Finance and Operations Specialist [Remote]

Work at Blissway: Opportunity for Impact Every Day ✨

Blissway is a startup that simplifies toll collection and dramatically improves highway safety. We are multiple startups in one: Deep Tech, AI/ML, Hardware, SaaS, and IoT. For the past five years, we have built a nearly insurmountable technological lead in tolling, a roughly $200B global industry expected to double in the next decade. We work for toll authorities and state DOTs, and we own the whole system, from the roadside camera to the final bill, so every vehicle we see becomes one accurate toll transaction and nothing more. While our competitors have thousands of employees, we operate with a lean but growing team of less than 30. Our impact is visible on the massive Interstate Highway System connecting every major US metro (except Juneau, AK—sorry, Juneau).

The Mission

Our technology runs on some of the busiest toll roads in the country, and our growth depends on a tight, well-run business behind it. You'll report directly to our founder and CEO and take as much off his plate as you can handle, including owning Blissway's finance and operations: the numbers, the workflows, and the systems we'll scale on. You'll see up close how a startup gets built: the decisions, the problems, and the details that make it all work. Your scope will grow as you do.

You'll begin with:

• Finance: Run the numbers that drive the business. Lead monthly reporting to the founders, including budget vs. actuals and a cash forecast. Own the monthly close and work with our outside CPA firm on tax and year-end.

• Operations: Run the deals and decisions that keep the company moving: negotiate vendor and service agreements, manage leases like the private road where we test our technology, and decide when a contract needs outside counsel. When something is slowing the team down, you find it and fix it.

• Billing and payments: Run the systems that can't break. Customer invoicing, including milestone billing for public agencies, along with collections, vendor payments, payroll, and benefits. Much of it is already automated, and we want to keep it that way.

You are a good fit if...

• You have drive: You take extreme ownership. If a number doesn't tie out, you find out why. If a process is missing, you build it. We are outcomes focused, not hours focused. You know when a major project calls for an extra push.

• You think clearly: You cut through noise. You can look at a P&L or an aging report, spot what's wrong and explain what to fix first.

• You communicate clearly: In writing and in person, you get to the point. Founders, employees, customers, and vendors always know where things stand: what's owed, and what's due next.

• You spot and flag gaps proactively: You don't wait to be asked. You spot the lapsing insurance policy, the under-billed contract, the filing coming due, or the cash crunch three months out, and you raise it early with a recommendation.

• You see finance and operations as a system: You treat the books, payroll, and billing as a system you can build, not a pile of tasks. You automate what repeats, document the rest, and set up controls so the same mistake can't happen twice. "We've always done it this way" bothers you.

• You are detail obsessed: You juggle payments, customer invoices, filings, and renewals and nothing falls through the cracks. Every number has backup, every deadline is on a calendar, and every invoice goes out on time.

• You learn fast: You may have closed the books before, or you may simply respect it as a job that the business can't function without. You don't need to have done every part of this job before if you pick up new systems quickly, ask the right questions, and don't need to be shown twice.

• You have technical foundations: You don't need to be an engineer, but you're curious about how our products work and how we make money from them. You're comfortable with automations, integrations, and AI tools, and you'd rather build a workflow than repeat a task.

• You value working together in person: You’re excited to work alongside the team at our Denver office. This role is in-office on Mondays, Wednesdays, and Fridays, with flexibility to work remotely on Tuesdays and Thursdays.

• Bonus points: Experience with public agency or government contracts (milestone invoicing, required backup documentation, long payment cycles). A CPA or progress toward one is a plus, not a requirement.

This might be you if...

You want your work to make a difference every day. You're drawn to the pace of a startup and the stability of a profitable business with long-term contracts. You love getting things done, and you'd rather own finance and operations end to end than one slice of it at a big company. You're excited to build the systems we'll scale on.

Backgrounds we'd love to hear from: You might be in operations at a fast-growing startup, a couple of years into consulting or Big 4, or something else entirely. We care far more about how fast you learn and how much you own than whether you've held this exact job before.

The Interview Process

We're a selectively small team, which means a deliberate and thorough interview process with 3-4 interviews and a final paid work trial. In exchange, you get real autonomy from day one and direct access to the people setting the company direction.

The Essentials (Health & Wealth)

• Relocation Support: We are excited for you to join the team at our engineering office in Denver. We value in-person collaboration and daily team lunches and we provide a relocation bonus to help you get here.

• Personalized Health Coverage (ICHRA): We don’t believe in one-size-fits-all healthcare. We provide a monthly allowance for you and dependents so you can choose the individual plan that actually fits your life.

• Investing in Your Future: 401(k) matching up to 4%.

• Peace of Mind: Transparent compensation. Company-sponsored life & disability insurance.

• Early Stage Equity: Competitive equity package. Every year, we facilitate a tender process that gives you the opportunity to sell your vested shares at the same valuation as our investors.

Rest & Recharge

• High-Trust Time Off: 4 weeks of untracked PTO. We don't micromanage your calendar; we focus on your impact. Take the time you need to stay sharp and inspired.

• Family First: 12 weeks of paid parental leave for birth and adoptive parents. We want you present for the moments that matter most.

• The Deep Breath (Sabbatical): Every 5 years, take 12 weeks of fully paid leave . Go travel, write a book, or master a new hobby—then come back and tell us all about it.

Fuel & Community

• The Blissway Kitchen: Whether it’s breakfast to start your day or our daily group lunches, we keep the team fueled.

• Snacks Autonomy: Our kitchen is fully stocked and we mean it—if we’re missing your favorite fuel, just add it to the request list.

• The "BlissTrip": An annual 4-day getaway for the team and significant others.

• Monthly Beats: Game nights, escape rooms, and dinners to celebrate the grit we put in.

• Continuous Learning: Tuition reimbursement for courses, programs, and conferences that sharpen your craft.