The Retail Ladder Group Start a Conversation

Fractional Chief Strategy Officer

Elevating brands.
Strategy over guesswork.

The Retail Ladder Group brings enterprise-level retail rigor to brands and programs at every stage of growth — from emerging designer, to retail-ready, to organizational scale.

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Sherieka Smallwood-Morgan, Founder & Fractional Chief Strategy Officer — 20+ years leading enterprise retail strategy at Macy's, Inc.

Company Overview

Enterprise structure, built for growing brands

The Retail Ladder Group is a strategic consulting firm helping brands and organizations build the structure, strategy, and systems needed to launch, grow, and scale in retail.

Led by a 20-plus year retail strategy executive from Macy's, Inc., the firm bridges the gap between big-box discipline and independent-brand agility — translating enterprise playbooks into practical, right-sized strategy for teams that don't have a corporate bench to lean on.

Who We Serve

Two kinds of climb, one strategic partner

Whether you're a single brand or the organization behind hundreds of them, the strategy work is the same discipline applied at different altitudes.

Ready-to-Scale Retail Brands

Businesses with product-market fit seeking fractional strategic leadership to structure operations, refine go-to-market strategy, and scale into wholesale and marketplace channels.

Incubators & Accelerator Programs

Organizations — pledge programs, chambers, fashion incubators, and supplier diversity councils — seeking to design or strengthen learning curricula, mentorship structures, and growth processes for member brands.

Core Capabilities

Five ways we get involved

01

Fractional Chief Strategy Officer

Ongoing strategic leadership for retail-stage brands that need executive-level direction without a full-time hire.

02

Retail Launch & Wholesale Growth Consulting

Go-to-market strategy for entering and scaling within wholesale and marketplace channels.

03

Brand Incubation & Accelerator Curriculum Design

Building the learning content, mentorship structure, and growth processes that power cohort-based brand programs.

04

Retail Operations Optimization

Governance, training, and reporting infrastructure that brings enterprise-grade discipline to growing organizations.

05

Speaking Engagements & Workshops

Sessions for organizations and cohorts on scaling in retail, brand strategy, and supplier development.

Track Record

What the strategy has built, so far

Two decades inside one of retail's largest vendor ecosystems, translated into a body of work that speaks for itself.

20+ yrs
Drove enterprise merchandising strategies to grow brands at every stage — from $50K to $50M — developing assortment, financial, and marketing plans that increased sales, profitability, and visibility.
Mentorship
Mentored brands to understand retail industry best practices, merchant requirements, and benchmarks for success; identify opportunities and minimize threats to building strong retail partnerships; and deconstruct business operations to align with stronger growth.
275+
Architected the operating model, governance structure, and cross-functional workflows for The Workshop at Macy's — transforming a brand-development program into a full accelerator delivering access, capital, and opportunity to 275+ brands through in-person and e-learning curriculum, merchant toolkits, business grants, and structured onboarding pathways.
$50M+
Developed long-range financial and inventory strategies supporting $50M+ in annual sales and 25% year-over-year growth, using market performance and market trends to identify growth opportunities and optimize business outcomes.
  • Contributed to driving $3B in sales and $2B in emerging brand spend across retail partnerships.
  • Designed governance, training, and reporting infrastructure adopted enterprise-wide for supplier and vendor programs.

Professional Background

Sherieka Smallwood-Morgan

Founder & Fractional Chief Strategy Officer. Twenty-plus years at Macy's, Inc., architect of The Workshop at Macy's, and lifelong translator of enterprise retail strategy into growth plans that smaller teams can actually run.

Speaking & Panels

  • WBENC — Women Owned in Retail: Navigating the Road to Success
  • Harlem Fashion Row Sustainability Summit — Driving Sustainable Growth
  • Scaling in Retail with The Fifteen Percent Pledge

Let's Talk Strategy

Ready to climb to the next level?

Whether you're a brand ready to scale or a program ready to strengthen its next cohort, let's talk through where structure is missing.

retailladdergroup@gmail.com Connect on LinkedIn