Top Tech Jobs & Startup Jobs in Chicago, IL

Own Perk’s global go-to-market engineering strategy, architecture, tooling, and roadmap. Build production-grade Clay automations, Salesforce integrations, orchestration systems, and AI-agent workflows using code and modern data infrastructure. Automate prospecting, seller workflows, account intelligence, and revenue operations while measuring commercial impact. Lead and develop a senior international team, partner with sales and revenue leaders, and establish engineering standards for scalable, monitored, tested, and recoverable systems.

Manage full-cycle enterprise SaaS sales across North America, including outbound and inbound lead generation, prospect demos, solution selling, follow-up, negotiation, and closing. Build and maintain C-suite relationships, develop pipeline through outbound prospecting, maintain accurate Salesforce records, collaborate with marketing on lead qualification, and communicate Perk’s value proposition to diverse stakeholders. The role is based near Boston or Chicago and requires in-person work three days per week.

Own and grow a portfolio of SMB customers by strengthening relationships, increasing product usage, identifying upsell and cross-sell opportunities, and supporting retention targets. Conduct data-driven business reviews and presentations, resolve account issues, coordinate product integrations, and collaborate with internal teams on go-to-market strategies. The role requires strong communication, prioritization, analytical, and customer relationship skills in a fast-growing travel management environment.

Manage the full enterprise sales cycle across North America, including outbound prospecting, inbound lead management, product demonstrations, solution selling, negotiations, closing, and some account management. Build and maintain a qualified pipeline, develop C-suite relationships, communicate Perk’s value proposition, maintain Salesforce records, and collaborate with Marketing to improve lead generation and qualification.

Manage a portfolio of SMB customers in North America to drive adoption, retention, upsell and cross-sell. Build strong client relationships, run data-driven business reviews, identify growth opportunities, coordinate product rollouts, and resolve account issues to maximize customer value and meet quarterly targets.

Own and deliver high-complexity onboarding projects for Travel, Expense and Invoice products, often involving ERP integrations. Coordinate finance, IT, and external partners, design advanced custom setups, apply financial expertise for Invoice modules, manage integrations, resolve escalations, and mentor junior implementation team members to ensure successful rollouts, adoption, and go-lives.

Lead complex onboarding projects for Travel, Expense, and Invoice products, often involving ERP integrations. Coordinate stakeholders (finance, IT, PMs, external partners), design advanced setups, guide invoice module adoption, resolve escalations, coordinate technical teams, and mentor junior implementers to ensure smooth rollouts and successful go-lives.

Lead North America field marketing to drive demand and pipeline for B2B SaaS. Develop regional strategy, run ABM and integrated campaigns, manage events and budgets, align closely with sales and SDRs, hire and manage a small team, and use data and AI to optimize performance and ROI.

Manage a portfolio of enterprise travel customers, build relationships with decision-makers, increase product adoption, identify expansion opportunities, and drive retention and revenue growth. Provide data-driven business reviews and presentations, resolve account issues, coordinate product integrations, and collaborate with AmTrav and Perk teams. The role requires strong communication, prioritization, analytical, and client relationship skills in a fast-paced SaaS environment.

Own Perk’s US and UK PR strategy, building Tier 1 financial and business media relationships, shaping corporate narratives, securing earned coverage, and profiling C-suite executives. Manage proactive, reactive, and crisis communications; translate AI and technology developments into compelling stories; coach spokespeople; oversee PR agencies; and use AI tools, coverage data, and performance metrics to improve PR operations and demonstrate ROI.