Company Audit for — Ship It Nation

The Modern Systems Audit

Executive Summary

Company Overview

Core Offer

• Freemium YouTube content for lead generation

• Subscription plans ($79–$321/month) with NFL and Golf strategy, projections, and tools

• Private Discord community (~1,600 members) with direct access to experts and discussions

Growth Snapshot

• Year 1: $600K → Year 2: $1M → Year 3: tracking ~$1.9–$2M

• ~55% profit margins

• 11.5K-person email list, lightly monetized (sales blasts only, no nurture)

• Strong retention and lowest churn ever last month

What’s Working:

• Strong founder-led brand and trusted reputation in DFS space

• High engagement community inside Discord, strong retention metrics

• Organic growth without paid ads or affiliate clutter

• Clear pricing structure and premium positioning

Biggest Bottlenecks/Risks:

• Business is founder-dependent — retention/LTV tied directly to Tyler’s personal involvement

• Customer service consumes 5–8 hrs/week of founder time with no ticketing or triage

• Onboarding is weak — no “Start Here” path, new members risk being lost on Day 1

• No operating rhythm or shared decision rights between founders (no plan for reinvestment vs. cash extraction)

• Email list underutilized — no onboarding or retention automations

• Risk of partner misalignment — Mike prefers maximizing distributions and short-term horizon, Tyler wants reinvestment and long-term growth

Quantifiable Pain:

• 5–8 hrs/week of Tyler’s time lost to support

• Founder stuck “in” the business → limited ability to pursue growth levers (newsletter, partnerships, product expansion)

• New member experience not systematized → potential churn risk as audience scales

Top 3 Challenges

1. Customer Service Bottleneck — Support lives in a shared inbox, no macros or ticketing. Tyler handles 80% of issues personally.

2. Weak Onboarding — No structured “Day 1 → Day 7” experience, leading to preventable churn and high support volume.

3. Leadership & Alignment — No shared reinvestment plan, no clear decision rights, risk of partnership misalignment.

High-Level Opportunity

• Reclaim 5–8 hrs/week of Tyler’s time to work on growth rather than firefighting.

• Increase LTV further through better onboarding, reducing early churn and raising upgrades.

• Create leverage: Tyler moves from “sales and support guy” to strategic leader.

• Build AI-powered customer service that resolves 90%+ of tickets without founder involvement.

• Set a 2–3 year plan that satisfies Mike’s desire for cash while funding smart growth bets.

NOW vs FUTURE

The Roadmap

PHASE 1: GET CLARITY

Objectives

• Align on a 2–3 year vision and strategic posture

• Define founder roles, decision rights, and reinvestment rules

• Establish an operating cadence from annual to weekly

• Create scorecards and accountability for each founder

• Resolve “fork in the road” tensions early to prevent friction later

Why this first

• Vision reduces noise: clear “yes” and “no” filters for work

• Identity clarifies what Ship It Nation can win at longterm

• Rhythms turn strategy into habits and habits into results

• Early agreement on decision rights prevents growing risk of getting stuck and resentment

Risks if We Skip This

Phase 2: BUILD FOUNDATION

The Prerequisite for AI & Automation

Current Challenges

• Information and processes live across WordPress, MemberPress, Discord, AWeber, and Gmail

• Status and ownership live in people’s heads; no ticket reasons or CS reporting

• Onboarding materials exist but are not embedded end-to-end

• No documented SOPs for support, onboarding, or repurposing

Optimized Future State

• One place for goals, roles, SOPs, meeting rhythms, and status

• Help desk and knowledge base as the backbone for AI assistance and macros

• Operating cadence from annual intent → quarterly goals → weekly priorities

• AI-readiness: structured context so AI can draft accurately and route correctly

Foundation Impact

• Hours saved: 25–40 hrs/month by moving support to help desk and macros

• Error reduction: 50–65% fewer repeated questions and access issues

• Speed: Faster time-to-first-value via guided onboarding

• Staff efficiency: Tyler recovers 5–8 hrs/week; support/dev handles 90% of tickets

• Revenue impact: Lower early churn and more systematic upgrades

What Happens If We Skip the Foundation?

