Top Tech Jobs & Startup Jobs in Chicago, IL

The Chief of Staff will oversee operational projects, refine strategies, and support leadership in a fast-paced scaling environment.

Directs presale operations, overseeing intake, quoting, RFPs, proposals, testing, peer reviews, process improvement, and technology adoption. Leads managers and staff, resolves cross-functional conflicts, develops talent, manages budgets and performance, and analyzes capacity, output, and customer trends. Partners with Underwriting, Actuarial, Sales, and product stakeholders to deliver accurate, competitive, timely responses for Life and Supplemental Health products.

The Director of Site Acquisition leads the Site Acquisition Team, managing land campaigns, coordinating with teams, negotiating contracts, and driving project pipeline growth for renewable energy projects.

Provide onboarding and ongoing group and individual training on policies, procedures, competencies, and laboratory information systems; develop and update training materials; serve as procedural/compliance resource; support leadership on quality/service metrics; create improvement plans, maintain training records, assist with high-volume workflow and travel to client sites for training.

Prepare and review property accounting tasks including financial reports, cash and accrual journal entries, bank reconciliations, tenant billings, A/P review, rent roll postings, owner distributions, escalation settlements, and ensure schedules tie to the general ledger using real estate accounting software. Coordinate with property management, auditors, and tax preparers, maintain documentation, and meet monthly reporting deadlines.

Coordinates U.S. Customs entry documentation and high-volume import clearance processes. Reviews brokerage files, classifies invoices using tariff references, enters and transmits AMS and HTS data, prepares customs forms, files ISF documentation, obtains government releases through ABI, monitors rejections, and supports delivery, invoicing, audits, and customer inquiries. Maintains compliance with U.S. Customs standards and required documentation procedures.

Lead linguistic quality for an account: edit and proofread localized content, perform translations and reviews, define quality expectations, run LQAs and RCAs, liaise with Apple SMEs, manage linguistic assets, coach and onboard linguists, track KPIs, and drive corrective actions and arbitration.

Sell Convr's AI-driven underwriting platform into large commercial P&C insurers. Identify, negotiate, and close enterprise SaaS deals with C-suite stakeholders, develop relationships, generate leads through networking/referrals, and leverage deep P&C underwriting or enterprise software expertise to drive revenue and inform product-market fit.

Lead design and implementation of the software QA program: define QA strategy, build and manage QA teams (internal/offshore), select tools, implement test automation and performance testing, monitor metrics and defects, drive continuous improvement, and support M&A activities.

Lead a full rebrand and repositioning, define marketing strategy for institutional and crypto audiences, build a premium brand identity, partner with commercial leadership to drive measurable impact, and grow a small AI-augmented marketing team to shift market perception toward institutional credibility.