Head of Design (Arbitrage)

📍 Job Overview

Job Title: Head of Design (Arbitrage)

Company: UPSTARS

Location: Kyiv, Ukraine (Remote Option Available)

Job Type: FULL_TIME

Category: Design Leadership / Operations

Date Posted: 2026-09-22

Experience Level: 10+ Years

Remote Status: Remote OK

🚀 Role Summary

• Lead and manage a diverse design function encompassing Visual Graphic & Motion Design, Motion Creators Design, Visual Graphic & Motion App Design, and Product Design.

• Drive strategic development and operational efficiency for a high-volume creative production team, focusing on performance marketing and B2B services within the iGaming and technology sectors.

• Implement and refine design production processes, ensuring high throughput, quality, and timely delivery of creative assets for media buying and affiliate marketing.

• Foster a culture of continuous improvement, data-driven decision-making, and cross-functional collaboration to maximize the impact of design on key business metrics like CTR and conversion rates.

• Develop and mentor Team Leads and individual contributors, building a robust management structure and a high-performing design organization.

📝 Enhancement Note: This role is positioned as a senior leadership role within a product IT company specializing in technological solutions and B2B services, particularly in the iGaming sector. The "Arbitrage" in the title, combined with the emphasis on performance creatives, media buying, and affiliate marketing, strongly suggests a focus on direct response advertising and performance optimization rather than traditional brand design. The operations aspect is critical, focusing on the scalable production and optimization of creative assets.

📈 Primary Responsibilities

• Oversee and direct four distinct design teams: Visual Graphic & Motion Design, Motion Creators Design, Visual Graphic & Motion App Design, and Product Design.

• Set clear performance objectives, conduct regular evaluations, and implement Individual Development Plans (IDPs) for all team members, fostering professional growth.

• Recruit, onboard, and develop Team Leads to build a strong, capable management layer within the design department.

• Strategically allocate team priorities and workloads across different design disciplines to align with urgent business objectives and team member competencies.

• Analyze existing design production processes, identify bottlenecks, and implement solutions to enhance overall team productivity and output.

• Standardize and optimize the creative production workflow, from briefing and prioritization to execution, review, and final delivery, ensuring consistent quality and volume.

• Establish and maintain a transparent workflow for task management, ensuring a seamless process from initial brief to final asset handover.

• Collaborate closely with media buying teams to implement and analyze A/B/n testing of creatives, evaluating the impact of different formats and styles on CTR and conversion rates.

• Coordinate design operations effectively with cross-functional teams including Marketing, Media Buying, and Product to ensure cohesive campaign execution and strategic alignment.

• Report on the performance of the design function to C-level executives, articulating the impact of design on key performance indicators, highlighting challenges, and advocating for necessary resources.

• Develop and execute the strategic roadmap for the design function for the next 6-12+ months, ensuring alignment with the overall company business strategy.

• Define the optimal team structure, roles, and required competencies, actively participating in the recruitment and integration of new designers and leadership talent.

• Drive the adoption of automation, AI tools, standardized templates, and Design Systems to accelerate creative production and improve efficiency.

• Manage the budget for the design department, including tools, stock resources, and freelance/outsourced services, and champion resource requests at the C-level.

• Make informed decisions in ambiguous situations and assume accountability for business outcomes resulting from those decisions.

• Stay abreast of the latest trends in advertising creatives, platform formats, banner networks, and native advertising, adapting the team's approaches accordingly.

📝 Enhancement Note: The responsibilities heavily emphasize operational efficiency, process management, and direct impact on performance metrics, aligning with a "Head of Operations" within a design context, rather than a purely creative director role. The focus on "Arbitrage" and "Media Buying" reinforces this.

🎓 Skills & Qualifications

Education: While not explicitly stated, a Bachelor's degree in Design, Graphic Arts, Marketing, Business Administration, or a related field is typically expected for a leadership role of this caliber. Advanced degrees or certifications in management or specific design disciplines are a plus.

Experience: Minimum of 10+ years of progressive experience in design, with a significant portion focused on leadership and management within performance-driven environments.

