Senior Director, Digital and At-Scale Success Programs

Summary

Join Restaurant365, a SaaS company revolutionizing the restaurant industry, as a Senior Director of Digital and At-Scale Success Programs! Lead the development and execution of scalable success initiatives supporting our customers. Reporting to the Chief Customer Officer, this role blends digital strategy, customer lifecycle expertise, financial understanding, and operational execution to deliver impactful customer experiences. You will lead a team building automated journeys, self-service tools, and programs to accelerate customer value, drive product adoption, and improve growth and retention. Collaborate with various teams (Product, Marketing, Customer Success, Operations) to align efforts. This leadership role requires building and mentoring a high-performing team focused on digital success strategies, content, automation, and engagement programs.

Requirements

• 10+ years of experience in Customer Success, Customer Experience or Digital Programs in a B2B and/or B2C SaaS environment
• 5+ years of leadership experience
• Proven success in building and scaling at-scale and digital customer success programs across diverse customer segments
• Strong understanding of SaaS metrics (NRR, GRR, churn, TTFV)
• Experience with tools like Gainsight, Salesforce, Pendo, and webinar platforms
• Experience in a multi-SaaS product environment
• Strategic thinker with hands-on execution capabilities
• Excellent collaboration and program management skills
• Prior ownership of SMB or long-tail customer success programs
• Experience scaling CS in high-growth or product-led SaaS companies
• Background in Customer Marketing, Onboarding, and/or Digital CS Operations

Responsibilities

• Define and lead the digital and at-scale success vision and roadmap aligned to customer lifecycle stages (onboarding, adoption, renewal, expansion)personas, key customer outcomes and “moments that matter”; build and execute a multi-channel engagement model combining automated, in-app, and low-touch human interactions; partner with Marketing, Product, Support, Systems, Data and CS Ops to align content, tools, and timing across the journey
• Design and deploy automated customer journeys and usage-based triggers using tools such as Gainsight, Salesforce, Pendo, and/or Marketo; leverage email campaigns, learning resources, 1: many programs and customer communities to support self-service and education; incorporate AI to help manage and optimize digital touchpoints for engagement, usage, and retention
• Develop office hours, webinars programs, cohort-based training programs, and other scalable engagement formats with key partners in Professional Services, Education Services and Customer Success Management (CSMs); establish repeatable and automated onboarding and adoption tracks tailored to customer segments and use cases in collaboration with Product, Marketing, Systems, Data and CS Ops; ensure digital initiatives are measurable and contribute to customer value, NRR, GRR, and CSAT improvements
• Partner with Product on in product learning, usage, guidance and AI to help customers optimize their usage and value of the R365 platform; collaborate with CS leadership to align digital programs with high-touch CSM efforts for a hybrid model; partner with CS Ops to build key analytics, dashboards and reporting to track program performance and drive data-informed decisions
• Build, lead, and mentor a high-performing team responsible for digital success strategy, content, automation, and engagement programs; establish clear roles, goals, and career development plans for team members; promote a culture of innovation, accountability, and continuous improvement

Preferred Qualifications

Previous ERP, Business Software and/or Restaurant experience is a plus

Benefits

• Comprehensive medical benefits, 100% paid for employee
• 401k + matching
• Equity Option Grant
• Unlimited PTO + Company holidays
• Wellness initiatives