The Copy-Paste Sales Package
Someone digs up the last "similar" deal and spends days—or weeks—recalculating estimates and manually updating proposals and contracts line-by-line.
For Consulting & Implementation Firms
Every proposal
starts from zero.
It shouldn’t.
Not generic templates. Not gut feel. Your actual project history.
Winning proposals land in your client’s hands before your competitor schedules their scoping call. Leeward Compass calibrates every opportunity against your firm’s real delivery actuals — a defensible, client-ready package in minutes instead of a deal-stalling scoping guessing game your margins pay for.
Calibrate a Real Opportunity →
15 minutes · your own history · not a canned example
Live product · sample data
Clarity in every current.
The Problem
Your best data never
makes it into the bid.
Your firm has completed dozens of projects. The lessons exist. The data exists.Nobody has time to use it.
Gut-Feel Pricing & Wishful Timelines
Estimates get shaped by what the client wants to spend rather than what past projects actually cost. Scope creep and margin loss begin before the contract is even signed.
Trapped Institutional Knowledge
The real post-project truths—cost overruns, materialized risks, and schedule delays—stay locked in scattered folders and individual heads, never informing the next bid.
Proposals That Look Like Everyone Else’s
Because they are. Relying on generic scope language removes any connection to your firm’s real outcomes—giving clients zero reason to choose you over the competition.
Why this keeps happening
A generic AI tool guesses. A static template repeats the past. ChatGPT doesn’t know what your last implementation actually cost, and your template library doesn’t know it ran six weeks over.
Leeward Compass calibrates — because every estimate is built from your firm’s own closed projects, not a public model’s training data.
The Anchor
Every number in Compass traces back to a real, completed project — not a guess, not a benchmark, not a template.
How It Works
Your institutional knowledge,
finally doing its job.
See how Leeward Compass takes your team from guessing to winning.
Phase 01
Retrieve
AI identifies up to 5 comparable projects from your delivered work — by application, scope, and complexity. Every match shows its similarity score.
Raw Input
Phase 02
Calibrate
Analyzes actual vs planned budget and timeline variances, the risks that materialized, and the lessons learned. Budget rationale explains the gap against client expectations in dollars.
Calibration
Phase 03
Generate
Produces your complete sales package, scope-driven — select 5 scope areas and only those 5 appear. No irrelevant sections, no manual cleanup.
Final Output
Who It Serves
Built for the whole
deal team.
One platform. Three stakeholders. Each gets what they actually need to move the deal forward.
Sales & Business Development
Win faster. Defend less.
Walk into every conversation with a client-ready package in minutes. Calibrated budget ranges, scope tied to your firm’s actuals, and a clear story for why the number is right.
Delivery & Practice Leads
Scope what you can actually deliver.
Stop inheriting optimistic proposals. See comparable projects, real variance, and the risks that materialized — before you’re asked to sign off on the SOW.
Executive & Finance
Protect margin. Repeat what works.
Every estimate is anchored to delivered history, not wishful thinking. Fewer write-offs, more predictable forecasts, and a closed-loop system that gets sharper with every project.
Client Perspective
What sales leaders
are saying.
“Leeward Compass is a genuinely useful tool for consulting and delivery teams. It doesn't just support external proposal responses — it also streamlines the internal collateral needed for reviews and approvals... removing a lot of friction in getting to a confident, evidence-backed result, both outside and inside the organization.”
S
Senior Sales Executive
Global Enterprise Software Firm
What You Get
Eight artifacts.
Minutes, not days.
The complete sales-to-contract package — each one generated in minutes, every one consistent with the others, all grounded in the same project evidence.
Budgetary Estimate
A ±10% calibrated range sent before the formal SOW, so the client sees a defensible number early and the deal doesn't stall on price.
T&M Statement of Work
Scope-driven terms for time & materials engagements, written in your firm's language and calibrated to past actuals.
Fixed-Price Statement of Work
Fixed-fee scope, assumptions, and boundaries built from your firm's real delivery history.
T&M Ordering Document + Exhibit
Commercial contract package for time & materials engagements, ready for execution under your existing contracts (MSA/CSA).
Fixed-Price Ordering Document + Exhibit
Fixed-price commercial contract and exhibit, ready for execution under your existing contracts (MSA/CSA).
