Top Tech Jobs & Startup Jobs in Milwaukee, WI

Leads the Tooling engineering team responsible for developer experience, CI/CD, deployment automation, release workflows, observability, internal developer platforms, and AI-assisted engineering tools. Partners with Infrastructure, Security, and Product Engineering leaders to improve reliability, engineering productivity, software delivery performance, and developer satisfaction. Sets technical direction, manages roadmaps, coaches engineers, and drives cross-functional platform initiatives.

Generate qualified enterprise sales pipeline through outbound prospecting, cold calling, account research, decision-maker identification, and persistent follow-up. Schedule discovery calls and demos, maintain accurate Salesforce records, collaborate with Account Executives and cross-functional teams, support enterprise marketing efforts, and improve territory coverage, data quality, and prospecting workflows. The role focuses on restaurant and franchise accounts with 15–500 locations.

Develop fullstack web applications, enhance platform performance, collaborate on high-impact opportunities, and ensure stable, scalable solutions. Engage in rapid iterations and be a committed team player.

Lead and build Toast Retail’s Mid-Market sales function from the ground up. Manage and coach Account Executives while personally closing complex grocery, liquor, and convenience retail deals. Develop repeatable sales processes, qualification frameworks, business cases, proposals, forecasting practices, and competitive positioning. Partner cross-functionally with Product, Marketing, Enablement, Finance, Deal Desk, and Onboarding to support enterprise implementations and product improvements. Hire and develop a high-performing team, establish benchmarks, and transition from a player-coach role to full team leadership.

Leads customer education strategy and self-serve learning experiences to improve customer success and business outcomes. Owns educational content, webinar programs, customer playbooks, and training initiatives. Uses qualitative and quantitative data to identify learning gaps, measure engagement, reduce support needs, improve CSAT, and optimize content. Partners cross-functionally with Customer Success, Marketing, Product, subject matter experts, and customer teams while managing large projects, timelines, deliverables, and operational readiness for new products and features.

Own the strategy, roadmap, packaging, and go-to-market evolution of Pluralsight’s AI, Cloud, and Security learning solutions. Design blended learning programs, define expert perspectives, identify content and lab components, monitor market needs, and use customer and learner data to improve outcomes. Partner with Product, Sales, Marketing, Curriculum, Engineering, and Services teams, support strategic enterprise deals, manage solution benchmarks, and drive adoption, renewals, and revenue growth.

Own and evolve Pluralsight’s Cloud and Security solutions portfolio across expert positioning, solution design, roadmap, packaging, go-to-market, and performance. Develop blended learning offerings using courses, labs, assessments, and instructor-led training. Partner with Product, Sales, Marketing, Engineering, Services, customers, and subject-matter experts to launch differentiated solutions, support strategic deals, track KPIs, and continuously improve outcomes using market insights, data, and customer feedback.

Own and lead the technical direction of a major codebase section while designing, building, testing, documenting, and maintaining secure, scalable API-based decisioning products. Partner with product, engineering, and security teams on agile delivery, troubleshoot production issues, meet SLA requirements, and participate in an on-call rotation.

The Product Manager will lead internal tech initiatives, focusing on data-heavy systems and datasets, ensuring scalability and alignment across teams.

Own and improve Composer’s brokerage and trading operations, including trade lifecycle management, account servicing, escalations, reconciliations, controls, and risk workflows. Partner with Product, Engineering, Compliance, and Operations to define requirements, implement scalable solutions, support launches, analyze operational trends, and lead cross-functional initiatives in a regulated environment.

Serve as a strategic finance partner for a subscription business by leading forecasting, monitoring KPIs, building cohort and unit economics models, evaluating investments, and providing actionable insights. Collaborate with business leaders, Marketing, Product, Risk, Operations, and Accounting on financial decisions, revenue recognition, process improvements, scalability, and automation. Present recommendations to decision-makers while supporting an inclusive, collaborative Finance culture.

Support pre-sales and post-sales for SLED customers: demonstrate CrowdStrike Falcon, run demos/POVs, advise on endpoint, cloud, identity, and AI security, drive onboarding/adoption/expansion/renewals, partner with Account Executives, mentor peers, and perform occasional customer travel.

Design, build, and support high-throughput, low-latency LLM inference and data pipelines; collaborate with data scientists to post-train and evaluate models; implement scalable, production-ready systems with strong testing, monitoring, and performance focus; mentor engineers and iterate on architecture, reliability, and user-facing AI applications.

Build and maintain cloud cost monitoring, alerting, and optimization tooling. Develop automation, cost allocation/tagging, data pipelines, dashboards, and integrations with billing APIs. Support FinOps processes, implement cost guardrails, troubleshoot cost systems, participate in on-call rotation, and collaborate with senior engineers and product teams to drive cost-efficient infrastructure and reporting.

Provides technology support for commercial real estate applications, managing ServiceNow tickets, resolving incidents, performing light application support, maintaining data, and implementing non-technical configuration updates. The role also supports business process analysis, vendor issue resolution, technology changes, and internal user assistance through email and ticketing workflows. Responsibilities include troubleshooting software and hardware, maintaining network systems, gathering project data, and mentoring team members.

Leads a 12-person application security practice conducting code audits, vulnerability research, and secure design reviews. Oversees technical delivery, client relationships, project staffing, utilization, profitability, recruiting, and team development. Provides hands-on technical direction across source-code security work, determines investments in tooling and methodologies, and integrates AI-assisted auditing and research into team workflows. The role also owns practice P&L and supports engineers’ conference, publication, and open-source contributions.

Lead the Application Security Practice, overseeing team performance and business growth while delivering high-quality security consulting services and fostering innovation through AI integration and research contributions.

Provides executive-level architectural and advisory leadership for ServiceNow ePro transformation programs. Builds trusted relationships with senior clients, aligns business strategy with enterprise architecture and governance, recommends solutions, develops roadmaps and business cases, and supports sales planning and partner relationships. Creates technical presentations and white papers, presents at industry forums, mentors consultants, leads knowledge transfer, and influences cross-functional teams delivering complex ServiceNow initiatives.

Lead the Claude Corps talent and people operations pod, managing early-talent recruiters and HR coordinators. Own high-volume screening and selection, employer-of-record employment lifecycle processes, onboarding, payroll, benefits, compliance, employee relations, and performance issues. Build scalable, AI-assisted recruiting and HR workflows, manage multi-state employment operations, improve efficiency, and grow team capabilities as fellowship cohorts expand.