Top Tech Jobs & Startup Jobs in Chicago, IL

Lead strategy and execution for ServiceTitan's Fintech product suite, owning roadmap, P&L, and product delivery for payments and embedded finance. Manage product teams, partner with engineering, negotiate commercial partnerships with processors and lenders, drive adoption and revenue, ensure compliance and risk controls, and report performance to executive leadership.

Owns sales enablement strategy and change management for high-priority Upsell and Fintech initiatives. Responsibilities include prioritizing initiatives, coordinating cross-functional planning, translating product and process changes into training and communications, creating enablement content, delivering training, aligning senior stakeholders, and measuring adoption and effectiveness. Requires enablement experience, sales or account management knowledge, strong communication, project prioritization, and proficiency with CRM, LMS, eLearning, and project tracking tools.

Advises Product, Sales, Implementations, and Customer Success using deep Property Care trade expertise. Represents the company at industry conferences, manages trade-organization relationships, develops market perspectives, supports prospect conversations, guides complex implementations, and translates customer feedback into product and business priorities. The role requires a former senior operator with direct oversight of operations and technology, enterprise-scale experience, strong market credibility, and fluency in service agreements, technician routing, route optimization, compliance, and multi-location operations.

Leads sales compensation strategy and operations across more than 500 production roles. Develops and evaluates incentive plans, benchmarks industry practices, presents recommendations to senior leaders, manages payouts and accruals, improves processes through automation and AI, and partners with Sales, Finance, HR, and Operations. Directs and develops a high-performing compensation team.

Manage concurrent enterprise ServiceTitan implementations from initiation through close. Lead discovery and requirements gathering, configure client environments, conduct software training, create workflow resources, monitor risks, and coordinate with delivery, data, training, and product teams. Serve as the primary client contact while ensuring timelines, implementation quality, platform adoption, and long-term client success. The role requires 20–30% travel for client on-site engagements.

Lead and build a data science and analytics organization focused on operations and finance analytics. Define and execute an applied AI/ML roadmap (including LLMs and agentic systems), hire and mentor teams, partner with stakeholders to translate problems into production AI capabilities, and collaborate with data engineering and platform teams to ensure data quality, orchestration, and evaluation.

Design and implement automated cloud security controls across multi-cloud environments. Integrate security into CI/CD pipelines, harden infrastructure and IaC, manage IAM and secrets, advance container and workload security, protect AI/ML systems and data, and support monitoring, detection, and incident response for cloud applications.

Own the long-term technical success of strategic enterprise accounts by advising on ServiceTitan configuration, workflows, integrations, and best practices. Build stakeholder relationships, lead technical discovery, resolve complex issues, support adoption, analyze usage data, deliver business reviews, and partner with Product, Engineering, and Support. Coach users, manage technical initiatives, maintain account records, and identify improvements that increase customer value and satisfaction.

Manages a SaaS Pro Sales team responsible for upselling products and services to existing customers. Oversees sales performance, forecasting, strategy, recruiting, onboarding, coaching, and customer relationships. Drives product adoption, retention, and customer success while partnering with Marketing, Product, Strategy, Customer Success, and Sales Leadership. Provides consultative guidance, influences product direction, and develops processes to improve team performance.

Serve as a trusted advisor to enterprise clients, driving product adoption, retention, and expansion. Manage ~50–100 accounts, create success plans and KPIs, monitor client health, coordinate cross-functional teams, identify upsell opportunities, and provide product feedback to inform roadmap and improve outcomes.