Top Tech Jobs & Startup Jobs in Chicago, IL

Leads FP&A and strategic finance for a B2B SaaS business, partnering with senior leaders on forecasting, revenue performance, growth investments, resource allocation, financial modeling, and business planning. Oversees a globally distributed six-person team, improves finance processes and decision support, and supports M&A and due diligence initiatives.

Leads and grows an engineering team responsible for customer-facing web, mobile, and backend products. Owns delivery, technical direction, architecture, reliability, hiring, coaching, and career development. Partners with Product and Design to prioritize work and deliver dependable releases. Establishes AI-assisted engineering practices, supports AI-powered customer experiences, and builds systems for scheduling, payments, client management, notifications, and integrations.

Direct global customer acquisition for ClassPass across paid media and brand marketing. Lead a multidisciplinary team, manage a multi-million-dollar budget, optimize paid social, search, app, and programmatic channels, and build upper-funnel campaigns across OOH, CTV, partnerships, and influencers. Partner with Creative, Lifecycle, CRO, Analytics, and Product on full-funnel growth, measurement, market launches, forecasting, and performance optimization.

Manage and scale global Apple and Windows endpoint fleets using Jamf and Intune. Develop scalable device-management runbooks for M&A, enforce security baselines, support systems integration, lead technical projects, resolve cross-functional workflow issues, and participate in IT escalation support. The role requires expertise in cloud platforms, identity and SSO, API integrations, endpoint compliance, security frameworks, regulatory requirements, and IT strategy.

Lead full-cycle technical recruiting for software engineering and platform roles. Partner with hiring managers on hiring plans, build pipelines for hard-to-fill positions, evaluate recruiting data and funnel metrics, and deliver an inclusive candidate experience. The role involves sourcing, stakeholder management, employer branding at industry events, cross-functional collaboration with People & Culture, and hiring across time zones in a fast-paced technology environment.

Leads and scales the enterprise Technical Account Management organization, managing managers and owning customer retention, renewals, expansions, and forecast accuracy. Builds executive customer relationships, oversees technical integrations, APIs, data migrations, and complex configurations, and partners with Product and Engineering on roadmap improvements. Establishes scalable processes, reporting, coaching frameworks, and risk management while serving as the senior technical voice for strategic accounts. Frequent travel is required for onsite customer meetings and industry events.

Leads global benefits governance, compliance calendars, plan documentation, HIPAA privacy and security, retirement plan oversight, leave and accommodation frameworks, vendor resilience, and benefits governance during acquisitions. Coordinates audits, remediation, risk programs, committees, and cross-functional partnerships while ensuring regulatory compliance, operational consistency, and continuity across more than thirty countries.

Build and operate reliable backend systems and APIs for high-traffic products. Responsibilities include distributed system design, data modeling, service architecture, performance tuning, automated testing, observability, incident management, and end-to-end feature delivery. The role partners with Product and Design, makes architecture decisions, mentors engineers, and applies AI-assisted development tools responsibly.

Leads demand generation and product marketing for Playlist’s Beauty & Wellness SaaS division. Builds an AI-native marketing function, launches new AI products, manages paid and organic acquisition, owns positioning and messaging, and oversees experimentation, lead quality, conversion, retention, and payback. Partners with sales leadership, hires and develops the marketing team, manages media budgets, and contributes to divisional strategy and thought leadership.

Leads global SMB sales for Playlist’s Beauty & Wellness division, owning revenue targets, sales strategy, multi-product motions, forecasting, pipeline management, and performance reporting. Builds and manages the sales organization, establishes playbooks for AI-native SaaS products, applies automation across sales processes, oversees hiring and incentives, and contributes to divisional strategy. Requires extensive sales leadership experience, strong analytics, commercial judgment, and the ability to operate in entrepreneurial, high-growth environments.