“I’ve been fortunate to grow with Portland Webworks since the very beginning,” says founder and CEO Justin Davis. “We’re here today because of our team’s commitment to the innovation and skill adoption required to navigate the ever-changing landscape of the internet since our founding in 1999.”
A lot has happened in the past 25 years. From the beginnings of the internet to today, the services we provide at Portland Webworks (PWW) and GovWebworks (GWW)–websites, custom software, and other digital services—have come a long way. At the same time, our management has grown and evolved with the company to form the powerful team we are today.
Here’s how the management team at Portland Webworks/GovWebworks came together.
Our growth as a team
In 1999, at the heart of the dot-com boom, Justin (age 25) registered the domain portlandwebworks.com. PWW was incorporated just before Christmas and Justin began trading web services for office space at 5 Milk Street in Portland’s Old Port.
In 2000, Justin’s cousin Chris Davis came on as Director of Technology to manage the on-premise servers, and Justin’s brother-in-law, Christopher Prinn, left his role at L.L.Bean to shape PWW’s creative vision as Director of Creative—leaving a lasting legacy until his passing in 2021.
Clients in those early years included the Nantucket Nectars “Juice Guys” and L.L.Bean, while public sector opportunities emerged with the Maine Office of Tourism contract in 2002. The family spirit also thrived as Justin’s mother, Jackie, kept the office running smoothly alongside a parade of office dogs.
Celebrating the first million in revenue in 2007, PWW won more public sector projects and brought on Tom Lovering from L.L.Bean in 2008 as Director of Business Development.
In 2011, Alison Schestopol came on to define the project management department, later becoming the Director of Project Management and Quality Assurance.
As the public sector focus grew with clients from from Idaho to Washington, Kevin Ferguson came on in 2013 as a software developer and rose to Director of Software Development in 2021.
In 2016, we added the public sector brand, GovWebworks, to highlight PWW’s specialization in digital innovation for government agencies.
That same year, Sarah Crossman and Hellen Fitzpatrick joined as project managers for the growing company. In 2019, Sarah became the Director of User Experience, and Hellen was appointed as Software Development Manager for the Drupal team in 2022.
From family connections to industry-leading professionals, the Portland Webworks’ story is about the people who’ve brought the talent, collaboration, and commitment to shape the path forward from 1999 to today.
Learn more about our management team members, listed below in order of seniority.
MEET THE TEAM
Justin Davis: Founder & CEO
I’ve been fortunate to grow with Portland Webworks since the very beginning. We’re here today because of our team’s commitment to the innovation and skill adoption required to navigate the ever-changing landscape of the Internet over the last 25 years since we began in 1999.
Portland Webworks was born into the dot com bubble and its subsequent burst. That was just the beginning of our unchartered path over the past 25 years through on-premise computing, the browser wars, the advent of cloud computing, and the bust and boom of economic expansions and recessions to keep things interesting.
I credit my team for its commitment to innovation and relentless skill adoption that allowed our organization to survive and thrive despite the ever changing landscape that the Internet has introduced to the world.
My day-to-day work is primarily in an advisory capacity. I’ve advised several internal and external initiatives this year including the Idaho Department of Health and Welfare’s idalink benefits application, modernization of an in-house revenue tracking software system, and tradeshow marketing and outside sales.
Chris Davis: Director of Technology
What I enjoy most about my work is how much it’s evolved since I first started. When I took on the technical director role at PWW in 2000, I began growing and learning alongside the company and industry. Over the years I’ve had the chance to dive into all the technical layers—from web software development and server administration to networking and hardware installation.
It’s rewarding to know we’re providing secure, stable environments that people can count on. Over the years, I’ve helped build hosting infrastructures that handle over 100 million requests and thousands of transactions every year. Despite all the demand, it’s gratifying when our servers maintain near-perfect uptime, which is a credit to our team’s commitment.
Supporting high-profile projects has been an especially meaningful part of my career at PWW. I feel fortunate to maintain environments for clients like the Washington Department of Social and Human Services, Missouri Department of Conservation, and Minnesota DEED and to contribute to their critical services by ensuring everything runs smoothly on the back end.
