Top Tech Jobs & Startup Jobs in Chicago, IL

Lead and scale business and GTM recruiting across multiple corporate functions. Develop talent acquisition strategies, workforce plans, hiring metrics, recruiting processes, employer brand initiatives, and candidate experience improvements. Build and mentor a high-performing recruiting team, advise senior leaders, and integrate AI and automation into sourcing, screening, assessment, scheduling, and pipeline management.

Lead Engine’s global events portfolio across conferences, executive experiences, partner and supply events, government programs, and first-party customer events. Own strategy, budgets, calendars, execution, brand experience, attendee recruitment, measurement, and monetization. Build scalable playbooks connecting events to pipeline, revenue, sponsorships, and partner participation. Manage multiple event motions across product lines while collaborating with brand, growth, partnerships, sales, supply teams, vendors, and agencies.

Own acquisition and retention growth for the weddings vertical by developing channel strategies, running experiments, scaling successful programs, and building lifecycle initiatives. Partner with Product and Sales to improve the wedding customer experience and roadmap, analyze performance data, execute hands-on growth work, and use AI to personalize programs and accelerate testing.

Lead Engine’s total rewards strategy across compensation, equity, benefits, job architecture, pay transparency, and geographic expansion. Advise executives on compensation and equity decisions, anticipate AI-driven workforce changes, build predictive analytics and market intelligence, modernize compensation technology, ensure compliance, and enable managers to communicate rewards effectively. The role requires deep expertise in compensation design, equity strategy, executive incentives, analytics, and scalable rewards programs in high-growth companies.

Own internal communications for Engine’s Go-To-Market organization, advising senior commercial leaders and translating strategy into clear messaging. Lead communications for sales kickoffs, QBRs, incentive rollouts, organizational changes, town halls, and executive updates. Partner cross-functionally, coach leaders, manage change communications, and develop AI-enabled workflows to scale communications while preserving leader voice and consistency.

Build and maintain Engine X performance dashboards, reporting frameworks, data models, and complex SQL analyses using Snowflake. Track card, booking, rewards, spending, and retention metrics; investigate anomalies; support A/B tests; document metric definitions; and communicate findings to product, finance, and leadership. Collaborate with analytics and data engineering teams to validate pipelines and improve data quality.

Lead FinTech product design from vision through execution, including payment experiences, billing portals, spend management, bill payment, insights, and credit card products. Partner with product, engineering, data, and executives to define user-centered solutions, simplify complex workflows, lead design reviews, improve feedback processes, and shape design strategy while mentoring other designers and raising the organization’s quality bar.

Lead partnership acquisition strategy for Engine’s transportation and trucking vertical. Identify, negotiate, and close enterprise partnerships across fleet payments, TMS, telematics, ELD, fuel networks, and industry associations. Build executive relationships, onboard partners, coordinate integrations and go-to-market launches, and track pipeline, signed partnerships, and revenue KPIs. The role requires enterprise sales or business development expertise, financial acumen, scalable partner-led sales experience, and familiarity with transportation, logistics, or fleet ecosystems.

Leads analytics for Pricing and Supply, managing a team of approximately eight analysts. Partners with cross-functional leaders to prioritize analytical work, build dashboards and decision frameworks, improve metric quality, and generate insights into pricing, supplier coverage, marketplace performance, conversion, margin, and customer behavior. Coaches analysts, establishes scalable analytics processes, and collaborates with data engineering teams to improve data models, tooling, and self-service capabilities.

Own the strategy and acquisition of high-value industrial partnerships across associations, franchise and dealer networks, GPOs, and technology ecosystems. Build pipeline from zero, engage executives, develop ROI-driven business cases, negotiate complex commercial agreements, and close scalable one-to-many partnerships. Collaborate cross-functionally to activate signed partners, generate referred revenue, measure performance, and develop a repeatable industrial partnerships playbook.