• Automations and AI lack context → errors and rework

• Founder remains the bottleneck for approvals and replies

• Dashboards exist but trust is low → gut-based decisions persist

• Costly rework later (rebuilding rules, renaming fields, re-linking flows)

PHASE 3: OPTIMIZE KEY PROCESSES

Process Optimization #1: Onboarding Spine + Lifecycle Emails

Process Overview

Current Problems

• No guided Day 1–7 path; users get lost after purchase

• Discord setup and notifications confuse older, mobile-heavy audience

• No lifecycle emails to drive activation steps

Optimized Future State

• 4-email welcome series with short Looms and checklists

• Pinned Start Here and Introductions channels in Discord with role-based prompts

• Mobile setup PDFs and quick links for Discord

• Behavior-triggered nudges for missed steps

Impact Summary

• Hours saved: 8–12 hrs/month via fewer basic tickets

• Speed improvement: Faster activation within first 72 hours

• Retention lift: Expected 10–15% reduction in early churn

Optimization #2: Help Desk + AI Draft Engine

Process Overview

Current Problems

• Email-only support with no routing, macros, or reporting

• Repeated questions and manual replies by founder

Optimized Future State

• Help desk (e.g., Help Scout, Freshdesk, Zendesk, etc) with macros, forms, reasons, and KB

• AI drafts and one-click approvals for edge cases

• Weekly CS report with top reasons and deflection rate

Impact Summary

• Hours saved: 12–18 hrs/month

• Error reduction: 50% fewer missed or delayed replies

• Visibility: Ticket reasons inform onboarding and product improvements

ROI - Process Optimizations

Totals (ops time only)

• Expected monthly hours saved: ~25–30

• Expected monthly labor savings: $2,125–$2,550 (at ~$85/hr blended)

• Expected annual labor savings: $25,500–$30,600

• Additional revenue upside: reduced churn and increased upgrades from better activation

Rollout Strategy (Proposal)

90-Day Implementation (Outcomes by Phase)

• Shared 2–3 Year Vision: Clear agreement on growth vs. cashflow goals and long term roadmap.

• Decision Rights & Guardrails: Documented rules for reinvestment, spending, and who decides what.

• Operating Cadence: Annual → quarterly → weekly rhythm that keeps founders aligned and focused.

• Accountability & Metrics: Simple scorecards so Tyler and Mike can see progress without debating.

• Foundation for Company OS: With alignment in place, we can build a Company OS that scales — instead of building systems on top of friction.

• Company OS Live: One central place for goals, roles, SOPs, and meeting rhythms so the team runs on rails.

• Help Desk & Knowledge Base: Ticketing system, macros, and CS reporting to cut support time and create data visibility.

• Onboarding Spine & Lifecycle Emails: “Start Here” flow + Day 1–7 onboarding experience to reduce churn and activate new members faster.

• Dashboards & Metrics: Real-time view of activation, churn, support load, and upgrades for data-driven decisions.

• AI-Ready Infrastructure: With data structured and processes documented, we can layer in automation and AI to remove repetitive work and scale without adding headcount.

• Frictionless Onboarding: 4-email welcome series, guided Day 1–7 path, and pinned Discord setup channels to get new members to first value in 48 hours.

• Behavior-Based Nudges: Automated reminders for missed steps to increase activation and retention.

• Help Desk Live: Portal, macros, and ticket reasons replace ad-hoc email support, giving real reporting and freeing Tyler’s time.

• AI Draft Engine: First-reply automation handles 70%+ of tickets with one-click approvals for edge cases.

• Compounding Flywheel: Every support interaction and onboarding step now generates data → fuels continuous improvement and future automation layers.

Readiness Score & Acceptance Criteria

Why Now?

• Stop losing 25–30 hours every month to repeatable support and onboarding friction

• Build the foundation to avoid scaling bottlenecks and partnership slowdowns

• AI won’t fix chaos, it multiplies it; the OS and help desk make AI safe and useful

• Fast feedback from metrics drives better decisions and faster iteration

Final Thoughts

• You get 30+ hours a month back to focus on the newsletter, partnerships, and high-leverage growth moves.

• Support and onboarding run without you, so you can take time off without worrying something will break.

• You shift from being the engine of the business to the driver of the strategy.

• You get a cleaner, more predictable business, one that runs on documented processes, not founder heroics.

• Metrics and dashboards show where growth is coming from and where money is leaking.

• You’re building an asset that isn’t just a brand and a list, it’s a system a buyer can trust, worth 2–3x more at exit.

Next Steps

1. Confirm interest – If you feel this direction is aligned, let us know. That’s the signal we need to continue moving forward together.

2. Roadmap call – We’ll schedule a follow-up session to walk through the 90-day roadmap in detail, clarify scope, and confirm priorities.

3. Finalize scope & pricing – Once scope is clear, we’ll share pricing options. This ensures the plan matches both your goals and resources.

4. Lock start date – When scope and pricing are confirmed, we’ll reserve your implementation slot.

Ready to take the next step?

About Modern Operators

• Damon Flowers has spent 20+ years helping companies grow from $3M to $50M+ in revenue, building operational systems, mentoring leadership teams, and driving sustainable scale. He brings deep expertise in aligning strategy, systems, and execution so founders can grow without burning out their teams.

• Mark Malian has spent the last 7 years in agencies helping brands generate growth strategies and then turning those plans into clean, automated systems that produce steady pipeline and shorten deal cycles.