My work touches most of the projects at PWW. People are sometimes uncertain what DevOps work entails, so I thought it would be helpful to include the following details:
- Expertise Across Systems and Software: From Linux systems (RedHat, CentOS, Ubuntu, Debian) and application servers (Tomcat, Jetty, JBoss) to various databases (MySQL, Oracle, PostgreSQL), I manage diverse technology stacks with an emphasis on uptime and performance.
- Infrastructure Architecture and Design: Designing infrastructures that deliver stability and scalability for complex deployments, high-availability setups, and virtualization (VMware ESX, MySQL replication, load balancing)
- IT Security and Networking: Security is at the core of my work, whether configuring firewalls, setting up VPNs, or monitoring systems for any potential intrusion, I ensure our network environment remains solid and secure.
Tom Lovering: Director of Business Development
I started as Director of Business Development in 2008. Although we’re a small team, we’re able to pivot from broad strokes to fine detail with ease. By that, I mean the ability to speak to a wide range of audiences with messages that resonate for all, while simultaneously being able to respond to the fine details of an RFP with a highly personalized and specific approach.
The results of our work impact the whole company, which is a responsibility we take seriously. There’s a push and pull as we build on our existing successes and talents, while working to stretch into new areas or relationships. Our team is always seeking to align with the various interests of our company. It can be challenging to get that balance right, but it keeps us on our toes! We fully embraced the public sector in 2016 with the launch of GovWebworks, and for many of us, the public sector focus helped align the work with our values.
There are many projects that are a source of pride for me. To single a few out, the Washington DSHS website remodel in 2016 was the first project where we proved that we could tackle a large-scale HHS project successfully. Our relationship with Minnesota DEED has been one of true partnership for many years, and has paved the way for our growth in the area of workforce development. Finally, our work in natural resources and conservation in Missouri, Colorado and Mississippi has been important for its impact on the environment. I’m proud to be a part of these and other important projects like them.
Background: Throughout my career, I always held a customer-facing role, either in sales or account management. During my previous job at L.L.Bean, I worked with PWW as a vendor and got to know Justin. When the BD job came up, it felt like a natural fit for me, and fortunately Justin thought so too. If you’ve met me, you can tell from my accent that I grew up in the UK, where I got a degree from the University of Sussex in Politics and American Studies. That degree has come in handy now that I find myself working with government clients where an understanding of legislation, funding, and acquisition is a big part of the job.
Alison Schestopol: Director of Project Management and Quality Assurance
I started as Director of Project Management & Quality Assurance in 2011. I genuinely enjoy working with our project management and quality assurance teams. Their dedication, attention to detail, and problem solving in the face of challenging work are inspiring, especially in the public sector, where our projects have a tangible impact and transform lives. Embracing Agile principles, our team adapts swiftly to changing requirements, keeping projects dynamic and responsive to our client’s needs.
We tackle complex tasks with a commitment to quality and service, making an impact that truly matters. The teamwork, adaptability, and passion make our mission to serve the public both fulfilling and rewarding. When challenges arise, our project teams don’t just survive; they adapt, innovate, and deliver results to delight our customers.
My experience in project management and Agile practices is supported by a number of certifications. I’m a Certified Project Management Professional and hold advanced Agile credentials, including PMI-ACP, Certified ScrumMaster, Certified Product Owner, and Certified Scrum Developer. I’ve expanded my Agile expertise with certifications in Agile Leadership Essentials, Agile Leadership for Organizations, and Agile Leadership for Teams, as well as Agile Facilitation.
Background: My past professional journey included roles such as Senior Project Manager at Abilis Solutions, Business Analyst and Project Manager at Diversified, and Beta Software Project Manager at IDEXX.
Kevin Ferguson: Director of Software Development
I started as a Software Developer in 2013 and became Director of Software Development in 2021. I’m really proud to be part of a team that is making a positive difference in the lives of people, and I love that we can bring the power of technology to enable meaningful change.
The Software Development team plays a very versatile role at Portland Webworks. We’re constantly balancing many different facets of the projects and business. Responsibilities include evaluating the new technologies, programming patterns, and techniques that are constantly evolving as we keep on top of industry best practices. At the same time, we’re gaining a deep understanding of our client’s domains and industries so we can better understand the challenges they face and how best we can apply the technologies available. Finally, we’re engineering custom solutions that best fit the challenges and constraints that are unique to the project and the client we’re working with. Many of the challenges we see are similar between clients, but no two projects are really the same. That’s what keeps the work we do interesting.
