Top Tech Jobs & Startup Jobs in Chicago, IL

Reviews and underwrites new merchant applications for KYC, AML, card-brand, processor, and regulatory compliance. Analyzes flagged transactions, merchant histories, and payment-processing statements to assess risk and recommend approvals or limits. Supports fraud detection and risk-management improvements, handles payment-related inquiries and escalations, and collaborates with internal teams and external partners.

Conduct outbound outreach through email, phone, and social channels; qualify prospects, identify business needs, schedule meetings and demos for Account Executives, track activity in sales tools, and meet sales KPIs. The role also requires staying informed about business management software and POS trends while building expertise through training and enablement.

Build Boulevard’s Product Intelligence function by developing product data foundations, pipelines, dashboards, experimentation practices, and customer behavior models. Partner with Product, Engineering, and leadership to deliver actionable insights, self-serve analytics, and productionized models. Establish scalable processes, instrumentation standards, statistical workflows, and data-driven decision-making across the organization.

Own Support Operations across systems, processes, reporting, and strategic initiatives. Administer and optimize Salesforce, Intercom, and Jira; build integrations, workflows, dashboards, automations, and KPI reporting. Partner with Support leadership and Revenue Operations to improve data quality, customer handoffs, change management, and operational scalability. The role requires cross-functional project management, technical aptitude, documentation, and proactive analysis of support trends and performance gaps.

Own and modernize Boulevard’s corporate IT environment, including identity, access, endpoints, SaaS applications, device management, onboarding, offboarding, and service delivery. Build scalable operating standards, automation, governance, documentation, metrics, and self-service workflows. Resolve complex technical issues, manage vendors, lead IT programs, and partner with Security, People, Finance, Legal, Engineering, and business leaders on compliance, continuity, and technology strategy.

Own and scale Boulevard’s go-to-market automation engine across Salesforce, Clay, LeanData, Gong, Outreach, and related systems. Build AI-driven enrichment, personalization, routing, lifecycle, call-insight, monitoring, and error-handling workflows. Partner with Sales Ops, Marketing Ops, Revenue Enablement, and Analytics to improve seller productivity, data quality, reporting, coaching, and pipeline generation. Document processes and identify automation opportunities that reduce manual work and support scalable revenue growth.

Leads 8–12 Onboarding Specialists serving SMB customers, owning activation velocity, forecasting accuracy, portfolio health, risk mitigation, coaching, and customer readiness. The role manages onboarding operations, reviews performance data and Gong calls, improves processes, coordinates cross-functional handoffs, supports capacity planning, and escalates customer risks. Success is measured by activation speed, forecast accuracy, CSAT, backlog reduction, milestone completion, and team development.

Lead Boulevard’s infrastructure transformation by defining cloud, DevOps, security, and reliability strategy. Manage and grow infrastructure and reliability engineering teams while architecting scalable AWS platforms, EKS containerization, Terraform and GitOps automation, CI/CD pipelines, observability, disaster recovery, database scaling, and compliance practices. Partner with Product, Services, Data Engineering, and Platform teams to provide secure, highly available, self-service infrastructure that supports business growth.

Leads a team of 5–8 engineers, balancing people management with technical leadership. Responsibilities include career development, roadmap delivery, architectural guidance, code reviews, hiring, incident response, team culture, and delivery management. Partners with Product Management and Design to build scalable, reliable, user-focused SaaS products while contributing hands-on technically and supporting remote, asynchronous collaboration.

Own the end-to-end vision and roadmap for Boulevard's AI Receptionist. Define how AI handles voice and text client interactions, design handoffs to humans, set success metrics (autonomous resolution, CSAT, adoption, retention), drive business outcomes and pricing, gather deep customer insight from self-care businesses, and lead cross-functional teams to deliver trustworthy, high-quality AI conversational experiences.