The AI Leadership Sprint

    Make AI your advantage. In four weeks.

    Cut through the noise, understand where your organisation really stands, and create an AI plan you can execute with confidence.

    Know where AI can create value for you, what it costs, who owns it, and what to do first.

    Book a fit callSee what it costs

    Remote or on site · Delivered by a CTO with 20+ years' experience

    Dane Eldridge, Founder of StackUp

    Dane Eldridge
    Founder, StackUp

    4 weeks
    Start to committed roadmap
    <9 hrs
    Of each leader's time
    10
    Working artefacts you keep
    12 months
    Platform access included

    The problem

    Consequential AI decisions, made without an independent picture

    Leadership teams are often asked to make consequential AI decisions without an independent picture of where their organisation stands. The Sprint cuts through the noise: we measure and benchmark where you are, and provide a senior, independent CTO with 20+ years of technology leadership experience to support your leadership team in designing the plan. Working with them, not reporting to them.

    Strategy

    Where you are actually trying to win, and where AI creates real value, not just theatre.

    Process

    Effective, simple processes to support your success: how projects get approved, how decisions are reviewed, how you stay ahead.

    Skills

    The AI skills across your organisation, and whether the right training is in place to make effective AI decisions.

    Every Sprint examines your organisation through these three lenses.

    How it runs

    Assess. Align. Commit.

    Four weeks to a plan your leadership team has committed to, then a month of executive support while it gets underway.

    Week 1
    Assess

    Opening alignment session. AI maturity and technology assessments run across your organisation and leadership team, benchmarked against other organisations.

    Weeks 2-3
    Align

    One-to-one leadership interviews, then two working sessions that lift your team's AI knowledge and build its judgement against its own evidence.

    Week 4
    Commit

    Decisions made, roadmap agreed, owners named. Your team leaves with a plan it has committed to.

    Weeks 4-8
    Support

    Executive support. Your CTO stays close as your team puts the plan into action, building momentum and confidence, and closing with a checkpoint on what you have achieved.

    Under 9 hours

    Per leader, across the four weeks. The platform does the discovery work that would otherwise be extracted from your team in workshops.

    12 months

    Of StackUp platform access included, so the roadmap stays live and measurable well beyond the engagement.

    What you receive

    The AI Leadership Pack

    Ten working artefacts, built with your leadership team and handed over for continued use. These are not slides. They are operating documents you will still be using long after the engagement is over.

    Where you are now
    • 01
      AI Maturity Benchmark Report

      Scored across every dimension, benchmarked against other organisations.

    • 02
      Tech Health Benchmark Report

      The state of the technology function underneath the ambition.

    • 03
      Leadership AI Skills Profile

      AI skills across your leadership team, individually and collectively.

    How you govern it
    • 04
      AI & Shadow AI Discovery

      What AI is already in use across your organisation, by whom, with what data.

    • 05
      Decision Rights & Ownership Model

      Who decides what, who is accountable for AI outputs, and what escalates.

    • 06
      AI Guardrails & Acceptable Use Policy

      What AI may do, what data it may touch, where human oversight is mandatory.

    • 07
      AI Project Evaluation Framework

      A repeatable scorecard and gate applied before anything goes live.

    Where you go next
    • 08
      Skills & Resourcing Plan

      What you actually need next: hire, train, buy, or partner.

    • 09
      Prioritised AI Roadmap

      Sequenced and prioritised, with a named owner against every item.

    • 10
      Board Pack & 90 Day Plan

      The summary your CEO takes to the board, plus the actions, owners and risks that follow.

    Who delivers it

    A senior, independent CTO. Not a consultant with a template.

    Sprints are delivered by senior technology leaders from our independent network, matched to your industry and situation. They are independent of StackUp, which is precisely the point.

    20+ years

    Of technology leadership experience, every engagement

    50+

    Technology leaders in our independent network

    7 countries

    Across Australia, the UK, the US and beyond

    The next step is a fit call, not a pitch. A 30-minute call to meet the right CTO, at no cost and no obligation. If the chemistry isn't right, we will propose someone else.

