Top Tech Jobs & Startup Jobs in Chicago, IL

Leads a 24x7 managed IT services practice across Service Desk, NOC, SOC, field services, and project delivery. Oversees service quality, operational metrics, escalations, capacity, utilization, financial drivers, and continuous improvement. Builds and develops high-performing teams, manages client health and executive escalations, supports retention and growth, and partners across Sales, PMO, Client Experience, and other practices to deliver consistent client outcomes.

Leads technical strategy across customer sales and success lifecycles. Advises sales teams, designs and demonstrates solutions, responds to RFPs, removes technical sales blockers, and owns technical wins. Develops customer success plans, supports onboarding and implementation, manages account strategy, provides ongoing technical guidance, and identifies expansion opportunities. Requires strong Red Hat, Linux, Ansible, OpenShift, cloud, DevOps, solution architecture, consultative selling, communication, project management, and customer relationship skills.

Designs, develops, tests, maintains, and troubleshoots Workday integrations with internal and external systems. The role gathers requirements, documents solutions, supports HR stakeholders, leads QA and system testing, monitors Workday releases, optimizes HR system performance, and provides technical guidance and training. It also serves as a subject matter expert in HRIS projects and collaborates with Finance and HR system teams.

Serve as a GRC subject matter expert on strategic and enterprise deal teams, supporting discovery, demos, POCs, workshops, customer onsites, and expansions. Advise prospects on multi-framework compliance, risk, privacy, trust, and governance programs. Validate AI-generated compliance responses, create enablement materials, train GTM teams, provide product feedback, and support post-sales handoffs. Travel approximately once per quarter.

Serve as the GRC subject matter expert on strategic and enterprise deal teams, advising prospects on compliance, risk, privacy, trust, and AI governance programs. Support discovery, demos, POCs, workshops, customer onsite engagements, and expansions. Develop enablement for GTM teams, validate AI-generated content, provide product feedback, and ensure effective post-sales handoffs. Requires deep hands-on GRC experience, customer-facing credibility, strong writing and teaching skills, sales-process knowledge, audit expertise, and practical AI fluency.

Own sourcing strategy and execution for niche, senior, and leadership engineering roles. Build technical talent pipelines through outreach, talent mapping, networking, and professional communities. Partner with recruiters and hiring managers to align priorities, provide market intelligence, and improve hiring decisions. Use data and AI sourcing tools to optimize pipeline performance, candidate engagement, and recruiting efficiency while developing scalable sourcing practices.

Develop new business for a staffing and project services company by identifying prospects, engaging decision-makers, building client relationships, and converting opportunities. The role involves networking, researching client needs, maintaining CRM records, collaborating with recruiting, account management, and marketing teams, supporting client retention and expansion, and identifying new markets and services. Flexible remote part-time or full-time hours are available, with potential for increasing responsibility in business development strategy.

Manage strategic enterprise and mid-market SaaS merchants, serving as a consultative partner and product expert. Own renewal strategy, drive platform adoption, demonstrate ROI, resolve escalations, facilitate business reviews, track portfolio metrics, and collaborate cross-functionally to improve retention, expansion, and merchant outcomes.

Manage international inbound ocean and air freight, including bookings, shipment tracking, carrier exceptions, customs coordination, Amazon FBA/AWD operations, and contract manufacturer documentation. Maintain landed costs, NetSuite inventory transactions, month-end reconciliations, EPR records, and freight invoice disputes. Provide shipment updates, coordinate forwarders and 3PLs, resolve CBP and Amazon issues, and identify cost savings and process improvements across U.S., EU, and UK marketplaces.

Leads complex operational analysis and issue resolution for MoneyPass network operations. Responsibilities include root-cause analysis, tactical planning, stakeholder collaboration, compliance enforcement, dispute and arbitration review, contract and pricing tracking, client communications, invoicing support, and validation of pricing and interchange setups. The role also supports AI adoption, operational process improvements, and data-driven recommendations to senior management.

Serves as the primary contact for MoneyPass financial institution clients, providing operational support, resolving service issues, coordinating internal and external partners, and managing client communications. Leads operational reviews, tracks service metrics, supports onboarding and product changes, escalates issues, recommends service improvements, and contributes to automation and process optimization. The role requires strong communication, organization, problem-solving, accountability, and client service skills.

Leads administration, maintenance, and governance of MoneyPass network operating rules supporting surcharge-free ATM access. Oversees compliance, rule updates, participant guidelines, disputes, arbitration, penalties, and the MoneyPass Locator. Partners with pricing, analytics, product, legal, strategy, and leadership teams to communicate regulatory and operational changes. Drives process improvement, automation, AI adoption, and data-informed operational excellence while translating complex rules into practical guidance for stakeholders.

Owns employee engagement program execution, including annual company offsites, department gatherings, vendor and contract management, budgets, travel safety, recognition fulfillment, inclusion events, and program administration. Builds scalable planning tools and automations using AI, coordinates stakeholders, tracks participation and costs, and evaluates programs through engagement and feedback metrics. Requires strong organization, communication, judgment with confidential information, and experience managing large events end to end.

Owns Aledade’s Annual Operating Plan and OKR performance management, driving accountability, execution, risk mitigation, and cross-functional alignment. Leads annual and mid-year planning cycles, refines the planning playbook, and prepares data-driven Quarterly Business Review materials. Partners with senior leaders and teams across Analytics, Field, Product, and other departments to coordinate dependencies, resolve roadblocks, and translate strategy into measurable outcomes.