Chief of Staff

Access to education starts with a safe, reliable ride to school. That’s why we built BusRight, a technology platform trusted by hundreds of thousands of Transportation Directors, Drivers, and Parents across 36 states to make school transportation safer, smarter, and more equitable. 

Following our Series B fundraise and over 100% year-over-year growth, we're hiring a Chief of Staff for Keith, Co-founder & CEO. This person will ride shotgun with Keith, working from our Brooklyn, NY office ~3 days a week as we think through and execute BusRight’s next phase of growth. 

This job description isn’t going to be like a normal job description. This is a transparent overview of what Keith needs help with, the characteristics of who he's looking to partner with, and what it’s like to work with him.

In 2026, Keith will spend almost all of his time focused on (i) developing a world-class company culture, (ii) hiring and nurturing the best-fit talent for BusRight, (iii) spending high-quality time with the team, (iv) deepening relationships with customers, investors, and the board, and (v) continuing to develop and articulate a vision for the team and BusRight community that we can all be proud of. 

What the CEO needs help with

• Goal & project management: Be a thought partner on Keith's annual, quarterly, monthly, and weekly goals, helping link them to daily activities (managed via Monday.com). When priorities shift, help adjust projects and timelines accordingly.
• Stakeholder & relationship management: Help craft a rhythm for engaging all key stakeholders and ensure the CEO's goals and daily activities leave space for meaningful relationship building. 
• Culture & decision support: The CEO can’t be in every room, Slack huddle, or conversation, so he'll lean on you to stimulate discussion, ask the right questions, and make decisions on his behalf to remove bottlenecks across the company.
• Efficiency & operationalization: Proactively recommend ways to streamline, eliminate manual work, and operate smarter. For example, operationalizing recurring activities like board meeting prep, conference presentations, customer on-site prep and follow-up, etc.
• Calendar & travel management: Support the CEO with scheduling, especially for travel to conferences, chapter meetings, department and company off-sites, and board meetings. We know it’s not glamorous work, but he'll be deeply appreciative of your support. This work won’t exceed 20% of the role.

Who we're looking for

We're seeking a self starter with a strong EQ. It’s a plus if you have an MBA, a couple of years in management consulting, or a few years helping scale a venture-backed company.

• You can manage yourself: You set clear priorities, stay organized, and keep commitments without someone checking in. You create structure where there isn’t any, create order when there’s chaos, and treat follow-through with precision.
• You lead with kindness and curiosity: You listen to understand, not just to respond. You’re empathetic, assume positive intent, and look for the underlying assumptions driving varying perspectives. Thoughtfulness matters here just as much as speed. We work hard, but we know there’s no shortcut for taking care of people.
• You write exceptionally well: You’ll be drafting communication on behalf of the CEO to key stakeholders, and you should be able to adopt his tone and produce clean, professional writing that doesn’t scream ‘ChatGPT’ wrote this.
• You are direct and succinct: Keith operates best with fast, clear, honest feedback (voice notes included). You can take complex information and boil it down into the ‘so what’ that matters.
• You can influence without a title: You’re comfortable managing up, disagreeing thoughtfully, and stepping into conflict when needed. Influence matters more than authority in this role.
• You are detail-obsessed: Nothing should fall through the cracks. You’ll effectively be managing two workloads: yours and the CEO's, so discipline and organization are essential.

What it’s like to work with Keith

The good:

• He'll celebrate your wins loudly. Expect voicenotes with excitement when he sees great work.
• He loves being challenged, and will encourage you to speak up with direct, thoughtful opinions in real time.
• He doesn't believe the only way to be great is through “100-hour work weeks.” If outcomes are strong, you’ll have flexibility in where, when, and how you do your best work.

The not so good:

• He wants to mentor, but is not always great at it. People tend to work best with him when they shadow, observe, and choose what to adopt based on their own style.
• He travels often, and between being on the road and carving out focused heads-down time, he's not always available on short notice.
• He has communication pet peeves: spelling errors, writing that looks unedited or AI-generated, and vague requests like “can we talk?” without context shared first.
• His energy fluctuates with the overall health and success of our customers and team members. He has a lot of patience, except when it comes to not calling customers or engaging with team members who need help. Nothing frustrates him more than learning a customer isn’t having a great experience with BusRight, and we didn’t do everything possible to turn their experience around.

Who Keith is outside of work:

• Animals bring him a lot of joy (fun fact: his pet bearded dragon is how he met his Co-founder, Phil).
• He's a kid at heart and unreasonably proud of beating his brothers and cousins in Nerf battles, wiffle ball, or ping pong.
• He's obsessed with being present and focused, and will geek out on morning and evening routines and ways to trade quick dopamine hits for fulfilling, in-the-moment experiences with the team, his family, and friends.

This Chief of Staff at BusRight will be joining a remote team of 70+ ‘BusRighters’ with hubs in New York City, Boston, Poland, and Austin. To get a feel for the team and culture, check out our company retreat in Mexico, this company commercial, and how we approach school bus conferences.