Top Tech Jobs & Startup Jobs in Chicago, IL

Own the full B2B SaaS sales cycle for acquiring mid-market senior living customers, from prospecting through contract execution. Responsibilities include consultative discovery, business-case development, tailored demonstrations, stakeholder alignment, deal strategy, quota attainment, Salesforce pipeline management, forecasting, and cross-functional collaboration. The role also involves regular travel to conferences, trade shows, and client meetings while representing Aline and generating new business opportunities.

Lead digital customer success and education programs for SMB and mid-market customers. Manage enablement specialists and product-focused customer success SMEs while developing scalable training, onboarding, lifecycle, adoption, and engagement programs. Partner with Marketing, Product, Sales, and Customer Success to improve product proficiency, retention, expansion, and time-to-value through digital campaigns, in-app guidance, webinars, knowledge content, and data-driven interventions.

Own net-new enterprise and strategic customer acquisition for a senior living SaaS platform. Manage the full sales cycle, including prospecting, discovery, business-case development, deal strategy, executive consensus, negotiations, forecasting, and contract closure. Maintain pipeline discipline, carry a quota, and collaborate with Marketing, Product, Solutions Consulting, Customer Experience, Revenue Operations, Legal, and leadership. Regular travel to conferences, trade shows, and client meetings is required.

Owns executive relationships with 1–3 strategic enterprise customers, driving adoption, retention, growth, and measurable business value. Responsibilities include developing multi-year success plans, leading executive reviews, monitoring customer health and renewal risks, managing escalations, influencing internal product and go-to-market strategies, and mentoring other customer success managers. The role requires strong executive presence, strategic account management, data-driven decision-making, and cross-functional leadership.