Monomoy Strategies Lighthouse

Navigate Smarter

Nearly half a century as CEO, CMO, CSO, and Inc. 500 Board Advisor. Now applying every lesson to help entrepreneurs transform their businesses with AI.

Bill Sifflard
Founder & Strategist

Meet Bill Sifflard

For nearly half a century, I've been in the arena — as entrepreneur, CEO, CMO, CSO, Inc. 500 board advisor, and executive coach. I've built and led companies across food service, energy, financial services, and building supplies manufacturing. I've recreated branding strategies for $300M companies, built sales organizations that achieved unprecedented growth, and coached hundreds of organizations from startup to scale.

What I've learned across all of it: every company reaches a moment where they must transform — or start to decline. That moment is happening right now for every business in America, and it's called AI. Through Monomoy Strategies, I help business owners navigate that transformation with the tools, strategy, and wisdom that only comes from doing it the hard way for decades.

“The way I see it, we either leverage AI in our business, or AI will leverage our business. The companies that harness these tools won't just keep up — they'll lead.”

Nearly Half a Century of Growth and Leadership

CEO, CMO & CSO — Multiple Industries

Served as chief executive, marketing, and strategy officer across food service, energy, financial services, and building supplies manufacturing — building organizations from the ground up and scaling them to industry leadership.

Inc. 500 CMO & Board Advisor

Served as CMO of an Inc. 500 company and as an executive board advisor — recreating complete branding strategies for $300M+ organizations and driving growth at the highest levels of business.

Built Sales Organizations with Unprecedented Growth

Designed, built, and led sales organizations that achieved results that set new benchmarks in their industries — combining strategic vision with ground-level execution.

Coached Hundreds of Organizations

As VP of Business Breakthroughs International — one of the world's leading business coaching organizations — consulted and coached hundreds of companies from early-stage startups to established enterprises seeking transformation.

The Forming → Norming → Transforming Framework

Every business goes through it: you form, you norm, then you must transform — or decline. Each major revenue threshold ($1M, $5M, $10M, $50M, $100M+) demands a new transformation. Companies that refuse to evolve don't plateau — they fall behind.

Now: AI as the Next Paradigm Shift

The AI revolution is the biggest transformation moment in 50 years of business. The companies that treat it like every other technology cycle will be disrupted by those that embrace it. Monomoy Strategies exists to make sure your business is in the second group.

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The Vibe Entrepreneur

Weekly AI insights for real business owners — not developers. Nearly half a century of business experience, applied to the tools that are reshaping every industry.

Practical tools. Real workflows. Honest lessons. Every Tuesday.

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Our Solutions & Tools

Smart solutions and tools built by entrepreneurs, for entrepreneurs. Each one combines cutting-edge AI with real-world business expertise.

🛠️ Tools

Software products you can use today

Featured

HeartbeatGuard

Runtime security monitoring for AI agents. 10 automated security checks run during every heartbeat cycle — from open ports and failed logins to credential rotation and suspicious processes. Your AI agent's security watchdog.

Free & Open SourceLearn More
Featured

OpenClaw Agent HQ

AI agent command center dashboard that puts you in control of your AI workforce. Manage, monitor, and optimize your AI agents from one powerful interface.

Pro Annual $39.99/yr • Lifetime $199Learn More
Featured

AIDEN — AI Executive Navigator

Your AI-Integrated Daily Executive Navigator. A proactive AI companion that learns your business, manages your day, and surfaces opportunities before you even ask. Built for busy executives and entrepreneurs who need a strategic partner, not just another chatbot.

Coming Soon

💡 Solutions

Services and platforms to grow your business

The Vibe Entrepreneur

A content platform and community for entrepreneurs who are embracing AI to transform their businesses. Weekly insights, strategies, and real-world playbooks from someone who's been building businesses for 45 years — now with AI as the ultimate force multiplier.

Free Newsletter — Launching SoonLearn More
Featured

The Beacon Method™

An AI-powered brand launch methodology that compresses 9-18 months of traditional brand work into 30-45 days. Seven sequential phases — from raw idea to market identity — guided by an AI board of four specialized models and signed off at every gate by an experienced executive. Your brand, navigated.

Custom EngagementLearn More

Branding & Web Development

Professional branding and web development services powered by AI and guided by decades of marketing expertise. From brand identity and messaging to modern, high-converting websites — we build your digital presence the right way.

Custom Pricing

Coaching & Custom Workflows

One-on-one coaching combined with custom-built AI workflows tailored to your operations. From lead nurturing to client onboarding, we design and deploy automation that saves you hours every week — guided by decades of executive leadership experience.

Custom Pricing

Our Vision

We're living through the most significant technological revolution since the internet. Artificial Intelligence isn't just changing how we work—it's redefining what's possible for businesses of every size.

"The lighthouse that guides entrepreneurs through AI complexity."

But with great opportunity comes great confusion. That's where Monomoy Strategies comes in. We bridge the gap between proven business strategy and the AI revolution, offering tools and wisdom that help entrepreneurs navigate smartly, not just quickly.

Because in a world moving this fast, experience isn't just valuable—it's essential.

Get in Touch

Ready to navigate the AI revolution with confidence? Let's start a conversation about your business goals and how our tools can help you achieve them.

Consumer Division

Personal Tools

Products built for everyday life — gifts, pets, fitness, and more. Made with the same AI-first approach we bring to business.

Explore Personal Tools