Top Tech Jobs & Startup Jobs in Chicago, IL

Lead full-cycle recruiting for complex Sales, Marketing, and Operations roles. Partner with senior leadership, develop multi-channel sourcing strategies, evaluate and close candidates, optimize recruiting funnels, and ensure compliant ATS and CRM tracking. The role also involves mentoring junior recruiters, leveraging AI and automation, improving hiring metrics, and delivering a high-touch candidate experience.

Generates new B2B business for WEX’s Valero fleet partner through high-volume cold calling, lead qualification, discovery, objection handling, proposals, and closing. Maintains a sales pipeline and customer records using CRM and sales tools, analyzes prospect transaction data, recommends fleet and fuel management solutions, gathers account approval information, and coordinates onboarding. Builds customer and internal relationships while supporting sales goals and staying current on products, industry trends, and competition.

Supports Sales Directors by responding to proposals, drafting tailored cover letters, managing Salesforce tasks and client contacts, coordinating travel and events, answering inquiries, and assisting with presentations and product training. The role involves consultant and client interactions, opportunity management, research, customer service, and sales team support. Travel is required 5–7 times annually.

Administer COBRA and Direct Bill plans, balances, employer accounts, and incoming files. Resolve internal questions, account discrepancies, and tier-three escalations using product and system knowledge. Communicate with departments, employers, consultants, brokers, and vendors through case management. Support peer training, process improvement, compliance with HIPAA policies, special projects, and quality and performance goals.

Manage approximately 100 middle-market corporate payment partners, serving as relationship owner and client advocate. Drive retention, profitable growth, contract renewals, pricing, quarterly business reviews, issue resolution, and cross-functional execution. Collaborate with leadership, operations, finance, legal, product, and technology teams to deliver roadmap initiatives, improve processes, resolve operational issues, and identify opportunities for additional services. Travel up to 30% and maintain frequent partner engagement.

Own territory growth and full-cycle B2B sales for complex HVAC, plumbing, and electrical contractor accounts. Develop strategic relationships, manage prospecting through close, maintain Salesforce pipeline data, and achieve sales targets. Partner with marketing and regional leadership to improve go-to-market strategies, sales processes, messaging, and playbooks. Mentor junior sellers and contribute to leadership development and future advancement opportunities.

Lead enterprise AI security architecture, strategy, governance, and secure-by-design implementation across cloud, hybrid infrastructure, software, and AI/ML environments. Design security patterns for LLM hosting, agentic systems, vector databases, and inference endpoints; translate regulatory requirements into technical standards; review complex architectures; implement AI security guardrails and policy enforcement; advise engineering and product teams; and mentor teams while influencing senior stakeholders.

Leads commercial strategy, growth, and relationship management for strategic global travel accounts. Builds executive-level partnerships, coordinates cross-functional teams, develops value creation roadmaps, expands WEX solution utilization, manages forecasts and charge volumes, conducts market analysis, and delivers revenue growth. Requires payments industry expertise, enterprise relationship management experience, financial modeling, data interpretation, and strong presentation skills.

Sell WEX telematics solutions to small and mid-sized fleets by managing a pipeline, negotiating and closing deals, upselling, forecasting MRR in Salesforce, collaborating with customer success and partners, and mentoring junior sales team members.

Develop and execute lifecycle and retention marketing strategies for B2B mobility customers. Lead multi-channel campaigns that improve engagement, product adoption, usage, satisfaction, and retention. Collaborate with business and digital marketing stakeholders, manage campaign risks, budgets, and deadlines, and measure performance through customer, revenue, churn, and retention metrics. Use segmentation, marketing automation, analytics, and AI tools to optimize campaign effectiveness and investment.