resume & portfolio site

Heather Ann Kelly — Predictive Analytics for Performance & Profit
Heather Ann Kelly at work

Small signals. Big returns.

I use predictive analytics to improve performance and profitability — in software and user experience, in aerial mapping, and in real estate.

Predictive Analytics · Design · Flight

Heather Ann Kelly

My career began at Expedia in brand and rebranding, then grew into website design and user experience at Microsoft.

Consulting took me to Boeing and into predictive analytics, where models showed that small adjustments across a global fleet could save millions in fuel. For two decades since, I’ve turned complex data into software and decisions that improve performance and profit.

Today I apply the same approach to land and real estate: aerial mapping that reveals risk and value across a property, and forty-two acres in Oregon’s Applegate Valley that I took from raw land to a permitted, income-producing property.

Along the way I founded nationally recognized companies, including Winerybound, a winery locator and deal finder that earned me Entrepreneur of the Year through Infiniti Motors.

The industries change. The goal doesn’t: see what’s coming, perform better, and protect the bottom line.

How I got here
Read the signal
A close-up detail
Change the outcome

Founder

of nationally recognized companies

Entrepreneur of the Year

awarded through Infiniti Motors · for Winerybound

20+ Years

brand, UX & software systems

Level 1 Sommelier

Court of Master Sommeliers

A Life in
Chapters

From brand to predictive analytics to land: one approach, five chapters.

Chapter I

Brand & web

It began at Expedia, working on the brand and its rebranding, and grew into website design.

Chapter II

Experience design

At Microsoft I designed web and software experiences, from research and personas to prototypes and executive dashboards.

Chapter III

Predictive analytics

Consulting brought Boeing, Ford, Zones, and Avanade, and predictive analytics: modeling fuel savings across Boeing’s global fleet.

Chapter IV

Real estate

Those threads, plus twenty years in wine and founding Winerybound, met on forty-two acres of raw land. I added value at every step: permitting, infrastructure, mitigation, and new revenue.

Chapter V

Fire & flight

Now I fly the data myself: a decade of piloting turned toward aerial models that predict risk and reveal value across a property.

Heather at work

Five chapters · One method

The common thread

Predict.
Perform. Profit.

Every chapter comes back to the same three steps: see what’s coming, operate better because of it, and protect the bottom line.

I.

Predict

See it before it happens.

In software & UX

I design analytics dashboards and systems that model outcomes, like fleet fuel savings, before anything changes.

In the air

I map terrain, vegetation, and fuel load to show where risk sits on a property before it becomes a loss.

In real estate

I study permits, fire risk, and use potential before investing, so every improvement targets a property’s highest and best use.

II.

Perform

Turn insight into better operations.

In software & UX

I research how people actually work, then design software that replaces ad-hoc workflows with one clear path.

In the air

I give owners and crews the terrain, access routes, and data they need to plan improvements.

In real estate

I sequence improvements so each one unlocks the next: access, infrastructure, mitigation, then income.

III.

Profit

Protect and grow the bottom line.

In software & UX

I build tools that help executives find sales gaps and savings worth millions, and act on them quickly.

In the air

I document terrain and mitigation to support property value, lending, and insurance.

In real estate

I turned raw acreage into a permitted property with several income streams, and 27 of 42 acres now mitigated and professionally landscaped.

Experience design work

Where I apply it today

0103

Software Systems & UX

Research-driven software that turns data into better decisions.

  • ClientsExpedia · Microsoft · Boeing · Ford · Vulcan · Zones · Avanade
  • MethodsBrand, web design, research, personas, prototypes
  • DeliveryAgile & waterfall · local & global dev teams
  • DeliversAnalytics dashboards, enterprise software & workflows
  • OutcomeLower costs, faster pivots, higher sales
See the systems

Real estate case study

From Raw Land
to Income Property

Love & Luck Ranch is where I test everything first. Each improvement was chosen to raise the property’s value and add a new way for it to earn.

Love & Luck Ranch in the Applegate Valley
  1. 1

    Entitle

    Secured county land-use approval for overnight guests, the permit that turned acreage into a business.

  2. 2

    Build access

    Built a commercial-standard access drive, the requirement that unlocked everything after it.

