Chief of Staff to the CTO

Description

Do you live for the moment a messy week resolves into a clean scorecard? Do you find yourself, unprompted, building the spreadsheet that nobody asked for but everyone ends up using? Do you geek out over a well-run meeting, a tight agenda, a follow-up that actually got followed up on? Do you want to sit one seat away from a CTO and learn how a real software business actually gets run? If so, keep reading.

RTA is looking for a Chief of Staff to the CTO. This role is the operational backbone of the CTO office, which spans Product Management, Software Engineering, QA, Infrastructure, Site Reliability, and Customer Support. You will own the reporting cadence, drive cross-team coordination, run point on release planning with Marketing, and keep the CTO's time and attention pointed at the things that actually matter. It is part program manager, part operations lead, part executive partner. None of those hats is full-time on its own. Together they are more than full-time, which is exactly the point.

We don't do silos. Our four delivery teams (Innovation, Roadmap, Customer Experience, DevOps) work shoulder to shoulder, and the Product Steering Committee keeps us all rowing the same direction. You will be in the middle of all of it.

A note up front: we care more about aptitude than checked boxes. If you don't hit every item on the list below but you have the wiring to pick it up fast, apply anyway. The learning curve here is vertical, and the people who thrive in this seat treated their last job as a launchpad rather than a destination.

What We're Looking For

In general, someone who:

• Feels at home being a member of a healthy team. This means they aren't afraid to mix it up or be held accountable by the team, and they are willing to hold others accountable as well. 
• Passionately cares about our clients and helping them be more successful. Our clients are fleet managers, parts clerks, automotive technicians, and they maintain everything from squad cars to school buses so that everyone comes home safely at the end of the day.
• Thinks of themselves less, while not thinking less of themselves. They are other-centric, compassionate, and self-assured.
• Is willing to lift boxes, clean floors, and hold doors if that's what it takes to get something done, because no job is beneath them.
• Takes ownership and initiative. They don't wait to be told what to do. They own their role and how to make it better.
• Loves to read, learn, grow, and stretch themselves. Bonus points for each book they've read by Patrick Lencioni.
• Is AI-native. Uses Claude, ChatGPT, or equivalent every day, and has views on what they're good and bad at. We will ask.

Specifically for this job, someone who:

• Owns the operational drumbeat: weekly C-suite tactical scorecards, Monthly Business Reviews, trimester board materials, and the monthly board-member check-in. Reporting isn't a fire drill, it's a rhythm.
• Builds and maintains the dashboards and metrics that feed the reporting cadence, instead of rebuilding them every cycle from scratch.
• Runs release coordination across Product, Engineering, QA, Customer Experience, and DevOps. Is the connective tissue when handoffs break.
• Partners with Marketing on go-to-market and communications planning for releases. Makes sure customer-facing messaging, enablement, and launch timing line up with what's actually shipping.
• Drives cross-functional initiatives end to end. New QA tooling rollout. AI workflow adoption push. A customer-impacting release. They don't all fit on an org chart, but they all need to get done.
• Preps the CTO for every meeting that matters. Talking points, context, what's changed since last time.
• Drafts internal communications: all-hands updates, board memos, Executive Team briefs, internal announcements. Writes clearly and structurally, with no fluff.
• Is a thought partner. Can push back on a half-baked idea respectfully, in private, before it leaves the room.
• Actively manages the CTO's calendar. Triages requests, defends deep-work time, sequences meetings logically, resolves conflicts before they show up.
• Handles meeting prep and follow-through: agendas built in advance, materials staged, action items captured and chased to completion.
• Supports inbox and Slack triage. Flags what needs attention, drafts responses for review, keeps low-value noise out of the queue.
• Owns travel planning, expense management, and other executive operations hygiene. This is real work, done at a high level, and it frees up CTO focus for the things only the CTO can do.
• Coordinates CTO Team logistics. Offsite planning, leadership team rhythms, executive guest visits.

Does this sound like you? Let's talk.

Key Results Areas (aka the Job Outcomes)

• The CTO's reporting commitments (weekly tactical, Monthly Business Reviews, board materials, monthly board check-in) are delivered on time, accurate, and visually clean, without becoming the CTO's job to assemble.
• Cross-team release coordination runs predictably. Marketing knows what's launching when. Customers don't get surprised by what shows up.
• The CTO's calendar reflects strategic priorities, not whatever filled the white space first.
• Commitments made in leadership meetings actually get done, tracked transparently, and closed out.

Feeling confident this is in your wheelhouse? Let's put that to the test.

