Finance and Operations Specialist

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 $15B 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).

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 month end, a payroll deadline, or an insurance renewal calls for an extra push.

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

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 been paid, 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 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 payroll cycles, vendor payments, customer invoices, filings, and renewals at once, and nothing falls through the cracks. Every account reconciles, 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 have studied accounting and be ready to own it. Either way, 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.

Bonus points: Experience billing public agencies 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.

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 will own the financial and operational engine that keeps Blissway running: the logistics, deadlines, and details that let the rest of the team build. This is an individual contributor role reporting directly to our founder and CEO. You'll also partner with our outside CPA firm on tax and year-end work.

• Keep Things Running: Handle vendor onboarding, contract records, and the day-to-day logistics that keep the company moving, and fix any process that's slowing the team down.

• Report and Flag: Deliver monthly reporting to the founders with budget vs. actuals and a cash forecast. Flag gaps, risks, and opportunities before anyone asks.

• Bill and Collect: Invoice customers accurately and on time, including milestone and contract-based billing for public agency customers. Follow up on receivables until they're paid.

• Pay and Track: Pay vendors on time with clear approvals, track and categorize company spending, and keep vendor records clean, including W-9s and 1099s.

• Close the Books: Own the monthly close: bank and card reconciliations, accruals, and a clean P&L, balance sheet, and cash flow on a predictable schedule.

• Handle the Small Contracts: Own Blissway's non-tolling agreements from draft to signature to renewal. That covers leases (like the private road we use for testing), vendor and service agreements, NDAs, and the many small contracts a growing company signs. Negotiate standard terms, bring in outside counsel when a deal needs it, and track obligations and renewal dates so nothing auto-renews or lapses by surprise. Tolling and agency contracts stay with the founders.

• Run Payroll and Benefits: Run payroll in Rippling and keep payroll tax filings current. Manage our ICHRA allowance, 401(k), and life and disability coverage. Manage Colorado FAMLI premiums and coordinate leave alongside our parental leave policy.

• Protect the Company: Own business insurance renewals and certificates of insurance for customers. Keep a compliance calendar of filings, registrations, and renewals so nothing lapses.

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, direct access to the people setting technical direction, and work that ships to roads in weeks, not quarters.

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.