  3. 3

    Add infrastructure

    Eight tents, a vintage Airstream, a VIP suite, bath facilities, an outdoor kitchen and bar, wayfinding, and remote-controlled lighting.

  4. 4

    Reduce risk

    Heat-mapped the property and mitigated 27 of 42 acres, self-funded first and then extended with an $18K grant, protecting value and insurability.

  5. 5

    Diversify income

    Layered overnight stays, a four-tier membership, events, a media lab, and wine sales onto one property.

The result is a turnkey, permitted guest property, and a repeatable playbook for improving land and the income it produces.

Visit Love & Luck Ranch

Software
Systems

Twenty years designing enterprise software, from start-ups to the Fortune 500. Every system began with one question, and was built to improve performance, profit, or both.

I.

Predict

Analytics and decision systems that show what’s coming.

No.01
Boeing fleet fuel dashboard

Boeing

Fleet Fuel Conservation

How do you show the butterfly effect of fuel loss?

Predictive analytics · Tableau · executive dashboards

Read the case

The problem

Boeing executives wanted to mine flight data for fuel savings as they planned the next generation of aircraft.

My role

Senior UX designer, working with a managing director, program manager, senior developer, data scientists, and researchers.

The system

An interactive visual story built on flight-diagnostic data and applied algorithms, letting executives move from fleet-wide savings to a single flight at a single airport. I customized the Tableau visualizations with developers.

The result

Executives could spot trends and model how small changes in flap settings, altitude, or routes would save fuel across the global fleet, informing routes, designs, and how pilots fly.

No.02
Alternate airport selection prototype

Boeing

Alternate Airport Selection

Can the choice be automated for dispatchers and pilots?

Decision-support system · desktop & iPad

Read the case

The problem

Choosing an alternate airport was a manual process for commercial clients, dispatchers, and pilots, often under emergency pressure.

My role

UX designer leading research and prototyping.

The system

I reviewed existing systems, studied how dispatchers use their monitor space, and interviewed pilots about emergency scenarios, then prototyped desktop and iPad versions built for fast data entry.

The result

A system concept that automates alternate-airport selection, so crews decide faster with the right references in hand.

No.03
In-vehicle experience study

Ford × Microsoft

In-Vehicle Systems

How can technology in a car help without costing safety?

Global research · next-generation systems

Read the case

The problem

After an early infotainment system failed with drivers, Ford and Microsoft needed a new way to put technology in the car.

My role

Supported the senior UX lead and research lead, cataloguing and synthesizing a global study of driving habits and competing systems.

The system

A consolidated body of research and conceptual designs covering buttons, knobs, touchscreens, haptics, and displays, and which technologies helped or intruded.

The result

Findings presented to senior engineering teams and CEO leadership at Ford and Microsoft, shaping safer, more ambient in-car systems.

II.

Perform

Enterprise systems and workflows that help teams work as one.

No.04
Zones sales order system

Zones

Sales Order System

What if everyone orders the same thing a different way?

CRM & order processing · 3 months

Read the case

The problem

Rapid growth left Zones, one of the world’s largest technology distributors, with every sales lead following an ad-hoc process.

My role

Senior UX designer under a director lead.

The system

Eight leadership interviews, four requirements workshops, heuristic review of the custom sales tools, and personas that mapped unique and overlapping usage, leading to a new prototype reviewed by leadership.

The result

One streamlined path to quote, sell, and follow up, with product-suggestion modeling to open more sales opportunities.

No.05
Sales pipeline CRM wireframes

Enterprise client

Sales Pipeline CRM

What do sales leads actually need to manage their pipeline?

CRM redesign · workshops with IT

Read the case

The problem

An aging CRM didn’t match how regional sales leads worked day to day.

My role

UX lead, partnering with IT, regional sales leads, and senior leadership.

The system

An analysis of the current system and code complexity with IT, then workshops where sales leads defined their ideal pages, data, and daily scenarios, consolidated into wireframes.

The result

Signed-off designs ready for IT build, focused on sales tracking and performance.

No.06
Avanade global intranet

Avanade

Global Intranet

How do international teams actually use their intranet?

SharePoint platform · 6 months

Read the case

The problem

Avanade’s SharePoint intranet no longer served its teams around the world.

