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.

Your mission is to drive architecture, technical strategy, and implementation of AI agents for Toast’s Team area which is part of the Fintech line of business. You will be one of the most senior technologists in line of business. The Team area is a mission-critical space on which our restaurants rely to manage their staff and optimize their labor. Beyond being on the forefront of agent development, your scope will also include enablement and leadership for how software is developed at Toast through adoption of bleeding edge spec driven development and other paradigms.

A day in the life (Responsibilities)

• Develop and drive an architectural vision to support the ambitious goals for agents and agent development
• Be an active participant and an authoritative technical voice in FinTech product strategy discussions
• Partner with the Team Management Director of Engineering and Sr. Director of Product to successfully deliver Team agent products from design to production
• Work closely with other Senior Principal Engineers to further the agent patterns and ecosystem across Toast as a whole
• Evolve an ever more efficient way of working through agents and spread it across Toast
• Work directly with the product manager for the Team Agent space, collaborating to drive vision
• Be hands on and actively participate in development on the Team Agent
• Mentor and develop technical leadership across Team, and Fintech

What you’ll need to thrive (Requirements)

• 15+ years experience designing and building highly scalable, mission-critical distributed and fullstack software systems
• 10+ years experience building and operating SaaS products, ideally AWS hosted
• 1+ years experience using the latest in coding agents
• A strong desire to lean all in on agentic development practices
• Passion for building autonomous agents
• Demonstrated ability to drive technical architecture for a company or highly scalable line of products
• A desire to work not only with technologists but also product owners and business leaders
• Ability and desire to draw big lines and boxes on a whiteboard paired with the ability to dig in and understand the ebb and flow of what the code is doing under load
• Ability and desire to communicate and influence at the executive level

What will help you stand out (Nonessential Skills/Nice to Haves)

• Experience designing agentic products
• Experience building systems that leverage LLMs and other ML models
• Experience with enterprise integration using Apache Camel
• Experience architecting event-driven distributed systems using Apache Pulsar
• Experience defining test, build and deploy strategies
• Solid understanding of workforce management
• Solid understanding of restaurant operations

#LI-HYBRID

#BI-Hybrid

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.

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

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 candidateaccommodations@toasttab.com.

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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 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.

Your mission is to drive architecture, technical strategy, and implementation of AI agents for Toast’s Team area which is part of the Fintech line of business. You will be one of the most senior technologists in line of business. The Team area is a mission-critical space on which our restaurants rely to manage their staff and optimize their labor. Beyond being on the forefront of agent development, your scope will also include enablement and leadership for how software is developed at Toast through adoption of bleeding edge spec driven development and other paradigms.

A day in the life (Responsibilities)

• Develop and drive an architectural vision to support the ambitious goals for agents and agent development
• Be an active participant and an authoritative technical voice in FinTech product strategy discussions
• Partner with the Team Management Director of Engineering and Sr. Director of Product to successfully deliver Team agent products from design to production
• Work closely with other Senior Principal Engineers to further the agent patterns and ecosystem across Toast as a whole
• Evolve an ever more efficient way of working through agents and spread it across Toast
• Work directly with the product manager for the Team Agent space, collaborating to drive vision
• Be hands on and actively participate in development on the Team Agent
• Mentor and develop technical leadership across Team, and Fintech

What you’ll need to thrive (Requirements)

• 15+ years experience designing and building highly scalable, mission-critical distributed and fullstack software systems
• 10+ years experience building and operating SaaS products, ideally AWS hosted
• 1+ years experience using the latest in coding agents
• A strong desire to lean all in on agentic development practices
• Passion for building autonomous agents
• Demonstrated ability to drive technical architecture for a company or highly scalable line of products
• A desire to work not only with technologists but also product owners and business leaders
• Ability and desire to draw big lines and boxes on a whiteboard paired with the ability to dig in and understand the ebb and flow of what the code is doing under load
• Ability and desire to communicate and influence at the executive level

What will help you stand out (Nonessential Skills/Nice to Haves)

• Experience designing agentic products
• Experience building systems that leverage LLMs and other ML models
• Experience with enterprise integration using Apache Camel
• Experience architecting event-driven distributed systems using Apache Pulsar
• Experience defining test, build and deploy strategies
• Solid understanding of workforce management
• Solid understanding of restaurant operations

#LI-HYBRID

#BI-Hybrid

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.

