Five ways Oisin shows up — chosen to match where you are.

AI Strategy & Roadmapping

Typical engagement: 4–8 weeks. Workshops + research + a roadmap your team will defend on its own.

From "we should use AI" to a sequenced plan your team will actually ship.

The goal isn't an inspiring deck. It's a roadmap that names the bets you'll make, the bets you won't, the constraints (regulatory, data, organizational) that will shape them, and the leading indicators you'll watch in the first 90 days.

• Opportunity mapping across product, ops, customer-facing and internal workflows
• Honest readiness assessment: data, talent, regulatory, customer trust
• Sequenced 12-month roadmap with named owners and budget envelopes
• Executive narrative — for the board, for customers, for hiring

AI Product Innovation

Typical engagement: 8–16 weeks. From concept to paying pilot.

Take a fuzzy idea from concept to a pilot customers will pay for.

Most AI demos are easy. The pilot that survives a real customer's procurement and legal review is not. Oisin works alongside your product and engineering team to design the workflow, choose the model(s), build the evaluation harness, and produce the artifacts buyers actually need.

• Workflow design with human-in-the-loop checkpoints where they earn their cost
• Model selection, prompt strategy and fallback architecture across multiple LLMs
• Evaluation: golden sets, regression tests, customer-acceptance criteria
• Pricing, packaging and the "first 90 days of usage" plan

Integration & Scale

Typical engagement: 6–12 weeks. Pairs well with an in-house engineering team.

Wire AI into the systems your customers already run on.

AI is rarely the limiting factor in adoption. The limiter is usually integration: CRM, ERP, payments, identity, the data warehouse, the support tool. Oisin has stood up integrations across Stripe, Salesforce, Ellucian and a long list of partner platforms, and brings a pragmatic playbook for doing it without halting product velocity.

• Reference architecture for CRM, ERP, payments and identity integrations
• Partner / vendor selection and contract negotiation
• API design reviews and data-model alignment with customer systems
• Operational readiness: monitoring, support tooling, incident playbooks

M&A & Post-Merger Integration

Typical engagement: Pre-close diligence through 6 months post-close.

Make the deal worth the deal.

Oisin has been on the buy side of an acquisition (an outcomes-tracking product in the education market) and the integration side of one of the largest US banking mergers (Wells Fargo–Wachovia, 100M+ visits per month). The patterns repeat: the value lives in the integration plan, not the term sheet.

• Technical and product due diligence — including AI / model IP, data rights and partner dependencies
• Integration thesis tied to the deal economics, not generic synergies
• Day-1, Day-30, Day-100 plans and the operating cadence to land them
• Customer-communication and retention strategy through the transition

Advisory & Fractional Leadership

Typical engagement: Monthly retainer. Board / exec advisory or interim Head of Product / CPO.

Senior judgment, on call, without hiring a full-time exec.

For founders, CIOs and product leaders who need a sparring partner who has done the job — not a coach who has only read about it. Engagements range from monthly board advisory to interim product leadership during a key hiring or transition window.

• Board / executive advisory on AI strategy and product roadmap
• Interim Head of Product, CPO or VP Engineering for 3–9 month windows
• Hiring support: scorecards, interview design, exec referrals
• Pre-fundraise narrative and technical-diligence preparation