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Open nowPosted 214 days ago

Senior Strategic Technical Advisor (AI Strategy)

Workable (global search)108,016 open roles

Where
Sofia, Sofia City Province, Bulgaria
Work mode
Remote
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Your applicationOpen nowSenior Strategic Technical Advisor (AI Strategy)Workable (global search) · Sofia, Sofia City Province, Bulgaria

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Early applications get read.

7.9% of postings close within 7 days. Measured by our own scanner across the market. Workable (global search) postings stay open a median of 7 days.

Share of postings closed within
  1. 1.6%1 day
  2. 3.6%3 days
  3. 7.9%7 days
  4. 14.9%14 days
  5. 34.0%30 days
This job: posted 214 days ago

Workable (global search) median: 7 days open

The posting

Senior Strategic Technical Advisor (AI Strategy)

Role Overview

The Senior Strategic Technical Advisor is a high-level technology leader responsible for shaping AI strategy, technical architecture direction, and long-term systems design across complex technology environments.

This is not a day-to-day engineering role.

This role exists to provide strategic technical clarity, architecture guidance, and decision-making support to leadership teams building modern, scalable technology ecosystems.

You are a seasoned technical leader who understands how to evaluate complex systems, identify risks and opportunities, and guide organizations toward sustainable, scalable, and secure technology strategies.

You operate comfortably at the intersection of AI, architecture, and executive decision-making.

You will collaborate with leadership, engineering, and product teams to inform technical direction, validate architecture decisions, and support innovation initiatives.

This is an outcomes-driven advisory engagement, ideal for experienced technology executives, principal architects, or AI leaders seeking flexible strategic involvement without a full-time operational commitment.

Core Responsibilities

Technology Strategy & Architecture Direction

  • Provide high-level guidance on long-term technology strategy, platform architecture, and scalable system design.
  • Advise on modern infrastructure patterns including cloud architectures, distributed systems, APIs, and platform engineering practices.
  • Support the evaluation and integration of AI technologies and emerging tools aligned with business objectives.
  • Review existing architecture and provide clear strategic recommendations for improvement, scalability, and resilience.

Strategic Technical Reviews & Deliverables

Produce high-impact strategic artifacts that support executive and technical decision-making.

This may include:

  • Architecture reviews
  • Technical evaluation reports
  • AI integration strategies
  • Threat modeling and risk analysis
  • Technology roadmap recommendations
  • Reference architecture frameworks

Deliverables should translate complex technical considerations into clear, actionable guidance for leadership teams.

Cross-Functional Collaboration

  • Work with product, engineering, analytics, and operations teams to align technology initiatives with organizational goals.
  • Participate in strategic discussions around product innovation, system scalability, and infrastructure planning.
  • Support leadership teams in evaluating trade-offs between speed, cost, complexity, and long-term maintainability.

Strategic Advisory Sessions

  • Facilitate periodic technical strategy reviews, design discussions, and advisory sessions with internal teams and stakeholders.
  • Provide independent perspective on critical technology decisions and help prioritize initiatives with the highest long-term impact.
  • Engagements may include architecture clinics, roadmap reviews, or advisory consultations with senior leadership.

Mentorship & Technical Leadership Support

Provide guidance to internal engineering leaders, architects, and technical leads.

Share best practices across areas such as:

  • AI implementation strategies
  • Modern architecture patterns
  • Scalable platform design
  • Security and risk mitigation
  • Technical governance frameworks

The goal is to strengthen internal technical leadership while accelerating strategic decision quality.

Requirements

Required Skills & Experience

  • Minimum 10+ years of experience in senior technical leadership roles such as:
  • Principal Architect
  • CTO / VP Engineering
  • Solutions Architect
  • AI or Platform Architecture Lead
  • Deep expertise in modern software architecture and distributed systems.
  • Strong understanding of AI technologies, machine learning systems, and emerging technology ecosystems.
  • Demonstrated experience advising or leading large-scale technology initiatives or platform transformations.
  • Excellent ability to communicate complex technical ideas in clear, strategic, and actionable terms.
  • Experience influencing executive-level decision making within complex technology environments.
  • Ability to operate independently in consulting or fractional advisory engagements.

Application Requirements

Applicants must submit:

  • A brief overview of recent strategic technology engagements or advisory work
  • A short statement outlining your technical leadership philosophy
  • A high-level portfolio of relevant strategic work, which may include:
  • Architecture reviews
  • AI strategy documents
  • Technology roadmaps
  • Design reviews
  • Strategic technical evaluations

Applications are reviewed confidentially, and shortlisted candidates will receive further details regarding the organization and project scope.

Ideal Candidate

  • Senior technology executive or architect with deep strategic experience
  • Comfortable advising across AI, architecture, and platform strategy
  • Strong systems thinker with a long-term technical vision
  • Able to quickly assess complex environments and provide clear strategic guidance
  • Experienced working with leadership teams on high-impact technology decisions

Benefits

Compensation

Compensation is structured as consulting or advisory fees, which may be Hourly advisory rates or Monthly strategic retainers, Project-based engagements aligned with experience, expertise, and strategic impact.

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