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.

The role

We are seeking a technically thorough and commercially aware Senior Tax Associate to own the group’s tax compliance and transfer pricing infrastructure across multiple legal entities spanning Malta, Denmark, the United States, and beyond. This is a newly created role that sits at the intersection of technical tax execution and strategic group finance, reporting directly to the Head of Group Finance.

The immediate mandate is clear: ensure full US and Maltese tax compliance and establish a defensible, OECD-aligned transfer pricing framework across the group in close collaboration with external tax advisors. Beyond compliance, this role will be a critical internal voice on tax risk, planning, and structuring as the business continues to grow across multiple jurisdictions.

This is not a back-office compliance role. The Senior Tax Associate will operate with a high degree of autonomy, manage senior external advisor relationships, and bring genuine technical depth to a business that is building its tax function for scale.

What you'll be doing

Tax Compliance & Reporting

• Own end-to-end corporate income tax (CIT) compliance across Group entities, ensuring accuracy, completeness, and timely submission.

• Manage deferred tax asset (DTA) and deferred tax liability (DTL) positions and movements across the group, arising from timing differences, with particular focus on refunds on Maltese taxes applicable upon the distribution of dividends and/or formation of a Maltese tax group (fiscal unit).

• Coordinate US federal corporate tax and state & local tax compliance for the group’s C Corporation, working with external US tax advisors to ensure timely and accurate filings.

• Oversee VAT/GST compliance in relevant jurisdictions within the Group, coordinating with local advisors and ensuring obligations are met within regulatory deadlines.

• Maintain a group-wide tax compliance calendar to ensure no filing deadlines are missed across any jurisdiction.

• Prepare and review tax provisions and disclosures for inclusion in statutory and management accounts.

Transfer Pricing (TP)

• Lead the development of Gentoo Media’s group transfer pricing framework in collaboration with external advisors, ensuring it is defensible and fit for purpose across all entities.

• Prepare and maintain complete TP documentation, including master file and local files, for all relevant jurisdictions.

• Design and implement intercompany pricing policies that reflect arm’s length principles and are consistently applied across the group.

• Monitor legislative and regulatory developments in transfer pricing across key jurisdictions and assess the impact on group structure and existing policies.

• Work with Finance, Legal, and external advisors to ensure intercompany agreements are in place, up to date, and consistent with TP documentation.

• Coordinate TP reporting obligations (e.g., Country-by-Country Reporting) and ensure timely submission.

Tax Advisory & Planning

• Provide timely, technically sound tax advice to the Head of Group Finance and CFO on transactions, restructurings, and new market entries.

• Identify tax planning opportunities to optimise the group’s effective tax rate without compromising compliance or reputational integrity.

• Assess the tax implications of business decisions, including intercompany transactions, new entity formations, and cross-border flows.

• Stay current on international tax developments and brief senior stakeholders on implications for Gentoo Media.

• Support the annual budget and forecasting process by providing accurate current and deferred tax forecasts.

Stakeholder & Advisor Management

• Own the day-to-day relationships with Big Four tax advisors, coordinating workstreams, managing deliverables, and reviewing outputs prior to sign-off.

• Act as the primary internal point of contact for all tax matters, liaising across Finance, Legal, and the wider business as required.

• Brief the Head of Group Finance and CFO on material tax positions, risks, and developments in a clear, commercially framed manner.

• Support external audit processes by providing accurate tax schedules, reconciliations, and technical documentation.

• Build strong working relationships across the group’s business units to ensure tax considerations are embedded in operational and commercial decision-making.

Who we're looking for

Education / Qualifications

• Bachelor’s degree in Tax, Accounting, Finance, Law, or a related field (required).

• ACCA/ACA or equivalent professional qualification (required).

• ADIT (Advanced Diploma in International Taxation) or CTA (Chartered Tax Adviser) - strongly preferred

• CPA (US) is advantageous given the scope of US federal and state tax obligations.

Experience

• 5–8 years of progressive experience in corporate and international tax, with demonstrable depth in compliance and transfer pricing.

• Big 4 background preferred (Deloitte, PwC, KPMG, or EY); in-house experience within a multinational group is also valued.

• Proven experience preparing or reviewing transfer pricing documentation (master file, local files, CbCR) in line with OECD guidelines.

• Working knowledge of Maltese tax legislation, including the full imputation system, the refund mechanism applicable upon dividend distributions, fiscal units/tax groupings, and deferred tax assets and liabilities is strongly preferred.

• Familiarity with Danish corporate tax and withholding tax rules are advantageous.

• Exposure to US corporate income tax (federal and state & local) is a material advantage.

• Experience managing external tax advisors across multiple jurisdictions, including coordinating deliverables and reviewing technical outputs.

• Comfortable operating across a multi-entity group structure with varied jurisdictional tax profiles.

Technical Skills

• Practical experience managing withholding tax obligations on cross-border dividend, royalty, and interest flows, and applying double tax treaty provisions to minimise leakage with relevance to i.e., the Malta-Denmark and Malta-US treaty networks.

• Strong command of OECD Transfer Pricing Guidelines and the BEPS framework, including Pillar Two awareness.

• Proficiency in tax compliance processes and tools; familiarity with ERP systems (Microsoft Business Central) is advantageous.

• Advanced Excel; ability to build and maintain deferred tax asset and liability tracking models and tax provision workpapers.

• Understanding of intercompany accounting and the tax implications of consolidation adjustments.

• Familiarity with EU anti-avoidance Directive, Mandatory Disclosure rules and controlled foreign corporation legislation.

Soft Skills

• High attention to technical detail combined with the ability to communicate complex tax positions clearly to non-tax stakeholders.

• Operates with strong autonomy – self-directed, organised, and able to manage multiple compliance deadlines without close supervision.

• Commercially aware: understands the business impact of tax decisions, not just the technical answer.

• Builds credibility quickly with senior internal stakeholders and external advisor partners.

• Proactive in identifying risk and escalating appropriately – does not wait to be asked.

• High integrity and discretion when handling sensitive group financial and tax information.

What we're offering:

At Gentoo Media, we’re redefining affiliate marketing in iGaming - and we know that great work starts with great people. That’s why we’re committed to fostering a supportive and inclusive environment.

Here’s what you can look forward to as part of the team in Malta:

• Hybrid working model - flexibility to split time between home and office

• Daily office lunches with varied menus to suit all dietary preferences

• Birthday Leave - a day off to celebrate your special day

• “Me Time” Day - a day dedicated to your wellbeing

• Annual Volunteer Day - support a cause that matters to you

• International health insurance, including dental coverage

• Career progression pathways and continuous guidance

• Anniversary rewards at 3, 5, and 10 years

• Personal learning budget + access to Udemy

• Annual €400 wellbeing benefit

• Mental Health Support through Richmond Foundation

• Team building budget

• Free office parking

• A vibrant culture with regular events, social gatherings, and team celebrations

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.