Business Coaching for Owners and Leaders
Great marketing doesn’t start with a campaign. It starts with a clear, honest understanding of your business and realistic expectations about what marketing can and can’t do for it.
Run With Vision is a business coaching program built on a foundation of communication: internal alignment, external branding, and the processes that connect the two. It helps owners and leaders clarify direction, strengthen how their business communicates — inside the team and out in the market — and turn ideas into focused, consistent action.
Why Small Business Marketing Fails
After 18 years in business, we’ve noticed the same patterns showing up again and again in small businesses whose marketing isn’t working:
- Benchmarking against the wrong examples
- Marketing before the fundamentals are clear
- Mismatched expectations
- Doing too many things at once
- Learning as you go, without a system
- Treating marketing as separate from the business
The Approach
This program draws on Cucumber Marketing’s own 18 years of running a business + serving our clients, combined with a framework informed by EOS (the Entrepreneurial Operating System). We couple it with branding and communication principles, so marketing gets treated as a business function, not an isolated activity.
Whether you’ve tried marketing before and it didn’t work, or you’re starting from scratch and want to do it well, this coaching digs past the surface. Instead of jumping straight to tactics, we look at your marketing as one piece of the bigger business picture — connected to your vision, your operations, and your team’s communication. Ready to grow? Book a discovery call with Helen here.
How it Works
Run With Vision: 8-Week Business & Marketing Foundations
Here’s a structure that takes the 6 key small business marketing problems and flips each into a week of the program, using EOS concepts as the scaffolding:
Week 1 — Vision & Core Focus
Problem it solves: marketing before fundamentals are clear
Define vision, mission, values, and — borrowed from EOS’s V/TO — your Core Focus (your niche and your “why”). Nothing marketing-specific happens until this is locked.
Week 2 — Know Your Real Starting Point
Problem it solves: benchmarking against the wrong examples
Map where the business actually stands — budget, team size, current traction — so Nike and influencer comparisons get replaced with realistic peer examples at your stage.
Week 3 — Setting Expectations & Defining Success
Problem it solves: mismatched expectations
Get explicit about what marketing can and can’t do in the next 6 to 12 months. Introduce a simple Scorecard (EOS-style) with 5-10 numbers that will actually indicate progress.
Week 4 — Audience & Positioning
Problem it solves: doing too many things at once
Narrow down who you’re actually talking to and what makes you different, so channel and tactic decisions in later weeks have a filter instead of “let’s try everything.”
Week 5 — Set Your First Rocks
Problem it solves: learning as you go, without a system
Set 1-3 Rocks (EOS’s 90-day priorities, scaled here to your first cycle) — specific, owned, deadlined marketing priorities instead of an open-ended list.
Week 6 — Align Internal & External Communication
Problem it solves: marketing treated as separate from the business
Make sure how the team talks internally matches how the brand talks externally — messaging, tone, and the operational processes that support both.
Week 7 — Build the Accountability Rhythm
Problem it solves: no system to build on
Introduce a lightweight weekly check-in (EOS’s Level 10 meeting, scaled down) — review the Scorecard, review the Rocks, use IDS (Identify, Discuss, Solve) on anything stuck.
Week 8 — Review, Learn, Set the Next Rocks
Problem it solves: closing the loop so nothing gets thrown away
Review what worked, what you learned, what to carry forward. Set the next round of Rocks — reinforcing that this isn’t a one-time sprint; it’s the first layer of an ongoing rhythm.