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

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 candidateaccommodations@toasttab.com.

---—

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.

About Kuda:

Kuda, which means ‘love’ in Shona, a Southern African language, is a fintech company on a mission to make financial services accessible, affordable, and rewarding for Africans.

Backed by over $100 million in funding from some of the world’s most respected institutional investors, we offer a better alternative to traditional finance by delivering services including free money transfers, remittance, business banking, and instant access to credit through digital devices.

Our team of passionate and diverse people works hard to break boundaries, carry one another along, do better every day, and share the love that defines us.

If you’re excited about working at a place where purpose, innovation, and impact connect, you’d be right at home with us.

Role Overview:

As the VP of Engineering (VPE) at Kuda, you will lead a world-class engineering organization of 100+ software and quality engineers distributed across four countries. Your mission is built on three core pillars: Scale, Delivery, and Compliance. You will be the engine of internal execution, responsible for scaling our human organization, driving operational excellence, and ensuring our technical systems remain robust as we expand globally. You will bridge the gap between high-level technical strategy and daily execution, fostering a culture of psychological safety, technical excellence, and rapid innovation.

Key Responsibilities:

1. Scaling the Human Organisation

• Lead, mentor, and grow a diverse, distributed engineering team of 100+, ensuring high levels of engagement and professional development.
• Establish clear career frameworks and performance standards that reward technical excellence and leadership.
• Foster a culture of psychological safety where engineers feel empowered to take calculated risks and innovate.

2. Operational & Delivery Excellence

• Own the internal execution of the product roadmap, ensuring high velocity without compromising on quality or security.
• Drive the adoption of modern engineering practices (e.g., GitOps, automated testing, CI/CD) to accelerate delivery cycles.
• Optimize engineering processes to reduce friction and improve the developer experience across all squads.

3. Technical Strategy & Scale

• Oversee the architectural integrity of our cloud-native, high-throughput, and low-latency financial systems.
• Ensure our core banking systems and microservices are built to handle millions of global customers.
• Drive cloud infrastructure consolidation to simplify maintenance and improve cost-efficiency.

4. Compliance & Security

• Partner with internal stakeholders to ensure all software delivery upholds the highest standards of security and financial compliance.

• Ensure readiness for evolving standards (such as ISO 20022, 22301, CBN Risk-Based Cybersecurity Framework, PCI-DSS, etc) and lead the implementation of advanced security features.

• Seasoned Technologist: 10+ years of engineering experience with a demonstrable background in building and maintaining high-throughput, low-latency financial systems.

• Proven Leadership: Previous experience leading large engineering organizations (100+) and building high-performance squads in a fast-paced, high-growth environment.

• Cloud-Native Expertise: Deep understanding of modern cloud infrastructure and distributed systems.

• Regulatory Knowledge: Experience navigating the security and compliance mandates of financial regulatory bodies.

Hard Skills:

• Expertise in software delivery metrics (DORA metrics) and process optimization.
• Strong grasp of architectural patterns for scalable fintech applications (12 Factor Apps).
• Experience with automated regression testing and security-first development (DevSecOps).

Soft Skills:

• Clear Communication: Ability to translate complex technical challenges into business impact for executive and other business stakeholders.
• Empathetic Leadership: A commitment to fostering an inclusive, safe, and high-growth environment for engineers.
• Strategic Thinking: Ability to balance immediate delivery needs with long-term organizational health.

Why join Kuda?

At Kuda, our people are the heart of our business, so we prioritize your welfare. We offer a wide range of competitive benefits in areas including but not limited to:

💜A great and upbeat work environment populated by a multinational team

📈Career Development & growth

😁Competitive annual leave plus bank holidays

🎁Competitive paid time off (Parental, Moving day, Birthday, Study leave etc)

💯Group life insurance

💖Medical insurance

🎁Well-fare package (Wedding, Compassionate and etc)

✅ Awardco

🏃‍♀️Goalr - employee wellness app

🥇Award winning L&D training

💒 We are advocates of work-life balance, working in a hybrid in office schedule

Kuda is proud to be an equal-opportunity employer. We value diversity and anyone seeking employment at Kuda is considered based on merit, qualifications, competence and talent.

We don’t regard colour, religion, race, national origin, sexual orientation, ancestry, citizenship, sex, marital or family status, disability, gender, or any other legally protected status. If you have a disability or special need that requires accommodation, please let us know.

