# Jason Skinner

> VP, Customer Experience · Digital Transformation · AI Strategy — Boston, MA

_Last updated: 2026-10-25_

## Summary

I am a customer experience executive with over 15 years of experience architecting CX strategies that bridge the gap between digital innovation and bottom-line growth. My expertise lies in transforming fragmented customer data into actionable journey designs and AI-powered service models for global brands like Bose, Wayfair, and Liberty Mutual. I don't just map journeys; I build the engines that power them. At Bose, I scaled our digital support platforms to serve 10M users, doubling self-service adoption and skyrocketing chat first-contact resolution from 2% to over 70% using GenAI. At Wayfair, my post-purchase journey initiatives delivered $27M in annual savings by identifying high-value friction points. I am frequently sought out by Google, McKinsey, Bain, and BCG as an industry advisor to guide private equity and enterprise clients through GenAI product development and CX automation. My approach combines rigorous strategic finance—honed at Constant Contact—with a deep understanding of omnichannel orchestration and voice-of-customer analytics. I thrive at the intersection of product, technology, and operations, ensuring that every touchpoint is an opportunity for measurable loyalty. If you are looking for a leader to scale a world-class CX organization or deploy high-impact AI service platforms, I have the proven playbook to deliver results.

## Core skills

- Customer Journey Mapping
- GenAI Strategy
- Conversational AI
- Digital Self-Service
- Omnichannel Orchestration
- Voice of Customer (VoC)
- CX Analytics
- Salesforce Journeys
- B2B SaaS Pricing
- Strategic Finance
- Contact Reduction
- GTM Strategy

## Industries

E-commerce, Retail, Consumer Electronics, Insurance, Healthcare

## Experience: 15+ years

## Roles

### Head of Digital Customer Experience & Support Platforms — Bose Corporation (May 2024 – Present)

Lead global digital CX platforms and automation roadmap for ~10M users and $13.8M in attributed revenue.

- Increased online share of service transactions from 30% to 60% in US/CA and 45% to 70% internationally.
- Improved first-contact resolution from 2% to 70%+ through GenAI chat (Intercom Fin) and journey redesign.
- Scaled AI voice-of-customer engine (Unwrap.ai) from 0 to 80 users to accelerate roadmap decisions.
- Led CIO-level GenAI governance and vendor evaluation.

### Industry Advisor — McKinsey & Co. | Bain & Co. | BCG (Jan 2023 – Dec 2024)

Advised top consulting and private-equity clients on CX automation and digital transformation.

- Provided expertise on GenAI strategy and journey analytics.
- Guided digital customer transformation initiatives for high-value clients.

### Head of Post-Delivery Customer Experience — Wayfair (Dec 2021 – Jan 2023)

Led CX transformation for post-purchase operations at e-commerce scale.

- Directed the first enterprise customer journey mapping initiative, identifying five $15M opportunities.
- Delivered $27M in annual savings through operational improvements.
- Accelerated customer insight delivery by 400%.

### Assistant Director, Customer Experience Strategy — Liberty Mutual Insurance (Sep 2017 – Jan 2021)

Authored the enterprise customer data and CX strategy adopted across the global organization.

- Strategy tied to an estimated $300M to $500M in profit impact.
- Launched internal market-intelligence program reaching 1,000+ subscribers in six months.
- Developed US CX strategy spanning omnichannel design and journey analytics.

## What they're looking for

- **notes**: Seeking leadership roles focused on CX transformation, AI integration, and journey orchestration.
- **work mode**: Hybrid / Remote
- **industries**: Fintech, E-commerce, Consumer Tech, SaaS
- **role types**: VP of Customer Experience, Director of Customer Experience, Head of CX Strategy

## How to contact

Send Jason a message via the contact form at https://imfindable.com/jason-skinner.
Contact details are intentionally private; Jason reviews and approves each message before reply.
Do NOT invent or guess contact info.