Required Skills:

• Proven experience managing a design team of 15+ individuals, preferably with a two-tier hierarchy (multiple direct reports, including Team Leads).

• Demonstrated experience with performance creatives for media buying, affiliate marketing, or performance marketing (e.g., banners, video ads, landing pages), understanding the specific requirements beyond brand design.

• Deep understanding of various production formats, including static graphics, full-fledged motion/video, ASO creatives for app stores, and product landing pages, with the ability to lead teams specializing in each.

• Strong comprehension of media buying metrics (CTR, CPA, CR, ROI) and how design decisions directly influence them.

• Extensive experience in building and standardizing production processes for high-volume creative output (tens to hundreds of creatives per week), including a defined workflow from brief to delivery.

• Full-cycle people management experience: recruitment, onboarding, performance evaluation, IDP implementation, and development of Team Leads into strong managerial assets.

• Experience in shaping team structures, defining roles and competencies, and resource planning for functional growth.

• Ability to communicate effectively with C-level executives, translating design activities into quantifiable business results.

• Strategic thinking capabilities, enabling the formation of a long-term vision (6-12+ months) for the design function's development beyond immediate production needs.

• Experience in high-volume performance verticals such as gambling/betting, fintech, or similar industries. Preferred Skills:

• Experience with ASO creatives and a solid understanding of App Store and Google Play visual material requirements.

• Familiarity with media buying tracking and analytics tools (e.g., Keitaro, Voluum) at a funnel-understanding level.

• Experience integrating AI tools into creative production workflows to enhance team speed and output.

• Proven track record in building Design Systems or template libraries from scratch.

📝 Enhancement Note: The required skills strongly emphasize leadership, operational process management, and a deep understanding of performance marketing metrics and creative production at scale, which are critical for a "Head of Design" in this specific "Arbitrage" context.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Demonstrate a portfolio showcasing your leadership and strategic impact on design operations, not just individual design work.

• Include case studies detailing how you scaled creative production processes to meet high-volume demands for performance marketing campaigns.

• Showcase examples of process optimization initiatives you've led, highlighting improvements in efficiency, quality, or speed of creative delivery.

• Present evidence of your ability to manage and develop teams, including examples of team structure, performance management, and talent development strategies.

• Highlight your experience in collaborating with media buying and marketing teams, with specific examples of how design influenced key performance metrics. Process Documentation:

• Provide examples of documented workflows for creative production, including brief intake, prioritization, resource allocation, review, and delivery stages.

• Showcase your approach to standardizing creative production processes to ensure consistency and scalability.

• Illustrate how you have implemented A/B/n testing strategies for creatives and analyzed the results to inform future production.

• Detail your methods for measuring and reporting on the performance and impact of the design function on business outcomes.

📝 Enhancement Note: Given the role's focus on operations and performance, a portfolio demonstrating process management, team scaling, and measurable business impact will be more critical than a traditional design portfolio.

💵 Compensation & Benefits

Salary Range: For a Head of Design role with 10+ years of experience, managing a large team in Kyiv, Ukraine, and with a strong focus on performance marketing, the estimated salary range is typically between ₴120,000 to ₴200,000+ per month (approximately $3,000 - $5,000+ USD per month), depending on the candidate's specific experience, proven track record, and negotiation.

Benefits:

• Remote Work Flexibility: Option to work remotely from hubs in Kyiv or Warsaw, or fully remote.

• Generous Paid Time Off: 20 paid vacation days, in addition to public holidays and sick leave.

• Comprehensive Health & Wellness: Medical insurance with top clinics and coverage for psychologist services via the Pleso platform.

• Benefit Cafe: Monthly budget to spend on personal preferences, hobbies, sports, etc.

• Engaging Events: Participation in masterclasses, team-building events, and corporate parties.

• Learning & Development Budget: Individual budget for courses, corporate English classes, workshops, and access to an online library.

• Mentoring Programs: Opportunities for professional guidance and career development.

• Performance Reviews: Regular performance reviews with clear career pathing.

• Individual Development Plans (IDPs): Structured plans for personal and professional growth.

Working Hours: Standard 40-hour work week, with flexibility and a focus on work-life balance, allowing for remote work arrangements.

