Round Table
Multi-Advisor Collaboration
Bring multiple advisors together in a single conversation. Get synthesized perspectives from multiple AI advisors on complex, cross-functional decisions.
Building the future of business advisory
AI-Powered Tools for Every Entrepreneur
CEO Sidekick gives entrepreneurs and small businesses a complete suite of AI-powered tools — from expert advisors to document templates, content creation, goal tracking, and more — so you can make smarter decisions, faster.
Our Mission
Leveling the playing field for every entrepreneur
Over 33 million small businesses in the U.S. alone operate without access to the executive guidance that larger companies take for granted. Most founders wear every hat — CEO, CTO, CFO, head of HR — while making critical decisions in isolation.
CEO Sidekick exists to change that. We provide an AI-powered advisory team that delivers enterprise-grade strategic guidance at a fraction of the cost of traditional consulting.
Our Vision
A world where no founder builds alone
We envision a future where every business owner — regardless of budget, location, or network — has instant access to world-class strategic advice whenever they need it.
By combining advanced AI with deep domain expertise across technology, law, HR, marketing, sales, and leadership, we are building the advisor that every entrepreneur deserves but few can currently afford.
6
AI-Powered Tools
33M+
Small Businesses Underserved
24/7
Availability
< $1
Per Consultation
The Founder
Built by a founder, for founders
Shannon
Founder & CEO
Shannon is a full-stack technologist and entrepreneur who has spent years helping businesses harness the power of data and technology. As the founder of Full Stack Data Solutions, a consultancy specializing in data engineering and analytics, Shannon saw firsthand how small business owners struggled to access the strategic guidance that larger organizations take for granted.
That gap — between the advice founders need and what they can actually afford — became the spark for CEO Sidekick. By combining deep expertise in AI, cloud architecture, and business operations, Shannon set out to build an advisory platform that puts a complete AI-powered business toolkit in every entrepreneur's pocket.
CEO Sidekick is bootstrapped and self-funded, reflecting Shannon's conviction that the best products are built with the same resourcefulness and grit that define the entrepreneurs they serve.
The Advisory Team
Seven specialized AI advisors — one key part of the toolkit
AI advisors are one of six tools in the CEO Sidekick suite. Each advisor brings deep domain expertise to help you navigate the challenges of running and growing your business.
Technology Partner
Virtual CTO/CIO
Technology and automation strategy advisor. Get guidance on tech stack decisions, digital transformation, and build vs. buy analysis.
Learn more
Executive Coach
Leadership Partner
Leadership development and strategic thinking partner. Prepare for difficult conversations, set OKRs, and develop as a leader.
Learn more
Legal Advisor
Contract & Compliance
General legal guidance and document review. Get contract red flags identified and understand business structure options.
Learn more
HR Partner
People Operations
Human resources guidance and documentation. Create job descriptions, develop interview questions, and build HR processes.
Learn more
Marketing Partner
Growth & Brand
Marketing strategy and brand development advisor. Plan campaigns, develop positioning, and optimize your marketing spend.
Learn more
Sales Partner
Revenue & Deals
Sales strategy and deal-closing advisor. Build your sales process, handle objections, and improve your close rate.
Learn more
Content Engine
Thought Leadership
AI-powered content generation for marketing and thought leadership. Create blog posts, social media, and marketing copy.
Learn moreWhat Drives Us
Our values
These principles guide every decision we make — from product development to how we interact with the entrepreneurs we serve.
Democratize Expertise
Every entrepreneur deserves access to the same caliber of guidance that Fortune 500 CEOs rely on. We make executive-level advice accessible and affordable.
Trust & Transparency
Your business data stays yours. We build with privacy-first architecture, never train on your conversations, and are always upfront about what AI can and cannot do.
Founder Empathy
We are founders building for founders. Every feature is shaped by the real challenges of running a business — because we face them too.
Speed to Impact
Answers in seconds, not weeks. Our advisors are available 24/7 so you can make informed decisions at the pace your business demands.
Ready to try the full toolkit?
Start with 15 free credits per month. No credit card required. Access all 6 AI-powered tools in seconds.