Alex Oumn,
Zen Mondays

Rich Webster, a prominent lifestyle business coach with over 300k followers on Instagram, partnered with Zen Mondays to transform the course delivery and community management of How To Work Less. Designed for solopreneurs, freelancers, and service providers, his course aims to empower professionals to achieve more freedom by working less and earning more.

Recognizing the need for a streamlined, scalable system to accommodate growing student enrollment and community interactions, we developed a comprehensive solution. Our team seamlessly integrated Circle with essential third-party tools such as Leadpages, Thrivecart, ConvertKit, Zapier, and Adevent. Additionally, we crafted a custom Notion workspace to manage the entire business and developed exclusive Notion templates as bonuses for the students, significantly enhancing the learning experience for over 350 participants.

In addition to technical enhancements, I assumed the role of course manager, ensuring that all student inquiries were promptly addressed and that course operations ran smoothly. Our strategic interventions not only enabled the course to generate over $600k in revenue and achieve Platinum community status on Circle—placing it among the top 10% of most interactive communities—but also significantly optimized Rich’s workload. By automating key processes and managing community interactions, we reduced Rich's active working hours to only 4 hours per week during live cohorts, consisting of two two-hour sessions each week.

The success of How To Work Less highlights the significant impact of thoughtful automation and proactive community management. By cultivating a supportive and engaging learning environment, we helped Rich not only meet but surpass his educational and business objectives.

Sophia Babb, an accomplished freelance coach with over 46k followers on Instagram, partnered with Zen Mondays to revitalize her 6-Figure Freelancer course. Aimed at guiding freelancers toward achieving $10k+ months, the course required a more dynamic and engaging platform to accommodate its growth. We facilitated a complete migration from Kajabi to Circle, significantly enhancing the community interaction and course management features.

We reimagined every aspect of Sophia's tech stack from scratch. Our comprehensive revamp included building out Circle automations and integrating essential third-party tools such as Calendly, Thrivecart, Flodesk, and Zapier. We also crafted a custom Notion workspace to manage the entire business and developed specialized Notion templates as bonuses for her students.

In addition to these technical enhancements, we provided extensive support in rewriting the course, optimizing the curriculum, presentations, and bonus materials to enhance the learning experience. We developed comprehensive branding assets for the community, presentations, emails, and her website to ensure a cohesive visual and user experience.

I assumed the role of course manager, promptly addressing all student inquiries and ensuring smooth course operations. Our strategic overhaul dramatically reduced Sophia’s operational workload, allowing her to focus solely on delivering live teaching sessions. Now, Sophia needs to actively work only two hours a week during course periods, freeing her up to concentrate on content delivery and strategic growth.

Michael Lightman, an influential figure in startup education, collaborated with Zen Mondays to launch his innovative Don’t Hate Your Deck course. Designed to transform ineffective pitch decks into compelling presentations that capture investor interest, the course targets tech startups looking to secure venture capital funding.

From the outset, we were tasked with creating the course on Circle from scratch, employing a tech stack that included Circle automations and essential third-party tools like Webflow, Thrivecart, ConvertKit, and Zapier. We built a dynamic course environment that supports both evergreen content and separate live group programs, offering flexibility to accommodate various learning preferences and scheduling needs. Additionally, we developed a custom Notion workspace to streamline course management and student interaction, enhancing the organizational efficiency of the course.

Although Don’t Hate Your Deck has only recently launched, early feedback has been overwhelmingly positive, with participants praising the clarity and actionable insights provided. Michael Lightman's course is poised to become an essential resource for any startup or organization aiming to improve their funding outcomes through better presentations.

Our collaboration with Michael highlights Zen Mondays' ability to tailor educational platforms to the specific needs of clients, ensuring that both content delivery and technical infrastructure align perfectly to facilitate learning and growth.

Jonathan Smart, alongside his partners, co-founded Caddy Clubhouse to professionalize caddying and create career pathways for both club and tour caddies. Their mission is to help aspiring caddies secure positions at top golf clubs and tours worldwide through training, community, and professional connections.

Before partnering with Zen Mondays, the team faced the challenge of building an entirely new platform from the ground up. They needed more than just a place for members to gather—they required a structured, scalable ecosystem that could simultaneously serve caddies and golf clubs, manage multi-product offerings, streamline course delivery, and drastically reduce manual administration.

We designed and launched a full Circle build that included two connected communities—one for caddies and one for club recruiters—supported by a complete architecture of paywalls, branded design, and engagement flows. Advanced automations were developed to handle certificate delivery upon course completion, Airtable-powered testimonial and review tracking for caddies, and streamlined recruiter workflows for purchasing and assigning training seats. To unify the experience, we integrated third-party tools such as Stripe, Airtable, Zapier, and Notion, creating a seamless backend system to manage both community and business operations.

To further strengthen the platform, we built a comprehensive Notion backend hub for team operations, integrated forms to capture and manage data, and developed engagement strategies designed to foster participation across both communities.

The result is a professional, dual-track Circle community that operates as a polished, automated, and scalable platform. Caddy Clubhouse now delivers a smooth user experience for caddies and clubs alike, while reducing the workload for its founders and positioning the business for continued growth on an international scale.

The success of Caddy Clubhouse showcases how thoughtful architecture and advanced automation can transform a complex vision into a scalable, high-impact reality.

Jamie Brindle, a veteran freelance strategist with over 16 years of experience—including collaborations with Fortune 500 clients like Google, Netflix, and Lionsgate—launched The Freelancing Program to help creatives and professionals build predictable, scalable freelance businesses. Through structured systems, community support, and live coaching, the program has already served over 1,500 freelancers worldwide.

When Jamie approached Zen Mondays, his program was hosted on Kajabi. Managing such a large community and course on Kajabi was clunky, with limited tools for engagement, automation, and scaling. The setup created unnecessary manual work for Jamie’s team and made it difficult to deliver a cohesive member experience.

We facilitated a complete migration of The Freelancing Program from Kajabi to Circle, including both course and community content, and carefully onboarded all 1,500 existing members into the new ecosystem without disruption. The build incorporated Circle architecture, subscription workflows, and paywalls designed for long-term scalability. To streamline operations, we implemented Circle automations for onboarding and member management, and we developed a custom Notion backend to centralize team processes. Additional integrations with Zapier, ConvertKit, and Calendly ensured that email sequencing, scheduling, and access were automated across the entire system.

To ensure sustainability, we also trained Jamie’s team to manage the backend with confidence, providing clear systems and documentation to support the community moving forward.

The result is a polished, subscription-based Circle ecosystem that reduces administrative complexity, improves the member journey, and frees Jamie to focus on strategy and delivery. The success of The Freelancing Program demonstrates how thoughtful migration and automation can transform large-scale programs into seamless, growth-ready platforms that serve communities worldwide.