI-powered automation, scalable workflows, measurable business outcomes, and product quality across a regulated global employment platform.

Own and scale product marketing, content, and sales enablement end-to-end: GTM messaging, launches, sales materials, competitive differentiation, and measurement to drive pipeline, deal acceleration, and win rates. Manage multiple senior initiatives, align cross-functional stakeholders, and use AI to scale output and optimize results.

Leads a controls support engineering team responsible for post-commissioned warehouse automation systems. Oversees technical issue resolution, escalations, resource allocation, documentation, system reliability, and customer satisfaction. Develops measurable cross-training programs across multiple controls platforms, tracks capability progress through KPIs and skills matrices, and mentors team members. Collaborates with software, mechanical, and site operations teams to improve system performance and support processes.

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.

Design, deploy, and manage machine learning models supporting client acquisition, retention, and reactivation. Develop Next Best Action, CRM, paid media, and personalization solutions using LLMs and traditional ML. Design and interpret experiments, analyze large-scale datasets, communicate recommendations to stakeholders, and collaborate with product, design, and engineering teams on product and infrastructure roadmaps.