Top Tech Jobs & Startup Jobs in Chicago, IL

Plan, execute, and optimize multi-channel B2B demand generation and ABM campaigns for the mid-market segment. Partner with content, product marketing, marketing operations, sales, and analytics teams to align targeting, messaging, enablement, and pipeline goals. Manage webinars, sales plays, direct mail, and other channels; monitor performance, conduct testing, optimize spend, maintain reporting, and translate campaign data into actionable recommendations. Use AI tools to improve personalization and execution.

Support the Chief Product Officer and Chief Technology Officer by managing calendars, travel, communications, meetings, events, and confidential priorities. Lead the Pakistan-based technical executive assistant team supporting Product and Technology leadership, establishing service standards, coverage models, and development paths. Coordinate across time zones, maintain organizational documentation, anticipate executive needs, and assist with special projects and cross-functional initiatives.

Manages sales and services operations for Implementation, Installation, and Customer Education teams. Improves workflows, customer onboarding, resource allocation, and performance through data-driven analysis. Partners with Sales, Support, Product, and leadership on strategic projects, forecasting, territory alignment, QBRs, reporting, and Salesforce dashboards. Oversees recurring business processes, identifies inefficiencies, and provides operational guidance in a high-growth SaaS environment.

Own full-cycle recruiting for sales and business-critical roles, from intake through offer and closing. Partner with hiring managers and senior leaders on candidate profiles, search strategy, market conditions, interviews, and offers. Build passive-candidate pipelines through sourcing, networking, referrals, and market mapping. Use recruiting metrics and ATS data to identify bottlenecks and improve processes while delivering an inclusive, consistent candidate experience.

Provides strategic and hands-on HR partnership to Engineering, Product, and R&D leaders. Responsibilities include manager coaching, performance management, employee relations, talent and compensation programs, engagement surveys, exit meetings, organizational effectiveness, risk identification, and policy application. The role supports globally distributed teams during a six-month transition period and requires strong judgment, confidentiality, communication, and operational execution.

Lead forecasting, budgeting, variance analysis, financial modeling, scenario planning, headcount planning, and executive reporting for go-to-market functions. Partner with senior leaders to connect financial performance with operational metrics, improve data quality, build dashboards, automate workflows, and support investment decisions. Collaborate across Accounting, Data, Revenue Operations, People, and Corporate FP&A to improve planning accuracy and business decision-making.

Own Motive’s global financial products compliance program across AML/BSA, sanctions, KYC/KYB, PEP screening, transaction monitoring, lending compliance, audits, and regulatory relationships. Develop policies and controls, ensure operational effectiveness, manage bank and card network partners, monitor regulatory changes, support compliant product launches, and establish governance across multiple jurisdictions including the US, Canada, and UK/EU. Build the compliance function and advise leadership on compliance risk.

Sell Motive's fleet management platform to large enterprise prospects across industries. Prospect, develop executive relationships, win RFPs, coordinate technical resources, meet revenue quotas, and use customer analytics to drive expansion and integrations.

Own the full sales cycle for mid-market fleets (50–174 trucks): prospect, qualify, demo, negotiate, and close new business. Drive outbound lead generation, meet revenue quotas, collaborate cross-functionally, manage trials, and maintain accurate forecasting.

Build and manage AI-powered workflows, agents, automations, and internal applications for Deal Desk and GTM teams. Identify automation opportunities, develop prototypes, scale solutions to production, integrate enterprise data and APIs, implement human validation and audit controls, optimize LLM costs, document tools, measure adoption, and train users. The role requires Deal Desk or RevOps experience plus practical knowledge of AI models, APIs, scripting, SQL/SOQL, Python, CPQ, CLM, Salesforce, and agentic platforms.