AI-Driven Engineering Leadership

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AI-Driven Head of Engineering

Grigoriy Dobryakov

I build engineering organizations where AI is embedded at every layer — how teams write and review code, how the product learns from data, how operational contours use signals. Not an initiative, not a department — a way of operating. Where companies hire VP Engineering and Head of AI separately, I cover both levels with unified accountability for results.

Market Segments

Where I create the highest value.

AI-Committed Organizations

Companies that have moved past the "exploring AI" stage and made a board-level decision: AI becomes the operating model, not a single-department initiative. They need a permanent owner — someone who is simultaneously accountable for people, delivery, and AI being embedded at every layer.

  • • Key benefit: AI embedded in the organization, not bolted on top.
  • • Expert role: permanent function owner, not a consultant with a roadmap.
  • • Message: where companies typically hire two people who don't speak the same language — one person with unified accountability.
  • • Engagement shape: priority is fulltime; entry via 30-day AI Engineering Diagnostic with a concrete deliverable.
  • • Typical profile: 150–1500 employees, PE-backed or post Series B with a board-level AI mandate.

Enterprise in AI Transformation

Large corporations with legacy landscapes where the cost of failure is high and business processes must not break during AI adoption. Focus: safe AI integration into running systems, controlled pace of change, and predictable timelines under governance constraints.

  • • Key benefit: AI in production without losing business continuity.
  • • Expert role: architectural and managerial guarantor of stability during transformation.
  • • Message: AI is embedded into the existing landscape with explicit governance rules, not a "big bang" replacement.
  • • Engagement shape: fulltime as HoE or Director of Engineering; with headcount limits — fractional with clear scope and practices handover.

AI Scale-up (Series B/C)

Fast-growing companies where the product is already flying, but AI practices are ad hoc: parallel initiatives, none in production, no clear owner. Focus: building an AI-driven engineering culture without losing development pace.

  • • Key benefit: AI in SDLC, product, and operations as a repeatable system — not one engineer's magic.
  • • Expert role: the adult in the room for founder-led companies, turning AI experiments into production practice.
  • • Message: mature AI engineering as an accelerator, not a constraint — speed with control.
  • • Engagement shape: mostly fulltime for scaling; fractional as a deliberate 3–6 month bridge with explicit responsibility boundaries.

Traditional Business (banks, retail, industry)

Companies that want measurable results from AI with a pragmatic approach and clear economics of change. Focus: cost reduction, profitability growth, and reliable transformation without chasing hype.

  • • Key benefit: AI as profit, not hype.
  • • Expert role: a bridge between proven practices and the new technology wave.
  • • Message: predictable outcomes in business language — unit economics, throughput, and cost-to-serve.
  • • Additional focus: when operational scale starts pressuring margins.

Cases

Evidence, metrics, and business outcomes.

Askona — AI leadership and enterprise architecture

Event-driven architecture, AI practices in production, and team enablement for sustainable growth in a large ecosystem.

  • • Context: 15M customers, $680M+ turnover, 20+ distributed teams, 40+ services.
  • • Action: enterprise architecture + hands-on AI leadership; AI bot over data lake (NL -> SQL), personally designed and trained next best offer ML model, order lifecycle timestamp tracker, AI-assisted coding in practical microservices, and dozens of training sessions for 100-200 participants each.
  • • Result: release cadence and T2M accelerated, platform reliability increased, cross-team friction decreased, and bottleneck visibility improved. Under my leadership, AI became the primary operating pattern across all levels, from management decisions to engineering execution.
Open case

UMI.CMS/UMI.RU — transition from boxed product to SaaS

Rebuilt the product lifecycle and engineering processes for a scalable transition to a cloud model.

  • • Context: 65k clients → 1M+ users.
  • • Action: engineering-function turnaround — department reorganization, engineering culture adoption, QA/DevOps rollout, and test farm scaling.
  • • Result: 50% revenue growth, controlled scaling, weekly releases instead of quarterly.
Open case

KORUS Consulting — turnaround and restored predictability

An engineering department in a B2B integrator under pressure: unstable delivery, strategic contract risk, and margin pressure.

  • • Context: B2B services with a high cost of failure and rising reputation risk.
  • • Action: turnaround — team rebuild, quality governance, test automation scaling, and de-escalation of critical client situations.
  • • Result: restored delivery predictability, higher profitability, and lower dependence on manual heroics.
Open case

PersonaClick — ML and personalization at scale

Modernized the personalization platform with ML and predictive analytics to remove infrastructure bottlenecks.

  • • Context: 199M+ user profiles.
  • • Action: engineering and platform evolution, ML/predictive analytics integration, bottleneck removal.
  • • Result: stronger cashflow and client retention, higher platform speed and stability.
Open case

Who This Is For

Different stakeholders get different, measurable value.

CEO / Founder

When you need an engineering organization where AI is the operating model — not one department's experiment — I take ownership of the whole function and free your time for strategy.

  • • Focus: AI as competitive advantage, not a cost center; managed growth without proportional overhead.
  • • Value: in 90 days you have a map — where AI works, where it doesn't, and who owns what.

CTO / VP Engineering

When you need one person you can trust with people, AI architecture, and delivery — not two separate hires — I cover all three levels with unified accountability for production outcomes.

  • • Focus: delivery predictability + AI embedded in SDLC + architectural trade-offs without accumulating technical debt.
  • • Value: C-level peace of mind, less management overload, AI in the pipeline as team practice — not one engineer's personal habit.

Head of AI / VP AI

When the AI roadmap exists but its translation into engineering practice stalls, I bridge the gap between architectural decisions and how teams actually work every day.

  • • Focus: production readiness of AI systems, team enablement, governance, and observability of the AI layer.
  • • Value: AI initiatives reach production instead of dying in pilots.

