Cheshire
Strategy

Strategic Roadmap — Cheshire Strategy
Need something shorter? See the 3-month Clarity Sprint →

The Strategic
Roadmap.

A structured six-month partnership to turn your small business marketing from chaos into a clear, working system you can confidently move forward with.

The Strategic Roadmap Program
Deep data-backed strategy + light implementation.
  • Clear positioning people immediately understand
  • Website improvements to drive your growth & increase results
  • A realistic content plan
  • A conversion funnel that’s set up and tracked properly
  • Trainings and a 12-month roadmap your team can follow

Starts at $9,500 Fixed Scope · Flat Fee
Strategy-first approach
Light implementation included
Plain-language deliverables

Businesses need clarity, confidence and a plan they can realistically follow.

The Strategic Roadmap program is built for businesses who are ready to stop reacting and start moving with intention, guided by an independent strategist who isn't trying to sell you the next step.

At the end of 6 months, you'll have:

Clear positioning and messaging that reflects your business

A sharper website with technical issues fixed and a better user experience

A content system and a plan you can realistically implement

A strategic paid and social amplification plan that's ready when you are

A working conversion funnel with analytics setup so you can make better decisions

Trainings, documentation, and a 12-month roadmap that can be implemented by anyone

Six months.
One strategic improvement at a time.

Each month builds on the last, combining strategy, clear action, and light implementation so you can stay focused on your business while your visibility moves forward.

Month 1
01

Positioning & Messaging

We make it obvious what you do and why it matters.


  • Define your ideal customer and core offer
  • Clarify your value and positioning
  • Build messaging that sounds like you
  • Identify keyword and visibility opportunities
Light Implementation Included
  • Homepage headline + subheadline update
  • Service page header refinement
  • Metadata updates for key pages

You leave with clarity, direction, and messaging that finally clicks

Month 2
02

Technical Foundation

We fix what’s quietly blocking your visibility and conversions.


  • Audit your website, SEO, and analytics setup
  • Identify technical issues and missed opportunities
  • Review local visibility and search presence
  • Prioritize the highest-impact fixes
Light Implementation Included
  • Fix key site issues (metadata, indexing, headers)
  • Clean up broken links
  • Improve GA4 tracking and key CTAs

You leave with a cleaner, more reliable foundation that supports growth.

Month 3
03

Content & Experience

We build a content system you can sustain and a site that converts.


  • Define your core content themes and priorities
  • Build a realistic 90-day content plan
  • Align messaging with how people currently navigate your site
  • Identify where UX is helping (or hurting) conversions
Light Implementation Included
  • Improve one high-priority page (hero, layout, CTAs)
  • Make UX clarity fixes across key sections
  • Update on-page messaging for better alignment

You leave knowing what to publish, with a site that supports it.

Month 4
04

Amplification Strategy

We map out how to scale your visibility, without wasting time or money.


  • Whether ads actually make sense for your business
  • Which platforms are worth your attention (and which aren’t)
  • Budget guidance and realistic expectations
  • How your funnel and audience need to align
Light Implementation Included
  • Set up ad account structure (if applicable)
  • Define audiences or keyword groups
  • Update social profiles for clarity and positioning

You leave with a clear path to scale, when you're ready.

Month 5
05

Funnel & Tracking

We make it clear how people move through your business, and what’s working.


  • Map your customer journey from first touch to conversion
  • Identify where people drop off or get stuck
  • Improve your funnel and conversion flow
  • Clean up tracking so your data is reliable
Light Implementation Included
  • Improve CTAs and form flow
  • Add internal links to guide conversions
  • Update or add key tracking events

→ You leave with data you can trust and use to make better decisions

Month 6
06

Systemize & Scale

We turn everything into a system you can run without us.


  • Review what’s working and where to improve
  • Turn key processes into simple, repeatable workflows
  • Build your 12-month visibility roadmap
  • 12-month strategic visibility roadmap
  • Prepare your team to take this forward
Light Implementation Included
  • Final messaging + UX refinements
  • Last metadata or tracking updates
  • Prioritized next-step recommendations

→ You leave with a system, a plan, and the confidence to keep moving.

What's always
in your corner.

Beyond the month-specific work, you’ll have consistent strategic support, and you'll always know what’s happening and what's coming next.

Monthly Strategy Call A focused 1:1 session to align, review progress, and plan what’s next
Written Action Plan Clear, prioritized next steps after every call
Light Implementation High-impact updates handled for you each month
Email Access Ask questions and get answers between sessions
Call Recording + Notes Full documentation so nothing gets lost
Ongoing Refinement Your strategy evolves as we learn what's working

By month six,
here's what changes.

You have clarity about where your business currently is, where it's going, and how to get there.

You stop second-guessing.

Every decision has a clear rationale. You know why you’re doing something, and why you’re not.

Tradeoffs become obvious.

You know which channels are worth your time and which aren’t, so you can say no with confidence.

You stop wasting money.

You’re only investing in what aligns with your goals, not what sounded good in someone else’s pitch.

Your team knows what to do.

Trainings, a roadmap, and a clear handoff mean the work keeps moving after we’re done.

Need deeper
execution?

The core program focuses on strategy and light implementation. If you want more hands-on execution, these can be layered in at the right time, either as separate projects or ongoing support.

Website & Messaging

Full Website Copywriting

Rewrite your homepage and key pages, refine your messaging, and restructure your site so everything works together.

Content Creation

Blog & Social Content

Monthly blog articles, social content calendars, caption writing, asset creation, and scheduling, so the plan gets executed.

Paid Advertising

Ads Management

Google Ads and Meta campaign builds, audience testing, creative direction, ongoing optimization, and monthly reporting.

Email Marketing

Nurture Sequences

Automated email sequences, campaigns, and newsletters, written and ready to send.

Funnel & CRM

Full Funnel Build

Landing pages, lead capture, CRM setup, and automation, all connected and working together.

Analytics

Advanced GA4 & Dashboards

Deeper tracking, funnel visibility, and custom dashboards your team can use.

Which engagement
is right for you?

Both programs share the same strategic philosophy. The difference is depth, duration, and how far you want to go together.

3-Month Program

The Clarity Sprint

The highest-impact strategic work from across all six months, compressed into 90 days for businesses that need fast momentum.

Duration 3 months
Monthly strategy call ✔ Included
Light implementation ✔ Each month
Positioning + messaging ✔ Month 1
Technical + SEO audit ✔ Month 1
Content + social strategy ✔ Month 2
Paid ads strategy ✔ Month 2
Funnel + tracking ✔ Month 3
Trainings + roadmap handoff ✔ Month 3
Depth per strategic area — Condensed

Let's plan
your destination.

Book a free 30-minute call. It's an honest conversation about where you are and what you actually need.