Top Tech Jobs & Startup Jobs in Chicago, IL

Supports venture capital clients by ingesting, transforming, mapping, and verifying portfolio financial data from Excel, PDFs, CSVs, and other sources. Improves AI agent workflows, prompt design, and automation protocols while collaborating with Customer Success, Product Support, engineering, product, and operations. Provides customer support and helps scale accurate, efficient data-processing workflows.

Leads group sales growth for a luxury resort by generating new business, converting inquiries, qualifying leads, conducting outreach, and achieving sales targets. Coordinates with property leadership and internal departments to fulfill contracted services and maintain client satisfaction. Responsibilities include property visits, site inspections, FAMs, direct sales calls, and attending trade shows. The role is remote within the U.S. and requires travel of up to 35%.

Lead BigTime’s product management team and next-generation AI-native PSA platform. Own product roadmaps, release sequencing, specifications, customer migrations, PM hiring and development, executive customer relationships, advisory board engagement, and cross-functional alignment. Also oversee the existing BigTime Delivery roadmap. The role requires building a new platform alongside an established product, shipping AI capabilities, managing distributed teams, and traveling periodically to Poland, customers, and industry events.

Own post-sales technical relationships for key clients, helping them optimize platform solutions, workflows, integrations, and AI-driven automation. Manage technical support SLAs, monitor client health and anomalies, deliver training, identify process improvements, and communicate feedback to Product and Engineering. Collaborate cross-functionally on escalations, feature roadmaps, account growth, and client retention while operating effectively in an evolving environment.

Leads and scales Square’s Central Region Field Sales organization, managing Sales Managers and Territory Account Executives. Responsibilities include territory and go-to-market strategy, pipeline and KPI management, field coaching, consultative selling, product expertise, team development, cross-functional collaboration, and regional revenue growth. The role builds a competitive, accountable, high-performing sales culture while representing Square with local business leaders and partners.

Leads enterprise data security and information governance by building data intake, catalog, marketplace, classification, lineage, and access-control programs. Translates privacy and security requirements into technical controls, self-service workflows, and governance documentation. Partners with Legal, InfoSec, engineering, product, and data teams to support compliant data use, AI/ML initiatives, and regulatory requirements including HIPAA, GDPR, and CCPA. Measures adoption, turnaround times, and governance maturity across a global SaaS organization.

Supports client pilots, onboarding, training, and adoption of an AI-powered legal platform. Designs and evaluates legal AI use cases for contract review, research, and drafting; gathers user insights, translates them into product feedback, and documents scalable deployment best practices. The role requires a completed J.D., strong communication, analytical judgment, curiosity about AI and workflow automation, and adaptability in a fast-paced, client-facing environment.

Grow and retain defined contribution assets under management across the Pacific Northwest by developing relationships with advisors, consultants, recordkeepers, and strategic partners. Execute distribution strategies, market investment products, advise partners on DC trends and regulations, respond to client needs, coordinate internal resources, and maintain CRM records. The role requires investment fluency, strong sales and relationship-management experience, relevant securities licenses, and substantial client travel.

Handles high-volume payment and refund support for business travelers by contacting hotels and vendors, obtaining receipts and folios, collecting updated payment details, issuing pre-authorization forms and virtual credit cards, resolving payment issues, and coordinating credit card reversals. Maintains accurate records and timely updates while managing multiple tasks in a fast-paced, back-office environment.

Generates qualified sales meetings for Account Executives through outbound prospecting and inbound lead qualification. Responsibilities include cold calling, personalized email and LinkedIn outreach, account research, CRM and pipeline management, territory planning, AI-assisted workflow optimization, and continuous sales coaching. The role requires developing expertise in enterprise Governance, Risk, and Compliance concepts while working hybrid in Chicago from 6:00 AM to 2:00 PM CT.