Stage 1
Read the Terrain
AI Readiness Assessment
Leadership intake survey, synthesis of alignment gaps, culture dynamics, and stakeholder readiness. Delivered in 2–6 weeks with a written report and 90-minute readout.
Trailhead Communications
Helping leadership teams navigate the human side of AI adoption.
From alignment and change strategy to the internal communications that make it stick.
Company Description
A boutique consultancy for the human side of AI.
Trailhead Communications is a boutique consultancy focused on the human side of AI adoption. I work with senior leadership teams — CHROs, CCOs, CIOs, and transformation leaders — at mid-market companies (200–2,000 employees), and with functional leaders at larger enterprises who are six to eighteen months into an AI mandate and hitting real friction.
The Problem I Solve
AI adoption is a leadership problem.
Most organizations don't struggle with AI because the technology doesn't work. They struggle because leaders moved fast on tools before aligning on purpose, guardrails, and culture.
The result is fragmented adoption, frustrated teams, and credibility that quietly erodes. I close that gap.
Brand Promise
One senior partner. The whole climb.
Trailhead sits at the intersection of AI, leadership alignment, change management, and communications — rather than treating AI adoption as a purely technical or operational rollout.
Clients work with Barbara throughout. Not a senior partner on the pitch and an analyst on the work. At this level of organizational sensitivity, that continuity is not a small thing.
Trailhead is the flexible, senior-level alternative to hiring a full-time change or communications leader during a period of rapid transformation.
Benefits & Typical Outcomes
82%*
of AI initiatives fail to deliver expected results — almost always due to people, not technology.
1:1
Senior access throughout — Barbara on every engagement, start to finish.
30–60
days to leadership alignment on AI scope and guardrails.
~70%
cost savings vs. a full-time senior change leadership hire.
* Source: McKinsey & Company / Boston Consulting Group research on enterprise AI initiative outcomes
What Success Looks Like
What leaders should see across the first 90 days.
30 days
- More consistent leadership messaging
- Fewer ad-hoc AI experiments
- Managers asking better questions
60 days
- More intentional, better-scoped AI efforts
- Clearer ownership and guardrails
- Learning discussed openly
90 days
- Improved decision quality
- Greater manager confidence
- Leaders feeling ahead, not reactive
Services & Engagement Model
Four stages. No required entry point.
Start with a diagnostic, jump to a workshop, or engage directly in advisory. Fixed-fee options keep procurement simple.
Stage 2
Align the Team
Leadership Alignment Workshop
Half-day facilitated session with senior leadership. Produces a shared AI narrative, documented guardrails, leadership commitments, and a success framework.
Stage 3
Prepare to Move
Change Infrastructure
Manager activation, use-case identification, change-champion network, and internal-communications capability building. Delivered on retainer over 3–6 months.
Stage 4
Navigate Forward
Advisory Retainer
Ongoing monthly working sessions and thought partnership with the engagement sponsor. Light lift for clients; high continuity for the initiative.
Why Clients Engage Trailhead
Senior partnership at the intersection no one else occupies.
- ✓
Sits at the intersection no one else occupies: AI, leadership alignment, change strategy, and communications in one engagement.
- ✓
Entry points at every stage — start with a diagnostic, jump to a workshop, or engage directly in advisory. No required starting point.
- ✓
Positionality a CHRO can't manufacture internally — an outside voice that names what the room already knows.
- ✓
Fixed-fee options for assessments and workshops — predictable cost, no procurement complexity.
Founder & Principal Consultant
Barbara Roos
- 25+ years in strategic communications and organizational change management
- 7+ years at Intel in senior communications leadership, leading programs affecting 5,000+ employees
- Deep expertise in leadership alignment, AI adoption change strategy, and internal narrative development
- Track record building change programs from the ground up — from diagnostic through implementation
- Advisor and facilitator to leadership teams navigating high-pressure AI mandates from boards and PE firms
- Facilitator for Starboard Collectives — peer cohort program for senior leaders navigating AI adoption
Ready to read the terrain?
Fixed-fee assessments and workshops. Advisory retainers for the long climb. Let's talk about where you are — and where the next 30 days could take you.
Start the Conversationbarbara@trailheadcommunications.comlinkedin.com/in/barbaratroos
Portland, OR
trailheadcommunications.com