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.
A day in the life (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. Senior Managers are expected to model best-in-class leadership practices while developing strong, autonomous team members.
- Mentor and develop emerging leaders across the organization, including new managers and senior team members. Senior Managers act as role models and leadership partners, sharing best practices, strengthening talent pipelines, and elevating the overall performance of the onboarding organization.
- 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. Operate as the business leader for your segments, driving results while identifying opportunities to scale and improve performance.
- 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.
What you'll need to thrive (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.
AI at Toast
At Toast, one of our company values is that we're hungry to build and learn. We believe learning new AI tools empowers us to build for our customers faster, more independently, and with higher quality. We provide these tools across all disciplines, from Engineering and Product to Sales and Support, and are inspired by how our Toasters are already driving real value with them. The people who thrive here are those who embrace changes that let us build more for our customers; it’s a core part of our culture.
Our Total Rewards Philosophy
We strive to provide competitive compensation and benefits programs that help to attract, retain, and motivate the best and brightest people in our industry. Our total rewards package goes beyond great earnings potential and provides the means to a healthy lifestyle with the flexibility to meet Toasters’ changing needs. Learn more about our benefits at https://careers.toasttab.com/toast-benefits.
The base salary range for this role is listed below. The starting salary will be determined based on skills, experience, and geographic location. In addition to base salary, our total rewards components include cash compensation (overtime, bonus/commissions if eligible), equity, and benefits. You can learn more about how we align pay with local labor markets in our Geographic Pay Zone Philosophy.
The base salary range for this role is listed below. The starting salary will be determined based on skills, experience, and geographic location. In addition to base salary, our total rewards components include cash compensation (overtime, bonus/commissions if eligible), equity, and benefits. You can learn more about how we align pay with local labor markets in our Geographic Pay Zone Philosophy.
The base salary range for this role is listed below. The starting salary will be determined based on skills, experience, and geographic location. In addition to base salary, our total rewards components include cash compensation (overtime, bonus/commissions if eligible), equity, and benefits. You can learn more about how we align pay with local labor markets in our Geographic Pay Zone Philosophy.
How Toast Uses AI in its Hiring Process
Throughout the hiring process, our goal is to get to know you. We use AI tools to support our recruiters and interviewers with tasks like note-taking, summarization, and documentation of interviews to ensure they can be fully focused on your conversation. All hiring decisions are made by people. To learn more: https://careers.toasttab.com/ai-in-hiring
Our Approach to Hybrid Working
We embrace a hybrid work model that fosters in-person collaboration while valuing individual needs. Our goal is to build a strong culture of connection as we work together to empower the hospitality community, regardless of location. Please visit the Locations page on our career site to learn more about our in-office expectations by region: https://careers.toasttab.com/locations-toast
Diversity, Equity, and Inclusion is Baked into our Recipe for Success
At Toast, our employees are our secret ingredient—when they thrive, we thrive. The restaurant industry is one of the most diverse, and we embrace that diversity with authenticity, inclusivity, respect, and humility. By embedding these principles into our culture and design, we create equitable opportunities for all and raise the bar in delivering exceptional experiences.
We Thrive Together
We embrace a hybrid work model that fosters in-person collaboration while valuing individual needs. Our goal is to build a strong culture of connection as we work together to empower the restaurant community. To learn more about how we work globally and regionally, check out: https://careers.toasttab.com/locations-toast.
Apply today!
Toast is committed to creating an accessible and inclusive hiring process. As part of this commitment, we strive to provide reasonable accommodations for persons with disabilities to enable them to access the hiring process. If you need an accommodation to access the job application or interview process, please contact [email protected].
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For roles in the United States, it is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.
Toast Boston, Massachusetts, USA Office
Toast’s headquarters is located in the heart of the Seaport District. Toasters are surrounded by art, culture, and delicious cuisine in one of the most bustling neighborhoods in Boston.
Early Careers
Toast's Early Careers program is designed to launch students' careers by integrating them into the company's vibrant culture and impactful work. Interns and co-ops are treated as full-time Toasters from day one, given meaningful projects, and provided with mentorship from industry professionals. The program emphasizes hands-on learning, collaboration across teams, and the autonomy for students to develop and showcase their skills, supported by consistent feedback. Toast offers opportunities across various departments, including technical roles like Software Engineering and Data Science, as well as non-technical roles such as Human Resources and People Operations.
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