Trailway Flight Plan
Prepared by The Bold Group
ETHOS STATEMENT
We deliver Go to Market peace of mind to entrepreneurs who are experts in their business and are passionate about driving results, but don't have expertise in selling.We do this by implementing systems to clarify messaging, generate hand raisers, create opportunities and ultimately close business.
The Main Thing
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$10,000,000 exit in early 2028
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$3,500,000 ARR in 2027
With X% net profit
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$2,000,000 ARR in 2026
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$1,000,000 ARR in 2025
1 Month
Get Calvin out of delivery and fully focused on sales.
1 Month Focus Areas
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Documentation
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Define Client Acceptance
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Marketing 101
Documentation
Sales Process
Client Onboarding
Campaign Setup
Service Fulfillment
Define Client Acceptance
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Importance
Knowing who to say no to is just as important as who to accept.
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Qualification
Establish clear client qualification filters to increase retention
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Alignment
Avoid misaligned customers to avoid churn
Marketing 101
Begin outbound email
Core purchase journeys and workflows
- Map main customer journeys – Email, LinkedIn content, referral.
- Establish main workflows – welcome flow, newsletter, appt reminders
Build LinkedIn personal brands
- Jeremy
- James
- Calvin
- Blake
3 Months
Add new clients to prove the system
3 Month Focus Areas
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Begin Pricing realignment
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Establish Steady Lead Flow
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Adjust and Optimize
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Q3 Planning
Establish Steady Lead Flow
Message Market Fit
Finish message market fit campaign and build predictable system
LinkedIn Monetization
Begin to monetize LinkedIn audiences
Put out great content, interact with every person and interact with the people you
Pricing Realignment
Legacy Client Transition
- Decide which clients, if any, will receive new pricing and when.
- Will all clients receiving a price increase get the same one?
Begin With Problem Clients
- Test messaging with people you are ok losing first.
Adjust and Optimize
Sales Process
Is there a way to make it shorter?
Outbound Campaigns
Once message market fit is established, continue running tests.
Account Management
- Do clients need/prefer weekly check-ins
- Do they access the real time dashboards?
Q3 Planning
Goal Assessment
How are things pacing to goal?
MIOs Establishment
Establish MIOs for the quarter for each team member.
- Massively Important Outcomes (not tasks)
- Continue having MIOs for each month and week.
6 Months
Improve the System at Every Stage
6 Month Focus Areas
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Finalize mid-tier offering
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Onboard XDR
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Build Referral Network
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Q4 Planning
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Scale Outbound System
Finalize Mid-Tier Service
Sales process
Can prospects start off at this service or will you only allow clients to get here after you have worked together on EOS?
Pricing
Variable vs. fixed package
Deliverable/Offering
Onboarding
Onboard XDR
Internal Sales Support
Bring either an SDR or BDR onto the team to help with internal sales to increase sales velocity
Client Account Support
External use to support client accounts
Build Referral Network
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Angel investors
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Private equity
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Marketing agencies
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Current customers
Reward System
What sort of reward will you offer for referrals? Cash or unique?
Q4 planning
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Goal Assessment
How are things pacing to goal?
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MIOs Establishment
Establish MIOs for the quarter for each team member.
- Massively Important Outcomes (not tasks)
- Continue having MIOs for each month and week.
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Goal Achievement
What needs to happen to MAKE SURE the goal is hit?
Scale Outbound System
LinkedIn outreach
Manual and automated
Cold Calling
Meta/YouTube video ads
Not sure if there is a fit here and would be interested to see some testing done.
1 Year
Goal: $1,000,000 ARR
1 Year Focus Areas
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Build robust upsell journey
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2026 Planning
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PR, News & Media
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Refine Outbound Process
Build Robust Upsell Journey
Creating a smooth progression path for customers to upgrade their services
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EOS to OOS Transition
Make it easy and obvious when customers need to move from EOS to OOS. Add QBRs into account management for consistent upsell conversation opportunities. Implement clear scripts, metrics, signifiers, and timelines.
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Additional Add-ons
Identify potential additional add-ons to EOS that create value and natural progression.
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Contract Terms
Optimize contract terms to facilitate smooth upsell process.
2026 Planning
Review
Review Clients, service split, revenue, other KPIs
Set Goals
- New clients
- Upsold clients
- Leads/Deals per marketing channel
- Do we want to have goals for % of leads per channel as to be diversified?
PR, News and Media
Key Publications
- Key national and global publications
- These will be incredible assets for marketing and sales
Content Strategy
- Newsletters, puff pieces and press releases
- Build a strategy to 'always have something going on'
Refine Outbound Process
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Vertical Analysis
Is there a global vertical that works best? Channel specific?
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Channel Performance
Identify highest performing channel
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Opportunity Identification
Identify greatest opportunity within each channel
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Channel Evaluation
Time to kill a channel?
18 Months
Build a System for Consistent Fast Growth
18 Month Focus Areas
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Grow Personal Brands
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Grow Product Line
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Hypergrowth
Grow Personal Brands
Speaking Engagements
- Speak where your customers are and about what they are interested in or what troubled by.
Podcast Appearances
- Speak where your customers are and about what they are interested in or what troubled by.
- Great marketing assets
Grow Product Line
Courses
Expand educational offerings through structured learning experiences
Workshops
Develop interactive sessions focused on specific skills and outcomes
Onsite Trainings
Provide customized learning experiences at client locations
Different Contract Models
Create flexible engagement options to meet varied client needs
Staff Augmentation
Offer expertise through embedded team member solutions
Hypergrowth
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Revenue Focus
Key in on $2,500,000 revenue goal and make that the key focus
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Marketing Investment
Increase ad spend and performance across all channels
- At this point we should have a predicable ROAS on all channels and can pick how much to multiply investment by in each channel
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Team Optimization
Audit all employees, vendors, partners, etc. to identify areas of improvement
- Remove dead weight
- The people who got you to where you are aren't always the team that will get you to where you want to go
2+ Years
Exit
2+ Years Focus Areas
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2027 Planning
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Position to Sell
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Scale Growth OS
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Plan the Next Step
2027 Planning
Review
Review Clients, service split, revenue, other KPIs
Set Goals
- New clients
- Upsold clients
- Deals per marketing channel
- Do we want to have goals for % of leads per channel as to be diversified?
Position to Sell
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Growth Consistency
Maintain predictable growth rate
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Digital Presence
Mature digital omni-channel presence
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Marketing Efficiency
Optimize ROAS and ROM
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Long-term Viability
Investor friendly long-term viability roadmap
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Technical Optimization
Reduce technical debt and reduce infrastructure costs
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Strategic Partnerships
Mergers & acquisitions
Scale Growth OS - Is this Possible/Desired?
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Consultant Model
Develop a framework to identify, train, and integrate specialized consultants who deliver our signature expertise and quality standards.
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Scalability
Engineer repeatable, documented processes that maintain quality while allowing for exponential growth across markets and service lines.
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Implementation
Deploy comprehensive training, quality control systems, and performance metrics to ensure consistent excellence throughout expansion.
Plan the Next Step
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Family Time
More time with family
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Travel
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Invest
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New Business
Start another business
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Adventure
Go to space?
This isn't the next business or income generator, but what does life after Trailway?
Appendices
Appendix A: Flight Plan Foundations
Appendix B: Ethos Statement Workshop
Appendix C: Core Offering Workshop
Appendix D: Customer Clarity Workshop
Appendix E: Trailway Roadmap
Appendix B: Ethos Statement Workshop
Appendix C: Core Offering Workshop
Appendix D: Customer Clarity Workshop
Appendix E: Trailway Roadmap
