Gwendolyn JillSan Diego

Operations + Design strategic partnerships

Everything I do is one of three forms of communication.

Operational

A system is how an organization talks to itself. Shared and clear, everyone moves together; locked in one person's head, it breaks the moment they look away. I find what works, what doesn't, and what was never written down, rebuild it at the source, and keep it documented and current. Keeping teams aligned protects people, money, and everything the business touches.

Systems buildingDocumentationPlaybooksVendor coordination

Experiential

Good experience design is intuitive. It tells someone how to engage and what to trust before they have thought it through. I map the journey so a process runs efficient and effortless, shaping what they hit first, what comes next, and the impression they leave with. Beyond aesthetics means fixing real friction points to serve output, and the output serves people.

InterfacesJourney mappingInformation architectureContextual inquiry

Visual

Visual storytelling is one of the oldest languages we have. When words fail, image bridges the gap by acting as a tool to reach each other. Consider the wonders of cave paintings, or the sand art a pufferfish carves over a week to court a mate. I turn that instinct into intentional and strategic visual direction that aligns with an organization's mission.

Art directionVisual systemsBrand identityIllustration

Selected work.

Looking for the full body of visual work? See my Visual Portfolio ↗
BeachHaus Rentals
← Case Studies

BeachHaus Rentals

RelationshipStrategic Partnership
DisciplineOperations + Design
Scope
Systems building Documentation Contextual inquiry Playbooks Information architecture Journey mapping Interfaces Vendor coordination Art direction Visual systems
Overview

An established, well-respected operation ran almost entirely on the founder's know-how. I turned that into a documented operating system the team can run and hand off, so its success no longer depends on any one person.

Impact
  • Accelerated onboarding
  • Put expertise on demand
  • Optimized workflows
  • Made the operation into a sellable asset
  • Helped restore work-life balance across the team
The business

BeachHaus Rentals is a founder-led collection of 25 luxury vacation homes along the North County San Diego coast. The founder runs it with a small local team and a service standard that has earned more than 4,000 five-star reviews, with sustainability built into every stay.

The problem

No documented processes, no single source of truth, and a tech stack the team called a spider web. New hires learned by osmosis, the same pain points kept resurfacing, and the team wanted a cleaner handoff.

What I did

Over a month of on-site contextual inquiry, I mapped how the business actually runs. Rather than reinvent the wheel, I designed and built a new operating system as a layer on top of the tools they already trusted, shaped around how the team actually works day to day. It is intuitive enough that the team finds the right answer fast, so the system carries the complexity instead of the people.

  • Onboarding documentation and playbooks, built from scratch
  • Communication guidelines for guests, owners, and contractors
  • Company rules and escalation paths, documented
  • The full tech-stack flow, charted for internal and external use, with fixes for its worst friction
  • A keyword search and an AI assistant that answers from the guide in real time, even when the team doesn't know the answer
  • A built-in recaps tool that replaced the end-of-day email thread
Design

Visuals coming soon. Generalizing details to protect client confidentiality.

The onboarding

I designed onboarding as a staged ramp, so a new hire moves from account and login setup, studying, and shadowing, to running the work with backup, to full independence: sales from inquiry to booking, pre-stays, and vendor coordination.

Hi, my name is Gwendolyn Jill Schwartzkopf. I'm from St. Louis, Missouri, and now live in San Diego, California.

The path

I started in graphic design at 16 and went on to earn a Bachelor of Science in 3D Computer Animation. After I graduated in 2014, an employer paid me to learn UI/UX, and my knack for seeing how broken systems feed into one another pulled me quickly into operations. Since 2020 I have worked as an independent strategic partner, building a practice that bridges imagination and execution.

Before digital tools, there was a sketchbook. I carried it everywhere, drawing what I had no language for yet, dreaming without constraint. Twelve years into working professionally in tech, I still aim to honor that origin.

What I care about

Land, animals, food, and the people caught in the middle of all three.

Manifesto

Work on technology that benefits the living, in all its forms.

Contact.

Direct: GwendolynJill@gmail.com