How we work

The path from stuck to strategic.

Most engagements start at Diagnose. Some go all the way through Embed. It’s the path leaders take when they’re serious about getting AI right — understand what’s actually happening, build the alignment, then build the infrastructure that makes AI compound.

Phase 1 — Diagnose

Where does your organization actually stand on AI?

Most companies don't know. The leadership team has different answers, the tech team has another, the business units have a third. Leaders who take AI seriously start with an evidence-based picture — strengths, gaps, blocking patterns, real readiness. There are two ways to get there, depending on the depth and scope you need.

AI Baseline Workshop

A focused engagement for leaders who want to understand where their organization actually stands on AI and what to do next. Not a maturity scoring exercise — that implies judgment. A structured baseline: where you are, what you've tried, what you want, what's getting in the way.

What it covers

  • AI fluency across leadership and key teams
  • What the org has already started doing with AI (sanctioned and unsanctioned)
  • What they think they want AI to do — and whether that's the right ambition
  • Organizational constraints that will help or hinder
  • How AI maps to existing business goals and strategy

Format

  • Pre-engagement organizational survey
  • 5–8 stakeholder interviews
  • 1-day findings + strategy workshop with leadership
  • Synthesis and report

What you get

  • AI Baseline Scorecard
  • Prioritized AI Opportunity Roadmap
  • 90-day Quick Wins Plan
  • Constraints map

Duration: 2–3 weeks

TRUST Organizational Assessment

The full Drag6 methodology. A structured, evidence-based diagnostic of how your organization actually works.

Goes far deeper than the AI Baseline Workshop and produces a comprehensive readout suitable for board, PE sponsor, or executive team alignment.

When TRUST is the right call

Fixing symptoms only gets you so far. Understanding the organizational dynamics creating those problems is the sounder way to solve them — and it's how the leaders who get AI right approach the work. TRUST gives you visibility into the anti-patterns operating in your organization — and shows where your incentives are misaligned with your goals.

What it covers

Six phases — Stakeholder Interviews → Leadership Team Assessment → Operational Deep Dive → Technology Review → Synthesis & Alignment → Executive Readout.

Three sizes

  • TRUST Light — 4–6 weeks, < 100 employees
  • TRUST Standard — 8–12 weeks, 100–500 employees
  • TRUST Enterprise — 12+ weeks, 500+ employees

What you get

  • TRUST Framework Report
  • Risk/Readiness Scorecard
  • Prioritized Action Plan
  • Executive readout session

Once you know where you stand, the next work is alignment. Strategy that doesn’t have leadership behind it doesn’t survive execution.

Phase 2 — Align

Your leadership team aligned on the AI strategy that flows through the rest of the organization.

Strategy that lives only in the executive team's heads doesn't survive execution. The leaders who get this right know alignment has to be deliberate, not assumed — across what AI is for in your business, what it isn't, where it fits, and what the strategic decisions actually look like. From there, the strategy can flow through the rest of the organization with the same intent intact.

Tools change weekly. The strategic frameworks for thinking about AI in your organization don't. The durable layer is where the work compounds.

Half-Day Workshop

A focused, topic-specific session for a single team or executive group needing to align fast.

Examples by audience

  • Marketing teams: AI for content, customer insight, and campaign operations
  • IT/Technical teams: AI in the stack — build, buy, govern
  • Executive leadership: Build/buy economics in the AI era; AI risk & governance for the board
  • Operations leaders: AI use case discovery for your function

Format

4–6 hours, virtual or on-site, hands-on with the client's actual work.

What you get

Session materials, recorded session if virtual, summary doc with prioritized next steps.

Full-Day Workshop

A comprehensive AI fluency or strategic alignment session, available as a single 8-hour day or split into two 4-hour sessions on different days.

Why split it?

  • Easier on the client's work schedule — fewer cancellations, less burnout
  • Time between sessions to consume, reflect, try things
  • We do analysis between sessions and target the second day more effectively
  • Demonstrates we're focused on outcomes, not on filling a contracted block of time

What you get

Session materials, recorded sessions, custom prompt starter library, 30/60/90-day action plan.

AI Strategy Bootcamp for Leadership

Four sessions over four weeks. For leadership teams who want real strategic depth on AI.