While we have a strong affinity for the public sector and open source technologies at PWW/GWW, there is really no limit to the types of projects we can take on. The diversity of clients and unique problems we’re trying to solve with each project means our work is never boring. At the same time, we have such a strong culture of support where everyone is looking for ways to pitch in and help. We’re constantly pushing ourselves further, and higher, but we’re never doing it alone.
I’ve always been drawn to challenging problems. Some days, that’s coming up with an algorithm or learning a new technology. Other days, it’s figuring out how we’re going to solve a system problem or overcome a communication challenge. At PWW, my career has transformed from solving discrete technical challenges, to managing system and team level challenges. I feel fortunate to support a team of such talented individuals that are solving problems together in ways that amaze me every day.
Background: My certifications include Scrum Product Owner and ScrumMaster through the Scrum Alliance. Before PWW, I was an Advisory Software Engineer at IBM and got my BS Electrical and Computer Engineering at Cornell University.
Sarah Crossman: Director of User Experience
I started as Director of User Experience in 2019, after almost four years as a project manager. Our team is as skilled at tackling complex functional issues that require analytical thinking as we are at bringing aesthetic polish and style to our software. We also help extend or modernize our clients’ brands into the websites or software applications we’re building.
Our team is instrumental in bringing order, logic, and beauty to whatever the new software solution requires. We address many issues including aging technology that doesn’t meet administrative and content ownership needs, websites that have become outdated over time, and manual or paper-based processes that need to be digitized.
We also do extensive user research to understand how to organize large amounts of content that needs an overhauled information architecture or how to target audiences whose needs are not well-understood or met.
There is a certain beauty in helping form the vision for a new product, building a design around that, and then working with our development partners to bring it to fruition for our users. I love the collaborative approach we take to every project and the way we help one another deliver our best work, both within the Creative team and across our various disciplines at PWW/GWW. In recent months, our creative services have involved more content strategy and migration-related work, so we’ve welcomed permanent and short-term content specialists to our team as well.
GWW’s focus on the public sector in recent years has been especially fulfilling. It’s incredibly satisfying to see the direct impact that our work is having on citizens and customers who need access to a service being offered by one of our public sector clients, and it emphasizes the importance of bringing together usable, intuitive, accessible, elegant, seamless experiences for our users.
Background: I’m a Certified Professional for Usability and User Experience through UXQB, the International Usability and UX Qualification Board, as well as a Certified Scrum Master and Product Owner through Scrum Alliance. Prior to joining PWW, I was a Project Manager at IDEXX Laboratories and Spurwink. I got my MS in Project Management at Boston University and BS in Elementary Education at the University of Maine.
Hellen Fitzpatrick: Software Development Manager
I started at PWW in 2016 as a project manager and became the Software Development Manager for the Drupal team in 2022. The Drupal team brings invaluable expertise and insight to our projects. Our team of developers brings a wide variety of skills to help our clients build award winning, reliable websites that make a difference. They know Drupal inside and out, customizing its features to create websites that are easy to use, secure, and accessible to everyone. By staying active in the open-source community, our developers keep up with the latest tools and trends, making sure every site we build for our clients meets the highest standards for security, transparency and accessibility.
What sets our team apart is their flexibility and problem-solving mindset. Our clients’ needs are unique, and our developers are pros at tackling complex challenges, adapting to evolving requirements, and collaborating with all kinds of stakeholders. They make sure every project is built to handle lots of visitors, performs smoothly, and looks great. By combining expertise with a passion for quality, we deliver exceptional solutions and we have fun doing it! ”
Background: I hold certifications from the Scrum Alliance as a Scrum Product Owner and ScrumMaster. Before PWW, I was a Project Manager, Implementation Consultant, and Product Support Consultant at Tyler Technologies.
Meet our teams
- Dev & DevOps Team Spotlight
- Drupal Team Spotlight
- Creative Team Spotlight
- Project Management Team Spotlight
- Quality Assurance Team Spotlight
Join our team
We’d love to hear from you. We have a variety of remote and hybrid positions available.
- Check out our current job openings
- Contact us with any questions
- See PWW/GWW clients: Portfolio of work
- Visit us on social media: LinkedIn, Facebook, Twitter, Instagram