Jacob Will Work For You

I grew as a generalist from a small office to a 10-figure acquisition. Hire me and we'll do it again.

Last fall, I quit my job after a decade at a very successful fintech company. I wanted to take a breather, launch Second Person, and spend time with my two young girls. Nine months later, I have a time-efficient writing habit¹, a daughter about to start preschool², and an itch to get back to business.

In the last decade, I have developed two distinct sets of employable skills that are visible to two distinct audiences. If you’re a former Nasdaq colleague, client, or skim my LinkedIn, you’d see industry expertise in banking and regulation, and experience building and selling enterprise software to banks. You’d imagine me a middle manager at Moody’s or Morgan Stanley. It’s a nice gig. I’ve worked with many nice people who have it. I don’t want it.

I have also spent the last decade writing online. I’ve made bets and predictions, stood for or apart from causes, and tried to make sense of the world. I have found readers and online friends who appreciate some talents that come through in my writing — insight, integrity, rational analysis, creativity, discipline — but who have little idea what I used to or want to do for a living.

This post is for the latter. I believe that the second set of talents is more valuable to the right employer than any specific industry or role experience. It’s also much harder for an employer to select for. If someone you know is looking to work with someone like me, consider this my “hire-me doc”. And for everyone else, this may still be an interesting read on how a particular career path felt like from the inside, not just as a list of bullet points.

Rogue Generalist

They say your natural talent is what everyone else seems surprisingly bad at. In my case, I’ve been surprised how naturally most people conform to the box of their defined role. They’re careful not to step on any toes and careful not to learn anything that might volunteer them for work outside their job description.

I’m the opposite of that.

I started my education in mathematics, then learned finance, then spent a decade moving to roles that required soft skills. I’ve vibe-coded collateral allocation algorithms and made financial models for paper mills. I’ve written software sales brochures, talked at conferences, and made award-winning slide decks on new financial regulations. I’ve encouraged despondent coworkers and placated angry clients. I ran classes on macroeconomics and how to crunch numbers in your head. I’ve made smart gambles at work, on sports, and on major global events. I made people laugh in the office a lot. Less than half of these were within my job description at any given time, and the other half created by far the more value.

I get burned out if my work is disconnected from any outcome anyone cares about. When that happens, I just go looking for something cared-about to do instead. I joined my last employer, Axiom SL, when we had 50 people with 100 hats to wear. Eleven years, one merger, and two acquisitions later, Axiom became Nasdaq — an excellent company with 9,000 excellent well-defined boxes for its employees to stay in. I quit to go somewhere small and do it all over again.

I’m a broad-scope generalist who loves rogue tasks and moving quickly. I’ve started practicing the use of AI to get even better at this, catching up on new subjects quickly and automating repetitive tasks.

If you’re running a team that has a lot of problems that need to be solved every day that don’t fit into any job description — problems you can’t write a job description for because there’s going to be a different set next week — you might want to hire me. At the very least, you should tell me what all these problems are because I like learning about all kinds of businesses and am definitely going to have some thoughts. Then you might want to hire me.

Factual Resume

Early Life

I grew up in Israel in a trilingual family of scientists. As a teenager, I skipped school a lot and placed in the top three in most national youth math Olympiads. In my mandatory IDF service, I did field research of advanced electro-optics systems. I completed a BSc in math and physics from the Hebrew University in Jerusalem in 2009.

After the military, I pivoted away from math and academia and took a hedge fund job day-trading interest-rate derivatives. Six months in, I read a copy of Fooled by Randomness that was on the office shelf and realized that none of us had any alpha or market edge. Excited by my encounter with finance but disillusioned with day-trading, I applied to business schools. I was a rather unusual MBA applicant. My GMAT score of 770 was in the top 0.5%, but my BSc grades were just average and my work experience, at age 23, was very limited. Kenan-Flagler Business School decided to take a chance on my potential, and I arrived at UNC Chapel Hill in 2011.

After mathematics, I found the MBA classes easy, TAed for two professors in my second year, and took extracurricular PhD courses in econometrics. What I struggled with was absorbing American corporate culture from scratch, from email etiquette to networking practice to what exactly counts as “business casual” in each industry. At the end of two years, I was just about acculturated enough to be employable.

I was interviewing in Atlanta for management consulting when my girlfriend at the time announced a surprise relocation to New York. I had a sole job offer in NYC, a modest fintech named Axiom Software Labs. The CFO was impressed by my military service. I was impressed by my future boss who explained how his team makes money without the obfuscating corporate-speak I’ve grown to expect in b-school. I took the offer.

Axiom SL → Adenza→ Nasdaq

Axiom SL is a provider of software that automates risk and regulatory operations for major financial institutions. In 2021, it was acquired by PE firm Thoma Bravo and merged with a capital markets fintech to form Adenza. In 2023, Nasdaq acquired Adenza for $10.5B to form the backbone of its internal financial technology division. I worked at Axiom from 2013 until 2024, with a short sabbatical in 2017 in which I got married, learned Spanish in Latin America, and did an internship at Jane Street.

Axiom was initially a provider of regulatory reporting, selling templates that would package client-prepared results in the format required by financial regulators. These reports required upstream processing of the raw information and derivations of various ratios and summary amounts. This was usually done by an array of consultants with spreadsheets. In 2013, Axiom was ready to expand into this lucrative niche by automating the data transformation and calculations within its own proprietary software platform.

