Chief of Staff to the CEO-AI First Executive Strategic PartnerNational Painting Group • Colorado • Full-Time (Hybrid)
Keep reading if...- You're someone who says "I've got it," and then actually does.
- You ask, "what can I take off your plate today?" ... and you just do it.
- You're AI-fluent. You build workflows across platforms, well beyond chat and search, and you can show them.
- You love running a lot of projects, you're highly organized, and thrive creating organization from chaos.
- You know how to think like a leader. You understand why a CEO's priorities are what they are, and you protect them... including the well-being of the CEO.
- You're ambitious, financially and in life. You have big goals and you're going after them.
- You want your work to add to your life, not take from it.
- You want to love where you work: the work itself, the people, and what the company stands for.
- You want to be empowered and given room to perform, because you love to perform. You don't want to be micromanaged.
- You're coachable, and welcome feedback - and you can take feedback without taking it personal.
- You're hungry to learn, grow and develop, as a professional and as a person.
Still with me?What it's like to work hereAutonomy. We're all adults, we're high performers, and we all have a job to do. We trust each other to do our jobs, and you won't be micromanaged. This is a culture of universal accountability, not hierarchy. We are accountable individually and collectively.
High performance. When you work here, you're surrounded by high performers, and we expect the same from you.
Investment in your development. We produce exceptional results by investing heavily in our people through ongoing internal training and development. It goes beyond training you in your role: it develops you as someone who creates and fulfills intentions, and it shows up in your entire life.
Performance, not hours. We believe your work should add to your life, not take from it. We don't do hustle culture or 60-hour workweeks. You can perform at a high level without sacrificing your personal life, and we've found that's exactly what unlocks performance. You should be able to conduct this role at a high level while fulfilling everything else that's important to you in your life. We'll help you do that.
Clarity of intention & alignment. Everyone you work with is clear on the objective, how we operate, where we're going, and the future we're committed to.
Strategy & patience. We have a clear plan, and we don't take shortcuts. Impeccable, thoughtful work is the source of our increasingly rapid growth.
The Big PicturePainting Business Pro is the largest and longest-running coaching program for painting contractors, with over 500 active members. We've grown that business by 500% over the last three years, and we expect that trend to continue for the next three years.
National Painting Group is our portfolio of painting companies, where we buy a minority stake in painting companies, grow them, and then help the partner ultimately exit, where we take over a majority stake of the business. We currently have 15 painting companies in our portfolio, 8 more in due diligence, and we expect to bring on 1 to 2 new partners every month in 2027.
But we also have plans beyond the painting industry. A lot of our core competencies, what makes us unique, and what we're building apply to business far beyond the painting industry.
Painting Business Pro, National Painting Group and what comes next all run through my calendar today. I can't run fast enough to keep up with the growth that is happening and I'm in the process of completely reimagining how I run and lead this company - and a big part of that is this role.
RequirementsThe RoleThis is an operate-and-build role. You'll take over my executive support on day one, then build the AI workflows, project system and meeting rhythm that let you act on my behalf. You'll sit alongside me, learn how I think, and earn the authority to act for me.
You'll be the person:- Being my strategic partner. Guard my time and energy. Decide which meetings happen, get shortened or move. Prepare every call so the intention is set and it's worth having. Be my eyes and ears on new-leader onboarding and 90-day plans.
- Running project management & accountability. Own the system for everything I own and assign, with clear owners, KPIs, deadlines and visible progress across my leadership team.
- Owning AI-first executive support. Inbox, calendar, travel, expenses, documents and vendors. Route email into meetings or task blocks, get clarity before anything reaches me, and build the workflows that keep this to 10 hours a week or less.
- Handling personal logistics. Mainly trips and vacations. This is a very small part of the role but needed.
- Running the rhythm around it all. Prep and follow-up for team meetings and group calls of 50-100 people, podcast and filming schedules, the alignment rhythm around our BlüPrint, and NPG's six annual events of 50-200 people. Let me do the stuff only I can do and support the scaled distribution of everything I'm building and creating internally and externally.
- Give me my time back. In your first 30 days, own email, calendar, logins and payments, meet every leader, and ship your first AI workflows. By day 90, 10+ hours a week back to me. By month 12, you act on my behalf in meetings and routine replies, run accountability from a live dashboard, and run our events from a playbook you built. This is a rough expectation and we'll work together to expand the role as you're ready for the next step into more accountability.
You'll work side by side with me and coordinate across our team, and your authority grows step by step: from "do what I ask" to an extension of me.
About You- You have 5-7 years supporting a CEO or founder, owning their inbox, calendar and the decisions inside them. This is required.
- You've built AI workflows across platforms (Zapier, Make, n8n, Claude, ChatGPT or similar) and you can demo them, with the hours they saved.
- You've run many projects at once with KPIs, owners and deadlines, and you've held a team to its commitments.
- You understand business strategy at a high level and use sound judgment to guide and protect a CEO's priorities.
- You write clearly, including in someone else's voice, and your discretion is absolute.
- You're an A player: highly organized, quick, decisive and proactive. You love to perform at a high level - it's fulfilling for you to kick ass.
Nice to have: event coordination, from 5-15 person team days to 200-person events.
Not required: home-services experience or a degree. Many great candidates come from senior Executive Business Partner or strategic EA roles with a founder or CEO, or an early Chief of Staff seat that's still hands-on.
BenefitsCompensation & Benefits- Base salary: $125,000-$150,000, depending on experience and track record.
- Performance bonus: 10-15% of base, tied to your 90-day and 12-month outcomes.
- Tech stipend: Open to discussion (Approx. $100-$150 p/mo)
- Health insurance: We offer various Medical, Dental, Vision programs, and contribute up to $400 p/month towards your selection.
- Unlimited PTO. You read that right. Unlimited. We hire high-accountability folks and top performers; you balance your time, and we encourage you to take the time you need, when you need it. You need to fulfill your accountabilities and as long as you're doing that, you can work whenever you want.
- Training & Development: We invest in you. Our first-in-class training & development programs foster personal & professional growth, and you'll have an all-access pass.
- The real benefit: a balanced work culture where you do meaningful work with people you respect and work alongside a founder who plans life alongside the business, without the sacrifice a role like this usually demands.
Location: Hybrid, based in Colorado. You'll rarely need to be in person day to day; you'll travel with me occasionally (under 10%) and join us in person for events, filming days and team days. Otherwise, work where you work best. This is a full-time role and your sole focus. You can expect to be in Fort Collins, Colorado 1-5 days a month for events or in person team meetings.
How to ApplyPlease submit all three:
- Your resume
- A short cover letter: why National Painting Group, and why this role
- A 1-2 minute video: you, on camera, telling us why you'd be a great fit
For a Chief of Staff, that video is also a work sample: show us how you communicate, clearly and concisely.
We won't consider applications without all three.What to Expect After You ApplyThis is an important role, and we're highly selective. Because we expect a lot of interest, we'll only reach out to the candidates we're moving forward with.
Your first step is a phone conversation with Vivian, who leads talent for our organization. Strong candidates then record short video answers to three questions about the role. From there, strong candidates move to a conversation with me, including a walk through our company, mission, vision, values, and how we work... And then through the rest of our process, which includes meeting several members of our team (we've found that to be one of the most important steps).
We move fast, because speed matters with the right people. If we're moving forward, you'll hear from us within 24 hours. If you don't, it means we didn't see the right fit this time, and we wish you the best in your search.
Job Type: Full-time
Location: Hybrid - Colorado
Apply by: November 30, 2026