Chief Digital Officer

When the digitalization roadmap needs to land as outcomes, I align business goals with engineering execution without losing manageability.

  • • Focus: AI initiative portfolio execution, transformation risk management, business–technology alignment.
  • • Value: digital projects reach production in a predictable mode.

HR / Head of Recruitment

A rare combination: engineering leadership + AI systems expertise in one profile — fills roles that would otherwise require two hires with coordination overhead between them.

  • • Focus: lower hiring risk for a complex combined role; explicit JD fit on scale, stack, and scope.
  • • Value: a candidate who is easy to defend to CTO and CEO simultaneously.

Chief Architect

When architectural integrity must survive AI transformation, I embed new practices without breaking the foundation or creating unmanageable AI technical debt.

  • • Focus: managed architectural debt, AI solution compatibility with the existing landscape, reliable change.
  • • Value: platform growth without increasing fragility.

Expertise

AI as an operating model — not one-off prompts, but a repeatable operating layer across three dimensions: SDLC, product, and operations.

What you get

  • AI as the operating model, not a feature — I diagnose where AI creates real leverage for your engineering organization right now, then embed it across three layers: how teams work, how the product operates, how operations use data.
  • Predictable delivery as a baseline — I start with what breaks delivery now: SDLC bottlenecks, architecture debt, organizational friction. Timelines and quality without black swans.
  • Leadership at scale — multiple teams and leads, clear ownership boundaries, growing people without diluting execution standards.
  • One person instead of two — where VP Engineering and Head of AI don't speak the same language, I cover both levels with unified accountability for business outcomes.

AI in SDLC

  • AI-assisted coding as team practice — not one engineer's personal habit, but a repeatable workflow with explicit standards and patterns handed to the whole team.
  • AI in testing and review — test case generation, defect analysis, AI in code review: faster cycle without lowering the quality bar.
  • Observability of AI in the production pipeline — model decision logging, human-in-the-loop checkpoints, audit trails; AI in production is visible and managed, not a black box.

AI in Product and Operations

  • Production-ready AI architecture — RAG with proper knowledge structure (not "dump a PDF into a vector DB"), agentic pipelines, recommendation systems; designed for real enterprise constraints: security, legacy, governance.
  • Event-driven AI — LLM as a consumer of event streams (Kafka, webhooks, monitoring alerts, CI events): intelligent event processing, not a chatbot.
  • AI in marketing and business processes — repeatable systems with measurable output, not "let's ask ChatGPT."

Stack and domains

  • AI layer: Anthropic Claude (API, MCP, tool use), OpenAI-compatible interfaces, Gemini; RAG/agentic patterns in enterprise contexts, n8n orchestration, Python + APIs.
  • AI tooling and protocols: Cursor IDE, Claude Code, MCP integrations, and tool routing for engineering and research scenarios.
  • Cloud and platform: AWS, Ansible (IaC), Docker Hub; hybrid / multi-region; virtualization and the VM layer.
  • Integration and events: Kafka, RabbitMQ, APIs, event-driven architecture.
  • Data and analytics: SQL, Elasticsearch, ELK, ClickHouse; vector stores.
  • Quality and delivery: phpunit, Cypress, CI/CD, automated testing pipelines.
  • Enterprise integrations: 1C, Bitrix, ERP / WMS / BI, SAP.

Methods

  • • AI Engineering governance: observability, prompt injection defense, data isolation, human-in-the-loop.
  • • Engineering governance and operational delivery discipline.
  • • Agile planning and execution practices (planning / review / refinement).
  • • CI/CD, test automation, quality gates, release reliability.
  • • DevOps, IaC, SRE thinking for sustainable operations.
  • • Legacy modernization with controlled architectural debt.

Why this matches market expectations

  • • I lead multiple teams and managers and build a repeatable delivery model — not heroics from individuals.
  • • AI in SDLC is not one-off prompts but a managed operating layer (governance, observability, clear ownership).
  • • Positioning is grounded in real production cases: Askona — RAG and event-driven AI at $680M+ scale; PersonaClick — ML on 199M+ profiles; nextmoveengine.com — own AI system as "eat what I cook."
  • • In high-pressure environments I keep predictability without artificially slowing growth — through prioritization and transparent trade-offs.

Materials

A single hub with all public assets: blogs, videos, courses, community, project, and profiles.

Blogs and Articles

Practical writing on project management, engineering leadership, software delivery, and applied AI in production contexts.

Videos and Courses

Public video materials on engineering leadership, architecture, and practical AI operations.

Vstup.AI Community

"AI through the eyes of a technical manager with 25+ years in IT": role analysis, AI adoption patterns, orchestration, and SDLC integration.

Looking for an engineering organization where AI is a way of operating, not a separate initiative?

How we can work together

  • Fulltime Head of Engineering — permanent owner of the AI-driven engineering function; full cycle of people + delivery + AI architecture + culture. Horizon: one year and beyond.
  • Fractional — fixed weekly capacity, agreed scope (AI architecture review + team enablement + AI-in-SDLC roadmap), success criteria, and handover to an internal owner; fits headcount constraints or as a bridge to a permanent role.
Discuss Your Challenge

Entry offer: AI Engineering Diagnostic

AI Engineering Readiness Assessment — up to 5 days, async mode: interviews with key stakeholders, artifact review (architecture, delivery metrics, AI backlog), diagnostics across three layers (team/SDLC, product, operations).

Deliverable: AI Engineering Readiness Map — current state, top-3 highest-leverage points, 90-day plan with named owners and success criteria. Concrete enough to execute without external help.

Funnel: Diagnostic → fulltime (on mutual fit) or fractional (with limited scope/budget) or off-ramp with plan handover. All three outcomes are honest and agreed upfront.