Top Tech Jobs & Startup Jobs in Chicago, IL

Lead end-to-end onboarding projects for mid-market hospitality SaaS customers, from sales handoff through go-live, adoption, and transition to Account Management. Define timelines and deliverables, coordinate cross-functional teams, lead customer meetings, manage risks and escalations, and monitor adoption and onboarding success metrics. The role requires hospitality expertise, project management experience, multilingual communication in English, Portuguese, and Spanish, and strong customer relationship skills.

Leads North American mid-market customer onboarding for a hospitality software platform, managing onboarding project managers and coaches while personally overseeing strategic accounts. Responsibilities include team development, account assignment, escalation management, PMS implementation guidance, performance tracking, cross-functional coordination, partner management, and improving time-to-live, deployment quality, customer satisfaction, and early retention.

Leads North American mid-market customer onboarding for Cloudbeds, managing onboarding project managers and coaches while personally overseeing strategic accounts. Responsibilities include team development, account assignment, escalation management, implementation quality, training, performance tracking, cross-functional handoffs, partner coordination, and consultative workflow redesign for hotel customers. The role requires hotel operations or hospitality technology experience, PMS implementation expertise, customer-facing team management, project-management discipline, and familiarity with Salesforce and AI tools.

Lead the North American mid-market onboarding team while personally overseeing strategic hotel accounts. Manage onboarding project managers and coaches, improve implementation quality and time-to-live, resolve escalations, and ensure smooth handoffs to Account Management. Coach and develop team members, manage account assignments, coordinate consultants and internal partners, and use Salesforce dashboards, AI, and automation to identify risks and streamline operations. Provide consultative guidance to hotels transitioning from systems such as Oracle Opera.

Lead North American mid-market customer onboarding for Cloudbeds, managing onboarding project managers and coaches while personally overseeing strategic accounts. Own team development, account assignment, escalation management, implementation quality, time-to-live, CSAT, Hypercare, and retention metrics. Partner with Sales, Account Management, Support, Professional Services, Product, and external consultants to deliver successful hotel PMS implementations and improve customer workflows. Use Salesforce, dashboards, AI, and automation to improve regional performance and reduce administrative work.

Leads Cloudbeds’ Customer Recovery team, overseeing retention, risk triage, executive escalations, and cross-functional Fire-Team interventions for at-risk hospitality accounts. Coaches and develops Recovery Coaches, manages recovery operations, drives proactive save motions, and converts customer-risk insights into product and process improvements. Partners with Product, Engineering, Support, Sales, and CS Operations to improve customer outcomes using AI tooling, automation, and Salesforce reporting.

Hunt for new hospitality clients, build prospect lists, execute high-volume outbound outreach and cold-calling, deliver virtual and in-person product demos, develop local partnerships, attend events (under 10% travel), represent Cloudbeds in the market, and consistently meet or exceed sales targets.

Lead and scale mid-market onboarding from contract to go-live and handoff. Build frameworks, SOPs, metrics, and staffing plans; improve deployment velocity, quality, training, and early retention. Manage escalations, partner cross-functionally with Sales/Product/Support/Account Management, and coach a distributed team to deliver repeatable, high-quality multi-property implementations.