Top Tech Jobs & Startup Jobs in Chicago, IL

Own and evolve Flexport’s implementation methodology, create standardized playbooks, and lead client implementations from award through steady-state delivery. Scope awarded business, build project plans, coordinate cross-functional teams, manage critical paths, report status and risks to leadership, adapt plans as conditions change, and capture lessons learned to improve future implementations.

The role manages financial planning and analysis, oversees cash flow, collaborates with leadership, and requires strong analytical skills and project management.

Designs and leads AWS-native data foundations for enterprise AI applications, including knowledge graphs, ontologies, semantic layers, vector indexes, retrieval systems, and LLM grounding datasets. Builds Python and SQL pipelines using AWS services, establishes data models and governance standards, integrates identity-based access controls, and monitors data and retrieval quality. The role also mentors engineers and citizen developers, sets technical direction, and communicates with cross-functional stakeholders.

Generate qualified outbound and inbound sales pipeline through personalized calling, emailing, social, video, and text outreach. Research target accounts, map personas, qualify prospects, schedule discovery meetings for Account Executives, maintain CRM accuracy, and meet activity and opportunity targets. Collaborate with marketing and sales on account strategies, campaigns, messaging, and follow-up. Share market and prospect insights to improve demand generation, sales processes, and conversion performance.

Leads the Builders Risk underwriting division by managing a portfolio, evaluating complex construction risks, and driving profitable growth. Oversees underwriting strategy, carrier capacity, pricing, broker relationships, referrals, and production goals. Manages, recruits, trains, and evaluates a team of underwriters while partnering with product, claims, actuarial, and division leadership. Requires advanced technical underwriting expertise, sound judgment, and travel for client and industry engagements.

Lead and deliver bank valuation engagements for financial reporting, including loan portfolios, core deposit and customer relationship intangibles, and financial instruments. Manage staff, oversee projects and client relationships, apply multiple valuation standards and methodologies, perform financial statement and quantitative analyses, and provide defensible conclusions for regulatory and tax contexts. Hybrid role with occasional travel.

Lead the global revenue marketing strategy for a B2B SaaS company, integrating demand generation, ABM, digital, web, lifecycle, events, partner marketing, and growth programs. Build and lead a global marketing organization, generate predictable pipeline, accelerate acquisition and conversion, optimize campaigns through experimentation, and partner with Sales, Customer Success, Product, Communications, and Marketing Operations to drive measurable commercial results.

Leads integrated marketing plans and complex marketing materials while supporting marketing directors on strategic initiatives. Builds internal client relationships, manages feedback, coordinates multifunctional teams, and oversees outside vendors. Ensures projects are delivered according to scope, brief, timeline, and budget. Requires at least five years of relevant experience and vendor-management expertise, with healthcare or agency marketing experience preferred.

Sales Representatives engage with customers to identify their sleep needs, explain product benefits, nurture relationships, and maintain store presentation to exceed sales goals.

Leads budgeting, forecasting, management reporting, and financial performance analysis. Partners with executives and business leaders to evaluate results, risks, opportunities, and operational drivers. Develops executive summaries, financial models, reporting packages, and standardized processes across regional markets. Supports annual operating plans, quarterly forecasts, business reviews, financial systems improvements, automation, and strategic decision-making while collaborating with accounting and business finance teams.

Lead design and implementation of the EisnerAI platform, integrating data, governance, AI agents and applications. Drive model evaluation, post-training optimization, agent development (TaxPrepBot, DocIntake, etc.), and ensure data governance and responsible AI practices across enterprise solutions.