Top Tech Jobs & Startup Jobs in Chicago, IL

Leads a mid-market B2B SaaS sales team by managing pipeline activity, forecasting, quota attainment, prospecting, negotiations, and performance. The role coaches account executives, drives outbound-sourced ARR growth, aligns execution with company goals, improves sales processes, manages hiring and performance, and develops team career paths. It collaborates with sales, marketing, business operations, and enablement leaders to achieve revenue objectives.

Own Salesforce administration, configuration, security, data quality, integrations, maintenance, governance, and roadmap contributions. Translate stakeholder needs into scalable declarative solutions, troubleshoot complex platform issues, manage connected GTM applications, support releases and deployments, improve adoption through training, and maintain documentation. Partner with Sales, Marketing, Customer Success, Finance, Product, and Engineering to enhance reporting, automation, and platform usability.

Own and optimize Fleetio’s go-to-market systems and data workflows across Salesforce, Clay, ZoomInfo, RingLead, LeanData, Zapier, and Slack. Responsibilities include data enrichment, deduplication, routing, automation, integration monitoring, documentation, governance, vendor management, and cross-functional partnership with Sales, Marketing, Customer Success, Revenue Operations, and Salesforce administrators.

Own the monthly sales commission process, including payout calculations, validation, adjustments, and payroll handoff. Analyze sales funnels, pipeline health, conversion, and revenue attainment while building executive reports and dashboards. Support territory design, capacity planning, and target-setting through data analysis. Improve recurring workflows with automation and AI, resolve discrepancies, document business rules, and collaborate cross-functionally across revenue and support teams.

Build and manage revenue operations for SDR, Solutions Consulting, and Partnerships teams. Own reporting, dashboards, pipeline analysis, operating reviews, lead routing, deal registration, workflow design, and process improvements. Partner with GTM Systems and executive leaders on strategic projects and technology roadmap priorities. Use AI and automation to accelerate analysis, surface insights, and reduce manual work while independently prioritizing competing demands.

Build and maintain Fleetio’s marketing website, including high-converting landing pages and customer funnels. Develop user-facing web experiences, optimize performance, SEO, accessibility, Core Web Vitals, and conversion rates, and integrate headless CMS solutions. Collaborate cross-functionally on technical scoping and delivery, conduct code reviews, monitor analytics, mentor developers, and connect web initiatives to marketing and pipeline goals.

Own and operate reseller partner onboarding and ongoing enablement programs across technical training, sales, marketing, certifications, and product updates. Build curricula, playbooks, and partner-facing content; coordinate Product, Marketing, Sales, Support, and Legal stakeholders; track onboarding, engagement, ramp, and certification metrics; and maintain partner enablement records in Salesforce and related tools.

Build and manage strategic reseller partnerships across fleet management, telematics, and VAR segments. Responsibilities include sourcing and closing new partner agreements, onboarding and enabling partners, growing existing accounts, negotiating commercial terms, managing joint business plans, supporting QBRs and co-selling, tracking pipeline and revenue in Salesforce, and collaborating with Sales, Marketing, Product, Legal, and Partnerships leadership.

Leads Fleetio’s global brand strategy and expression across visual identity, content, thought leadership, social, video, PR, sponsorships, and experiential activation. Manages the in-house brand and content team, agency partners, creative operations, and brand standards. Drives narrative evolution, awareness, share of voice, content performance, executive visibility, and activation of Fleetio’s NASCAR partnership.

Lead and scale a team of 8–10 outbound SDRs, driving predictable pipeline generation and improved funnel conversion. Develop outbound strategy, coach prospecting and objection handling, diagnose bottlenecks, enforce activity and quality standards, and partner with Sales, Marketing, and RevOps. Present performance and pipeline insights to senior leadership while building a culture of accountability, resilience, and continuous improvement.