Top Tech Jobs & Startup Jobs in Chicago, IL

Serve as the CEO's strategic and operational right hand at an AI LegalTech startup: prepare executive/board/investor materials, build financial models and decks, contribute litigation expertise to product content, validate LLM-generated analyses, drive cross-functional execution, manage company operations (recruiting, vendor administration, OKRs), represent the CEO, and handle special projects across finance, legal, and partnerships.

Owns the product backlog and translates user needs into JIRA tickets, user stories, and acceptance criteria. Partners with Product Management, Engineering, QA, and cross-functional stakeholders on prioritization, release planning, testing, and delivery. Monitors feature adoption, gathers feedback, advocates for end users, and supports business cases and ROI analysis. The role requires understanding healthcare workflows and facilitating communication among technical and business teams.

Own quality engineering for high-throughput payment systems by architecting automated regression, performance, stress, and load testing. Build emulators for external payment systems, integrate quality gates into CI/CD pipelines, validate microservices, event-driven architectures, and databases, and use Prometheus and Grafana for observability. Apply AI-assisted testing, synthetic data generation, and edge-case analysis while mentoring engineers and preventing incidents through telemetry-driven testing and post-mortems.

Own quality engineering for high-throughput payment systems by designing automated regression suites, performance and load tests, quality gates, external-system emulators, observability-driven test environments, and AI-assisted testing workflows. Partner with feature teams and product leaders to improve reliability, scalability, security, and transactional accuracy. Mentor engineers, support incident prevention, and embed automated validation throughout the software development lifecycle.

Design secure, scalable payment infrastructure solutions for prospective and existing customers. Lead technical discovery, map complex payment flows, create architectures, demos, proposals, proofs of concept, and implementation handoffs. Advise on tokenization, PCI scope reduction, processor connectivity, payment portability, resiliency, and compliance. Partner with Sales, Account Management, Product, Engineering, and customer technical teams, provide launch oversight, influence product strategy, and develop reusable integration assets and reference architectures.

Design, develop and support cloud applications using Cloud Foundry and Node.js. Apply object-oriented design and SQL (HANA). Work with APIs and eventing, use VS Code. Prefer SAP CAP/BTP and SAP experience. Collaborate in agile/SCRUM teams, communicate effectively, take ownership, and ensure high quality.

Senior full-stack developer to build scalable SAP BTP applications using Node.js, CAPM, and SAP UI5/Fiori; integrate with S/4HANA and third-party systems; optimize performance, ensure secure deployments, and follow Agile practices.

Build and maintain large-scale data processing pipelines using Apache Spark (PySpark/Scala) and Python. Design ETL workflows, implement distributed data processing, use version control (Git), and work with cloud platforms (GCP/AWS/Azure).

Provides high-level executive support to the CEO and leadership team, managing complex calendars, travel, meetings, confidential matters, and follow-through. Writes and edits executive and company-wide communications, coordinates all-hands and leadership events, prepares Board materials, and supports change communications. Improves executive-office workflows using Microsoft 365, AI tools, templates, trackers, and repeatable processes.

Lead and oversee volunteer HR operations: supervise/train HROs, manage recruiting and onboarding via Dover ATS, maintain HR documentation and systems, run meetings and strategic HR initiatives, support Executive Director on DEI and people strategy, and cover day-to-day volunteer HR duties.

Design and launch interactive podcast content (quizzes, polls, listener challenges), integrate elements with hosts, track engagement metrics, experiment with tools, and improve audience interaction.

Volunteer WordPress Developer to migrate and maintain a content library, build new features, and create custom themes, plugins, and widgets. Work remotely for ~5+ hours/week, attend weekly meetings, and respond within 24 hours to support an active nonprofit volunteer team.

Design, develop, test, deploy, monitor, and support enterprise integrations using the Boomi platform. Connect systems such as NetSuite, SAP, D365, Workday, Salesforce, and other applications through APIs, EDI, databases, files, messaging, and cloud services. Perform data transformation, error handling, optimization, troubleshooting, documentation, and production support. Lead integration workstreams, manage deliverables and deployments, conduct code reviews, define reusable standards, collaborate with stakeholders, and mentor junior developers.

Owns enterprise integration architecture across multiple projects and teams using the Boomi platform. Defines reference architectures, integration standards, API strategy, security, runtime topology, deployment models, monitoring, and governance. Oversees design, development, testing, code reviews, production support, performance, and migration roadmaps. Architects integrations among ERP, CRM, HCM, database, file, messaging, and cloud systems; leads stakeholder discussions, estimates effort, documents solutions, and mentors developers.

Design, configure, and operate SailPoint Identity Security Cloud for enterprise-scale identity governance. Own joiner-mover-leaver automation, connectors, integrations, RBAC and SoD policies, access certifications, provisioning, troubleshooting, platform reliability, audit evidence, documentation, and roadmap improvements. Partner with security, IT, HR, application owners, and compliance stakeholders while supporting critical production issues through on-call and escalation responsibilities.

Own Linktree’s production AI platform, including pipelines, model and prompt versioning, evaluations, monitoring, rollback, cost, latency, and reliability. Drive internal AI adoption through tooling, agent workflows, and enablement across Product, Engineering, Marketing, and Support. Establish practical governance for data handling and vendor risk, make build-versus-buy decisions, align AI investment with business priorities, and mentor engineers and analysts.

Lead Roo’s sales organization and integrated revenue strategy across its veterinary staffing marketplace. Responsibilities include designing territory and coverage models, allocating headcount and budget, improving forecasting and quota attainment, scaling go-to-market playbooks, building enablement and coaching programs, managing CRM and sales tooling, planning organizational capacity, and aligning Product, Marketing, Finance, and Data around revenue priorities. The VP will also lead hiring, performance management, and major sales process and compensation transformations.

Build and lead Roo’s Revenue Operations function, owning the operating model, HubSpot architecture and governance, forecasting, pipeline management, reporting, capacity planning, lead management, and conversion optimization. Partner with Sales, Marketing, Customer Support, Finance, and Data to improve revenue efficiency and predictability. Apply AI to reduce operational work, hire and develop a lean team, and expand RevOps capabilities across the organization.

Lead client discovery and executive engagement to identify high-value AI and data opportunities. Translate ambiguous business problems into use cases, hypotheses, MVP scopes, business cases, and measurable KPIs. Facilitate workshops, prototype solutions using AI-assisted and low/no-code tools, and partner with technical teams to develop scalable solutions. Manage client alignment, scope, risk, adoption, and change communication while connecting technology investments to business value.

Lead complex client-facing AI and data programs from strategy through delivery, coordinating multi-geo teams and partners. Own roadmaps, budgets, margins, risks, escalations, client relationships, and measurable business outcomes. Partner with technical leaders, provide executive reporting, identify account expansion opportunities, and coach project managers and consultants. The role requires strong program management experience in consulting or professional services, familiarity with modern data and AI platforms, and willingness to travel up to 50% per month.

Leads complex, client-facing data and AI programs from strategy through delivery. Responsibilities include managing roadmaps, scope, budgets, margins, risks, forecasting, change control, executive communications, partner coordination, and measurable outcomes. The role orchestrates multi-geo teams, coaches delivery professionals, manages stakeholder relationships, and improves delivery methodologies across consulting engagements.