📝 Enhancement Note: The salary estimate is based on industry benchmarks for senior design leadership roles in Ukraine, considering the specialized nature of performance marketing and the iGaming industry. The benefits package is extensive and aligns with modern tech company offerings.

🎯 Team & Company Context

🏢 Company Culture

Industry: Product IT company focused on technological solutions and B2B services, with a strong presence in the iGaming sector. The company also holds a B2B license for gambling services in Ukraine, emphasizing its commitment to a legal and transparent market.

Company Size: While not explicitly stated, the requirement to manage a design team of 15+ people, coupled with the mention of scaling projects and a "dream team," suggests a mid-to-large-sized organization, likely employing several hundred to over a thousand employees.

Founded: Founded prior to 2026, with the company actively scaling projects and its team in 2026. The company has a history of launching successful projects recognized by industry ratings.

Team Structure:

• The Design function is structured with a clear hierarchy, led by the Head of Design, who manages multiple Team Leads responsible for specific design disciplines (Visual Graphic & Motion, Motion Creators, App Design, Product Design).

• This multi-layered structure indicates a focus on specialization and efficient management of a large, diverse design output.

• Collaboration is expected to be cross-functional, involving close partnerships with Marketing, Media Buying, Product, and other departments to ensure design efforts are aligned with business goals. Methodology:

• Data-Driven Performance: A core methodology involves leveraging data from media buying metrics (CTR, CPA, CR, ROI) to inform and optimize creative production. A/B/n testing is a key component of this.

• Process Optimization & Automation: The company emphasizes streamlining workflows, identifying and eliminating bottlenecks, and implementing automation, AI, templates, and Design Systems to increase production efficiency.

• Agile & Iterative Approach: The focus on high-volume, performance-driven creatives suggests an iterative approach where designs are rapidly produced, tested, and refined based on performance feedback.

• Strategic Planning: A long-term vision for the design function (6-12+ months) is crucial, requiring strategic planning that aligns with broader business objectives.

Company Website: https://career.upstars.com

📝 Enhancement Note: The company culture appears to be performance-oriented, valuing efficiency, data-driven decisions, and rapid iteration, common in high-volume performance marketing and iGaming sectors. The emphasis on "no bureaucracy" and "freedom of action" suggests an agile and modern work environment.

📈 Career & Growth Analysis

Operations Career Level: This role represents a senior leadership position, a "Head of" level, responsible for a significant function within the company. It sits at the intersection of design leadership and operations management, with a strong emphasis on the latter. The scope includes strategic planning, team building, process engineering, and direct impact on business performance.

Reporting Structure: The Head of Design reports directly to C-level executives, likely the CEO, COO, or a Chief Product/Marketing Officer, indicating the strategic importance of the design function to the company's success. They are responsible for managing Team Leads, who in turn manage individual contributors.

Operations Impact: The Head of Design is directly accountable for the performance and efficiency of the entire design function, with a critical role in optimizing creative assets that drive key business metrics such as Click-Through Rates (CTR), Conversion Rates (CR), Cost Per Acquisition (CPA), and Return on Investment (ROI) for media buying campaigns. Their decisions and team's output have a tangible and measurable impact on the company's revenue and profitability.

Growth Opportunities:

• Strategic Leadership Expansion: Potential to expand responsibilities into broader GTM strategy, product marketing leadership, or even overseeing related operational functions beyond design.

• Advanced Operations & Process Engineering: Opportunities to deepen expertise in scaling operations, implementing advanced automation, and driving significant business process re-engineering across departments.

• Executive Influence: Continued opportunities to influence company-wide strategy and operations through direct engagement with C-level leadership and by demonstrating the value of design operations.

• Industry Specialization: Deepen expertise within the high-growth iGaming and performance marketing sectors, becoming a recognized leader in design operations for these verticals.

• Mentorship & Team Development: Further develop leadership and coaching skills by nurturing future leaders within the design team and potentially across other operational areas.

📝 Enhancement Note: The career trajectory for this role moves beyond traditional design management into a strategic operational leadership position, with significant potential for growth into broader executive roles focused on performance and GTM strategy.

