Senior Onboarding Manager Hotels/Sports & Entertainment

Toast

1d•$115,000 - $234,000•Hybrid

About The Position

Toast creates technology to help restaurants and local businesses succeed in a digital world, helping business owners operate, increase sales, engage customers, and keep employees happy. The Senior Onboarding Manager, Enterprise Hotels & Sports + Entertainment, reports to the Director of Onboarding and leads a team of Hotel and Sports + Entertainment (S+E) Onboarding Consultants responsible for delivering complex enterprise implementations. In this role, you will own the performance, development, and operational success of both segments. While Hotels and Sports + Entertainment are distinct lines of business, they share many of the same implementation motions and customer needs, allowing for strong alignment in how the teams operate. You will be the primary leader for the Sports + Entertainment segment, one of Toast's fastest-growing lines of business, while also partnering closely with the leader of our other Enterprise Hotels team. This provides a built-in thought partner for collaboration, strategy, and operational planning while maintaining clear ownership of your segments. As a Senior Manager, you will be expected to anticipate challenges, build scalable solutions, influence cross-functional strategy, and elevate the performance of both your team and the broader onboarding organization.

Requirements

4+ years of experience in implementation, professional services, onboarding, or operational leadership within a SaaS, hospitality, or technology-driven environment, including 2+ years of experience leading and developing high-performing teams.
Proven success leading complex enterprise implementations or large-scale rollout programs, with the ability to balance strategic planning with operational execution in fast-moving environments.
Demonstrated ability to design and scale operational processes, frameworks, or systems that improve implementation consistency, forecasting accuracy, and team efficiency.
Strong data-driven leadership skills, with experience using operational metrics and reporting to diagnose performance challenges, identify trends, and drive strategic improvements.
Exceptional communication, professionalism, and executive presence, with the ability to confidently influence senior internal stakeholders and engage with C-suite customer leaders.
Trusted to represent Toast in person through customer meetings, leadership forums, and industry events, with the ability to command the room, influence outcomes, and uphold Toast’s brand with credibility and professionalism.

Responsibilities

Lead, coach, and develop a high-performing team of Onboarding Consultants, setting a high bar for project management discipline, customer consultation, and operational excellence.
Mentor and develop emerging leaders across the organization, including new managers and senior team members.
Own the performance and strategic direction of the Enterprise Hotels and Sports + Entertainment segments, with accountability for go-live execution, implementation velocity, customer satisfaction, and operational efficiency across both portfolios.
Maintain deep visibility into pipeline health, team capacity, and project execution, proactively identifying risks, forecasting resource needs, and ensuring enterprise rollouts remain on track.
Drive strategic operational improvements across the segment, designing and implementing scalable frameworks, processes, and best practices that improve forecasting accuracy, implementation consistency, and team efficiency.
Serve as the subject matter expert for both Enterprise Hotel onboarding and Sports + Entertainment onboarding, providing guidance on complex implementations, advising cross-functional partners, and establishing standards that improve enterprise rollout success.
Act as the primary escalation leader for complex enterprise implementations, confidently guiding teams through high-impact challenges while reinforcing structured problem-solving and strong customer partnership.
Influence and align cross-functional partners including Sales, Solutions, Customer Success, OTC, CARE, Product, and Operations to drive successful enterprise outcomes and remove operational barriers.
Leverage data, operational metrics, and post-mortem analysis to diagnose systemic challenges, anticipate risks, and build strategic improvement initiatives that elevate onboarding performance.
Demonstrate exceptional executive presence and communication, representing the onboarding organization in leadership forums, cross-functional initiatives, and high-stakes customer conversations with senior and C-suite stakeholders.
Lead through ambiguity and organizational change, proactively identifying opportunities for innovation while driving clear direction and momentum for the team and broader onboarding organization.