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The Customer Success Manager, Enterprise is responsible for driving long-term retention and growth across a portfolio of high-value Enterprise accounts ($50k+ ARR) with dedicated, high-touch coverage. You will act as a trusted advisor to restaurant and hospitality executives and operators, ensuring they realize measurable ROI from Restaurant365s platform, including Accounting, Operations, Workforce, Payroll/HR, and BI solutions. You own account outcomes across adoption, renewal, and expansion, leveraging data, executive engagement, and cross-functional coordination to deliver Gross and Net Annual Retention targets for your book of business. How youll add value: Customer Leadership & Value Realization Become a primary strategic partner to finance, operations, and brand leaders within each account, building multi-threaded relationships across executives, operators, and back-office teams. Co-create and maintain Customer Success Plans that connect R365 capabilities to concrete business outcomes (labor, food cost, speed to close, AP automation, visibility, etc.). Lead Business Impact Reviews (BIRs) and Executive Business Reviews (EBRs) on a regular cadence, telling a data-backed ROI story, highlighting adoption wins/gaps, and aligning on a 612 month roadmap and expansion opportunities. Translate product capabilities into restaurant-relevant narratives for owners, CFOs, franchise leaders, and GMs, grounded in KPIs like prime cost, food cost %, labor %, and location-level profitability. Account Health, Risk Management & Forecasting Own the health and risk profile of your portfolio, ensuring accurate health/risk scores, documented reasons, and active mitigation plans for at-risk customers. Run intentional risk plays for at-risk accounts (e.g., implementation stalls, product gaps, expectation gaps) in partnership with AEs, Support, Product, and Services. Maintain a reliable renewal forecast, with the majority of renewals forecast 90 days before term and minimal surprise churn within 60 days of renewal. Use R365, Gainsight, Salesforce, Domo, Gong, and dashboards to monitor usage, module adoption, and financial outcomes, and to prioritize actions across your portfolio. Executive & Cross-Functional Leadership Orchestrate cross-functional teams across Sales, Implementation, Support, Product, Billing, and Professional Services to resolve issues, advance strategic initiatives, and deliver on customer outcomes. Co-own expansion strategy with AEssurfacing Customer Success Qualified Leads (CSQLs), shaping deals to align with customer strategy, and ensuring smooth execution and adoption post-sale. Partner with Product and CS leadership to bring structured customer feedback (e.g., gaps in workflows, UX, reporting) that influences roadmap and go-to-market motions. AI-, Data- & Automation-Enabled Customer Success Use AI and automation (e.g., Gong insights, Gainsight rules/CTAs, R365 reporting and alerts, templated playbooks) to: Scale BIR/EBR prep and follow-up. Generate health and risk insights from product usage and financial data. Automate low-touch communications (e.g., success plan nudges, value summaries, renewal reminders). Continuously refine portfolio operating rhythms, cadences, and workflows to increase coverage and impact per CSM using automation and orchestration tools (Gainsight, SFDC, https://monday.com, Domo, etc.). Operating Discipline & Internal Contribution Maintain high-quality CRM and Gainsight hygiene (health scores, success plans, timelines, risk notes, activities) that gives leadership and partners a true, near-real-time view of your portfolio. Contribute to CSM enablement by sharing templates, playbooks, EBR decks, and best practices, and by contributing to org-wide improvements in tools and processes. What youll need to be successful in this role: 35+ years in a B2B SaaS Customer Success Manager or Account Management role, preferably in vertical SaaS or complex, multi-stakeholder environments. Experience working with multi-location or franchise restaurant groups or adjacent industries (hospitality, retail) is strongly preferred. Restaurant365 experience strongly preferred (as a user, implementer, or advisor), or hands-on experience with a comparable restaurant back-office / workforce platform. Demonstrated success owning renewal and expansion outcomes for a portfolio of mid-to-large ARR customers, with clear stories of risk mitigation and growth. Comfortable using data and dashboards (operational metrics, usage data, financial outcomes) to drive decisions and customer conversations. Hands-on experience with CS and GTM tools (e.g., Salesforce, Gainsight, Gong, Freshdesk, https://monday.com, Domo or similar). AI & Automation Skills .