Careers at Lightyear

Transform your career

We are on a multi-year journey to fix a wildly consequential and under-appreciated industry. We’re looking for people who want a hard problem, a small team, and colleagues who expect a lot of them.

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Why this work matters

A trillion dollars of spend,
still run
by hand

Telecom is over a trillion dollars of mission-critical spend that still runs on email threads, PDFs, and spreadsheets. We’re replacing that manual coordination with software, data, and agents that can actually do the work.

Who we’re looking for

Smart, intrinsically motivated, and coachable

At Lightyear, we succeed when our teammates are smart, intrinsically motivated, and coachable. Smart means you reason from first principles and can explain how you got there. Intrinsically motivated means you do not wait to be assigned the work that matters. Coachable means you can take direct feedback and act on it. Beyond that, we look for people who push themselves, and the people around them, with a constant itch to improve.

Working here

What our team says

I really appreciate how grounded Dennis and the leadership team is, how straightforwardly they give us the state of the company. I’ve always felt secure in my job while getting the other benefits of startups, like moving fast and having a small close knit team.

Tracy · Senior Software Engineer

Our values

The five ideas we run on

These are the principles we use to make decisions, work together, and hold ourselves to the highest possible standards.

Our identity.

We are on a mission and focused on achieving it above all else. We are here to win. We expect performance, and being part of this team is something earned every day rather than granted once. The standards apply to everyone, including the people who set them.

A relentless focus on recruiting and talent quality. Intellectual honesty about performance, in reviews and company-wide. A willingness to make hard calls when they are needed instead of kicking the can out of fear.

Our intellectual posture.

A beginner’s lack of ego allows for the most innovative ideas and the fastest growth in capability. However big or successful we become, we want to stay beginners. We stay curious, we welcome the obvious question, and we keep a healthy degree of paranoia.

We change our minds without apology or shame. We ask “if we were starting Lightyear today, would we build it this way?” and then act on the honest answer. We separate the strength of an argument from the seniority of the person making it.

Our growth philosophy.

We are on a multi-decade path to transform enterprise telecom. It is a game of nuance and detail that compounds every day at the margins: vendor coverage, data, process, product. One percent better every day becomes magnitudes over a long enough timescale.

We invest in tooling, documentation, and process improvements that will not pay off this quarter. We run retros after wins as well as losses. We develop our team for the long term.

Our tempo.

Opportunities decay, and the cost of waiting is almost always higher than the cost of action. When we say we will do something, we do it. We solve problems with the least process and resourcing required, and we stay decisive in the face of uncertainty.

We do what we said we would, on a timeline that feels slightly uncomfortable. We default to making the decision rather than scheduling another meeting about it. We ship the B+ version this week instead of the A+ version next quarter, unless the stakes require otherwise.

Our approach to stewardship.

We collectively own Lightyear, and we treat it the way we would treat an asset we want to be worth more in twenty years than it is today. Long-term thinking on every meaningful decision, rational frugality, and good judgment when nobody is watching.

We make decisions on a ten-year horizon, especially when the one-year decision would be different. We treat company money as if it were our own. We hold ourselves to standards that do not require enforcement.

Benefits and perks

Covered, vested, and trusted

Remote-first, high-trust
No location restrictions. We trust our team to manage their own schedules around what matters, whether that is family, focus time or a midday run.
Flexible time off
Paid time off without accrual limits, approved by your manager and grounded in trust and ownership.
Paid holidays
Twelve for rest and time with loved ones. The 13th is chosen annually by the team in our very serious, very fun Battle of the Holidays.
Health insurance
National health, dental, and vision, with 100% coverage on base plans for employees and 80% for dependents. Plus FSAs and a $50K life policy.
401(k)
Through Guideline, and you can start contributing from your first paycheck. We match 50% up to 3% of salary.
Company stock
Option grants that vest over four years, with more grants available based on performance.
Bi-annual team events
Twice a year we bring the whole team together, once in NYC and once in a new city.
Swag
A custom swag box when you start, plus fresh gear at every team event.

Interviewing at Lightyear

Our process is intentionally challenging and transparent

A quick 15-minute Zoom chat with a member of our People team. It’s a chance to confirm alignment on the role, answer any early questions, and get an early sense of culture fit.