Head of Technology and AI Strategy

Golabs Tech | Costa Rica | Full-time

Golabs Tech is looking for a Head of Technology & AI Strategy to shape the company’s technology direction and lead the development of its AI practice.

This is a senior strategic leadership role focused on understanding where the technology market is moving, assessing competitive and emerging technology signals, and turning those insights into clear priorities for the business. The role also leads Golabs’ AI function, strengthening internal capabilities, guiding experimentation, and developing a commercially relevant AI portfolio.

The Head of Technology & AI Strategy reports directly to the CEO and works closely with the board of directors.

Responsibilities

Technology Strategy & Competitive Positioning

• Define Golabs’ technology strategy based on industry developments, competitive activity, client needs, and emerging technologies.
• Assess technology trends and shifts in client demand to determine where Golabs should invest, build capabilities, or change direction.
• Turn external technology and competitive signals into clear recommendations, priorities, and action plans for executive leadership.
• Advise the CEO and board on technology opportunities, risks, investments, and strategic positioning.
• Manage technology OKRs and report progress, results, and key findings to executive leadership.
• Lead decisions related to technology investments, platforms, tools, partnerships, and market positioning.

AI Practice Leadership

• Lead the development of Golabs’ AI practice, including team capabilities, operating processes, priorities, and areas of specialization.
• Define the company’s AI portfolio, priority use cases, and value proposition based on market demand and validated internal work.
• Structure AI initiatives around clear business objectives, value hypotheses, and measurable success criteria.
• Evaluate the business impact and ROI of AI initiatives as they move from experimentation into broader adoption.
• Identify and manage strategic technology and AI partnerships.
• Lead internal AI training initiatives and strengthen AI fluency across the organization.
• Develop case studies and documented use cases that support commercial discussions and market positioning.

Commercial & Advisory Support

• Support sales and business development efforts where senior technology or AI expertise is required.
• Advise clients on AI strategy, use cases, adoption priorities, and implementation approaches.
• Lead high-level client conversations to understand business challenges, identify opportunities, and define potential consulting engagements.
• Build and review technical and strategic proposals with the commercial team.
• Identify opportunities to expand existing accounts by connecting client needs with Golabs’ technology and AI capabilities.

External Presence & Internal Culture

• Represent Golabs at industry events, webinars, conferences, and client-facing sessions.
• Communicate complex technology and AI topics clearly to both technical and business audiences.
• Help build an internal culture that encourages autonomy, ownership, learning, and experimentation.
• Travel domestically and internationally when required.

Presence & Culture

• Represent Golabs at industry events, webinars, and conferences, with the ability to present clearly, explain complex topics, and lead meaningful conversations.
• Support the development of an AI-oriented internal culture built on autonomy, ownership, and experimentation.
• Travel domestically and internationally when needed.

Requirements

• 15 to 20 years of experience in technology, including at least 10 years in senior leadership or strategic roles.
• Academic background in systems engineering, computer science, or a related technical field. Business training or executive education is strongly valued.
• Strong business judgment and the ability to connect technology decisions with market opportunities, client needs, and financial outcomes.
• Deep technical fluency in applied AI — including machine learning models, AI architectures, and emerging technologies — with the ability to engage substantively on technical topics with clients and stakeholders.
• Experience building, managing, or scaling technology or AI teams.
• Experience in consultative sales, technical pre-sales, technology advisory, or a similar client-facing environment.
• Ability to guide senior clients through AI strategy and translate business challenges into technology initiatives.
• Experience working directly with CEOs, executive leadership teams, or boards of directors.
• Experience managing OKRs, strategic priorities, and performance metrics.
• Advanced English for regular interaction with US-based clients and stakeholders.
• Based in Costa Rica and employed through local payroll.
• Preferred: Valid US B1/B2 visa.

Why This Role

• You will help define Golabs’ technology direction instead of executing a vision already decided by someone else.
• You will have real autonomy over technical, investment, and positioning decisions.
• Your work will directly influence Golabs’ growth, client relationships, AI strategy, and market positioning.