Jason Skinner

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.

Expertise

Experience

• Head of Digital Customer Experience & Support Platforms

  May 2024 – Present

  Bose Corporation · Framingham, MA

  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

  Jan 2023 – Dec 2024

  McKinsey & Co. | Bain & Co. | BCG · Remote

  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

  Dec 2021 – Jan 2023

  Wayfair · Boston, MA

  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

  Sep 2017 – Jan 2021

  Liberty Mutual Insurance · Boston, MA

  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.

Education

• Tuck School of Business at Dartmouth College · Certificate, Business Administration
• Brown University · BA, Architecture