Strategic Solutions for Growing Small Businesses
We help business owners build the structure, systems, and strategy needed to grow with confidence.
What We Do
The Ottley Group is a Boston-based business consultancy that partners with consumer-facing small businesses to solve the strategic and operational challenges that stall growth. We blend enterprise-level strategy with hands-on implementation to help business owners move from reactive to resilient.
We don’t sit on the sidelines—we step in.
Whether you’re expanding locations, reworking internal processes, or trying to get a handle on your margins, we help you build smarter systems and stronger strategies that support lasting success.
We believe scaling is a skill—and we’re here to help you master it.
About Our Founder
With a foundation built on years at global firms like EY, PwC, and Reebok, our founder and chief strategist, Keenan J. Ottley, brings more than a decade of experience translating complex financial and operational systems into practical strategies for small business success. Since launching The Ottley Group, he has worked with small-to-medium-sized businesses across Massachusetts helping founders navigate growth, access funding, and implement scalable solutions that stick.
Combining deep corporate expertise with a hands-on, community-rooted approach, he specializes in bridging the gap between local business realities and institutional opportunities whether through grant strategies, internal process design, or positioning within Boston’s broader business ecosystem.
At the heart of The Ottley Group is a commitment to helping small business owners scale with structure, clarity, and staying power. If you’re ready to grow your business sustainably or solve the challenges getting in your way, we’re ready to help.
Who We Serve
Solo or Early-Stage Founders
Owners With Multiple Locations
Real Estate Entrepreneurs
Our Services
Our services are designed to bring structure, clarity, and momentum to businesses that are ready to grow but unsure of how to do so. Whether you're optimizing operations, planning expansion, or reevaluating your business model, we offer practical, enterprise-grade solutions tailored to real-world challenges.
- Internal Audit & Risk Assessment
- Operational Audits & Process Reviews
- End-to-End Process Mapping & Optimization
- Internal Control Design & Implementation
- KPI & Performance Metrics Development
- Cost Structure Analysis & Margin Improvement
- Workflow Automation & Efficiency Initiatives
- Root Cause & Bottleneck Analysis
- Deal & Transaction Analysis
- Buy-Side & Sell-Side Due Diligence
- Deal Structuring & Negotiation Support
- Financial Modeling & Forecasting
- Revenue Model Development & Optimization
- Budgeting & Long-Term Forecasting
- Working Capital & Cash Flow Optimization
- Scenario Planning & Financial Sensitivity Analysis
- Performance Dashboards & Reporting
- Full Lifecycle Project Management (Initiation to Closeout)
- Budget Monitoring & Cost Control
- Cross-Functional Coordination (Architects, GC, Vendors)
- Schedule Development, Risk Management, & Change Control
- New Business Strategy Rollouts
- Strategic Roadmap Development & Execution Oversight
- Change Management & Communication Planning
- Operating Model Redesign
- Organizational Readiness Assessments
- Go-to-Market Strategy Execution
- Market Analysis & Competitor Benchmarking
- Strategic Planning Facilitation
- Revenue Stream Diversification
- Customer Experience Journey Mapping
- Digital & Data-Driven Strategy Alignment
Our Clients
Working with Keenan as a strategic consultant was one of the best decisions we’ve made at Integral Studio. He brought clarity, structure, and high-level thinking to our vision as a music tech company. From the very first session, Keenan helped us refine our mission, prioritize our roadmap, and uncover opportunities we hadn’t fully tapped into. His ability to balance creative ambition with operational focus was invaluable. Keenan doesn’t just offer advice—he becomes a real thought partner. Highly recommend to any founder looking to sharpen their direction and accelerate growth.
Keenan was instrumental in helping me take CascentualTherapy to the next level. Expanding into a storefront was a major move for my business, and having his strategic support made all the difference. From evaluating locations and navigating lease terms to budgeting for build-out and creating a launch plan, Keenan brought clarity and confidence to every step of the process. He understood my vision for a wellness-centered spa and helped me bring it to life in a way that felt both authentic and sustainable. If you’re a small business owner looking to grow, I can’t recommend Keenan enough.
Coming out of the pandemic, Pink & Pretty was faced with numerous challenges. Like many small businesses, we were encountering setbacks that almost led to us closing our doors. Keenan stepped in at a critical time and helped us completely restructure the business. His guidance was not just strategic—it was hands-on and deeply invested. From refining our operations to helping implement a strategic plan that fit our vision as a Black woman-owned nail salon, Keenan brought the clarity and structure we needed to move forward. He didn’t just advise—he partnered with us and helped lay the foundation that we’re still building on today.
