Head of Technology

About UpShift Media

UpShift Media is a lean, AI-first publisher network. We build and grow high-intent comparison and review properties across crypto, iGaming, and sports betting, competing with much larger teams by moving faster and operating smarter.

We're now investing in an ambitious new platform for one of our fastest-growing categories, and we need a senior technology leader to build it.

About the role

We are looking for a senior Head of Technology to architect and build a new, feature-rich platform from the ground up.

You'll own the technical vision and architecture, lead the engineering effort, report to the founder, and partner closely with a Product Manager to turn a deep, ambitious roadmap into shipped features, fast. You'll make the big technical calls, set the standards the build runs on, and keep the platform quick, reliable, and ready to scale as the category grows.

This is a senior leadership role for someone with a proven track record. You are technical enough to architect and set direction, and experienced enough to lead, not a solo developer, and not a hands-off manager either. As the platform and the team grow, the role grows with them.

What this role is built to own

A senior technical mandate for someone who architects and builds a new platform from the ground up.

The platform. Architect and build a new, feature-rich platform, and own the decisions that shape it.
Delivery with product. A deep roadmap turned into shipped features alongside a Product Manager.
Engineering leadership. Architecture, standards, and technical direction; leading the build.
Scale & reliability. Performance, data, security, and uptime as the platform grows.

Who you'd be joining

Upshift Media is a lean, AI-first team of fewer than seven people (the two-pizza rule, on purpose). We run on four values: We Own Outcomes · We Run on AI · We Get Shit Done · We Grow Together. You'd report straight to the Founder and own the technical direction and build of a brand-new platform — not a backlog handed down through layers.

It's also a place to level up fast: you'll build with the most advanced AI and automation workflows in the industry every day, and leave world-class at AI-driven engineering — the kind of operator any company fights to hire.

The deal: fully remote — work whenever and wherever you do your best work (small HQ in Cyprus); a competitive base plus a high-margin performance bonus; co-working covered if you're outside Cyprus; and once a year we fly the whole team to Cyprus to celebrate. We hire culture-first — only apply if you genuinely share these values.

What you'll own

The platform

Architect and build a new, feature-rich platform for a fast-growing category, and own the technical decisions that shape it.

Set the architecture, stack, and engineering standards from day one.
Design for a deep feature roadmap, performance, and scale from the start.

Delivery, with product

Partner with a Product Manager to turn the roadmap into a prioritized, shippable build.
Own delivery cadence, quality, and the trade-offs between speed and scope.
Break an ambitious roadmap into features that ship without stalling.

Engineering leadership

Lead engineers and vendors, set the technical bar, and grow the team as the platform grows.
Own code quality, review standards, and how the team ships.

Data, performance, reliability & compliance

Build in analytics, tracking, and clean data from the start.
Own performance, uptime, on-call, and security as the platform scales.
Build to GDPR and consent, geo and age-gating, and the compliance requirements of a regulated category from day one.

AI tooling & automation

Use AI-assisted development and internal tooling to build faster without lowering quality.

What success looks like

Early on, you've set the architecture, stack, and plan with the founder and product, and the first features are shipping.
In the first months, a real, feature-rich version of the platform is live, fast (strong Core Web Vitals), and stable, and the delivery cadence is predictable.
Over time, the platform scales cleanly with the category, the roadmap keeps shipping, and the engineering function grows behind a clear technical standard you set.

What we're looking for

You should have:

8+ years in engineering, including real ownership of architecture and a team.
A proven track record building and scaling a feature-rich web platform or product, with real examples of what you shipped and its impact.
Senior or lead experience owning architecture and technical direction end to end.
Strong command of modern web stacks, architecture, performance, data and tracking, and building for scale.
Real experience partnering with product managers to turn a roadmap into delivered features.
The ability to lead engineers and set standards, while staying close enough to the build to make the hard calls.
A practical command of AI-assisted development and tooling.
Clear communication and strong Central European Time overlap.

Nice to have

Experience building products in iGaming, sports betting, crypto, or another performance-marketing, compliance-sensitive category.
Experience taking a platform from zero to a mature, high-traffic product.
Familiarity with affiliate tracking, attribution, and partner integrations.
DevOps, cloud infrastructure, and security experience.
Experience hiring and growing an engineering team.

What this role is not

This is not a maintenance or keep-the-lights-on role, you're building something new.

It is not a solo-developer role, you'll lead the build and partner with product, not carry it alone. And it is not a hands-off manager role, you set the architecture and technical direction and stay close to the build.

Why join

The biggest thing we offer isn't a list of perks, it's that you will get better here. The people who join us leave sharper than they arrived, because we train, review each other's work, and grow as a team rather than in silos.

You'll grow, on purpose. Honest feedback, shared playbooks, and skills that compound. If you want to be sharper in a year than you are today, this is the place for it.
We go hard, and we enjoy it. High intensity and a high bar when it counts, and a team that doesn't take itself too seriously the rest of the time.
A small, senior team of specialists. Fast decisions, no bureaucracy or bloat, and real ownership from day one, startup speed at a high standard.
AI-first and data-driven. We use the best tools and let real data, not hunches, settle decisions, so your work compounds instead of getting redone.
Real ownership. You own a brand-new platform end to end, from architecture to shipped features.
Flexible remote work with clear expectations and fast feedback.
Competitive compensation based on experience, skill level, and scope.

How to apply

Send:

A short note on why this role fits your background.
Two or three platforms or products you built or led, ideally with measurable outcomes.
An example of a feature-heavy roadmap you delivered, and how you worked with product to ship it.
How you use AI in your engineering workflow.