    Book a fit call

    Investment

    Two delivery formats

    The engagement is the same in both. Each includes the full artefact pack, 30 days of executive support, and 12 months of the StackUp platform so the roadmap stays live.

    Format 01 · Remote
    From $20,000

    AUD, plus GST

    Every session delivered remotely over video, across the four weeks plus 30 days of support.

    Format 02 · On site
    From $30,000

    AUD, plus GST and travel

    The same engagement, with sessions delivered in person at your premises rather than over video.

    Pricing scales with organisation size. Payment is 50% on signing and 50% on completion. Travel and accommodation for on-site engagements are additional and agreed before booking.

    Book a fit callCompare platform plans

    Where the Sprint sits

    Foundation. Momentum. Advantage.

    The Sprint is the first stage. What follows is a decision you make at the checkpoint, with evidence in front of you, not a commitment you make now.

    Stage 01

    Foundation

    This Sprint · 4 weeks + 30 days support

    Measure where you are, build your leadership team's AI skills, and agree a roadmap your executives own.

    This engagement
    Stage 02

    Momentum

    Ongoing

    Execute against the roadmap with your CTO still involved, so the thinking moves from the sessions into how the team operates.

    Stage 03

    Advantage

    Continuous

    Re-measured every quarter. Advantage accumulates as skills and evidence build on each other.

    Questions

    Frequently asked

    Fewer than nine hours per leader across the four weeks: a 90-minute opening session, a 60-minute one-to-one interview, two 2-hour working sessions and a 2-hour closing session. The assessment platform does the discovery work that would otherwise consume weeks of your team's calendar in workshops.

    A senior, independent CTO with 20 or more years of technology leadership experience, drawn from our network and matched to your industry and situation. You will know exactly who they are, and have a no-cost fit call with them, before anything is signed.

    A fair question, and worth answering directly. The CTO who delivers your Sprint is independent. They come from our network, not our payroll, and their reputation depends on giving you a straight answer rather than a convenient one. The assessment measures your organisation whether or not you ever spend another dollar with us, and roadmaps regularly conclude “fix these three things first, and don't buy any AI tooling this quarter”, because that is what the evidence says. The platform's job is to make the evidence trustworthy and keep the roadmap live. It isn't the recommendation.

    Most assessments produce a maturity score and a slide deck. The Sprint starts with measurement, benchmarks you against other organisations, then puts an experienced CTO alongside your leadership team to build skills and a roadmap they own. The assessment is the evidence, not the product.

    The Sprint works either way. The process lens looks at how AI decisions get made, approved and reviewed across your organisation, which matters whether or not you write a line of code. Where you do build software, that lens goes deeper into your delivery practice.

    The engagement is the same. On-site means the sessions are delivered in person at your premises rather than over video. On site is from $30,000 plus GST and travel, agreed before booking, and scales with organisation size.

    Yes, and they often are the reason the engagement starts. Board members are welcome in the opening and closing alignment sessions, and the Board Pack is written to be presented rather than translated.

    Thirty days of executive support follow, closing with a checkpoint on what you have achieved. Most leadership teams then choose to keep their CTO involved, commonly a quarterly leadership session or an ongoing fractional arrangement. That is a conversation at the checkpoint, not a commitment now. Your platform access continues for the full 12 months either way.

    It won't select your vendors, write your prompts, or build your agents. It exists to make sure those decisions get made against a sound structure, not to make them for you.

    Interviews are conducted openly, and what you share may appear in the report and be attributed to you. If there is something you would prefer kept confidential, or reported without attribution, say so at the time and it will be honoured.

    From $20,000 remote and from $30,000 on site plus travel, scaling with organisation size, plus GST. Both include 12 months of StackUp platform access. Payment is 50% on signing and 50% on completion.

    Find out whether the Sprint is right for you

    A 30-minute fit call with the CTO we believe suits your situation. No cost, no obligation, and no pitch.

    Book a fit call