Top Tech Jobs & Startup Jobs in Chicago, IL

Lead complex enterprise SaaS sales for engineering firms across North America. Manage the full sales cycle from qualified leads and discovery through pilots, procurement, negotiation, and multi-year contract close. Build relationships with executives, engineers, and internal champions; generate outbound pipeline; represent the company at industry events; and collaborate with Product, Marketing, and Customer Success to support onboarding and expansion.

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.

Deliver customer-facing technical training in data engineering and AI through virtual and onsite sessions. Create tailored courses, projects, certifications, and assessments aligned with customer roles, tools, and business outcomes. Partner with Customer Success, Sales, Product, and Content teams to design blended learning paths, drive platform adoption, and improve measurable skills. Support diverse technical and non-technical audiences across time zones, with occasional onsite travel and success metrics tied to customer satisfaction, bookings, and professional services revenue.

Leads the architecture, development, and support of enterprise data warehouses, lakehouses, dimensional models, ETL/ELT pipelines, and governed data products using Microsoft Fabric and related tools. Ensures data quality, security, scalability, performance, and reliability for analytics and reporting. Partners with technical and business stakeholders, documents data solutions, guides architecture decisions, mentors team members, and drives continuous improvement of data engineering standards and practices.

Lead two engineering teams of 8–10 engineers, owning delivery, quality, capacity planning, sprint execution, OKRs, hiring, retention, and professional development. Establish scalable engineering processes, quality gates, testing standards, observability, and continuous improvement practices. Partner with Product Managers on roadmap execution while providing technical guidance on architecture, APIs, backend systems, infrastructure, and frontend platforms.

Provide excellent customer service, promote and sell products, maintain attractive merchandising and displays, process payments, manage inventory and stock (cycle counts, SKU checks, replenishment), handle guest queries and complaints, ensure store cleanliness and FIFO for perishables, assist with deliveries and vessel safety duties as needed.

Create short-form finance and Excel content that demonstrates TabAI workflows, engage and educate audiences across social platforms, experiment with formats and insights, collaborate with TabAI on prompts and creative direction, and drive subscriptions via affiliate links while building a personal brand.

Leads complex enterprise customer implementations from closed-won commitment through go-live, adoption, measurable ROI, and account health. Owns implementation plans, milestones, risks, technical coordination, customer onboarding, executive updates, value realization, and process improvement. Partners across Sales, Product, Engineering, AI, and customer teams while identifying expansion signals. The role requires strong enterprise stakeholder management, technical understanding of integrations and workflows, and regular customer-site travel.

Lead new-business sales and business development for FX trading and pre-trade risk technology across North America. Build relationships with Tier-1 to Tier-3 banks, liquidity providers, venues, and senior decision-makers; manage prospect pipelines, RFI/RFP responses, product demonstrations, negotiations, and closures. Exceed regional targets, provide market intelligence, support product strategy, and collaborate with product, development, IT, QA, support, and professional services teams.

Develop and close strategic mid-market and enterprise business for Build.io in the US. Own the full sales cycle, including prospecting, discovery, technical evaluation, negotiation, procurement, and closing. Build relationships with technical and executive stakeholders, manage pipeline and forecasting, drive account expansion, and help shape the company’s enterprise go-to-market strategy.