🌐 Work Environment

Office Type: The company offers a hybrid work model with options for working from physical hubs in Kyiv and Warsaw, or a fully remote setup. This provides flexibility and choice for employees.

Office Location(s): Key physical hubs are located in Kyiv, Ukraine, and Warsaw, Poland. The remote option extends the geographical reach for talent acquisition.

Workspace Context:

• Flexibility & Choice: Employees can choose to work from a company hub for collaborative environments or work remotely, catering to different preferences and needs.

• Technology-Centric: Given the company's focus on technological solutions and automation, expect a modern tech stack and tools to support remote and hybrid collaboration, including robust communication platforms and project management software.

• Collaborative Culture: Despite remote options, the company values teamwork and collaboration, evidenced by team-building events and the expectation of close interaction with cross-functional teams. The hubs likely facilitate in-person collaboration and team cohesion.

Work Schedule: A standard 40-hour work week is expected, aligning with full-time employment. The emphasis on "work-life balance" and "freedom of action" suggests a culture that values results over strict adherence to hours, provided objectives are met. The remote options further support flexible scheduling within reasonable operational boundaries.

📝 Enhancement Note: The blend of physical hubs and remote work options reflects a modern approach to talent management, aiming to attract and retain top talent by offering flexibility while still fostering a sense of community and collaboration.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A review of your application, resume, and portfolio to assess alignment with the core requirements, particularly leadership experience in performance creative production.

• Hiring Manager Interview: A deep dive into your experience managing large design teams, understanding of performance marketing metrics, process optimization strategies, and leadership philosophy. Expect scenario-based questions related to team management, resource allocation, and conflict resolution.

• Team/Cross-Functional Interviews: Meetings with potential peers or stakeholders from Media Buying, Marketing, or Product teams to assess collaboration style, communication skills, and understanding of their respective functions.

• C-Level Interview: A strategic discussion with senior leadership to evaluate your vision for the design function, ability to align with business strategy, financial acumen (budget management), and overall leadership potential within the company.

• Portfolio Presentation: A dedicated session to present a curated selection of your work, focusing on case studies that demonstrate your operational leadership, process improvements, team development, and impact on business metrics.

Portfolio Review Tips:

• Focus on Operations & Impact: Prioritize case studies that showcase your experience in scaling design operations, optimizing production workflows, and driving measurable results (CTR, CPA, ROI).

• Structure for Clarity: Organize your portfolio around key responsibilities: team management, process development, cross-functional collaboration, and strategic planning. Use clear headings and concise descriptions.

• Quantify Achievements: Whenever possible, use data and metrics to demonstrate the impact of your initiatives. For example, "Increased creative production by 30%," or "Improved CTR by 15% through A/B testing."

• Highlight Leadership: Include examples of how you've built, mentored, and managed teams. Showcase your approach to talent development and fostering a high-performing culture.

• Demonstrate Strategic Thinking: Explain the "why" behind your decisions and how your design strategy aligned with broader business objectives.

• Prepare for Q&A: Be ready to discuss your methodologies, challenges faced, lessons learned, and how you would approach specific scenarios relevant to UPSTARS' business.

Challenge Preparation:

• Process Design Exercise: You might be asked to outline a process for managing a high volume of creative requests, including prioritization, resource allocation, and quality control.

• Strategic Vision Presentation: Prepare to discuss your vision for evolving a design function in a performance-driven environment over the next 6-12 months, including potential use of AI and automation.

• Team Management Scenarios: Be ready to answer questions about managing underperforming team members, resolving conflicts between team leads, or scaling a team rapidly.

📝 Enhancement Note: The interview process is designed to assess not only design leadership but also strong operational management, strategic thinking, and the ability to drive business results in a performance-focused environment. The portfolio review is a critical component for demonstrating these operational capabilities.

🛠 Tools & Technology Stack

Primary Tools:

• Design Software: Proficiency with industry-standard design tools is assumed, but the focus will be on managing teams that use them effectively. This includes Adobe Creative Suite (Photoshop, Illustrator, After Effects), Figma, Sketch, etc.

