I’m Jake an NYC based early-stage startup operator

Employee #3 at Cassidy$14M fundingCo-founder of Interviews by AI$100k+ revenueSharing my learnings on TikTok50k+ followers

Jake Rosenthal with a microphone
@jakerosenthal_

Work

Cassidy

Cassidy is an AI Agent platform that lets business teams automate work around how their organization actually operates – connecting to the tools, documents, and knowledge already in place, with the governance, permissions, and reliability IT needs to scale agents safely across the company.

I joined as employee #3 five of us in a WeWork in New York City. Over the last 2.5 years I’ve been a generalist product person, marketer, first sales engineer, and early customer success lead as we pivoted from a PLG motion to enterprise sales-led. As each team took shape, I trained its founding members on the playbooks I’d built. Today, the team is 30+ people. Revenue has grown 35x+. To date, I’ve helped close our largest customers, like OneDigital, which has onboarded 6,000 employees to Cassidy.

How one role became the next

  1. Product

    First I helped scope many of the core features – speccing, designing, and shipping whatever the product needed next.

  2. Marketing

    Then I stood up our social channels and started bringing prospects in.

  3. Sales engineer

    Those people we attracted needed demos, so I built the demo environment and became our first SE.

  4. Customer success

    Once we closed those deals, we needed them to succeed – so I built our first CSM trackers and onboarding playbooks.

  5. GTM

    Led our rebrand and identity. Today I own inbound and the landing page.

An Interviews by AI practice question with voice recording
UI of a user answering a generated question

Interviews by AI

A nights-and-weekends AI tool my friend and I built for interview prep. We started with a simple AI interviewer and kept shipping – better prompts, more roles, tighter feedback loops – until it became a real product people paid for. Past $100k in revenue, 80k+ users, and still growing without a full-time team behind it.

Revenue
$100k+
Users
80k+
Jake's TikTok profile with 52.5K followers and popular AI videos
Feed of some of my most popular videos

TikTok

I share what I’m learning about AI, startups, and building in public – the same lessons I’m picking up at Cassidy and on side projects. Teaching forces the clarity. The audience has grown past 50k followers, with sponsorships and partnerships along the way from teams like Zapier and Replit.

Followers
50k+
Past partners
Zapier, Replit

How I work

Early-stage operator

My formal background is in product management, but the work that fits me best is building from zero – standing up the motion, writing the first playbook, and growing into whatever the company needs next.

  • Product sense

    Spotting gaps, shaping the problem, and shipping the first version.

  • UI / UX design

    I get ideas on paper quickly so teams can react to something real, not a slide deck.

  • Storytelling

    Making the value clear enough that people move – in marketing-led and sales-led motions alike.

  • AI systems

    I build complex AI workflows end to end, for clients and in-house alike – the kind teams actually run on.

Personal

I moved from Montreal to New York City to pursue early-stage AI startups — mission: learn by doing and teach by doing with AI. Outside of that, here’s what fills the rest of my time.

  • Jake at the World Cup final in an Argentina jersey
    World Cup final
    Soccer

    I play and watch as much as I can. Favorites: Barça and Chelsea.

  • Jake's R&B vinyl collection on wall shelves
    Favorite vinyls
    Music

    I love R&B, collect vinyl, and sometimes write songs for fun.

  • A clover club cocktail next to a bottle of Beefeater gin
    Clover club
    Cocktails

    I make cocktails for friends and family whenever we get together.

About

So, to recap
here’s my story so far.

I grew up in Montreal and went to McGill University. After school I moved to Toronto for consulting at Publicis Sapient – big finance and government clients, real product work – but it didn’t take long to realize startups were more my thing.

On the side I co-launched interviewsby.ai with a friend. It grew past $100k in revenue and 80k+ users, and I started sharing what I was learning about AI and building on TikTok, which grew to 50k+ followers (including partnerships with Zapier and Replit).

Through that work I met Justin Feinberg, co-founder of Cassidy. I joined as employee #3 in New York – five of us in a WeWork – and have worn nearly every hat as we grew into an enterprise sales-led company: product, marketing, sales engineering, customer success, and now GTM.