How Outsourcing Works for Jessica Flugge:The Hospitality Blueprint for Scaling Trust & Execution with AI
What does it take to build trust, execute at a high level, and scale operations in an increasingly technology-driven world?
In this episode of How Outsourcing and AI Works, host Brad Stevens sits down with Jessica Flugge, founder of Cherwell Consulting, to explore lessons from her extensive career across global hospitality, corporate finance, operations, consulting, and entrepreneurship.
Jessica shares three principles that have shaped her career: build trust, continuously learn, and execute. She also discusses how authentic relationships, consistent follow-through, and genuine curiosity can create stronger teams and more effective leaders.
The conversation also explores Jessica’s journey from Marriott and Ritz-Carlton to launching her own consulting firm and developing an AI-powered hospitality venture designed to help operators act faster, improve existing tools, and create greater transparency across organizations.
Whether you’re a founder, executive, franchise leader, hospitality professional, or entrepreneur looking to scale more effectively, this episode offers practical insights on building credibility, strengthening execution, embracing technology, and turning operational expertise into meaningful business growth.
Check out all the episodes of How Outsourcing Works:
Story to Scale: Nail Your Personal Narrative & Build the Team to Amplify It
Too many leaders stay stuck—not for lack of vision, but clarity. This session introduces Atomic Storytelling, the proven framework top U.S. leaders use to clarify their message and grow influence. Learn how to connect authentically and scale your impact with purpose-driven storytelling.
Upcoming
How Outsourcing Works for Tom Fox and His Podcast Network
Content bottlenecks can stall your best ideas. This session shows how one podcast network scaled from 20 to 50+ shows with Virtual Assistants and smart systems. Learn how blending VAs with AI tools can 10x your output and finally clear your creative backlog.
How Outsourcing Works - Accounting and Bookkeeping
Struggling to keep up with bookkeeping while growing your business? This session reveals how Virtual Accounting Pros help reduce overhead, cut stress, and bring financial clarity. Learn practical, affordable strategies business owners are using to stay on track—without doing it all alone.
How Outsourcing Works - Roofing
Roofing leaders know growth isn’t just more jobs—it’s smarter operations. This session shows how Virtual Assistants help streamline estimates, scheduling, and follow-ups, freeing you to focus on profit. Learn how to scale faster, cut overhead, and stay competitive with lean, offshore support.
How Outsourcing Works - Jon Ostenson
Franchise growth doesn’t have to mean burnout. This session reveals how top franchisees use Virtual Assistants to cut costs, streamline ops, and scale faster. Learn about high-profit non-food models, avoid common mistakes, and get a playbook to launch smarter with offshore support.
The COO Guide to Offshore Scaling— Without the Headaches
Ready to scale without bottlenecks? This session reveals how U.S. companies streamline operations and cut costs with top-tier offshore Virtual Assistants. Learn proven workflows, tech stacks, and surprising roles COOs are outsourcing to scale smarter—no matter your company size.
How Outsourcing Works - Sales Acceleration
Want to boost sales without burning out your team? This session shares 33 proven strategies—from automation hacks to smart VA delegation—that simplify operations and drive growth. Learn how to scale smarter, faster, and more profitably with real tactics you can use immediately.
How Outsourcing Works for Jabez LeBret and Business Automation
Discover how Jabez LeBret uses offshore outsourcing, automation, and Virtual Assistants to streamline operations, improve productivity, and create more time for high-value work. This session explores practical delegation strategies, the importance of clear communication, and how businesses can combine AI tools with human connection to scale smarter without losing authenticity.
How Outsourcing Works for Aaron Schmookler and Building High-Impact Teams
Learn how Aaron Schmookler and Outsource Access approach leadership, culture, and team connection to build stronger, more adaptable organizations. This session explores practical strategies for improving employee engagement, creating mission-driven teams, and fostering meaningful workplace relationships through intentional leadership, communication, and scalable systems.
How Outsourcing Works for Alex Bratton and AI-Powered Business Scaling
Explore how Alex Bratton and Brad Stevens use AI, automation, and Virtual Assistants to help businesses scale smarter and operate more efficiently. This session covers practical AI implementation strategies, productivity tools, and real-world examples of digital staffers that reduce low-value work, improve decision-making, and empower teams to focus on higher-impact activities.
How Outsourcing Works for Ankit Patel and AI-Driven Global Resourcing
Learn how Ankit Patel combines global resourcing, AI, and automation to help businesses scale smarter and operate more efficiently. This session explores real-world applications of production-level AI, industry-specific outsourcing strategies, and automation workflows that improve training, streamline operations, and boost customer conversion rates for growing businesses.
