Chief of Staff
January · New York City
Collections today works like an emergency room. The doctors carry too many patients, everyone arrives at their worst moment, and nobody has their chart. We're making it primary care. January personalizes interactions and optimizes decisions across every stage of consumer credit. We started in the hardest, most broken stage, because if it works there it works anywhere.
Most consumers want to pay what they owe. They want a way out, not a break. We've serviced over $20 billion in debt across more than 20 million consumers. We see more people with charged-off loans each year than all but the top five US banks. Those consumers rate us about 50% higher than the banks that lent them the money. Creditors net over 30% more because we collect more and charge less.
Most AI strips the human out of the work. We use it to make someone's hardest financial moment more human. The more human we make it, the more people recover. Now we're moving upstream, catching people before they default and building across every stage of the consumer credit lifecycle. The consumer in collections today is the consumer who gets approved tomorrow.
About the Role
We're moving from a single product to several. How we plan, decide, and communicate should grow accordingly. This role drives that transformation.
As Chief of Staff you'll report directly to our Founder and CEO, Jake. You'll be his closest partner on how January decides and executes. You'll represent him when he's not in the room. You are not an executive assistant. You won't manage a calendar.
Here's the work:
Drive our six-week planning cycle, so teams keep reflecting on the problems that matter most every week instead of only during planning week.
Own the operating reviews where we admit what's off track and decide what to do about it.
Run triage between reviews, so slippage surfaces weeks before the cycle closes rather than at the end of it.
Run diligence on the bets we're weighing next. Unit economics, what has to be true, what would kill it, in a memo leadership decides from.
Build the board deck and the narrative behind it, and own the investor updates between meetings.
Make our performance legible and tell the story behind it, wins and misses both, on a cadence people can count on.
Take the problem everyone agrees matters and nobody owns, and own it.
You fret over our decision cycle. Every minute ahead is an advantage. So you'll attack whatever slows us down. People will bring you decisions nobody asked them to bring you.
You'll shorten the distance between what we learn and what we do. If a team needs constant communication to get something done, we organized it wrong. You push decisions down to whoever has the most context, coach them if they need it, then get out of the way.
You'll partner with BizOps on the orphaned problems, supplying the single-threaded ownership those efforts lack. You get a kick out of building something and handing it to someone else. The legos aren't yours to keep.
We've built the strongest team in the company's history. We love how fast new people make an impact. One hire doubled the effectiveness of a key machine learning model in their first week.
What We Need
You obsess over iteration speed above almost everything else, and not just your own. You make already strong teams think clearer and move faster.
You treat prescription before diagnosis as a sin.
You ask the fewest, most important diagnostic questions nobody else in the room thought to ask, then act on the answer the same week.
You think in base rates. Mauboussin and Kahneman sit on your shelf. You'd rather be handed a messy dataset than a clean summary. A book like Psychology of Intelligence Analysis sounds exciting rather than academic, even if you haven't read it yet. You ask what would convince you that you're wrong, then go looking for it.
You believe subtraction is underrated. Clausewitz's line resonates with how you operate: "The talent of the strategist is to identify the decisive point and to concentrate everything on it, removing forces from secondary fronts and ignoring lesser objectives." A dozen things done well beats two done perfectly and ten done badly.
You cut what a decision needs to the fewest stakeholders and the fewest facts, then ask why not now. You're just as ruthless with what you send other people, telling them what doesn't matter as readily as what does, and asking what someone needs rather than building the deck nobody wanted. You think in OODA loops.
You build the first version with no team, no budget, and no playbook, and you build it to outlast you.
You prize truth-seeking and truth-telling over the tyranny of politeness. You hold opinions carefully, until you can argue the other side better than the person holding it. You write so the argument can happen in public. You want that back from us in the moment, not saved for a 1:1.
You already push LLM tooling deep into your own work and want to go further than anyone has let you. You'll build the skills and workflows the rest of the company runs on.
People who've done PE or VC and then gone operating have usually worked at every altitude, from the board deck to the spreadsheet nobody wanted to build. So do people from strategy and operations at companies that moved fast. Those reps are what we're after, wherever you got them.
4+ years of experience. Mostly we're looking for intellectual firepower.
How We Work
Initiative beats permission. You don't wait to be told, and you don't ask for sign-off on a call you can reverse.
Speed beats perfection. You run tight loops, act at 70% on reversible calls and adjust as you learn. Fast loops beat slow ones.
Candor beats comfort. You'd rather hear a hard truth early than a polite sidestep that wastes everyone's time.
Writing beats the average meeting. A good memo works while you sleep.
AI runs through everything here. We built our own code reviewer that beats the alternatives. Our voice AI handles most inbound calls with zero hallucinated payments. Engineers ship 3-4x the PRs they used to. You'll push it further into the work than almost any company you've worked at.
We operate at every altitude. No one here lives only on Mount Olympus, not even the leaders. We get into the trenches to learn the ground truth, then refine our information flows so ground truth climbs as fast as direction comes down.
We build in person, five days a week in our office in Nolita. Jake is in every day. This job runs on the conversations you can't schedule.
As a New York City-based company, we are dedicated to transparent, fair, and equitable compensation practices that reflect our commitment to fostering an environment where all team members are valued and supported. We encourage individuals from all backgrounds to apply.
We are an equal opportunity employer committed to diversity and inclusion in the workplace. We do not discriminate based on race, color, religion, sex, sexual orientation, gender identity, national origin, disability status, age, veteran status, or any other legally protected characteristic.