Restaurant365 · 5 months ago
Senior Director, Digital and At-Scale Success Programs
Restaurant365 is a SaaS company disrupting the restaurant industry, seeking a strategic, data-driven, and customer-centric Senior Director of Digital and At-Scale Success Programs. This role involves leading the development and execution of scalable success initiatives to enhance customer experiences and drive product adoption.
AccountingProductivity ToolsRestaurantsSaaSSoftware
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
Qualification
Required
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
Preferred
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
Company
Restaurant365
Restaurant365 is an enterprise management software for restaurants that provides accounting, inventory, scheduling, and payroll solutions.
Funding
Current Stage
Late StageTotal Funding
$437.5MKey Investors
ICONIQ GrowthBessemer Venture Partners
2024-05-15Private Equity· $175M
2023-05-19Private Equity· $135M
2019-06-27Series C· $88M
Recent News
2025-09-17
Company data provided by crunchbase