Monomoy Strategies

Navigate smarter in the age of AI.

Forty years of business leadership, translated into a system for entrepreneurs who refuse to be left behind. Know where you are. See what's coming. Leap before the water changes.

“You either harness AI in your business, or you hand your future to those who do.”

— Bill Sifflard

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The Vibe Cycle

Where are you right now?

Every business cycles through the same three phases — at every revenue milestone, at every scale.

Setting Sail
Launch

High energy, high uncertainty. Whether you're starting something new or steering an existing business into a new chapter, you're proving this phase can float. The danger isn't complacency — it's mistaking enthusiasm for readiness.

Watch for: mistaking motion for progress.
Underway
Level

Revenue is consistent. Things feel good. Comfortable water is a warning, not a reward — the channels beneath you are silting up while the surface looks fine.

Watch for: “what got us here” stops getting us further.
The Passage
Leap

Every business must eventually transform. The best companies leap proactively — they dredge the new harbors while the current water still looks fine. Only three out of ten companies make it through the Passage. Seven go down. Preparation is the difference between the three and the seven.

Watch for: waiting until the old model stops working.
“Comfortable water is a warning, not a reward.”

Pick the phase that made you wince. That's your current water.

Take the phase diagnostic →5 questions · 60 seconds · no email to start
Identify Your Harbor

Where are you headed?

Revenue tells you where you've been. Harbors tell you where you're going. Six dimensions every business must dredge.

H
Human Capital
Your Crew

Talent, leadership depth, and the roles you haven't filled yet. Do you have the right people to grow past where you are today?

A
Acquisition
Your Market

Marketing and sales bringing new prospects in. Where you fish — outward-facing, measurable, compounding when it's working.

R
Reputation
Your Brand

How you're known. Trust, authority, industry position. If you disappeared tomorrow, would your market notice and care?

B
Build
Your Product

What you offer — quality, innovation, differentiation. Is your product meaningfully better or different from your competitors?

O
Operations
How You Run

Systems, processes, infrastructure. Could the business run smoothly for 30 days without you? If not, you're the bottleneck.

R
Retention
Your Customers

Keeping what you've caught — loyalty, lifetime value, referrals. Not the same harbor as acquisition. Most businesses confuse them.

“Revenue is dessert. It's what you get when the harbors are healthy.”

The harbor you're ignoring is the one holding you back. Find it.

Score your six harbors →Six ratings · radar chart · results emailed to you
Bill Sifflard, founder of Monomoy Strategies
About Bill Sifflard

Forty years of growth and leadership.

For 40 years I've been in the arena as an entrepreneur, president, CEO, and consultant. I have built and led companies across multiple markets and industries. I built marketing and sales strategies for Fortune 500 companies, achieving unprecedented growth, and consulted and coached with hundreds of businesses from startup to scale.

What I've learned across all of it: every company reaches a moment where it must transform or start to decline. What wasn't there 10, 20, or 40 years ago was the ability to leverage AI to make that transformation. At Monomoy Strategies, we help businesses navigate those waters with tools, strategy, and hard-won wisdom that only comes from decades in the trenches.

“You either harness AI in your business, or you hand your future to those who do.”
Read the full story →

Pick your next move.

A done-for-you engagement, a newsletter, a coaching certification, or a direct line to me. Choose the path that fits where you are.

Available now🪔
The Lantern

Your business, built to be found, chosen, and remembered. SEO, brand, website, automation, and AI — rebuilt for the AI era.

Start with The Audit →
Coming soon📬
The Vibe Entrepreneur

Weekly thinking on AI, growth, and the leap. Delivered Tuesdays and Thursdays.

Launching soon
Coming soon🎓
Vibe Coach Training

Certification program for coaches running client work in the age of AI.

Launching soon
Coming soon✉️
Talk to Bill

For press, speaking, or partnership inquiries. Direct line.

Launching soon