Developing Clients

Axiom didn’t have a training or onboarding program. I learned the software by reading the manual, playing around, and asking the platform devs dumb questions. In my first year at Axiom, I was the main developer on two solutions: FFIEC 009, a computation of banks’ net foreign exposures, and a calculation engine of Basel III risk-weighted assets.

The solutions performed to spec but didn’t gain traction beyond a few clients. Banks had pre-existing workflows for both regulations, and even if these were expensive and unreliable we didn’t know how to sell them on the upgrade. I built both solutions for functionality at the cost of accessibility, which didn’t help close sales either.

From 2014-2017, I was sent to on-site implementations of Axiom’s products at Morgan Stanley, PNC, RBC, MUFG, and SVB (RIP). I learned three important things behind enemy lines.

First: clients want a lot more from a software vendor than a solution that performs ABC by XYZ date. They may want assurance that they’re in line with competitor best practices, “phone a friend” for emergencies, validation, an impressive story, or a scapegoat. It took a while for me to understand all of this and finally develop the “soft skills” business school was supposed to teach.

Second: clients aren’t paying for creativity or initiative.

Third: thank God I didn’t become a management consultant. Hotels and bar tabs get old fast.

Back at Axiom HQ, I also became involved in recruiting. I traveled to colleges, interviewed applicants, and developed the company’s first technical aptitude test for candidates. Talent evaluation is the most difficult thing I tried my hand at. Thankfully, one guy was hired against my recommendation and became one of my most competent collaborators and a good friend.

Product Management

After I rejoined the product team, our big break came with the publication of the Single-Counterparty Credit Limits (SCCL) rule in August 2018. The process for building a solution for this at large vendors would involve subject matter experts analyzing the rulebook, product managers writing specs, developers building and testing, and marketers creating brochures and decks. If every link in the chain is competent and it goes smoothly, this takes about 12 months.

I started building SCCL with one developer (the one I recommended against hiring) and one rules analyst. We worked in an agile way, turning rule diagrams to code modules and specs to marketing slides as we went. 10 weeks after the rule came out I showed a working demo of SCCL to our first client, complete with a brochure explaining the rules and a slide deck explaining the business case. Our solution was ultimately purchased by 14 out of the 25 US Banks that were subject to the rule, earning Axiom several million in ARR.

Eventually, Axiom also grew in complexity and team size. In 2021, I was managing a new product for the Brazilian market that involved a fragmented team across four different countries. My work involved connecting the silos, translating requirements to specs for developers in Ukraine and explaining our technical capabilities to client managers in LatAm.

I wonder how this project would have worked in 2025 with a good LLM. The tasks that kept everyone waiting, like translating rules from Portuguese or writing unit tests, can mostly be automated. The high value human tasks, like understanding the client’s true pain points and deciding on priorities and trade-offs, would be easier with a smaller, proactive team. Enterprise AI transformation still feels slept on, I’m excited to be in the generation that gets to figure this out.

After the merger and Nasdaq acquisition, product management moved mostly outside the New York office. Our team was re-christened as “pre sales”. I spent a lot of 2023-24 planning go-to-market strategies with Salesforce, putting together demonstrations and PowerPoints, and preparing talks for client roundtables and conferences. My remaining product responsibilities were becoming harder and harder to do, with every decision having to get approval from more stakeholders and executed through longer processes.

Though I still got the satisfaction of helping close multi-million deals, the day-to-day work lost a lot of its appeal. In June 2024, I told my boss that I wanted to leave. I spent two months tying up loose ends and transferring knowledge, then said goodbye to the team in August. I’m happy to provide references and recommendations from my time at Axiom/Nasdaq, it was time well spent.

Looking Forward

Things I’m looking for in my next job, in descending order of importance:

• A boss worth following into battle and a talented team that cares about their work. The main reason that writing/coaching isn’t my plan A is that it’s lonely work, I’m stronger in a squad.

• A winner: a company whose offering is best-in-class, or a startup that is sincerely trying to become one (as opposed to building hype and raising money, sorry “web 3”). From my experience, a lot of company culture is downstream from profit margins.

• A culture that values initiative and autonomy over protocol. I don’t need something crazy to be happening every day, but my chaos-thriving talents are wasted if there’s no chaos.

• A salary I can raise a family on, or an equity position with a time horizon in the 2020s. I have plenty of runway from saving my Axiom salary ($250k pre-tax TC in 2024), but I also need to feed the kids.

• I’m flexible geographically (within the US — I’m a permanent resident) with a preference to live near NYC or Berkeley. I actually enjoyed hybrid work for balancing maker and manager schedule, but I’ve also successfully worked remote from 2020-2024 and don’t mind being in the office full-time if the work requires it.

• I don’t care how trendy your industry is, how impressive my job title, how fun it is to talk about at parties. I keep the professional professional, and I find every business interesting in itself.

If you are:

• A team of engineers/researchers that needs a head of ops to keep things running and start developing a process.

• A startup that wants a fractional CFO to grow with as you approach Series A.

• A growing fintech looking for a product strategist to pivot or launch a new line.

• A lean private equity firm that’s going to make a killing with AI transformation.

• Someone who knows of an even better fit and can’t wait to tell me about it.

DM or email me at yashkaf@gmail.com, I look forward to working with you.

1. Over these months I’ve gotten much better at planning/structuring each essay in my head, which I mostly do on long walks. I spend the same amount of time *thinking* about each post, but the number of sat-at-my-desk hours each posts takes is now small enough now that Second Person wouldn’t be impacted by me going back to work full time.

2. That’s her in the cover photo, three and a half years ago.