Top Tech Jobs & Startup Jobs in Chicago, IL

Leads the strategy, architecture, transformation, delivery, and operations of cloud platforms, enterprise networks, data centers, and foundational technology services. Owns infrastructure separations, modernization, reliability, automation, observability, cost optimization, and IT operations evolution. Partners with engineering and enterprise technology leaders, manages strategic vendors and budgets, and develops a high-performing technical team while delivering scalable, secure infrastructure for global operations and AI-enabled workloads.

Own Flodesk’s company-wide forecasting, planning, subscription revenue modeling, three-statement financial model, board reporting, and FP&A automation. Partner with the CFO and cross-functional teams on strategic decisions, scenario analysis, unit economics, and executive reporting. Design auditable workflows using AI and automation, establish controls and documentation, manage the FP&A roadmap, and deliver prioritized ad hoc analysis.

Owns the full sales cycle for litigation-focused law firms, from inbound and outbound prospecting through discovery, demos, trials, proposals, negotiation, and close. Manages territory pipeline, forecasting, CRM accuracy, stakeholder engagement, and customer handoffs. The role focuses on winning new B2B SaaS business, protecting ACV, supporting expansion, and helping develop a repeatable mid-market sales playbook.

Leads and develops a team of GTM engineers building AI agents, workflows, integrations, and internal infrastructure for marketing, sales, and customer success. Establishes engineering standards, documentation, review, ownership, and rollback practices; partners on roadmap planning; manages technical vendor relationships; and coordinates transitions from prototypes to long-term engineering ownership. The role remains hands-on while hiring, mentoring, and improving team operations in a fully remote environment.

Lead product design for Brex’s Travel and Expenses platform, owning design direction from ambiguous problem definition through shipped execution. Design intuitive financial workflows, AI-assisted experiences, policy tools, and reimbursement products. Partner with Product, Engineering, Research, and Data; conduct research; define system models; contribute to design systems; facilitate alignment; present decisions; and mentor designers.

Own the partner enablement strategy from onboarding through certification, designation, and recertification. Build sales, technical presales, deployment, implementation, and MSP learning tracks; coordinate content, labs, assessments, boot camps, and partner events. Manage LMS governance and certification data while measuring time to readiness, partner revenue impact, pipeline contribution, delivery quality, and customer health. Collaborate with Channel leadership, Sales and Technical Enablement, Technical Services, and partner executives to improve programs and launch partner designations.

Build Boulevard’s Product Intelligence function by creating product data foundations, instrumentation strategies, analytical models, dashboards, and self-serve tools. Partner with Product and cross-functional leaders to analyze funnels, retention, cohorts, segmentation, and feature adoption, translating findings into clear recommendations. Establish scalable analytical processes, improve data quality, and influence product and business decisions through compelling narratives and visualizations.

Owns sales execution for a California territory, including territory planning, prospecting, pipeline and CRM management, value-based selling, forecasting, quota attainment, competitive analysis, and collaboration with product, support, and sales engineering teams. The role requires SaaS, security, or DevOps closing experience, strong enterprise relationship-building skills, and willingness to travel to clients as needed.

Leads the organization’s leave and workplace accommodation programs, supervising specialists and managing complex, high-risk cases. Oversees ADA interactive processes, FMLA and other protected leaves, return-to-work planning, vendor relationships, audits, reporting, compliance, policies, training, and confidential records. Partners with HR, Benefits, Payroll, Legal, Employee Relations, and operational leaders to resolve escalations, improve processes, manage risk, and ensure consistent administration across jurisdictions.

Leads and develops a commercial account executive team responsible for renewals, base management, transactional sales, retention, expansion, forecasting, and quota attainment. Owns pipeline reviews, deal coaching, discount approvals, recruiting, onboarding, and succession development. Partners with Renewals and Customer Success to manage account health and churn risk, while using AI tools to improve forecasting and productivity. Requires B2B software sales leadership, MEDDPICC experience, CRM proficiency, and 25–50% travel.