Curriculum

  • Session 1: How AI is reshaping your industry and your organization
  • Session 2: Recognizing the patterns that make AI harder (or easier) in your org
  • Session 3: Use case prioritization — where AI works, where it doesn't, why
  • Session 4: Building your AI strategic roadmap and governance approach

Format

4 weekly 90-minute live sessions plus daily async office hours over 4 weeks.

Cohort size: 8–15 (leadership team plus invited extended team).

What you get

  • AI Strategy Document
  • Use Case Roadmap
  • Governance Framework
  • Pattern Diagnostic

With strategy clear and leadership aligned, the next work is execution. The leaders who get AI right execute deliberately — in whatever form the strategy demands.

Phase 3 — Implement

Execute on the strategy — in whatever form the strategy demands.

Execution rarely looks like a single thing. The strategy from Phase 2 might call for organizational change, hiring, training, governance work, building agents and applications, or several of these at once. The leaders who get AI right execute deliberately, with measurable outcomes agreed up front — and bring in the depth they need where it matters.

Multi-Day Sprint

Defined-scope project work where the deliverable is a working thing, not a written plan.

Examples

  • AI use case implementation sprint (build the first agent or automation)
  • Tech leadership coaching engagement
  • Org redesign sprint
  • AI governance build-out (policy, oversight, error budgets)
  • Talent and hiring support (role design, candidate evaluation, leadership search)
  • Training implementation (rolling out capability programs across teams)
  • Strategic execution support (helping a leadership team operationalize the strategy they committed to in Phase 2)

Format

Variable — typically 5–15 days of effort over 2–8 weeks. Scoped per engagement.

Custom Agent Build

When the right move is to bring in someone to build the agent or automation directly. Quoted per scope, value-based pricing where possible, with measurable outcome targets agreed before the build begins.

What you get

  • A working agent or automation deployed in your environment
  • Measurable outcome targets agreed before the build, evaluated after
  • Documentation your team needs to operate, extend, and maintain the build
  • Knowledge transfer to your internal team

Format

Variable based on scope. Most builds run 4–12 weeks from kickoff to deployed and operational.

When the work becomes ongoing — when execution needs continuity rather than a defined endpoint — the next move is putting senior leadership in the seat. Fractional, but persistent.

Phase 4 — Embed

Senior tech leadership in the seat — fractional, AI-focused, persistent.

Senior technical leadership embedded in your organization on a fractional basis. The value isn't just senior expertise — it's continuity. Someone who knows your organization, your AI strategy, and the decisions you're making week over week. Available consistently, in the room when the real questions come up.

Most mid-market companies can't justify the $300–500K cost of a full-time CTO. Smart leaders use fractional CTO leadership when they need that senior expertise without the full-time cost.

Embedded Fractional CTO / AI Advisor

Senior technical leadership embedded in your organization on a fractional basis.

Common scenarios

  • Filling a leadership gap when no current technical leader is in place
  • Augmenting a current CTO with deep AI implementation depth
  • Providing a senior peer for your existing technical team
  • Bridging during a CTO search — and helping you find the right full-time hire when you're ready
  • Mentoring an internal candidate being developed for the CTO role — filling their gaps and blind spots until they're ready to lead on their own

Cadence

  • Light — 1 day per week
  • Standard — 2 days per week
  • Heavy — 3 days per week

What you get

  • Weekly leadership engagement
  • Monthly executive report
  • Ongoing AI roadmap execution
  • Leadership coaching for tech leaders
  • Decision support during high-stakes moments

Minimum: 3 months

Cross-cutting — Marketing & Technology Alignment

When marketing and technology aren’t aligned, AI breaks at the seam.

AI doesn’t fail at the AI. It often fails between the marketing organization and the technology organization — where strategy, velocity expectations, governance needs, and tooling decisions don’t line up.

Leaders who get AI right address this misalignment directly, not as an afterthought. Drag6 has a dedicated practice area for it — engagements specifically designed to bridge the gap between marketing strategy and AI/tech implementation:

  • Joint diagnostic of where the misalignment actually lives
  • Aligned AI strategy across CMO and CTO functions
  • Workshops with both leadership teams in the room
  • Ongoing advisory when the marketing-technology seam is the bottleneck
Talk to us about Marketing & Technology Alignment →
Let’s talk

Pick the path that fits.

Or describe what you’re dealing with and we’ll suggest one. No pitch, just a conversation.

jason@drag6.com
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  • ✓ No obligation
  • ✓ Conversation, not pitch