• Project Management & Workflow: Tools like Jira, Asana, Trello, Monday.com, or similar platforms for task tracking, workflow management, and team collaboration.

• Collaboration & Communication: Slack, Microsoft Teams, Google Workspace for daily communication, file sharing, and team coordination.

• Asset Management: DAM (Digital Asset Management) systems or cloud storage solutions for organizing and distributing creative assets.

Analytics & Reporting:

• Performance Tracking: Familiarity with platforms used for tracking ad performance, such as Google Analytics, Mixpanel, Amplitude, or similar.

• Media Buying Platforms: Understanding of how design performance is tracked within platforms like Google Ads, Facebook Ads Manager, and affiliate tracking software.

• Data Visualization: Tools like Tableau, Power BI, Looker Studio (formerly Google Data Studio) for creating dashboards and reports to communicate design impact to C-level.

CRM & Automation:

• CRM Systems: While not a primary focus for this role, an understanding of how design assets integrate with CRM or marketing automation platforms might be beneficial.

• Automation Tools: Experience with tools for automating repetitive design tasks, workflow triggers, or reporting processes. This could include scripting, Zapier, or specialized design automation software.

• AI Tools: Familiarity with AI-powered design tools for content generation, image enhancement, motion graphics creation, or workflow optimization (e.g., Midjourney, Stable Diffusion, generative AI for video).

📝 Enhancement Note: The technology stack emphasizes tools that support high-volume production, collaboration, data analysis, and automation, reflecting the operational demands of the role. A strong understanding of how design integrates with performance marketing technology is key.

👥 Team Culture & Values

Operations Values:

• Teamwork & Collaboration: A strong emphasis on working together, both for project execution and for social activities. The company fosters a supportive environment where team members contribute to collective success.

• Positivity & Drive: A culture that encourages enthusiasm for work, finding joy in accomplishments, and deriving energy from challenging tasks, feedback, and peer interactions.

• Opportunity & Growth: Commitment to providing clear career paths, performance reviews, mentorship, and training to support employees' professional and personal development.

• Boldness & Ambition: A willingness to take on ambitious projects and challenges, push boundaries, and pursue significant goals.

• Openness & Proactivity: Encouraging direct and honest communication, valuing diverse ideas and feedback, and rewarding proactive contributions.

• Efficiency & Automation: A core operational value that drives the company to automate routine tasks, allowing employees to focus on higher-value activities and professional growth.

• Freedom & Autonomy: A culture that minimizes bureaucracy and empowers individuals with the freedom to act and make decisions, fostering ownership and innovation.

Collaboration Style:

• Cross-Functional Integration: The design function is expected to work closely with Marketing, Media Buying, and Product teams, requiring strong communication and alignment to achieve common business objectives.

• Process-Oriented Feedback: A culture that encourages open discussion and feedback on processes, with an aim to continuously improve workflows and efficiency.

• Knowledge Sharing: Encouraging the sharing of best practices, learnings from experiments, and insights across teams to foster collective learning and development.

• Experimentation: A willingness to experiment with new approaches, tools, and methodologies in design and production, supported by data analysis and performance metrics.

📝 Enhancement Note: The company culture is a blend of high-performance expectations common in aggressive growth sectors, combined with a modern, employee-centric approach that values collaboration, growth, and autonomy.

⚡ Challenges & Growth Opportunities

Challenges:

• Scaling Creative Production: Managing the demand for a high volume of performance creatives while maintaining quality and efficiency will be a significant, ongoing challenge. This requires robust process engineering and team management.

• Adapting to Market Trends: The fast-paced nature of performance marketing and iGaming means staying ahead of evolving creative trends, platform algorithms, and competitor strategies.

• Balancing Speed and Quality: Ensuring that rapid creative production does not compromise the effectiveness or quality of the assets, especially under tight deadlines.

• Cross-Functional Alignment: Effectively coordinating with multiple departments (Media Buying, Marketing, Product) that have distinct priorities and require different types of creative output.

• Team Development & Retention: Attracting, developing, and retaining top design talent in a competitive market, particularly those with specialized skills in performance creative.

