Proposal - Jake Cutler

notion image
Proposal: Comprehensive Operations + Notion Systems Audit
Prepared for: Jake Cutler
From: Damon Flowers & Mark Malian, Modern Operators

Current Situation

You’ve built real traction in a nuanced business (small business lending + partner-driven deal flow), but the business is still being run on your back.
Right now, you’re the only person actively using the system, and the “Notion project” has turned into an 8-month detour instead of the leverage play it was supposed to be.
As you try to scale (and raise capital), a few constraints are creating drag and risk:
  • Adoption is at zero: you have contractors and partners, but the system is not usable for them yet, so everything routes through you
  • Notion technical debt: multiple consultants have made changes you did not approve, and each new person tries to rebuild instead of building on what already exists
  • Permissions and guest access are a core requirement, but the current architecture makes it hard to share the right information with the right people
  • Sales execution needs a clean home: you need a way to manage opportunities end-to-end while selectively sharing deals, templates, and workflows with 1099 sales partners
  • PDF-heavy workflows live elsewhere (and for good reason): critical deal documents are handled in Google Drive, and the system needs to support that reality instead of fighting it
  • Support + SOPs are blocked: the team cannot follow documented process if there is no simple, trustworthy “home base”
You don’t need “more features.” You need clarity, simplicity, and an architecture that makes adoption inevitable, with complexity kept behind the scenes.
This audit is the third-party diagnostic to identify what’s actually broken, why it’s broken, and the shortest path to a system your team will adopt.

Goals

This audit will help you:
  1. Get team adoption unstuck by designing a “don’t make me think” experience for contractors and partners
  1. Fix the architecture and permissions path so guest access is possible without a brittle, manual setup
  1. Create a sales execution center that supports your referral + 1099 model (and does not require you to be the bottleneck)
  1. Design clean handoffs for document-heavy deals so PDFs and deal packages are organized, trackable, and easy to collect without breaking your current workflow
  1. Unblock SOPs + support enablement so you can document once and delegate repeatedly
  1. Leave with a prioritized roadmap for the next 30/60/90 days, including “what to fix first” and what to ignore
By the end of this engagement, you’ll know exactly what to keep, what to simplify, and what to rebuild, so you can scale without the system becoming the constraint.

Proposal: Stabilization Audit + Advisory (Built on What You Already Have)

What You Get

Phase 1: Stabilization + Discovery (Week 1)
We’ll run structured 60–90 minute interviews and working sessions to understand how work actually moves through the business today, and identify the fastest “unblock” path without forcing a rebuild:
  • You (founder)
  • 1-2 key sales partners
  • 1–2 support or back office operators (if applicable)
  • Any current Notion builder or developer you want involved
We’re diagnosing:
  • Where work gets stuck
  • Where it duplicates
  • Where you are still the “human API” between people and information
  • What adoption blockers are real (and which are just symptoms)
We’ll also review your current stack and artifacts:
  • Current Notion workspace structure (companies, contacts, opportunities, partner areas)
  • Permissions and guest access approach (what’s been tried, what broke, why)
  • Sales workflow: opportunity management, deal stages, templates, qualification, and follow-up
  • Document-heavy deal flow (PDF collection, storage, and handoff)
  • Dev + product tracking (what exists, what’s missing, what’s too complex)
  • SOP/support enablement vision (what “good” looks like for your team)
Phase 2: Simplify + Permissions Path (Week 2)
We map your current environment to a simplicity-first, adoption-first model to identify:
  • Foundation gaps: where the architecture makes adoption, permissions, or scale impossible
  • Simplification plan: how to create a “front stage” that is obvious to use, with complexity hidden behind the curtain
  • Permission strategy: the simplest model that will actually work for partners and contractors
  • Highest-leverage build order: what to fix first to create momentum (sales, support/SOPs, dev/product, marketing)
Phase 3: Keep / Simplify / Rebuild Decisions + Roadmap (Week 3)
You’ll receive a clear audit report that includes:
  1. Current State Assessment: What to keep as-is, what to simplify, and what is creating technical debt
  1. Root Cause Analysis: Why adoption is failing today (and how to reverse it)
  1. Quick Wins List: The first changes you can implement in 7–30 days
    1. 30/60/90 Roadmap: A prioritized plan that sequences improvements without breaking what already works
  1. Blueprints: Recommended architecture patterns for sales, partner areas, and SOP/support enablement
  1. Next Steps Options: Clear pathways for implementation (DIY, your current team, or with us)
We’ll also hold a 60-minute presentation + consulting call to walk through findings, answer questions, and align on the plan.

