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About the Role

This role drives the transformation of how January plans, decides, and communicates as the company expands from a single product to several. The Chief of Staff will be the closest partner to the Founder and CEO, representing him and leading strategic initiatives.

Responsibilities

• Drive the six-week planning cycle, ensuring continuous reflection on key problems.
• Own operating reviews to identify and address off-track initiatives.
• Run triage between reviews to surface slippage early.
• Conduct diligence on potential bets, including unit economics and critical success factors.
• Build board decks, manage investor updates, and craft performance narratives.
• Make performance legible and communicate wins and misses consistently.
• Take ownership of critical, undefined problems.
• Identify and eliminate bottlenecks in the decision-making cycle.
• Shorten the gap between learning and action by pushing decisions to those with context.
• Partner with BizOps on orphaned problems, providing single-threaded ownership.
• Build and transfer ownership of initiatives.

Requirements

• Obsession with iteration speed, both personal and team-wide.
• Ability to make strong teams think clearer and move faster.
• Practice of diagnosis before prescription.
• Skill in asking critical diagnostic questions and acting on answers swiftly.
• Thinking in base rates and comfort with messy datasets.
• Belief in the power of subtraction and focusing on decisive points.
• Ruthless prioritization of decision-making factors and stakeholders.
• Ability to build a first version with minimal resources.
• Commitment to truth-seeking and truth-telling.
• Ability to hold and argue opinions effectively.
• Proficiency in writing for public argument.
• Experience pushing LLM tooling into work and a desire to innovate further.
• Experience in PE, VC, or fast-paced strategy/operations roles.
• 4+ years of experience, with a focus on intellectual firepower.

Skills

• Strategic planning
• Operating reviews
• Triage management
• Diligence and analysis
• Board deck creation
• Investor relations
• Performance reporting
• Problem-solving
• Decision-making
• Cross-functional collaboration
• Project management
• LLM tooling
• Communication
• Writing

Location

• New York

Work Type

• Onsite

Experience Level

• 4+ years

About the Company

• 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.
• Initiative beats permission.
• Speed beats perfection.
• Candor beats comfort.
• Writing beats the average meeting.
• 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.
• 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, four to five days a week in our office in Nolita. Jake is in every day. This job runs on the conversations you can't schedule.

Equal Opportunity

• 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.