Top Tech Jobs & Startup Jobs in Chicago, IL

Acquire and grow mid-market customers for AI-powered customer experience, contact center, unified communications, and business communication solutions. Generate pipeline through prospecting, referrals, networking, partners, and inbound opportunities; manage complex multi-stakeholder sales cycles; conduct consultative discovery; develop account plans; present solutions; maintain CRM data and forecasts; use AI-enabled sales tools and analytics; and collaborate with marketing, partners, solution consultants, customer success, and product teams.

Build end-to-end product features with a backend focus: schema and API design, UI work in React/TypeScript, GCP/Terraform infrastructure, CI/CD, DB performance tuning, production ownership, and product decision-making using AI coding tools.

Build and iterate full-stack systems powering AI agents, from user-facing experiences through orchestration and deployment. Research agent orchestration, prompting, and model alignment approaches; collaborate with Product, Design, and Engineering to improve usability; document findings, share technical learnings, and participate in reviews and technical discussions.

Support end-to-end onboarding of HR, payroll, benefits, and leave clients. Configure HRIS platforms, migrate and validate employee and payroll data, establish benefits EDI and GL integrations, coordinate cross-functional workstreams, maintain implementation plans, and ensure smooth handoffs to service teams. The role also improves workflows through automation and AI while managing client expectations, timelines, testing, and go-live readiness.

Support senior leaders by managing complex calendars, meetings, travel, communications, presentations, action items, and confidential information. Coordinate cross-functional priorities, prepare executives for meetings, track follow-ups, improve workflows, and support special projects in a fast-paced healthcare organization.

Leads Hint’s brand growth agenda, annual planning, integrated campaigns, innovation strategy, commercial partnerships, and consumer engagement across social, creators, partnerships, and experiential channels. Owns campaigns from brief through launch, guides creative development, aligns cross-functional teams, establishes performance measures, and drives brand and commercial results. Develops high-performing teams while balancing strategic leadership with hands-on execution in a fast-moving consumer marketing environment.

Manage a portfolio of 15–25 customers, owning renewals, retention, upsells, customer health, account planning, and revenue growth. Serve as a trusted product advisor, lead business reviews, provide data-driven insights, collaborate cross-functionally, and mentor CSMs. The role requires senior stakeholder engagement, quota-carrying experience, CRM forecasting, project management, and occasional travel while working remotely during Eastern Time hours.

Acquire new enterprise and mid-market customers, expand existing accounts, manage complex B2B software sales cycles, build pipeline, engage executive buyers, lead proposals and negotiations, partner with presales and internal teams, maintain accurate forecasts, and meet or exceed revenue targets. The role requires data management or governance sales experience, consultative selling, channel expertise, account expansion skills, and effective use of AI tools for sales productivity.

Lead customer implementations and migrations of H1’s SaaS and data solutions. Own project plans, customer deliverables, KPIs, communications, and cross-functional coordination across Professional Services, Customer Success, Product, and Engineering. Improve scalable services processes, manage high-visibility initiatives, communicate technical updates, and advocate for customers while ensuring high-quality delivery and satisfaction.

The Head of Sales leads the sales organization, owning strategy, pipeline performance, forecasting, sales process, quota execution, and new business growth. Responsibilities include coaching sales leaders and representatives, establishing accountability and deal-review disciplines, expanding into new markets, managing strategic opportunities, partnering with Marketing and Commercial teams, and representing the company at industry events. The role requires building repeatable sales operations and improving win rates, deal velocity, and forecast reliability.