Senior Principal Software Engineer, Go to Market Experiences

Toast Toast · Enterprise · Boston, MA +1 · R & D : Engineering : Customer Experience Platform

This role is for a Senior Principal Software Engineer focused on the Go To Market (GTM) Experiences at Toast. The primary responsibility is to define and drive the multi-year technical strategy and architectural evolution for platforms that shape customer engagement, onboarding, support, and product-led growth. The role involves leading technical direction for a broad ecosystem, including AI-assisted capabilities and agent tooling, ensuring these systems work together as a unified platform to improve customer outcomes and operational efficiency. While AI is mentioned as a component of the systems being built, the core craft of the role is platform engineering and technical strategy, not direct AI/ML model development.

What you'd actually do

  1. Define and drive the multi-year technical strategy for the GTM Experiences LOB, ensuring alignment with company goals and long-term customer experience outcomes.
  2. 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
  3. Evaluate and de-risk major technical investments such as platform migrations, vendor integrations, and large-scale architectural changes.
  4. Ensure that systems across onboarding, support, and growth operate as a cohesive, extensible platform rather than disconnected point solutions.
  5. Partner with product, design, Care, Onboarding, and Growth leadership to translate strategic goals into scalable technical solutions that improve outcomes and operational efficiency.

Skills

Required

  • 10+ years of experience in software engineering
  • strong background building and evolving large-scale distributed systems
  • strong background building and evolving customer-facing platforms
  • Demonstrated experience defining technical strategy or architecture for complex platforms spanning multiple systems and teams
  • Strong systems thinking
  • platform design expertise
  • ability to operate across organizational boundaries
  • clarity to a complex ecosystem
  • drive alignment across teams
  • translate investments into measurable improvements
  • Strong communication skills
  • articulate complex technical ideas clearly to both technical and non-technical stakeholders
  • track record of mentoring senior engineers
  • raising the overall engineering bar

Nice to have

  • Experience working on customer experience platforms
  • workflow systems
  • other complex operational software environments

What the JD emphasized

  • AI-assisted capabilities
  • AI-assisted support systems
  • intelligent systems and agents