Hi, I'm Keenan Bennett

I love homes, and the companies reinventing everything around them: how we find them, buy them, build them, and care for them. For 13 years, my work has followed the industry's biggest changes, from Porch, Zillow, and Pacaso to an award-winning luxury builder.

Get to know me

Keenan Bennett on the Seattle waterfront

Strengths

Results. Relationships. Teams.

The three things I've built at every company, from category-creating startups to an award-winning builder.

Results
Owning the number
Pipeline, conversion, and closing are where I'm most at home. I like being measured, and I like hitting the mark.
Relationships
Understanding the decision
A home holds a family's hopes, so the choice is emotional before it is financial. I listen for what matters most and help families move forward with confidence, from the first call to the signed contract.
Teams
Growing the people around me
I set a high bar and work beside the team to reach it. Watching people I've coached grow into leaders is the best part of the job.

Keenan Bennett smiling at an evening event

About Keenan

I learned to read a room before I learned to sell a home.

I started out waiting tables to get by. I left Bellevue College to help open four restaurants and worked my way from server to manager. I didn't know it then, but those years shaped everything that followed. I learned to read a table, notice what people need before they say it, and make them feel taken care of. I've used those lessons in every sales conversation since.

That instinct has carried me through nearly every seat of the home decision: a home-services startup, a builder's sales office, real estate technology, my own business, and luxury co-ownership. Each time, I was asking people to trust something new.

Today I lead the client journey at The Custom Home Company, 425 Magazine's 2026 Best Builder. I'm still curious about why people decide, what helps a team win, and what the next great home company will look like.

At home, I'm a proud father of two, and I get to do life with the most incredible woman by my side. They're the reason I care so much about what home means to other families.

The Story

The path that brought me here.

Every stop taught me something about people and the places they call home. Start with today, or choose any year.

The Porch sales team forming a high-five tunnel in the office

Porch displays inside Lowe's stores during the 2014 nationwide launch

2013 – 2016

Porch Group

Senior Sales Account Executive · Seattle

Venture-backed · $100M raised by 2015 from Lowe's, Founders Fund, and Valor

I started where home services were being reinvented: a new marketplace that launched nationwide in more than 1,700 Lowe's stores in 2014. The pace was high and the work was simple: make the call, earn the meeting, and sign the partner.

~1,400Partner agreements signed

Top 2%Net-new revenue, company-wide

2×Salesperson of the Year; Mentor of the Year, 2015

Every call was about someone's home. Even a small project carried real hopes, and that never left me.

The full Porch team in Seattle, many in Porch shirts, making the roof sign with their hands — The Porch team, Seattle

Keenan Bennett during his time at BDR Homes

A finished BDR Homes townhome with cedar and blue lap siding

Redmond Retreat townhomes sign listing Keenan Bennett as sales representative

2016 – 2018

BDR Homes

Community Sales Manager & Assistant Project Manager · Bellevue

Private Eastside builder · Investor-funded communities

Next, I crossed to the builder's side of the table. Selling new homes across three Eastside communities, I learned to keep buyer expectations, builder economics, and the job site moving in step.

8New homes sold

$22MTotal sales volume

20%Investor return, delivered early

A sale only counts if the project still works for the builder and the investor.

Keenan with the Zillow sales team on a sunny Seattle rooftop

Zillow Group Q4 2018 Top Performer award presented to Keenan Bennett

2018 – 2020

Zillow

Sales Executive · Seattle

Publicly traded on Nasdaq

I sold advertising and technology to real estate agents across Florida, managed from Seattle. It taught me how much the first conversation matters, and how quickly trust is won or lost.

18%Sign-up conversion vs. 3.5% average

242%Of goal, Q3 2018

220%Of goal, Q4 2018; 178% in Q3 2019

Most leads aren't lost on price. They're lost in the first few minutes.

Keenan Bennett on the Seattle waterfront in golden evening light

A portrait by West Sound Photography of a woman framed by green houseplants

Modern farmhouse exterior with stone and board-and-batten siding, photographed by West Sound Photography

2020 – 2021

Building My Own

Founder, West Sound Photography · Seattle

Self-funded startup

I joined a title and escrow startup with former Zillow colleagues and helped build its brokerage partnerships. When COVID brought a furlough, I built West Sound Photography, a portrait and real estate business with paying clients, and tested for a year whether it could scale.

