The Lonely Entrepreneur exists because founders are overwhelmed, isolated, and unsure who to trust—especially in an AI-driven economy.
We believe:
We are all lonely entrepreneurs.
Our mission is to build the most trusted place entrepreneurs go for answers, support, and execution.
At the center of The Lonely Entrepreneur is a growing community of founders, operators, and business leaders who connect with each other, share insights, and access resources that help them build and grow companies.
Entrepreneurs engage with this community through discussions, events, social platforms, and collaborations.
Within this ecosystem, entrepreneurs may access several offerings designed to support them at different stages, including:
- Learning Community (LC) – the only 1 stop shop for entrepreneurs
- Sidekick Consulting – 1:1 consulting for $5M–$25M businesses
- Entrepreneur Survival Guide – a system for navigating entrepreneurship in an AI-driven world
- MichaelGPT – an AI assistant trained on the experience of founder Michael Dermer
Learn more at:
https://lonelyentrepreneur.com
About the Role
This role is responsible for growing and activating The Lonely Entrepreneur community.
This is not a traditional moderation role.
The primary responsibility is expanding the audience of entrepreneurs engaging with The Lonely Entrepreneur across social platforms and online communities.
The role has three primary objectives:
1. Grow the entrepreneur community (approximately 60% of the role)
Expand the reach and participation of The Lonely Entrepreneur community across social platforms and digital ecosystems.
2. Drive engagement inside the community ecosystem (approximately 25% of the role)
Support meaningful participation within the community, including discussions, events, and the Learning Community platform. Knowledge of Mighty Networks or other community platforms is important.
3. Generate Revenue from the community (approximately 15% of the role)
Key Responsibilities
Community Growth (Primary Focus)
Grow the entrepreneur audience around The Lonely Entrepreneur by engaging communities across social platforms and digital ecosystems.
Responsibilities include:
- Engaging entrepreneurs across social platforms such as LinkedIn, X (Twitter), Instagram, Facebook groups, Reddit, YouTube, and TikTok
- Identifying and participating in conversations happening in entrepreneur and business communities
- Sharing founder insights, stories, and lessons to expand the reach of the community
- Identifying emerging discussions and bringing them into The Lonely Entrepreneur ecosystem
- Building relationships with leaders of entrepreneur communities and founder networks
- Supporting partnerships with accelerators, incubators, and business organizations
- Helping expand the visibility and influence of The Lonely Entrepreneur community
Community Engagement
Support active participation within The Lonely Entrepreneur ecosystem.
Responsibilities include:
- Encouraging discussion and participation within the community
- Responding to member questions and connecting them with helpful resources
- Starting discussion prompts and founder conversations
- Highlighting meaningful insights shared by members
- Identifying members who may need additional support or resources
Learning Community Engagement
Support engagement within the Learning Community platform by helping members get value from available resources.
Responsibilities include:
- Helping members navigate the platform
- Encouraging participation in discussions
- Promoting coaching calls and events
- Helping members connect learning resources to real business challenges
Events and Founder Discussions
Support community programming including:
- Founder discussions
- Group coaching calls
- Community conversations
- Workshops and special events
Responsibilities include scheduling, reminders, moderation, and follow-up.
Member Recognition and Success Stories
Help highlight the achievements and insights of community members.
Responsibilities include:
- Identifying member success stories
- Capturing founder lessons and insights
- Sharing community wins across platforms
Community Revenue Pathways
As relationships develop with community members, help identify opportunities where entrepreneurs may benefit from additional support such as:
- Learning Community membership
- Coaching calls
- Events or programs
- Sidekick consulting
All recommendations must be trust-based and focused on helping entrepreneurs succeed.
Data, Reporting, and Systems
Responsibilities include:
- Maintaining community records in HubSpot
- Tracking growth and engagement metrics
- Supporting CRM workflows and automation
- Providing weekly updates on community activity and growth
Required Qualifications
- 5+ years experience managing online communities or membership-based platforms
- Experience growing an online audience or community
- Strong social media engagement skills
- Experience working with entrepreneurs, founders, or small businesses
- Experience using CRM systems (HubSpot preferred)
- Strong written communication skills
- Highly organized and able to operate independently
Preferred Experience
- Entrepreneur or founder communities
- Business consulting or coaching environments
- SaaS or subscription-based platforms
- Content distribution or social media growth
- Experience organizing online discussions or events
How Success Is Measured
Success in this role will be measured by:
Community Growth
Growth in the number of entrepreneurs engaging with The Lonely Entrepreneur community.
Community Engagement
Participation in discussions, events, and interactions across the ecosystem.
Community Revenue Impact
Participation in offerings such as the Learning Community and Sidekick consulting.
Application Questions
Please include answers to the following questions when applying.
1. Community Growth Plan
In 300 words or less, describe three ways you would grow The Lonely Entrepreneur community in the first 90 days.
2. Community Example
Provide one example of a community, audience, or platform you helped grow. Include:
- the platform
- starting audience size
- current audience size
- what actions you personally took to drive growth
Why This Role Matters
Entrepreneurs succeed when they have a trusted community around them.
This role is responsible for helping build that community—expanding its reach, strengthening engagement, and ensuring entrepreneurs find the support they need.
Pay: $65,000.00 - $75,000.00 per year
Benefits:
Work Location: Remote
