Director, Engineering

CarTrawler

Tech that takes you places We’re CarTrawler, the global travel tech company behind seamless connections between people, places and possibilities. From powering car rental to creating smarter ways to move, we make travel smoother for millions worldwide. Our culture is built on curiosity, collaboration and craic where every idea counts and every journey matters. Ready to make an impact? Let’s go places together. As we evolve from a single-category leader into a multi-product travel platform, we are building the next generation of B2B connectivity, blending modular architecture, unified product experiences and AI-powered intelligence. This is a pivotal leadership role at the centre of that transformation. We are seeking a strategic and execution-focused Director of Engineering to lead engineering delivery across our multi-product B2B platform. This role is accountable for engineering outcomes across Product Engineering, Platform Engineering and Engineering Excellence. You will shape engineering strategy, steward architecture direction, embed modern AI-enabled practices and ensure predictable, high-quality delivery at scale. You will play a key role in transitioning CarTrawler into a multi-travel platform business, balancing platform evolution with operational excellence. What you will do as a Director of Engineering

Datadog

Datadog is seeking a Director, Technical Account Management (TAM) for the EMEA region to join our high-growth organization and world-class Technical Post Sales (TPS) Team. You will own the strategy, growth, and execution of a team of 25–30 today, with a clear mandate to scale to 50–70+ over the next two to three years. You will be building organizational infrastructure, developing first-line leaders, and establishing scalable processes before they're needed. TAMs are technical experts who provide paid "white glove" technical services to our largest customers, supporting adoption and providing guidance across the comprehensive Datadog product suite. A TAM is held in high regard as an expert and trusted advisor for how IT Operations translates to business value. This is a senior leadership role where you will set the technical post-sales vision for all of EMEA, own executive relationships with key accounts, evangelize the TPS offering at scale, and grow services revenue across the region. At Datadog, we place value in our office culture—the relationships and collaboration it builds and the creativity it brings to the table. We operate as a hybrid workplace to ensure our Datadogs can create a work-life harmony that best fits them. WHAT YOU'LL DO: * Scale the EMEA TAM organization from 25–30 to 50–70+, hiring first-line leaders, designing team structures, and building systems that sustain quality through rapid growth. * Lead a team of managers and senior TAM ICs across EMEA, ensuring customer success, retention, and expansion at high standards of technical delivery. * Own the commercial strategy for the TPS program, partnering with Sales to position, price, and sell TAM services as a core part of the Datadog value proposition. * Define and execute regional OKRs aligned with global TPS goals, driving accountability through your leadership team each quarter. * Lead executive-level recruiting and build a leadership pipeline from within, developing managers who can in turn scale their own teams. * Serve as executive sponsor for strategic EMEA accounts, engaging at the C-suite level to reinforce value, resolve escalations, and identify expansion opportunities. * Partner with global TPS, Product, Sales Engineering, CS, and Enablement to standardize and evolve the TAM offering, customizing for regional needs where warranted. * Establish operational rigor: clear metrics, health scorecards, capacity planning, and forecasting to give full visibility into team performance and customer outcomes. * Drive talent development programs such as performance reviews & career growth plans, focusing on building future leaders within the organization and motivating, growing, & retaining top talent.   WHO YOU ARE: * 8+ years leading Professional Services, TAM, or Sales Engineering teams, with demonstrated success scaling an organization from fewer than 25 to 50+ headcount. * Experience managing managers: you hire and develop first-line leaders and have a track record of building leadership depth within your orgs. * Commercially minded, with direct experience selling or co-selling services and a history of growing services revenue; you position TAM as a value driver, not a cost center. * Technically fluent across infrastructure, cloud platforms (AWS, Azure, GCP), observability, and monitoring, credible with practitioners and C-level executives alike. * A strategic operator who pairs vision with execution: you set direction, build the systems to support it, and develop your team's ability to operate independently. * 3–5+ years earlier in your career as a TAM, Solutions Architect, or equivalent client-facing technical IC, giving you firsthand credibility with your team. * Willing and able to travel up to 50% of the time across the EMEA region.   BONUS POINTS: * Experience redesigning organizational structures mid-growth: building new team shapes or specializations as a business scales. * Track record evangelizing cloud adoption, observability, or security to C-level and board-level stakeholders across EMEA. * Hands-on experience with Datadog or other leading cloud monitoring and observability platforms. * Multilingual or deep experience navigating multi-cultural teams across EMEA markets. Datadog values people from all walks of life. We understand not everyone will meet all the above qualifications on day one. That's okay. If you're passionate about technology and want to grow your skills, we encourage you to apply. BENEFITS AND GROWTH: * Best-in-breed onboarding * Generous global benefits * Intra-departmental mentor and buddy program for in-house networking * New hire stock equity (RSUs) and employee stock purchase plan (ESPP) * Continuous professional development, product training, and career pathing * An inclusive company culture, able to join our Community Guilds and Inclusion Talks Benefits and Growth listed above may vary based on the country of your employment and the nature of your employment with Datadog. ---------------------------------------------------------------------------------------------------------------------------------- About Datadog:  Datadog is the leading observability and security platform for the AI era, providing businesses with unified visibility across the technology stack to manage complexity at scale. It brings applications, infrastructure, data, models, and security into one place, using AI to detect and resolve issues before they impact customers. Trusted globally by Fortune 500 companies and high-growth AI leaders, Datadog enables businesses to move faster with clarity and confidence. Learn more about #DatadogLife on Instagram, LinkedIn, and Datadog Learning Center. ---------------------------------------------------------------------------------------------------------------------------------- Equal Opportunity at Datadog: Datadog is proud to offer equal employment opportunity to everyone regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity, veteran status, and other characteristics protected by law. We also consider qualified applicants regardless of criminal histories, consistent with legal requirements. Here are our Candidate Legal Notices for your reference.  Datadog endeavors to make our Careers Page accessible to all users. If you would like to contact us regarding the accessibility of our website or need assistance completing the application process, please complete this form. This form is for accommodation requests only and cannot be used to inquire about the status of applications.  Privacy and AI Guidelines: Any information you submit to Datadog as part of your application will be processed in accordance with Datadog’s Applicant and Candidate Privacy Notice. For information on our AI policy, please visit Interviewing at Datadog AI Guidelines.

Toast

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 * 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 Location: Remote (within Ireland) or Hybrid (Dublin) #LI-Remote   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 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 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.