FounderTurned a COVID furlough into a business of my own

0 → PaidBuilt West Sound from nothing to paying clients

OwnerRan every part of the business for a year

Photographing homes taught me to see the moment a buyer stops and pictures their life inside.

Oceanfront Pacaso home at sunset with terraced stone, green roofs, and an infinity pool

Modern Pacaso home with walls of glass in fresh snow among pines

2021 – 2023

Pacaso

Sales Principal, Market Advisor · Remote

Venture-backed · $215M raised, including a SoftBank-led round · $1.5B valuation, 2021

Pacaso created a new category, luxury co-ownership. I closed the region's top-priced homes and fastest sales, and buyer insight from my calls helped shape which homes Pacaso bought. When sales moved in-market, I was the last remote seller kept.

$74.9MSold across 141 interests, 20+ markets

TopPerformer, 2021–22

70+Reps trained in discovery, objections, closing

A second home is where families make their best memories. Helping them get there never felt like a transaction.

The full Pacaso sales team on a coastal bluff above the Pacific; Keenan is on the far right in a black Pacaso shirt — The Pacaso team, California coast · Keenan, far right

Modern custom home by The Custom Home Company at dusk with the Bellevue skyline behind

Primary bath in a custom home with a freestanding tub, oak vanity, and arched mirror

July 2023 – Present

The Custom Home Company

Vice President · Fractional since July 2026

Private design-build firm · Remote / Bellevue

I lead the client journey for a luxury design-build firm on the Eastside and in Seattle, with a team of 15+. I've hired about half and equipped our veterans with AI and modern tools. I also build the brand by hand: every website, flyer, mailer, apparel piece, card, and press detail. Together, we've earned magazine features and 425 Magazine's 2026 Best Builder.

9Home contracts, $2.5M–$7M each

15+Team members led

2026425 Magazine Best Builder

Awards follow when a team believes in the work. I'm proudest of the people who earned them.

The Custom Home Company team gathered around a shuffleboard table — The Custom Home Company team, Greater Seattle

Keenan at the Best of 425 celebration at sunset, standing among lit marquee letters

What's Next

The right people and the right idea have a way of finding each other.

This year, a former employer recruited me back as Regional Director. It wasn't the right fit, so I stayed with The Custom Home Company in a fractional role, and it made my next step clear: a team doing something new around the home, from services to new ways to own to the future of building, open to ideas and ready to take them to market.

5×Zillow's average inbound conversion. More revenue from leads a company already pays for.
$74.9MSold as a top performer at Pacaso. I own a number and hit it.
220+Salespeople trained or mentored. Teams that grow, and stay.
20%Investor return delivered early at BDR. I think like an owner.

If you're building the future of the home, I'd love to hear about it.

Brands

Companies and communities I've been proud to be part of.

Approach

Raise the bar, then help every person reach it.

Start with the customerEvery process, script, and hire should make the client's decision easier.
Coach in the momentThe best training happens on live deals, not in a conference room.
Let the numbers talkData shows where deals stall. Fix the system, not just the person.
Win as a teamThe scoreboard is how far the people around me go.
Sweat the detailsThe difference lives in what most people miss, from a proposal to a business card.
Push throughHard moments are where teams find their edge. I stay steady and find the way through.

AI as a competitive edge. ChatGPT, Claude, and Gemini are part of my every day. They make my teams faster, leaner, and more focused on clients.

Outside work, I coach. I help run youth camps with FlexWork Sports and ProCamps, and since 2021 I've coached for a local youth sports organization, where I serve as board vice president, and for the Y. Kids teach you fast what real encouragement looks like.

Keenan, right in a grey shirt, coaching young players at a youth baseball camp

Connect

Let's connect.

I enjoy meeting founders, builders, investors, and anyone shaping the future of the home. If something here sparks an idea, grab a time.

Greater Seattle · LinkedIn

30 minutes

Grab time on my calendar.

Pick a time that works for you. No agenda needed. Just bring what's on your mind.

Choose a time