Top Tech Jobs & Startup Jobs in Chicago, IL

Serve as the technical lead in the pre-sales process for aviation software prospects. Responsibilities include technical discovery, tailored product demonstrations, proof-of-concept ownership, RFP responses, API and integration discussions, demo environment maintenance, objection handling, and communicating customer feedback to Product and Engineering. The role also develops technical collateral, supports sales enablement, and helps onboard Sales Executives.

Leads integrated paid search and SEO strategy across client accounts, managing campaigns, budgets, bidding, keyword strategy, technical SEO, content optimization, measurement, and performance analysis. Presents recommendations to clients, identifies growth opportunities across emerging search channels and AI-driven discovery, mentors junior team members, and collaborates with media, analytics, creative, web, UX, and account teams.

Own the strategy, development, launch, and performance of a new AI wedding product from zero to one. Responsibilities include defining the roadmap, market positioning, trustworthy AI behaviors, rapid prototyping, user testing, measurement, unit economics, and use of proprietary marketplace and behavioral data. The role also partners with executive, engineering, design, marketing, and data science leaders to shape company-wide AI direction.

Own full-cycle enterprise sales for Astra’s payments and financial technology platform, from prospecting through procurement, technical review, legal, and signature. Build executive relationships, navigate complex multi-stakeholder deals, displace incumbent providers, forecast pipeline, and develop outbound strategies. Partner with engineering, integrations, and compliance teams while influencing product and go-to-market strategy. Mentor account executives and apply AI tools to improve research and sales workflows.

Own Kestra’s enterprise demand-generation strategy, account tiering, ABM programs, multi-channel campaigns, paid acquisition, nurture, conversion, measurement, budget allocation, and agency partnerships. Build target-account programs from product, community, web, GitHub, and firmographic signals, partnering with Sales, Product Marketing, Growth Engineering, and Business Development to generate and progress qualified enterprise pipeline. The role is a hands-on senior individual contributor position focused on account-level engagement and pipeline outcomes.

Manage small business and mid-market customer relationships, driving adoption, retention, renewals, and expansions. Build success plans and playbooks, conduct QBRs and EBRs, analyze product usage, deliver enablement, understand recruiting workflows, and communicate customer needs cross-functionally to Product and Engineering. Maintain expert knowledge of the GoodTime platform while building executive relationships and recommending features, settings, and modules that improve customer outcomes.

Partners with business development leaders to acquire and manage high-net-worth clients. Provides investment advisory, financial planning, estate and tax planning, customized investment proposals, portfolio reviews, asset allocation recommendations, and proactive client communication. Supports referral-based business development through prospect meetings and custodian-sponsored events while delivering personalized wealth management services.

Conduct complex investigative research and analysis on individuals, companies, and entities for due diligence, disputes, investigations, and risk engagements. Gather information from public records, databases, media, regulatory filings, and human sources; synthesize findings into actionable reports and client briefings. Coordinate remote research consultants, manage multiple projects, maintain accurate records, and support time-sensitive client needs. The role requires strong analytical, communication, organizational, and research skills, proficiency with Microsoft Office, and willingness to travel as needed.

Manage full-cycle technical recruiting from requisition intake through placement. Source specialized talent, screen candidates, build pipelines, partner with hiring managers, prepare candidates for interviews, and manage multiple requisitions. Use ATS, VMS, sourcing platforms, automation, and AI-enabled recruiting tools while collaborating with recruiting and delivery teams to meet hiring priorities and submit qualified candidates.

Develop and productionize machine learning models and predictive analytics using Python, Databricks, PySpark, SQL, and Delta Lake. Build scalable data science workflows, resolve healthcare data quality and entity-resolution issues, and apply Master Data Management practices. Partner with engineering, product, analytics, and business teams to deliver governed, HIPAA-compliant solutions. Perform exploratory analysis, feature engineering, model evaluation, deployment, documentation, and data lineage management for healthcare and member engagement initiatives.