Technical Project Manager (Software Company)

Technical Project Manager

About Castle Rock ITS

Castle Rock ITS empowers transportation agencies to create roadway knowledge that improves safety, trust, and reliability.

We are the creators of SaaS platforms in the transportation sector. Our customers are government agencies. Our products are modular and share a common code base, but they are highly configurable.

Each of our client deployments is a unique combination of software ecosystem’s modules and settings. The systems are mostly cloud-based but some are on-prem. . Our platform uses common code but with high levels of configuration to meet individual client needs and preferences.

We don't just deliver software. We build deep, long-term partnerships with every customer we serve.

The role

We're hiring a Technical Project Manager to own a portfolio of 4–5 client deployments, from launch through ongoing operations and maintenance.

You'll be each client's trusted partner and the bridge to our internal Product Development and Operations teams. Launches are intense and detail-heavy. Once a system is live, the work shifts to deepening the relationship and helping the client get more from it.

This seat is for someone who can grasp the details of a complex, configurable platform quickly and run with it independently. You don’t need a deep software background, but you do need to keep many moving parts straight at once in your mind.

You’ll be in very frequent contact with clients and internal teams, so strong communication is central to the job, including the ability to explain ideas verbally and visually.

What you'll own

This seat has five core roles.

• Deployment leadership. Lead new client launches and new rollouts for existing clients, from kickoff to go-live. Own the plan, the timeline, and the configuration decisions that make each deployment fit. You’ll walk the client through the process, being clear, reliable, and dependable along the way.
• Client partnership. Hold regular check-ins with your clients that deepen each relationship. Track to-dos from these meetings and make them happen. Spot opportunities for improvement, and share how other customers are using the products.. Help us keep information flowing across our client base so every client knows about the latest product features and offerings. Assist with building new relationships with new customers.
• Release planning with Dev and Ops. Plan rollouts, upgrades, and patches with our engineering teams. Track them and report back to your clients. Bring clear requirements and timing so developers can stay focused on building.
• Performance reporting. Track each client's KPIs and system stats. Deliver monthly progress reports that show the value of their system.
• Scopes and billing. Write clear, accurate scopes of work, and manage client billing on time.

Your first 90 days

You'll take charge of on two major deployments:

• A new deployment for a new client, taken from kickoff toward go-live.
• A major upgrade for an existing client.

By day 90, success looks like this:

• Both projects are on track, and both clients trust you as their go-to person.
• You know the product ecosystem well enough to make configuration decisions and talk through trade-offs with engineers and clients.
• You've captured what you learned in our knowledge bases (Confluence, JIRA) so the next person ramps up faster than you did.

How we'll measure success

Measurable

What it tracks

1.

Milestones on track

Delivery milestones in your active projects that are on schedule

2.

Release plans on time

Rollout, upgrade, and patch plans shared with Dev and Ops by the agreed lead time

3: Open client issues past due: Client issues older than the agreed response window

4.

Client satisfaction

Every client in your portfolio rates their experience working with you at 5 out of 5

Our core values

We hire, promote, and measure against these five core values.

• Creativity. We offer the most innovative, thoughtful products in our market. In this seat, you find smart ways to combine modules and settings to solve each client's real problem.
• Can-Do Attitude. “It wasn't built to do that” or “that’s not possible” is the opposite of how we think. You figure out a way with the team instead of shutting down ideas, or each other.
• Client/User Obsession. Our clients should feel they can totally depend on us, and their eyes should light up when we roll out solutions.
• Caring. We treat our teammates, clients, and end users with patience, compassion, and respect. We take time to understand where others are coming from, work as one team, and follow through, because we care how things turn out for the people we serve.
• Competence. We know our craft and we do it right. We think critically, work thoroughly, and get to the root of the problem. When we don’t know something, we find out. We own the results, so clients can count on us to get the job done well.

You'll thrive in this role if

• You plan before you execute. You break a launch into milestones, map out dependencies, and spot risks early, then keep the plan current as things change.
• You love puzzles and systems. Working out how a configurable platform fits together energizes you.
• You learn independently. You dig into documentation and hands-on experiments to get yourself up to speed, gathering your questions to set yourself up for deep learning when bring your questions to the team
• You protect developer focus. You batch your questions, come prepared, and know what's urgent and what can wait.
• You communicate clearly. You're as comfortable explaining an API to an agency director as you are explaining a client's needs to an engineer.
• You love getting things done, with people. You enjoy building relationships and seeing projects through to the finish.
• You build process as you go. We're growing, and you'll help shape how we run deployments.
• You love helping others grow and succeed. Just as others will help you thrive, you do the same for them: you share what you know, collaborate generously, pitch in however you can, and are reliably there when people need you.

What you bringRequired

• 4+ years managing software projects, ideally SaaS implementations or client deployments.
• Experience running several client relationships/projects at the same time.
• Strong technical savvy. You understand front ends, back ends, APIs, configuration, and cloud environments well enough to talk through them with technical and non-techical people.
• Expert-level Jira and Confluence. Fluent in Slack, Excel or Google Sheets, and Word or Google Docs.
• Literate and numerate. You write clear scopes and reports, and you're comfortable with KPIs, data, and billing.
• Comfortable using AI tools such as Claude in your daily work.

Nice to have

• PMP certification.
• Experience with transportation agencies, intelligent transportation systems (ITS), or other public-sector and government-agency clients.

This role probably isn't for you if:

• You’d rather "jump into the work" than plan it out. Launches need someone who looks ahead, sets the timeline, tracks dependencies, and sees problems coming weeks before they land.
• You need a complete playbook before you can move. Our processes are still evolving, and you’ll often be the one writing them.
• You’d rather hand technical questions to someone else than dig in yourself. We expect you to work through the docs, Confluence, and the product before escalating.
• You prefer to focus on one project at a time. You’ll be juggling 4–5 clients at different stages, often switching between them in the same day.
• “It wasn’t built to do that” is your first instinct when facing a challenging question from a customer. Clients will push the platform in new directions, and we need someone who starts by asking how it could work.
• You’d rather keep client relationships transactional. After launch, the job is building trust over months and years.
• You keep what you learn in your head. We rely on people writing things down so the whole team gets smarter.

Logistics

• Location: Fully remote.
• Residence: You must reside in one of these U.S. states:

-Oregon

-Washington

• California
• Arizona
• Minnesota
• Michigan
• Louisiana
• Texas
• District of Columbia
• Travel: 2–5 trips per year.
• Team summit: Once a year, in person, in Portland.
• Compensation: $90,000-$115,000 with bonus eligibility, generous benefits, and room for growth

How to apply

Send your resume, along with short written answers (a paragraph or two each) to these two questions:

• Tell us about a time you had to learn a complex technical system quickly. How did you get up to speed, and how did you keep track of what you learned?
• Describe a time a client asked for something their system “wasn't built to do.” What did you do?

We read these answers as closely as your resume, so please be sure to submit them with your application.

We look forward to meeting you!

Pay: $90,000.00 - $115,000.00 per year

Benefits:

• 401(k)
• 401(k) matching
• Dental insurance
• Health insurance
• Life insurance
• Paid time off
• Parental leave
• Vision insurance

Application Question(s):

• What are your salary requirements?
• What US state do you reside in?
• Are you willing to undergo a background check?
• Tell us in a few sentences about a front-end, a back-end, or an API for a software product you helped deliver as a project manager at a previous job

Experience:

• Project management: 4 years (Required)

Location:

• United States (Preferred)

Work Location: Remote