How Outsourcing Works for Chad Nikkel and Scaling Service Businesses
Discover how Chad Nikkel and Brad Stevens help small and medium-sized businesses scale through better leadership, optimized systems, and strategic outsourcing. This session explores the key pillars of business growth, common scaling bottlenecks, and practical ways service-based companies can use offshore talent and AI to improve operations, communication, profitability, and team performance.
How Outsourcing Works for Chip Dodd and Operational Business Support
Explore how Chip Dodd uses offshore professionals, automation, and AI tools to improve efficiency, maintain compliance, and support long-term business growth. This session highlights practical outsourcing strategies for healthcare and service-based businesses, showing how integrated remote teams can streamline operations, strengthen remote work systems, and free local staff to focus on higher-value responsibilities.
How Outsourcing Works for Chris Medhurst and Scaling Restaurant Operations
Learn how Chris Medhurst and District Taco use outsourcing, offshore talent, and operational systems to support rapid franchise growth and improve efficiency. This session explores how strategic delegation in catering, customer service, and accounting helped streamline operations, strengthen team support, and drive measurable business growth while maintaining high-quality customer experiences.
How Outsourcing Works for Dave Wheeler and Technology-Driven Business Scaling
Discover how Dave Wheeler and T-Source IT help businesses scale through smarter technology strategies, systems integration, and operational efficiency. This session explores common technology challenges growing companies face, practical ways to reduce manual work and redundancy, and how outsourcing and automation can support scalable, streamlined business operations.
How Outsourcing Works for Eric Dykes and EOS-Driven Business Growth
Explore how Eric Dykes and Brad Stevens use EOS principles, delegation systems, and offshore talent to help businesses scale more effectively. This session covers practical strategies for removing leadership bottlenecks, building accountability through clear processes, and empowering teams so entrepreneurs can focus on high-value work and long-term growth.
How Outsourcing Works for Eric Farewell and Entrepreneurial Growth
Discover how Eric Farewell and Brad Stevens use outsourcing, personal development, and intentional leadership to create sustainable business growth without burnout. This session explores the role of Virtual Assistants in freeing up time, the importance of emotional and personal well-being for entrepreneurs, and practical strategies for building a business that supports both performance and quality of life.
How Outsourcing Works for Ford Saeks and AI-Powered Business Growth
Learn how Brad Stevens and Ford Saeks use outsourcing, AI, and operational systems to help businesses scale more efficiently and sustainably. This session explores practical outsourcing strategies, the importance of cultural integration and process documentation, and how combining AI with skilled offshore talent can improve productivity, streamline operations, and support long-term business growth.
How Outsourcing Works for Jonathan Smith and Tactical Business Communication
Explore how Jonathan Smith and Brad Stevens apply negotiation frameworks, tactical empathy, and effective communication strategies to business growth and leadership. This session covers practical negotiation techniques, the psychology of understanding different perspectives, and how better listening, delegation, and AI-powered insights can strengthen relationships, improve decision-making, and support scalable business operations.
How Outsourcing Works for AI-Enhanced Business Scaling
Discover how businesses are combining offshore Virtual Assistants and AI tools to streamline operations, improve customer support, and scale more efficiently. This session explores practical outsourcing strategies, real-world AI workflows, and the benefits of integrating managed offshore teams with automation to create stronger systems, better communication, and sustainable business growth.
How Outsourcing Works for Jay Graves and Operational Business Scaling
Learn how Jay Graves and Brad Stevens use outsourcing, automation, and Virtual Assistants to help businesses scale more efficiently and focus on higher-value work. This session explores practical delegation strategies, the importance of documenting processes, and how integrating offshore team members with AI tools can improve productivity, operational support, and long-term business growth.
How Outsourcing Works for Joe Koufman and Scalable Team Support
Discover how Joe Koufman and Brad Stevens use outsourcing, operational systems, and Virtual Assistants to improve productivity and support long-term business growth. This session explores how offshore team members can become fully integrated contributors across administrative support, marketing operations, content production, and CRM management while helping businesses create more efficient and scalable workflows.
How Outsourcing Works for John Hall and AI-Driven Business Scaling
Discover how John Hall and Brad Stevens use outsourcing, AI tools, and operational systems to help businesses scale more efficiently. This session explores practical strategies for integrating Virtual Assistants into social media management, KPI tracking, market research, and sales workflows while leveraging AI and automation to improve productivity, streamline operations, and support long-term growth.
How Outsourcing Works for John Francis and Entrepreneurial Business Support
Learn how John Francis and Brad Stevens use outsourcing, Virtual Assistants, and operational systems to create leverage and support business growth. This session explores practical ways offshore team members can assist with marketing, CRM management, event coordination, and back-office operations, helping entrepreneurs focus on higher-value work while building more efficient and scalable businesses.