What’s in it for you?

Ready to make a serious impact? Millions of people already rely on Calendly, and we’re still in the midst of exciting product growth — it’s a fantastic time to join us. Everything you’ll work on here will accelerate your career to the next level. If you want to learn, grow, and do the best work of your life alongside the best people you’ve ever worked with, then we hope you’ll consider allowing Calendly to be a part of your professional journey.

About the team & opportunity What’s so great about working on Calendly’s Engineering team?

Calendly is the scheduling automation and meeting lifecycle platform used by millions of users for eliminating the back-and-forth emails to find the perfect time — and so much more. We are looking for an experienced and hands-on leader in the product development space.

This is an exciting opportunity to create, drive, and evangelize a vision for Calendly’s shared services platform. In this role, you will lead a group of engineers that build critical core services depended upon by the wider product development organization.

Why do we need you? Well, we are looking for an experienced Engineering leader who will bring operational maturity, technical subject-matter expertise, and the ability to empower the wider product development organization.

A day in the life of a Sr. Director of Engineering at Calendly

On a typical day, you will be working on:

• Defining and executing the vision and strategy for a key product area aligning with the Calendly’s goals and priorities
• Supporting and mentoring a team of managers and engineers, providing technical guidance and coaching on their career development
• Driving innovation and adoption of new technologies and methodologies that enhance Calendly’s services
• Ensuring the quality, performance, security, and scalability of a product line of business following best practices and standards
• Collaborating with other engineering teams, product managers, and stakeholders to understand the business requirements and deliver solutions that meet or exceed expectations
• Driving innovation and adoption of new technologies and methodologies that core capabilities and user experience

What do we need from you?

• 15+ years of software engineering experience, with at least 10+ years in a leadership role
• Experience helping to build and scale an AI-first engineering organization, including integrating AI/ML capabilities into core services, developer workflows, and product strategy
• Experience leading high-performance engineering teams
• Experience building highly-available distributed back-end systems
• Comfortable working as a change-agent, and drive adoption of modern engineering methodologies
• Knowledge of cloud platforms, such as GCP and their services and tools
• Experience operating in both high-growth startup technology companies and larger, more established organizations, with the ability to adapt leadership style and processes to each
• Strong communication, collaboration, and problem-solving skills
• Passion for delivering high-quality products and services that delight customers
• Ability to iterate and ship fast
• The ability to work in our San Francisco office 2 days per week
• Authorized to work lawfully in the United States of America as Calendly does not engage in immigration sponsorship at this time

Tier 1 Salary Hiring Range

$328,320—$426,816 USD

Tier 2 Salary Hiring Range

$300,960—$391,248 USD

Tier 3 Salary Hiring Range

$273,600—$355,680 USD

The ranges listed above are the expected annual base salary for this role, subject to change.

Calendly takes a number of factors into consideration when determining an employee’s starting salary, including relevant experience, relevant skills sets, interview performance, location/metropolitan area, and internal pay equity.

Base salary is just one component of Calendly’s total rewards package. All full-time (30 hours/week) employees are also eligible for our Top Performer Bonus program (or Sales incentive), equity awards, and competitive benefits.

Calendly uses the zip code of an employee’s remote work location, or the onsite building location if hybrid, to determine which metropolitan pay range we use. Current geographic zones are as follows:

• Tier 1: San Francisco, CA, San Jose, CA, New York City, NY
• Tier 2: Chicago, IL, Austin, TX, Denver, CO, Boston, MA, Washington D.C., Philadelphia, PA, Portland, OR, Seattle, WA, Miami, FL, and all other cities in CA.
• Tier 3: All other locations not in Tier 1 or Tier 2

If you are an individual with a disability and would like to request a reasonable accommodation as part of the application or recruiting process, please let your Recruiter know when first connecting with them. Calendly is registered as an employer in many, but not all, states. If you are located in Alaska, Delaware, Hawaii, Idaho, Iowa, Montana, Nebraska, North Dakota, Rhode Island, South Dakota, and West Virginia, you will not be eligible for employment. Note that all individual roles will specify location eligibility.

All candidates can find our Candidate Privacy Statement here

Candidates residing in California may visit our Notice at Collection for California Candidates here: Notice at Collection

This role may require occasional travel for company events, team collaboration, or offsites.