Qualifications

OK, the boring HR part of the job posting that looks like every other posting out there, but it's necessary:

• 2 to 4 years of experience in some combination of: program or project management, release management, agile delivery, executive assistant or business operations support, technical product management, or a prior Chief of Staff role. Title doesn't matter, pattern does.
• Proficient with Microsoft 365 (Outlook, Word, Excel, PowerPoint).
• Experience with virtual collaboration tools like Zoom and Teams.
• Excellent written communication. Clear, structured, no fluff. If your cover letter reads like generic AI output, we will notice.

Bonus points and nice to haves:

• SaaS background, especially vertical SaaS or B2B with a non-tech-native customer base.
• Working knowledge of agile delivery (scrum, kanban, SAFe, or similar). You don't need to be a certified scrum master, but you should know how a healthy delivery process feels and what breaks it.
• Hands-on with Jira, Confluence, HubSpot, Intercom. Our actual stack.
• Experience supporting a CTO, CIO, CPO, or VP Engineering directly.
• You've built a scorecard or dashboard from scratch (not just maintained someone else's).
• You've run a release train, an incident review, or a leadership offsite.
• Triple Yahtzee if you've sat in board prep cycles, even from the bench.

The Bottom Line

You've made it this far, so congratulations. We are really looking for ideal team players, with an almost frightening intensity around making things run well, the discipline to make a reporting rhythm look effortless, and a passion for serving the people on either side of them.

Compensation & Work Location

• Total compensation for the role is between $110k and $120k DOE. 
• This is a full-time, in-office role based at RTA HQ in Glendale, Arizona, working side by side with the CTO and the broader leadership team.
• This position is classified as exempt and is not eligible for overtime pay,

Why Top Talent Chooses RTA

We invest in our people — period.

• 401(k) with 6% Safe Harbor match (100% vested day one) 
• Flexible PTO model designed to support work-life balance and manager-approved time off 
• Cigna PPO and HSA medical plan options with company contributions ($780–$1,950 annually)
• Garner Health HRA program: up to $1,000 individual / $2,000 family reimbursement opportunity
• Wellness rewards up to $350 annually
• Virtual care and mental health support resources
• Company-sponsored benefits including dental, vision, EAP, life, STD, LTD, legal plan, and identity theft protection options
• Additional employee perks, wellness initiatives, and discount programs

The Part We're Most Proud Of

• 99% of employees say RTA is a Great Place to Work® (Certified 3 years running)
• 30% ARR growth — two years straight
• We are an AI-forward company building for the future
• Big growth. Real benefits. Strong culture. A team that delivers.

About Us

RTA has been established since 1979 and has the reputation of providing the best customer service in the market. Our purpose is to help fleets succeed. We pride ourselves on creating a caring, family-oriented atmosphere for both staff and clients, and love that our work makes a positive impact on all the lives we touch. Our clients carry kids in school buses, first responders in emergency vehicles, patients in ambulances, food and medical supplies in trucks, and people just taking the bus or train to work. We do meaningful work, and we want our clients to have the best tools available to them.

Our office spaces are open, spacious, and colorful, with an abundance of natural light. We come together often as a company to enjoy freshly baked desserts or awesome lunches, and genuinely enjoy each other's company. We offer some pretty unique perks and benefits, as well as all the standard ones. We're happy to talk through all the options.

Physical & Travel Requirements

This role has the following physical and travel requirements:

• Ability to sit or stand for extended periods
• Ability to work at a computer for prolonged periods
• Ability to travel up to 10% (minimal travel based on business needs)

Heading to RTA HQ?

Coming from the east side? You'll enjoy waving at the traffic going the other way while never having to stare at the blinding sun. It only takes about 25 minutes to get here from downtown Scottsdale in the mornings. We are located close to Arrowhead Mall, with quick access to the 101 from multiple directions. If all of this sounds like you, and your type of company, then click apply. Seriously, we've asked you four times now, and you are still reading. Bonus points for being thorough.

Reasonable Accommodation

RTA is committed to providing reasonable accommodations for qualified individuals with disabilities. If you need a reasonable accommodation to complete the application process or perform the essential functions of this role, please notify us at hr@rtafleet.com.

Employment Notices

Employment with RTA is at-will. This means either the employee or the company may terminate the employment relationship at any time, with or without cause or notice, subject to applicable law.

Employment with RTA may be contingent upon successful completion of a background check and other pre-employment screenings, consistent with applicable law.

We cannot accept student visas or provide sponsorship at this time.

Equal Employment Opportunity

RTA is an equal opportunity employer and does not discriminate on the basis of race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status, or any other protected status under applicable law.