My role

UX lead across research, design, and rollout.

The system

Persona workshops with IT based on page-view analytics, validated with remote surveys and card sorts, followed by internal roadshows while developers built and tested custom components.

The result

A validated experience and a compressed production schedule, since building and roadshowing happened side by side.

No.07
Microsoft LEX learning personas

Microsoft LEX

Online Learning Platform

Everyone learns differently. What do they share?

Research · personas · learning dashboards

Read the case

The problem

Microsoft needed to understand how developers around the world learn and collaborate online.

My role

UX researcher and designer.

The system

Interviews with developers of different ages, skills, and countries, turned into personas and journeys for the platform’s dashboards.

The result

Shared patterns that helped the team optimize training and collaboration tools across the LEX ecosystem.

No.08
Software delivery process work

Software delivery

Taming Delivery Chaos

How do you stop team chaos from eating profit margins?

Agile & waterfall · process design

Read the case

The problem

Siloed teams, constant rework, and haphazard communication were raising costs and burning people out on a large project.

My role

Worked with the technical lead as UX designer and acting project manager.

The system

Documented where the churn came from, realigned cross-functional teams to shared best practices and development lifecycles, and built reusable tools, including BI dashboards on team performance.

The result

A clear case to senior leadership for better practices, protecting morale, budgets, and margins. Best practices work. Period.

III.

Profit

Commerce, products, and companies built to grow revenue.

No.09
Microsoft subscription P&L dashboards

Microsoft

Global Subscription P&L

Where are the gaps in sales, store by store?

Power BI · custom code · agile

Read the case

The problem

Executives needed to review subscription profit and loss globally, by product, revenue stream, and store.

My role

Senior UX designer with data analysts, scientists, and global development teams.

The system

Journey maps built with finance teams, and dashboards comparing in-store and download sales by region, campaign, and product, with sensitive data protected through layering and color-coding in the design.

The result

Executives could find sales and distribution gaps quickly and pivot strategy fast.

No.10
Bing Dream Trip Builder

Microsoft Bing

Dream Trip Builder

Can travelers preview a dream trip before they buy it?

Interactive prototype · commerce

Read the case

The problem

Travelers want to picture themselves on a trip before they buy it.

My role

Worked with a senior UX designer on the flows and produced the executive video demo.

The system

A map-to-destination experience with built-in video editing for a personal trip preview, plus shopping for what to pack.

The result

A funding-ready demo that paired a better planning experience with new sales for related businesses.

No.11
CenturyLink Field experience

Vulcan

CenturyLink Field Experience

What happens when a stadium responds to its crowd?

RFID · beacons · mobile · think tank

Read the case

The problem

Vulcan wanted think-tank concepts for the most technologically advanced stadium in the world.

My role

Senior UX designer, co-leading the vision.

The system

Day-in-the-life storyboards aligning RFID, beacons, and a custom app with location, timing, purchases, and return on investment, including crowd-driven “hive mind” moments.

The result

Concepts for leadership funding review, and an honest lesson: technology should serve the fan, not just the sale.

No.12
Winerybound

Founder · Winerybound

Winerybound

What if finding a winery, and a great deal there, took one search?

Winery locator & deal finder · Entrepreneur of the Year

Read the case

The idea

Wine lovers needed one place to find wineries near them and the best offers to visit and buy.

My role

Founder, leading the brand, the product, and the business.

The system

A winery locator and deal finder connecting wine lovers with wineries and their offers.

The result

National recognition, and Entrepreneur of the Year awarded through Infiniti Motors.

Love & Luck Ranch

Permitted guest property · glamping, events & production
Jacksonville, Oregon
loveandluckranch.com

Divine Fire Foundation

Conservation, mapping & wildfire resilience
Applegate Valley, Oregon
hello@divinefirefoundation.com

Winerybound

Winery locator & deal finder
Entrepreneur of the Year, via Infiniti Motors
winerybound.com

Artemis Aerial

Drone mapping & aerial services
WingtraOne VTOL platform
[Add link]

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Let’s
Talk

Whether it’s a software system, a property, or the land around it, I’ll help you see what’s coming and improve the numbers that matter.

Write to me
© 2026 Heather Ann KellyApplegate Valley · Southern Oregon