Senior Director, Digital and At-Scale Success Programs

Restaurant365 is a SaaS company disrupting the restaurant industry! Our cloud-based platform provides a unique, centralized solution for accounting and back-office operations for restaurants. 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!

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 that benefit and support our customers. 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. This team will also partner very closely with our product teams to drive in-product onboarding and adoption. This leader will oversee and often orchestrate work cross-functionally to align 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, 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.

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 in this role:

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.

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

This position has a salary range of $169,000-$270,000. The above range represents the expected salary range for this position. The actual salary may vary based upon several factors, including, but not limited to, relevant skills/experience, time in the role, business line, and geographic location. Restaurant365 focuses on equitable pay for our team and aims for transparency with our pay practices.

Comprehensive medical benefits, 100% paid for employee

401k + matching

Equity Option Grant

Unlimited PTO + Company holidays

Wellness initiatives

$169,000 – $270,000 a year