Senior Program Manager of Manager Enablement, Toast

• 5-8 years of experience delivering high-impact enablement, training infrastructure, leadership development curriculum, or performance coaching strategies within a fast-paced SaaS, Fintech, or fast-growth tech environment
• Demonstrated ability as a senior leader to align cross-functional VP and Director-level stakeholders, manage massive programmatic changes, and drive process discipline across fragmented teams
• Proven domain expertise navigating both transactional/queue-based operational environments (Customer Care/Support) and relationship-driven commercial environments (Customer Success/Account Management)
• A strong portfolio of work demonstrating the ability to take an ambiguous, loosely defined objective and turn it into a scalable, repeatable corporate program
• Bachelor’s degree required, with an advanced degree in Adult Learning, Organizational Development, or a related discipline highly preferred
• Power-user familiarity with modern customer stacks, learning tools, and data analytics dashboards (e.g., Salesforce, CRMs, LMS tools, and AI platform assistants)

Desirable

• The Manager Enablement Program Manager is the strategic architect responsible for enabling, scaling, and governing the holistic onboarding, continuous development, and coaching infrastructure for people managers globally across Customer Care and Customer Success (CS). This senior individual contributor role defines how Toast builds its leadership bench and empowers managers to transform talent into high-performing contributors within a complex operational ecosystem
• Serving as a thought leader within the Enablement organization and a trusted partner to Care and CS Directors and Senior Leaders, this role bridges the gap between leadership development and business-critical KPIs
• Serving as a thought leader within the Enablement organization and a trusted partner to Care and CS Directors and Senior Leaders, this role bridges the gap between leadership development and business-critical KPIs. By applying advanced data analytics, adult learning principles, and modern AI tools, you will build a predictable, scalable ecosystem that equips managers to drive consistent team performance across key metrics such as CSAT, and Net Revenue Retention. This role will guide managers through the governance of high velocity tech changes to policy, procedure, and platforms to ensure high adoption and clear post enablement impact
• By applying advanced data analytics, adult learning principles, and modern AI tools, you will build a predictable, scalable ecosystem that equips managers to drive consistent team performance across key metrics such as CSAT, and Net Revenue Retention. This role will guide managers through the governance of high velocity tech changes to policy, procedure, and platforms to ensure high adoption and clear post enablement impact
• Strategic Program Management & Governance
• Design, contract, and scale end-to-end Manager Training & Enablement programs aimed at robust bench building, leadership development, and continuous professional growth
• Partner with Care Operations, CS and CSO leadership to shape the overall manager investment strategy bringing consensus and acquiring buy-in to a shared vision and roadmap
• Build and govern standardized coaching playbooks, behavioral rubrics, and coaching certifications to ensure global manager consistency and talent transformation
• Establish operational rhythms and governance frameworks that empower managers to effectively leverage insights tools and drive high-impact coaching sessions with AI based manager 1:1 dashboards and transcription analysis
• AI Coaching Modules & Ecosystem Innovation
• Architect and transition the standard manager training lifecycle into a closed-loop system by designing, piloting, and scaling autonomous AI coaching modules and simulation systems
• Integrate AI voice and text-based role-play tools into a manager "practice arena" to simulate high-complexity coaching, performance management, and alignment scenarios to assist managers with the development of their direct reports
• Optimize modern AI tools and LLM-based tech to build engaging, hyper-personalized manager support tools that empower leaders to be highly effective
• Tailored Enablement Delivery & Architecture
• Develop specialized, distinct enablement pathways that address the priority KPIs of Customer Care (TTR/C (Time to Resolve/Close), CSAT (Customer Satisfaction), Transfer Rate, and AHT (Average Handle Time)) and CSM KPIs (Save Rate, Churn Mitigation, Downsell prevention)
• Drive key manager KPIs in Coaching Compliance, Coaching Effectiveness, and Manager Engagement
• Design, build, and iterate on the onboarding design for new managers, including newly promoted, as well as the continuous development and enablement of tenured managers
• Ensure managers are deeply versed on organizational, product, and process changes, and fully equipped to translate those changes effectively to their teams during Huddles and dedicated coaching sessions to ensure adoption and effective application by their agents
• Influence, Analytics & Evaluation
• Align and influence cross-functional Senior Leader and Director-level stakeholders as a trusted thought partner, managing massive programmatic changes across distributed teams
• Proactively identify global areas of opportunity to support managers and leadership, providing ready solutions backed by a high rigor of analytical and performance assessment
• Lead as a Center of Excellence globally, evaluating behavioral opportunity areas and structuring remedial manager initiatives both internally as well as shared with BPO partners
• Establish robust post-enablement measurement frameworks to evaluate learning impact, leveraging AI analytics to track real-world performance improvements and core business KPIs