About Stephanie
Stephanie Reese
Executive | Fractional Chief Operating Officer (COO)
The Proper Group Executive
Stephanie Reese is a transformational operations leader with more than 15 years of experience helping organizations scale sustainably, modernize infrastructure, and expand into new markets. Known for turning complexity into clarity, she specializes in building scalable systems, embedding AI and automation into workflows, and aligning cross-functional teams to deliver measurable growth.
Stephanie’s career spans SaaS, consumer goods, and global marketplace businesses. She has overseen international expansions, post-crisis stabilizations, and large-scale cultural modernizations. As COO of bookingkit, she drove a 65% revenue increase while reducing headcount through automation and lean process redesign: improving per-employee profitability and managing $204M in customer funds. Earlier, she spearheaded Spoonflower’s European expansion, scaling EMEA revenue from $1.4M to $9M and building the Berlin operations from the ground up.
With experience bridging finance, product, people, and operations, Stephanie delivers both rigor and resilience. She is recognized for cutting attrition by 50% through modern HR initiatives, implementing AI-enabled efficiency improvements that reduced manual work by one-third, and leading cultural change that empowered global teams.
At The Proper Group, Stephanie leads fractional COO engagements, supports operational transformations, and contributes to the firm’s intellectual property in AI-enabled scaling and operational excellence. She helps organizations stabilize during disruption, scale during growth, and expand globally with confidence.
Stephanie is based in Chicago, IL, and serves clients nationally and globally. Outside of work, she is passionate about building motivated teams, mentoring leaders, and creating operational models that balance efficiency with humanity.
Comprehensive Offerings:
Operational Transformation & Scalability
- Process redesign and system optimization to unlock growth
- Cross-functional alignment with OKRs, KPIs, and executive dashboards
- Turnaround leadership during periods of disruption or change
AI & Automation Integration
- Workflow automation and AI adoption strategies
- Data-driven decision frameworks and reporting systems
- Infrastructure modernization to improve scalability and throughput
Global Expansion & Market Entry
- Operational setup and scaling in new geographies
- International financial modeling, compliance, and supply chain frameworks
- Cultural adaptation strategies for global teams and customers
Financial Stewardship & Compliance
- Full P&L oversight across multimillion-dollar budgets
- Risk management and governance frameworks
- Customer fund management and compliance with GDPR and global regulations
People & Culture Modernization
- Career pathing, compensation transparency, and retention initiatives
- Executive coaching for operations and cross-functional leaders
- Building high-performing, motivated, and aligned teams
Fractional Executive Leadership
- Fractional COO engagements (short- and long-term)
- Interim leadership during stabilization or transition
- Advisory support for founders, boards, and executive teams
📍 Based in Chicago, IL — serving clients nationally
🗓 Book a complimentary consultation
📧 sreese@theproper.group