wes smithe

operator

wes smithe

operator

About me

About me

About me

I’ve spent the last decade building and running a SaaS platform in the short-term rental space — owning product, operations, and the systems behind how the business runs.

Along the way, I’ve worked across every layer of the business: leading people, raising capital, meeting with customers, building partner relationships, developing major integrations, and rebuilding core infrastructure to support growth.

I work best in complex businesses where progress is constrained by broken systems — stepping in to simplify, align, and rebuild how things actually operate.

perspective

Throughout my journey, I've found growth is often constrained not by ideas and effort, but by the systems underneath them:

  • Product and operations out of sync

  • Speed competing with stability

  • Legacy decisions making it harder to scale

I've spent years inside this tension, observing similar patterns with customers and prospects.

This is the gap I’ve worked in — isolating root causes and rebuilding systems to support how the business actually runs.

philosopy

The goal is better systems, faster execution, and cleaner outcomes—not more noise.

High agency

I step into ambiguity and move things forward without waiting

Systems-first

I dig in to understand how things actually work before change

Outcome-driven

I focus on high-impact problems the company and customers face

Tech-forward

I use modern tools and AI to improve speed, clarity, and output

approach

I step into businesses where systems are limiting growth and execution.


My work typically involves:

  • Leading product and platform overhauls to match how the business actually operates

  • Simplifying workflows and reducing operational overhead

  • Aligning integrations, data, and payments into cohesive systems

  • Turning fragmented tools into scalable infrastructure

  • Applying AI to real workflows — not surface-level outputs

experience

Direct — CEO & Founder

2018 Present

  • Founded a full-stack SaaS platform for professional operators

  • Raised $12M across Seed and Series A

  • Serve as Chairman of Board of Directors

  • Led product vision and platform architecture

  • Developed major platform and marketplace integrations (Airbnb, Vrbo, Stripe, etc.)

  • Operated across product, engineering, operations, and go-to-market

  • Drove key partnerships and strategic initiatives

  • Navigated company through multiple phases of growth and restructuring

  • Currently leading efforts to rebuild core systems for scale

See my LinkedIn profile for additional work experience and background.

opportunity

I’m currently leading Direct through a major platform rebuild and broader company transition, including team reorg and bringing in an experienced COO to support the next phase.

For the first time in a decade, I’m open to exploring what’s next — particularly roles where I can work with companies that need to simplify, modernize, or rebuild the systems they rely on to operate.

I'm also open to select advisory or build engagements where systems need to be simplified or rebuilt.

Based in Charleston, SC

Based in Charleston, SC

Based in Charleston, SC