Investment & Timeline

Price: $3,500 (one-time payment)
Timeline (3 weeks total)
  • Week 1: Discovery interviews + workspace review
  • Week 2: Systems analysis + architecture and permissions strategy
  • Week 3: Audit report + roadmap + presentation call
Proposed Start Date: Monday March 9th, 2026, or Next available start after your return from the conference (upon payment and signed agreement).

Optional: Ongoing Advisory (After the Audit)

This audit is designed to give you clarity and a plan fast.
If you want support implementing the plan without getting pulled back into another 6–8 month detour, we can continue with a lightweight advisory engagement.
What advisory looks like
  • Weekly 60-minute working session
  • Async support in between sessions for quick decisions and reviews
  • Prioritized execution plan so you fix one thing at a time (without breaking what already works)
  • Guidance on permissions, adoption, and “front stage vs back stage” simplification as you roll changes out
Outcome: you move from “a roadmap on paper” to a system your team actually uses, with the founder no longer acting as the human API.

Why This Works for You

You’re not bad at Notion. You’re dealing with a common failure mode:
When the system gets complex before it gets adopted, adoption dies.
You’ve already lived through multiple consultant attempts, and you’re rightfully skeptical of anyone who wants to rebuild everything with their “signature system.” This audit is different because we’re not here to force a new flavor of Notion.
We’re here to give you:
  • Truth: what is actually breaking adoption (and what is just noise)
  • A permission strategy that works in the real world for 1099 partners and contractors
  • A simplification-first architecture that makes the right behavior the easy behavior
  • A sales execution plan that supports your referral model without you being the bottleneck
  • A roadmap you can execute one module at a time, without spinning for another 6 months
You’ve got momentum, investor interest, and a real business that is ready to scale. This audit makes sure your operating system becomes the lever, not the ceiling.

Next Steps

If this feels like the right move, here’s what happens next:
  1. We send a simple agreement + invoice
  1. You sign and pay ($3,500)
  1. We schedule your Week 1 discovery sessions
  1. You receive the audit report + 30/60/90 roadmap in Week 3
This is the fastest way to turn the last 8 months of Notion effort into a system your team can actually use, without another messy rebuild.
 

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About Modern Operators

Modern Operators is a systems-first growth partner for founder-led companies doing $500k–$10M who want to scale with clarity, calm, and predictable momentum. Instead of relying on heroic founders, scattered tools, or reactionary decision-making, MO equips teams with a modern operating system…a unified layer of vision, planning, execution, automation, and AI that allows the business to run smoother, faster, and more intelligently.
Co-founded by Damon Flowers and Mark Malian, Modern Operators brings together decades of deep operating experience, brand strategy, and systems design to help companies move from reactive growth to a stable, scalable rhythm.
  • Damon Flowers has spent 20+ years building and scaling companies from early-stage to eight-figure outcomes. He is known for architecting operating systems, transforming chaotic teams into aligned execution machines, and mentoring founders and leaders through the transition from “doing everything” to building a company that grows beyond them. His work blends strategic clarity, operational structure, and the practical integration of AI into day-to-day workflows.
  • Mark Malian brings 7+ years of experience in growth strategy, brand positioning, and systems automation inside agencies and product companies. His expertise lies in turning complex processes into clean, scalable systems…especially in marketing, sales, and customer operations, so teams can produce consistent pipeline, shorten deal cycles, and unlock predictable growth.
Together, Damon and Mark built Modern Operators to guide founders through a new era of business…one where clear structure replaces chaos, AI amplifies human capability, and a modern Company OS becomes the foundation for long-term, scalable success.