Senior Principal Software Engineer, Go To Market Experiences

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.

GTM Experiences defines how Toast engages with, supports, and grows customers across their entire lifecycle. This organization brings together Onboarding, Support, and Product-Led Growth (PLG) into a unified group responsible for designing and delivering a cohesive, end-to-end customer experience powered by intelligent systems and agents.

This team builds the platforms and experiences that shape how customers discover value, get started, receive help, and expand their use of Toast. We operate at the intersection of customer experience, agent experience, and product experience, developing systems that enable seamless transitions across lifecycle stages and channels.

GTM Experiences owns a broad ecosystem that includes customer onboarding journeys and activation systems, product-led growth surfaces and in-product engagement, customer support experiences and agent tooling, communications and engagement infrastructure, and AI-powered and agent-assisted lifecycle capabilities.

As Toast continues to grow, we are reimagining the customer lifecycle as a connected, intelligent platform rather than a set of siloed experiences. GTM Experiences plays a critical role in defining how these systems come together to deliver consistent, scalable, and high-quality experiences from first touch through long-term success.

About This Role

We are building the Customer Experience Platform that will define how Toast engages, supports, and grows customers at scale.

As a Senior Principal Engineer for GTM Experiences, you will serve as the LOB-level technical leader responsible for defining and driving the multi-year strategy that shapes how Toast delivers experiences across onboarding, support, and product-led growth. You will translate business strategy into coherent technical direction, align engineering investments with measurable customer and operational outcomes, and guide the architectural evolution to create a seamless customer journey.

This role extends beyond ownership of individual systems or services. You will help define how lifecycle stages connect into a unified experience and drive platform level decisions that unlock business outcomes. You will help define how core components of the support ecosystem — including AI-assisted capabilities, contact center infrastructure, agent tooling, and customer-facing support experiences — work together as a unified platform. You will partner closely with engineering, product, design, Care, Onboarding, and Growth leadership to establish a shared technical vision, make high-impact architectural decisions, and ensure that our platform scales with increasing complexity while improving customer outcomes.

Success in this role requires strong systems thinking, platform design expertise, and the ability to operate across organizational boundaries. You will bring clarity to a complex ecosystem, drive alignment across teams, and ensure our investments translate into measurable improvements in customer activation, retention, and support quality.

A day in the life (Responsibilities)

• Define and drive the multi-year technical strategy for the GTM Experiences LOB, ensuring alignment with company goals and long-term customer experience outcomes.
• Lead architectural direction for critical platform capabilities that support customer and agent experiences, including contact center infrastructure, AI-assisted support systems, internal agent tooling, onboarding and activation systems, product-led growth experiences
• Evaluate and de-risk major technical investments such as platform migrations, vendor integrations, and large-scale architectural changes.
• Ensure that systems across onboarding, support, and growth operate as a cohesive, extensible platform rather than disconnected point solutions.
• Partner with product, design, Care, Onboarding, and Growth leadership to translate strategic goals into scalable technical solutions that improve outcomes and operational efficiency.
• Establish architectural principles and engineering standards that support long-term platform scalability, flexibility, and velocity.
• Provide technical leadership and mentorship to senior engineers, helping raise the overall engineering bar across the GTM Experiences organization.
• Influence technical direction across multiple teams and functions, aligning stakeholders around shared platform decisions and long-term strategy.
• Leverage cutting edge AI tools to enhance your development workflow, improve velocity, and help pioneer new approaches to building - contributing to a culture of innovation and productivity across the team.

What you'll need to thrive (Requirements)

• 10+ years of experience in software engineering, with a strong background building and evolving large-scale distributed systems and customer-facing platforms.
• Demonstrated experience defining technical strategy or architecture for complex platforms spanning multiple systems and teams.
• Strong systems thinking and platform design experience, with the ability to connect individual services and tools into coherent technical ecosystems.
• Proven ability to lead high-impact architectural decisions and guide organizations through complex technical transitions.
• Experience influencing technical direction across teams and collaborating with product, design, and operational partners to deliver meaningful business outcomes.
• Strong communication skills and the ability to articulate complex technical ideas clearly to both technical and non-technical stakeholders.
• A track record of mentoring senior engineers and raising the engineering bar within an organization.
• Experience working on customer experience platforms, workflow systems, or other complex operational software environments is strongly preferred.

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.

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