Senior Director of Digital and At-Scale Success Programs

Employment Type: Full Time

Position Overview

Restaurant365 is a SaaS company disrupting the restaurant industry with its cloud-based platform for accounting and back-office operations. We are seeking a strategic, data-driven, and customer-centric Senior Director of Digital and At-Scale Success Programs to lead the development and execution of scalable success initiatives. Reporting to the Chief Customer Officer, this role combines digital strategy, customer lifecycle expertise, financial acumen, and operational execution to deliver impactful, at-scale, and tech-enabled customer experiences. This role will lead the team responsible for building automated journeys, self-service enablement, and one-to-many programs that accelerate time to value, drive product adoption, and improve growth and retention. The team will also partner closely with product teams to drive in-product onboarding and adoption. This leader will oversee and orchestrate cross-functional efforts across Customer Success, Marketing, Product, and Operations.

How You'll Add Value

Strategy & Program Leadership

• 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.

Digital Success & Automation

• 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.

Scaled Programs & One-to-Many Engagement

• Develop office hours, webinar 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, Net Revenue Retention (NRR), Gross Revenue Retention (GRR), and Customer Satisfaction (CSAT) improvements.

Cross-Functional Collaboration

• 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.

Team Leadership & Management

• 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.

What You'll Need to Be Successful

• 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).

Company Information

Restaurant365's culture is focused on empowering team members to produce top-notch results while elevating their skills. We’re constantly evolving and improving to make sure we are and always will be “Best in Class” ... and we want that for you too!