
Senior Director of Technology

Talent Team
Tijana Tadic
Inspired by the fastest and most resilient penguin species in nature, we're here to help our clients and players achieve more reach, high-quality traffic, and meaningful engagement. With over 17 years of experience, Gentoo Media is a leading affiliate in the online casino and sportsbook industry through our extensive portfolio of products and services, featuring our flagship websites AskGamblers, Time2Play, CasinoTopsOnline, WSN, Casinomeister, and our SaaS brand-protection tool Sitebee.
IMPORTANT: To be considered for this opportunity, please submit your updated CV in English.
The role
We’re looking for a hands-on Senior Director of Technology to own the delivery of our internal tools, tracking infrastructure, marketing tech stack, and website platforms, with the Director of Product reporting into this role. This isn’t a pure strategy role - you’ll roll up your sleeves to identify bottlenecks, implement critical fixes, and work closely with developers and business teams to drive measurable outcomes. You’ll lead a team of managers and engineers across multiple locations. Still, you’ll also act as a key problem-solver yourself, particularly on cross-functional challenges spanning tech, product, SEO, and marketing.
What you will be doing:
- Lead and mentor a team of tech managers and senior developers across multiple locations and time zones
- Own the engineering roadmap, processes, and delivery across our core platforms and tools
- Drive technical excellence, scalability, and security across our infrastructure and products
- Ensure that Tech collaborates closely with Product, SEO, Data, Design, and Commercial teams to align tech priorities with business strategy
- Improve workflows, deployment pipelines, QA processes, and engineering metrics
- Champion a culture of ownership, innovation, and continuous improvement
- Attract and retain top technical talent to support our growth
Who we are looking for:
- 10+ years of engineering experience, with 5+ years in leadership roles
- Proven experience scaling engineering teams in high-growth digital businesses
- Deep understanding of modern web technologies, cloud infrastructure (e.g. AWS), and scalable architecture
- Experience working with SEO-focused platforms, affiliate ecosystems, or performance marketing is a strong plus
- Experience working on the development of multiple websites across different markets and content management systems, such as Wordpress
- Strong grasp of Agile methodologies and product development lifecycles
- Excellent communication, prioritisation, and stakeholder management skills
- A bias toward action, paired with a strategic mindset and analytical rigor
What we are offering:
- Daily Office Lunches: Varied menu options, including vegan choices, for a delightful lunch experience.
- 25 Days of Vacation: Take advantage of our generous vacation entitlement to relax and travel.
- Birthday Leave: It's your special day, so you get a day off to celebrate it!
- 'Me Time Day': Take a paid day off to focus on self-care and your mental health.
- Volunteer Day: Give back to your local community and receive a day off for this generous act!
- Career Progression: We support your professional development and provide guidance to ensure your constant growth.
- Learning Budget: Enjoy diving into learning with Udemy and enhance your hard and soft skills.
- Annual Wellbeing Benefit: Each employee receives a €400 budget per year to allocate for purpose from the approved list, that will contribute to their overall wellbeing.
- Vibrant Office Culture: Enjoy our lively and supportive office atmosphere daily, complemented by a calendar of both in-house and external events and parties to foster connections with colleagues.
- Private Health Insurance: Generous coverage with a strong network of providers, including a sublimit for psychotherapy because we support your mental wellbeing, physical therapy specifically tailored for addressing potential impacts related to sitting jobs, and much more.
Get more out of Gentoo Media: https://www.gentoomedia.com/
At Gentoo Media, we are committed to fostering an inclusive, diverse, and supportive workplace where everyone feels valued, respected, and empowered. We truly believe that diversity makes us stronger and more innovative—driving us forward as we make our mark on the world. We welcome applications from all qualified candidates, regardless of age, gender, disability, sexual orientation, ethnicity, religion, cultural background, or any other characteristic protected under EU and local laws. Our recruitment process is fair, unbiased, and based solely on skills and business needs, ensuring equal opportunities for all. If you require any reasonable accommodations during the application or interview process, just let us know—we’ll be happy to support you. Join our team and be part of something unique while being your true self 🐧
Check out the benefits of working with Gentoo
Continuous learning is at the core of our culture. Whether it’s attending workshops, enrolling in online courses, or participating in industry conferences, we offer plenty of opportunities to grow your skills and broaden your knowledge. But more than that, we’re here to support your long-term career growth, empowering you to reach your full potential.
Your well-being matters to us. That's why we offer a wellness allowance that can be used towards gym memberships, yoga classes, or any other activities that promote your physical and mental health.
Your special day should be celebrated! That's why we offer birthday leave, so you can take the day off to relax, recharge, and enjoy your birthday however you may please. In addition, we give you the Me Day, an opportunity to find time for yourself, whatever that looks like to you. It is entirely up to you how you spend the day.
Giving back to our communities is important to us. That's why we offer a paid volunteer day, so you can dedicate your time to causes you care about, while making a positive impact in the world.
We believe that strong relationships foster creativity and collaboration! That's why we host regular social events to bring our team together outside of the work environment. Enjoy of our monthly drinks, Summer party, Christmas party and more!
Your health and peace of mind matter to us. That’s why we offer comprehensive health insurance with solid coverage and a trusted network, so you and your loved ones feel supported and protected, wherever you are.
Lunch is more than just a break, it’s your moment to recharge. We provide freshly prepared, nutritious (and seriously tasty!) meals to keep you energized, focused, and ready to tackle the rest of your day.

