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Head of Delivery

CDMXRemoteFull-time

AI Summary

Head of Delivery leads the design and stewardship of Capptus’ AI-first delivery system, aligning human judgment, systems thinking, and lightweight but rigorous processes to improve delivery across projects.

About this role

The Head of Delivery is the architect and steward of Capptus’ delivery operating system.

Their mission is to design a delivery environment where:

  • AI removes execution friction
  • Human judgment, taste, and systems thinking drive decisions
  • Small, high-leverage teams consistently outperform larger, siloed ones
  • Knowledge compounds across projects instead of resetting each time

Core Responsibilities (AI-First & System-Led):

1. Design the AI-First Delivery System (Primary Responsibility)

  • Define how work flows from idea → delivery → learning:
    • Where AI assists exploration, design, testing, and documentation
    • Where human review and judgment are mandatory
    • Where decisions must be explicit, documented, and reversible
  • Ensure all delivery roles operate in shared mediums:
    • Same artifacts
    • Same tooling
    • Same understanding of context
    • Minimal handoffs

2. Elevate Judgment as the Core Delivery Skill

  • Redesign delivery expectations so senior roles are evaluated on:
    • Quality of architectural decisions
    • Tradeoff clarity
    • Ability to frame problems, not just solve tasks
  • Institutionalize judgment rituals:
    • Lightweight decision reviews
    • Explicit assumptions and risk articulation
    • “What would make this decision wrong?” discussions
  • Protect time for thinking:
    • Architects and leads are not fully utilized

    • Slack is intentional, not waste
    • Judgment degrades under constant execution pressure

3. Operate Delivery as a Living System

  • Treat delivery as:
    • Inputs (scope, constraints, talent, customer context)
    • Flow (work in progress, dependencies, decisions)
    • Outputs (value, quality, margin)
    • Feedback (learning, reuse, improvement)
  • Identify and act on:
    • Bottlenecks
    • Feedback delays
    • Misaligned incentives
    • Over-optimization of local metrics
  • Use data (including Certinia) as signals, not commands.

4. Certinia as Observability, Not Control

  • Surface patterns and constraints
  • Track financial and delivery reality
  • Enable fast, informed decisions

5. Knowledge as a System Output

  • Every project must produce:
    • Reusable patterns
    • Decision rationales
    • What-worked / what-didn’t insights
  • AI is used to:
    • Extract learning from delivery artifacts
    • Summarize complex projects
    • Connect current teams with prior context
  • Knowledge ownership is explicit:
    • Assets are curated, pruned, and reused
    • Learning feeds back into future delivery design

6. Talent Development for Systems Thinkers

What the HoD Builds

  • Consultants and developers who:
    • Understand the full delivery system
    • Can reason across data, platform, business, and customer context
    • Specialize deeply in judgment-heavy domains

  • Clear progression:
    • From task execution → problem framing → system ownership → mentorship
  • Juniors are onboarded into thinking, not just doing:
    • Early exposure to decisions
    • Explicit explanation of tradeoffs
    • AI used as a learning accelerator

7. Customer as Part of the System

  • Customers are treated as:
    • Active participants in delivery
    • Decision-makers with constraints
    • Sources of feedback, not interruptions
  • SteerCos are:
    • Alignment forums
    • Constraint-renegotiation spaces
    • Shared judgment environments

Leadership Expectations

  • Optimize for long-term leverage, not short-term output
  • Make invisible work visible (decisions, tradeoffs, learning)
  • Use AI comfortably without surrendering responsibility
  • Protect buena onda while holding high standards

Think like a system architect, not a project manager.

Skills

AI-enabled Workflow DesignArchitecture LeadershipChange ManagementData-driven Decision MakingDecision Making FacilitationDelivery OrchestrationDelivery System MappingGovernance And Process DesignKnowledge ManagementLearning Systems DesignMentoring And Talent DevelopmentObservability And Metrics Using CertiniaPattern Extraction And ReuseProductivity ToolingRisk ArticulationSRE/devops ConceptsStakeholder AlignmentSystem DesignTrade-off Analysis

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