MEET THE FOUNDER & CEO
The Road to the High Desert: Hey, I'm Shawn!
Hi, I'm Shawn, the founder of Sir Paints A Lot.
When I originally started this painting company in the Willamette Valley, I was driven by a single desire: to bring much-needed professionalism to the painting industry and end the homeowner frustration that usually comes with hiring contractors.
Today, our Eugene operations are stronger than ever, and we've proven that the 'Wild West' approach to painting projects can be completely eliminated.
Now, after 13 years of refining our processes, honoring our warranties, and building an elite team, we are proud to expand our footprint.
We are bringing our proven, predictable painting systems across the mountains to serve homeowners here in Bend and the High Desert.
First with warranty-extending maintenance plans.
Pioneered free annual touch-ups during warranty
Husband, Father, and snorkeling enthusiast
Sir Paints A Lot was founded to address a glaring need in the painting industry: true professionalism and customer focus. Tired of the "Wild West" approach and homeowner frustrations with poor service, I set out to build a company where meticulous detail and robust systems would prioritize the client experience above all else.
Initially a solo effort driven by this vision, the demand for our customer-centric approach quickly grew. To truly impact the industry and serve more homeowners, building a like-minded team became essential.
The growth of Sir Paints A Lot is directly attributable to the exceptional individuals who now form our company. Each team member shares a commitment to quality, clear communication, and genuine customer care. Together, we've moved beyond what one person could achieve, implementing efficient processes that ensure consistently high standards and a positive experience for every client.
Our success isn't just about applying paint; it's about delivering a level of professionalism and service that was often missing in the industry.
We're proud to have built a company where serving the customer is paramount,
All thanks to the dedicated team that shares this fundamental principle.
We continue to paint a better experience, one project at a time.
2013 - 2026
History of Sir Paints A Lot
October 2013
Started in Billings, Montana as a 1 man painting business.
May 2014
The Derby family relocates to Eugene/Springfield Oregon for a new chapter in their journey. Shawn begins the process of setting up Sir Paints A Lot in Lane County
September 2015
Licesng done, tests, passed, Insurance paid. Sir Paints a Lot takes to the streets.
November 2016
Sir Paints a Lot hired our first employee
December 2016
Rose to the highest rated local painting company in Eugene and Springfield on Yelp, Google, Facebook, and Home Advisor.
Spring 2017
Our good work and referrals from awesome customers allowed us to hire 2 more painters.
July 2017
Painted the Copper Windmill Ranch
December 2017
Phoenix Inn Eugene hired us for our largest job of the year: we painted 102 bathrooms and the pool room.
June 2018
Protected the Alexis Diaz mural at 1061 West 2nd Ave
June 2018
Painted the interior and exterior and installed epoxy flooring in the Tour of Home at 1063 Lupine, Lot #51.
June 2018
Westmoreland Village hired Sir Paints for our largest job of 2018:
with the help of a trusted trade partner, we painted 26 four-plex units!
December 2018
Partnered with Mango Tree Coffee to feed a hungry child for a full year (and our clients got a delicious holiday gift)
June 2019
Sir Paints a Lot introduces industry leading warranty maintenance plan.
Our Premium home Care service is ONLY available to Customers who have had us paint the exterior of their home. Allowing us to expand our warranty plans out to 9 years!
August 2019
Completed our first free paint job for a home in Veneta with our charitable Paint It Forward program.
December 2019
The nerdy founder decides to document every step of the customer service process and hire our first administrator.
March 2020
Sir Paints a Lot created a process for finding high quality trade partners to diversify the work foce and deliver even better results.
Summer 2021
Technology expansion: We adopt a system that allows all company communication to be read by multiple people further assisting us in our goal of being a customer-focused company.
January 2022
The founder embarks on a massive software project that would streamline the estimating process for Sir Paints a Lot and hopefully many more contractors. Metric-based estimates guess work removed.
August 2022
The Founder steps away for 1 month to test the integrity of the processes we've built. The objective was to see if the team put together could maintain our vision, and they did.
December 2023
Spreading Joy with Toys for Tots!
After a year of dedicated hard work, Sir Paints A Lot partnered with Fred Meyer (who generously provided a special discount) to donate thousands of dollars worth of toys to Toys for Tots, bringing smiles to children in our community.
Spring 2024
A Step Back, A Step Forward for the Team.
While a significant move for the founder, this year marked Shawn's focus on empowering the team by mentoring a new sales leader in the Sir Paints A Lot way – putting the customer and solutions first.
July 2024
A Testament to the Team.
When a family emergency necessitated the founder's extended absence, the incredible Sir Paints A Lot team stepped forward, flawlessly executing our vision and proving the company's self-sufficiency – a true testament to their dedication and the strong processes in place.
Spring 2025
Growing Our Network.
Two driven team members transitioned to become independent contractors and valued trade partners, creating a stronger network and further extending the Sir Paints A Lot family.
2025
We've got a few cool things we are working on this year that we hope to share near the end of summer.
Spring 2026
We’re expanding to Bend, Oregon.
After earning trust in Eugene and the Willamette Valley, we’re bringing the same predictable, project manager led process to Central Oregon.
Built to end the “vacation mentality” of contracting.
From NW Crossing to Tetherow (and beyond), Bend homeowners can expect clear communication, clean execution, and long-term protection designed for High Desert conditions.
Ready? Book your estimate now.
Who We Are
Welcome to Sir Paints A Lot, your premier destination for interior and exterior protection in Bend, OR. We offer a perfect blend of quality, reliability, and peace of mind for High Desert homeowners.
Contact Us
Email Us: [email protected]
Call Us: (541) 600-8445
Address: Bend, OR 97702
Hours of Operation
Monday 7:00AM - 5:00PM
Tuesday 7:00AM - 5:00PM
Wednesday 7:00AM - 5:00PM
Thursday 7:00AM - 5:00PM
Friday 7:00AM - 5:00PM
Saturday Closed
Sunday Closed
Copyright 2026 Sir Paints A Lot | Bend . All rights reserved. CCB# 245616. Bend, OR 97702