Learning & Development Opportunities:

• Advanced Operations Leadership: Opportunities to deepen expertise in scaling operational functions, implementing advanced automation, and driving strategic process improvements beyond the design department.

• Performance Marketing Strategy: Gaining deeper insights into the intricacies of media buying, affiliate marketing, and performance analytics, becoming a strategic partner in revenue generation.

• AI & Future of Creative Production: Leading the charge in adopting and integrating cutting-edge AI and automation technologies to revolutionize creative workflows.

• Executive Communication & Strategy: Refining skills in presenting to C-level, influencing strategic decisions, and contributing to the broader business strategy of a growing IT company.

• Mentorship & Leadership Development: Opportunities to mentor junior leaders and contribute to the development of the broader leadership team within the company.

📝 Enhancement Note: The role presents significant operational challenges that are directly tied to business growth, offering substantial opportunities for professional development in areas critical to modern GTM and revenue operations.

💡 Interview Preparation

Strategy Questions:

• "Describe your experience building and managing a large design team in a high-volume performance marketing environment. What were your key strategies for ensuring efficiency and quality?"

• "How would you approach designing and implementing a new creative production workflow from scratch to handle hundreds of assets per week, including brief intake, prioritization, and delivery?"

• "Walk me through a time you used A/B testing of creatives to significantly improve CTR or conversion rates. What was your role, and what were the key learnings?"

• "How do you measure the ROI of a design function, and how do you communicate that value to C-level executives?"

• "What is your vision for integrating AI and automation into a performance creative production workflow, and what are the potential challenges?" Company & Culture Questions:

• "Based on your understanding of UPSTARS, how would you align the design function's strategy with our business objectives in the iGaming and B2B tech sectors?"

• "How do you foster a culture of collaboration and open communication within a geographically dispersed or hybrid design team?"

• "What are your core leadership principles, and how do they align with our company values of teamwork, positivity, boldness, and openness?"

• "Describe a situation where you had to make a difficult decision with incomplete information. How did you approach it, and what was the outcome?" Portfolio Presentation Strategy:

• Structure by Impact: Organize your presentation around key themes: Team Leadership, Process Optimization, Performance Impact, and Strategic

Vision.

• Case Study Deep Dive: Select 2-3 detailed case studies that best illustrate your operational leadership. For each:

  • Clearly define the problem/challenge.
  • Explain your strategic approach and the processes you implemented.
  • Quantify the results with specific metrics (e.g., % increase in output, % improvement in CTR, reduction in turnaround time).
  • Discuss the team's role and your leadership in managing them.

• Demonstrate Tools & Methodologies: Be prepared to discuss the specific tools, technologies, and methodologies you've used to achieve your results.

• Address Future Vision: Conclude by briefly outlining how your experience and approach would benefit UPSTARS, linking it to their stated goals of scaling and innovation.

📝 Enhancement Note: Preparation should focus on demonstrating operational expertise, strategic thinking, and a results-oriented mindset, rather than just showcasing creative aesthetics. The ability to speak the language of business metrics and process efficiency is paramount.

📌 Application Steps

To apply for this operations position:

• Submit your application through the provided link on the UPSTARS career page.

• Curate Your Portfolio: Select and prepare case studies that specifically highlight your experience in leading design operations, scaling creative production for performance marketing, implementing process improvements, and driving measurable business impact. Quantify your achievements with data.

• Optimize Your Resume: Tailor your resume to emphasize leadership experience, operational responsibilities, performance marketing knowledge, and quantifiable achievements. Use keywords from the job description such as "performance marketing," "creative production," "process optimization," "team management," and "ROI."

• Prepare Your Presentation: Rehearse a clear and concise presentation of your portfolio, focusing on demonstrating how your operational leadership and strategic approach can benefit UPSTARS. Be ready to articulate your vision and address potential challenges.

• Research UPSTARS: Familiarize yourself with UPSTARS' business in iGaming and B2B tech, their company values, and their commitment to a legal and transparent market. Understand their focus on automation and efficiency.

⚠️ Important Notice: This enhanced job description includes AI-generated insights and operations industry-standard assumptions. All details should be verified directly with the hiring organization before making application decisions.

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