How Outsourcing Works for Kelly Trimm and Franchise Brand Growth
Discover how Kelly Trimm and Brad Stevens use outsourcing, digital marketing systems, and offshore support to help franchise brands scale while maintaining consistency and authenticity. This session explores strategies for balancing corporate brand standards with localized marketing, improving operational efficiency through Virtual Assistants, and leveraging AI and digital tools to strengthen franchise growth and customer engagement.
How Outsourcing Works for Marissa Levin and Joyful Leadership Culture
Explore how Marissa Levin and Brad Stevens discuss building a joyful, scalable business culture through intentional leadership, strong processes, and people-focused growth strategies. This session covers practical approaches to operationalizing company values, creating psychologically safe workplaces, leveraging AI responsibly, and developing leadership systems that support long-term business success and employee engagement.
How Outsourcing Works for Home Service Businesses and Operational Growth
Discover how entrepreneurs in the home services and trades industries use outsourcing, Virtual Assistants, and automation to scale operations more efficiently and support long-term growth. This session explores practical delegation strategies, the value of offshore talent for operational and marketing support, and how businesses can create stronger teams by allowing leaders to focus on higher-value work and meaningful customer relationships.
How Outsourcing Works for Rhonda Meyers and Scaling Education Businesses
Learn how Rhonda Meyers uses outsourcing, Virtual Assistants, and operational systems to support growth across her education-focused businesses. This session explores how offshore support helped reduce leadership overwhelm, streamline administrative and HR processes, and create scalable systems that allowed her organizations to grow more efficiently while maintaining strong team support and operational consistency.
How Outsourcing Works for Ryan Rieches and Brand-Driven Business Growth
Explore how Ryan Rieches and Brad Stevens discuss the connection between personal branding, corporate culture, and scalable business growth. This session covers strategies for aligning executive visibility with company branding, navigating cultural integration during business growth and acquisitions, and using outsourcing, AI tools, and authentic communication to strengthen leadership presence and organizational trust.
How Outsourcing Works for Sarah Tourville and Brad Stevens on AI-Driven Business Scaling
Discover how Sarah Tourville and Brad Stevens discuss the growth of Outsource Access and the evolving role of outsourcing and AI in helping businesses scale more efficiently. This session explores strategies for operational growth, leadership development, process integration, and how AI-powered offshore staffing can support small and medium-sized businesses across multiple industries.
How Outsourcing Works for Steve Heroux and Scalable Sales Leadership
Discover how Steve Heroux and Brad Stevens use outsourcing and Virtual Assistants to scale content production, streamline operations, and support business growth. This session explores how offshore talent can assist with creative projects, lead generation, and operational support while allowing entrepreneurs and sales leaders to focus on strategy, thought leadership, and high-value business activities.
How Outsourcing Works for Tom Fox and Scalable Content Operations
Discover how Tom Fox and Brad Stevens use outsourcing, Virtual Assistants, and AI-powered tools to scale content production, streamline operations, and support business growth. This session explores practical outsourcing strategies for social media management, podcast production, and creative marketing while highlighting how offshore talent can help businesses remove operational bottlenecks and focus on higher-value work.
How Outsourcing Works for Tripp Guin and Commercial Real Estate Growth
Learn how Tripp Guin and Brad Stevens use outsourcing and Virtual Assistants to improve efficiency and support scalable growth within the commercial real estate industry. This session explores practical ways offshore support can assist with lead generation, client communication, CRM management, research, and operational tasks, helping entrepreneurs focus on higher-value activities and long-term business development.
How Outsourcing Works for Randall, Zach Coward, and Scaling Service Businesses
Discover how Randall, Zach Coward, and Brad Stevens use outsourcing, offshore staffing, and operational systems to scale businesses in the home and commercial services industry. This session explores how integrated offshore teams support routing, sales, accounting, and customer experience while helping companies maximize software tools, improve operational efficiency, and create scalable systems for long-term growth.
How Outsourcing Works for Betsy McAtee and Restaurant Operations Scaling
Learn how Betsy McAtee and Brad Stevens use outsourcing and Virtual Assistants to streamline operations and support growth at Dreamland BBQ. This session explores how offshore support helped improve financial reconciliation processes, reduce accounting bottlenecks, and create more operational efficiency, allowing leadership to focus on customer experience, restaurant operations, and long-term business growth.
