Fashionphile
6
min read
Having worked together at Nordstrom, Fashionphile's CTO trusted my ability to build and lead product organizations. When he needed to transform Fashionphile's technology approach in early 2020, this established relationship led to my joining as VP of Product. Our shared vision and previous success enabled me to attract key talent from Nordstrom who were eager to build something new.
Strategic Change Leader: Guided organizational transformation from service-centered to strategy-driven technology
Workshop Facilitator: Designed and led executive alignment sessions
Product Strategy Architect: Developed framework for identifying and solving systemic challenges
Technology needed to evolve beyond a service center role, but this transition risked alienating business units who feared:
Loss of influence over product direction
Reduced support for operational needs
Exclusion from strategic decisions
This tension manifested as a growing backlog of tactical issues, masking the underlying need for a new collaborative operating model. Many in the organization felt their voices weren't being heard by tech and executives, creating a disconnect between leadership vision and on-the-ground reality. We needed a way to tap into the creative problem-solving potential across all levels of the organization, bringing diverse perspectives into shaping our strategic direction.
Organizational Challenges
Limited previous exposure to product-led development
Resistance to changing established ways of working
Geographic distribution across US and Japan
COVID-19 forcing remote transformation
Cultural Challenges
Strong entrepreneurial culture resistant to structured processes
Existing relationships and influence networks
Trust deficit between tech and business units
Fear of losing autonomy
The workshop began with the marshmallow challenge. Executives paired up to build towers using limited materials - spaghetti, tape, string, and a marshmallow. This exercise:
Revealed tendencies toward over-ambition vs iteration
Demonstrated value of rapid prototyping and failing fast
Created openness to rethinking strategic approaches
The Marshmallow Challenge helped loosen creativity and drive problem-solving.
Following this ice-breaker, we moved into problem identification. Executives documented their challenges, and our workshop walls filled with issues ranging from operational hurdles to strategic roadblocks. Through focused discussion and dot voting, patterns emerged. What began as disparate problems formed into clear clusters.
A brief recess in our problem framing day - common everyday issues/symptoms posted on on the wall.
As we clustered issues, we found that most of the issues in the organization fell into six key problem areas:
1
Organizational Fragmentation
Teams working in silos without shared direction
Lack of clear ownership and accountability
Inconsistent understanding of company goals across departments
4
Financial Growth Constraints
Cash flow constraints limiting growth
Inefficient revenue capture in buying/selling process
Suboptimal pricing or transaction models
2
Gut-Based Decision Making
Decisions being made on gut feel rather than data
Limited data accessibility or understanding
Lack of consistent metrics for measuring success
5
Limited Market Position
Limited market penetration in luxury resale space
Customer retention challenges
Lower than desired customer lifetime value
Competitive pressure in the market
3
Poor Customer Journey
High volume of customer complaints/issues
Fragmented or confusing user journey
Inconsistent brand messaging and experience
6
Operational Inefficiency
Operational bottlenecks limiting growth
Manual processes causing inefficiencies
Training and scaling challenges with rapid growth
Lack of standardized processes
With these core problem areas, we established our overarching objective with six key supporting pillars:
Be the most sought-after brand for buying and selling ultra-luxury accessories, maintaining strong overall growth leading to IPO.
Unite Around Strategy
Drive clear communication of strategy and ownership at all org levels
Provide teams clear purpose through strategic planning and execution
Optimize Customer Experiences
Understand and address customer pain points in issue resolution
Improve shopper journey and brand/marketing messaging
Gain/Grow Marketshare
Increase penetration into ultra-luxe re-commerce sector
Drive greater awareness, customer growth, retention, and LTV
Grow the organization's data literacy and data pool
Place data in all key decision-making areas and processes
Gain Liquidity
Gain sufficient liquidity to meet growth plan
Optimize value-capture along buying and selling journey
Optimize ability to scale and train high learning curve competencies
Innovate processes/tools for high-volume, efficient throughput
Between Problem Day and Solutions Day, I conducted focused sessions with stakeholders to develop their ideas into comprehensive business cases. Using our "placemat" framework – a structured one-page template – stakeholders learned to:
Critically evaluate their proposals before presentation
Consider user needs and business impact holistically
Assess implementation risks and resource requirements
Quantify effort and potential return
These sessions helped transform initial concepts into well-reasoned proposals while teaching valuable product thinking skills across the organization.
The Placemat - a single page template for promoting ideation that's well-rounded and thought through.
An example of a filled placemat.
Structured Support System
Assigned dedicated product managers to each business unit
Established weekly open-door standup hours
Conducted process training sessions with each department
Product Director and Program Management Director served as key partners
On-the-Ground Presence
Prioritized in-person collaboration with non-remote teams
Regular physical presence in warehouse operations
Direct engagement with front-of-house specialists
Balanced remote and in-person communication channels
Grassroots Adoption
Identified and engaged unofficial leaders across organization
Built network of change champions beyond management
Created multiple access points for process understanding
Ensured consistent support across all organizational levels
Quantitative Outcomes
Generated 120+ strategic solutions from leadership team
Identified $30M in potential growth opportunities
Consolidated multiple problem streams into 6 core challenges
Organizational Transformation
Product and design teams maintained focus on strategic initiatives
Reduced context-switching from "problem of the day" interruptions
Established organization-wide transparency on all initiatives
United business units under shared strategic goals
Aligned departmental visions with core strategic pillars
Culture Shift
Repositioned tech as strategic driver within Fashionphile
Established customer-first strategy across organization
Created sustainable model for cross-functional collaboration
Built trust between tech and business units
Unexpected Market Dynamics
A significant oversight emerged as the pandemic evolved:
Initial Strategy: Built around accelerating growth seen during COVID
Reality: Failed to account for post-pandemic market normalization
Impact: Growth projections and solutions didn't consider market deceleration
Learning: Need for scenario planning in strategic frameworks
E-commerce sales plateau in week 14.
Strategic Resilience
The experience highlighted crucial lessons about strategic planning:
Market Assumptions
Over-indexed on pandemic-driven growth patterns
Needed broader range of market scenarios
Importance of building flexible, adaptable solutions
Vision Alignment
Successfully united teams around strategic pillars
But frameworks too rigid for rapid market changes
Need balance between focus and adaptability
Competition vs. Collaboration
Limited implementation capacity created competitive dynamics
Stakeholders invested significant effort in proposals that weren't selected
Disappointment affected team morale
Strategic Alignment Friction
Resistance to ideas being filtered through strategic pillars
Perception of ignored operational needs
Challenge to traditional influence patterns
Cultural Resistance
Some viewed the process as a power grab by technology
Resistance to moving away from service center model
Questions about decision-making authority
The project demonstrated how design thinking could transform executive strategy sessions while creating measurable business impact. The framework established continues to guide Fashionphile's strategic planning process, albeit with greater emphasis on market adaptability and scenario planning.