Proposal
Full client proposal with cover letter, executive summary, scope, benefits, and investment.
T&M Amendment
Change-order document for time & materials engagements when scope shifts after signature.
Fixed-Price Amendment
Change-order document for fixed-price engagements, with variance rationale built from comparable projects.
Also included
A Proposal Confidence Score that tells you how much evidence stands behind the estimate, a Delivery Hub that captures actuals and lessons as projects close, and one-click export to Word. Every closed project makes the next proposal sharper.
Why Compass
Guessing versus calibrating.
The difference between a win and a profitable project isn't the writing.
It's what the numbers are built on.
Everyone else
Leeward Compass
- Generic AI writes plausible scope languageCompass writes scope language that is specific and defendable, grounded in your actual delivered projects
- Templates repeat last quarter's assumptionsCompass calibrates each estimate against actual vs. planned variance from real projects
- Pricing anchored to what the client will payTheir tool prices from what was planned. Compass prices from what actually happened
- Lessons learned die in a closeout deckLessons from closed projects feed directly into the next estimate
- Every proposal starts at a blank pageEvery proposal starts with your firm's actual project evidence
Why We Built It
I lived this problem
for 25 years.
Over 25 years leading PMOs, enterprise consulting practices, and solution strategy — including more than a decade at Oracle and Siebel — I spent thousands of hours in the sales-to-delivery trenches. One truth became undeniable: the traditional proposal process is broken.
Modern consulting firms have completed dozens — sometimes hundreds — of successful projects. The lessons exist. The real cost data exists. But in a fast-moving sales cycle, nobody has time to mine it. Teams copy-paste old sales packages, guess at pricing, and make optimistic timeline promises that strain margins before the contract is even signed.
I built Leeward Compass to be the anchor I always wished I had: a calibration platform that turns your buried project history into automated guardrails for every future bid. Every estimate traces back to real, completed work — so your team can quote in minutes and protect the margin.
Hilary Atkinson
Founder, Leeward Advisory Services
Founder's Note
“Compass is the tool I wanted every time I sat down to scope a deal.”
The Track Record
- 25+ yrs
- Consulting & implementation leadership
- 100's
- Proposals, contracts, and change orders scoped, written, and defended
- 100's
- Procurement and executive reviews defending scope, price, and timeline
Compass isn't a general-purpose AI wrapper built by people who have never scoped a project. It's built on the way this work actually gets done.
Security & Data Ownership
Your project history is your most sensitive asset.
It's also the thing Compass needs to work. Here's exactly how we handle it.
Your data is isolated
Every firm gets its own tenant. Row-level security is enforced on every query — your projects are never visible to another customer, and never pooled.
You own your documents
Your projects, SOWs, and actuals remain yours. Export everything at any time. Cancel and we delete it.
Never used to train models
Your project data is never used to train AI models — ours or anyone else's. It is used to generate your proposals, and nothing else.
Encrypted in transit and at rest
TLS on every connection, encryption at rest, role-based access inside your account, and a full audit trail of document generation.
Where we are today
We are pre-SOC 2. We’re telling you that plainly rather than burying it, because if certification is a hard requirement for your firm today, you should know before the demo. We’re happy to walk your IT or security team through our architecture, hosting, and data handling in detail, and to complete your security questionnaire. Read the full security FAQ.
Founding Partners
Three firms. Founding terms.
Compass is live and we're onboarding our first three customers. Those three set the roadmap and keep their founding partner discount permanently.
Founding Partner Program
Limited to the first
3 signed firms
Initial pricing is set per firm based on your size and project volume. Founding partners lock in preferential terms - permanent discount off our standard rates and real influence over what we build next.
- Unlimited opportunities and generated proposals
- All eight artifacts, every time
- Delivery Hub for capturing completed project actuals and lessons
- Onboarding of your historical project data
- Direct access to the founder during rollout
- Admin and End User Training and Support
- A locked permanent discount off our standard rates for as long as you stay
Claim a Founding Slot →
No obligation · 15-minute demo on your own data
The Next Step
Bring one live deal.
We’ll calibrate it.
Fifteen minutes, your own project history, one opportunity you’re actually working. Not a canned demo. You’ll see the budget range, the comparables behind it, and the SOW — and you’ll know within the call whether this changes how your firm sells.