How Outsourcing Works for Cameron Herold and AI-Enhanced Business Operations
Discover how Cameron Herold and Brad Stevens use outsourcing, AI tools, and operational systems to improve productivity and scale business operations more effectively. This session explores strategies for integrating Virtual Assistants into high-level workflows, overcoming common outsourcing concerns, and combining AI with offshore support to help teams focus on higher-value strategic work.
How Outsourcing Works for Doug Smith and Restaurant Growth Strategies
Learn how Doug Smith and Brad Stevens use outsourcing, automation, and data-driven marketing to help restaurants scale more effectively. This session explores practical strategies for customer engagement, catering lead generation, operational support, and social-first marketing while showing how offshore staffing can streamline back-office operations and free restaurant owners to focus on long-term business growth.
How Outsourcing Works for Evan Nierman and Scalable Business Support
Discover how Evan Nierman and Brad Stevens use offshore talent, Virtual Assistants, and operational systems to improve efficiency and support business growth. This session explores practical outsourcing strategies for administrative support, marketing, SEO, and internal operations while highlighting how integrated offshore teams can help leaders focus on higher-value strategic work and long-term scalability.
How Outsourcing Works for Greenlight Cyber and Scalable Team Growth
Discover how Greenlight Cyber and Brad Stevens use offshore outsourcing, operational systems, and global talent to scale business operations more effectively. This session explores practical strategies for integrating offshore team members into leadership, sales, and technical roles while leveraging outsourcing to improve efficiency, expand capabilities, and support long-term business growth.
How Outsourcing Works for Matt Plapp and Restaurant Marketing Growth
Discover how Matt Plapp and Brad Stevens use outsourcing, customer engagement strategies, and operational systems to help restaurants scale more effectively. This session explores innovative restaurant marketing approaches, the importance of building customer databases, and how Virtual Assistants can support back-office operations, content production, and marketing execution to drive long-term growth and customer retention.
How Outsourcing Works for Waldo Waldman and Leadership Under Pressure
Explore how Waldo Waldman and Brad Stevens discuss leadership, preparation, and the power of collaboration in overcoming fear and uncertainty. This session covers practical strategies for building trust-driven teams, focusing on your “genius zone,” and using outsourcing and delegation to create stronger leadership capacity, operational efficiency, and long-term business growth.
How Outsourcing Works for Jeff Civillico and Personal Brand Growth
Discover how Jeff Civillico and Brad Stevens use outsourcing, AI tools, and Virtual Assistants to scale personal brands and streamline business operations. This session explores practical strategies for content management, relationship building, administrative support, and operational efficiency while showing how entrepreneurs can leverage offshore talent to focus more on creativity, leadership, and high-value work.
How Outsourcing Works for Dave Roberts and Cybersecurity Business Growth
Discover how Dave Roberts and Brad Stevens use offshore talent, AI tools, and operational systems to help businesses scale more effectively. This session explores how outsourcing can evolve from administrative support to specialized technical, sales, and leadership functions, while highlighting best practices for team integration, process documentation, and leveraging AI to improve productivity, efficiency, and long-term business growth.
How Outsourcing Works for Jonathan Whistman and Building High-Performance Teams
Discover how Jonathan Whistman and Brad Stevens explore the intersection of AI, outsourcing, and leadership to help businesses scale more effectively. This session covers practical strategies for leveraging offshore talent, creating high-performing and engaged teams, and using technology to enhance productivity while maintaining a human-centered approach to leadership, culture, and long-term business growth.
How Outsourcing Works for Armando Anderson and AI-Powered Business Growth
Discover how Armando Anderson and Brad Stevens combine AI, outsourcing, and strategic delegation to help businesses scale more efficiently. This session explores the practical use of custom GPTs, offshore talent, and relationship-driven growth strategies, highlighting how Virtual Assistants can support lead generation, business development, marketing, and operational tasks while enabling leaders to focus on higher-value opportunities and long-term growth.
How Outsourcing Works for Dustin Campbell and Culture-Driven Business Growth
Discover how Dustin Campbell and Brad Stevens explore the connection between organizational culture, outsourcing, and AI-powered business growth. This session covers practical strategies for building scalable teams, developing strong operational systems, and helping employees work in their “genius zone” while leveraging offshore talent and technology to improve efficiency, engagement, and long-term business performance.
How Outsourcing Works for Jessica Flugge: The Hospitality Blueprint for Scaling Trust & Execution with AI
What does it take to build trust, execute at a high level, and scale operations in an increasingly technology-driven world?
In this episode of How Outsourcing and AI Works, host Brad Stevens sits down with Jessica Flugge, founder of Cherwell Consulting, to explore lessons from her extensive career across global hospitality, corporate finance, operations, consulting, and entrepreneurship.