Carl Madi

The through-line

Carl Madi's fixed idea is that individual attention is not something a training company sheds as it grows. Stepful began with a cohort of 10 to 15 students whom he and his co-founder Tresia coached personally, and the claim he keeps returning to is that the same relationship survived the move to 20,000 monthly active students [1]. The doubt he quotes back at himself is the industry's: "Everyone told us this will not scale. You will not be able to get graduation rates of 75 to 80% when you have tens of thousands of students" [1]. His evidence that it did scale is not a metric but a repeated sentence in student reviews. Four years ago they read "Stepful was with me every step of the way," and, as he tells it, tens of thousands of students later they still do [1].

Running underneath that is a preoccupation with career mobility for working people, carried over from his time at Uber and Handy into building a healthcare training company aimed at the sector's skills gap [4][6].

On refusing to let scale dilute the service

The founding period was deliberately unautomated, and Madi treats that as formative rather than embarrassing. There was no product at first: they signed up the first fifteen students, split them between the two founders, and each founder coached their half "from the moment they started until they found the job" [1]. That meant manually creating Zoom links for every class and sending study material by hand [1]. It extended to the clinical training, where the founders were the students' first practice subjects for blood draws, an experience Madi describes in terms of the bruises it left [1]. Job placement was equally hands-on, done by calling hospitals directly and hustling to place people [1].

The point of retelling this is to set the standard the company is held to now. His formulation is unconditional: "We do whatever it takes for them to succeed and we will continue doing that no matter you know how many students we have thousands hundred thousand every student that goes through Stepful we're there for them at every step of the way" [1]. Reading student reviews is how he audits that promise, and he frames the exercise as a corrective for himself. A review from a divorced 43-year-old mother of five who had assumed she would spend her life "watching everyone else around" achieve things prompts him to say it "reminds me of why we do Stepful," and he reads it as proof that the company is "empowering people and it's there with them at every step of the way, which is incredibly important for us" [2].

On how the company got started

Madi began working on the idea in late 2020 and wanted to talk to an education expert, so he called Tresia, whom he had known from engineering school [1]. His test for the conversation was energy rather than logic: a call scheduled for thirty minutes ran for hours, and he uses the criterion that you finish "more energized than you are depleted" [1]. He then spent weeks unable to sleep on the strength of it, convinced that the idea would be big and would help large numbers of people upskill and find jobs [1].

The company was also shaped by an external ultimatum. Y Combinator's verdict on the founding pair was that they could not build the product themselves and needed someone on the team who could build the program, giving them three weeks to find a CTO [1]. Madi's search method was to work through who he knew who was "crazy enough to like join this business" [1]. What closed the hire was a photograph from the first cohort's graduation party, held in Central Park during the pandemic, with ten or twelve people holding the certificates that had got them into healthcare jobs [1]. Four years on, Madi's summary of the period is that they grew a great deal, launched many programs, hired well and went through a lot of ups and downs [1].

On career mobility and the healthcare skills gap

Madi traces his interest in creating career mobility for workers to his time at Uber and Handy, and describes carrying that motivation into Stepful's mission of closing the healthcare skills gap and delivering outcomes at scale [4][5][6].

Takeaways

• The core bet is that graduation rates of 75 to 80 percent can survive growth into the tens of thousands of students, against near-universal advice that they would not [1].
• Stepful launched with no product: the two founders each personally coached half of a 10 to 15 student cohort through training, clinicals and job placement [1].
• Madi treats consistency in student reviews across four years, specifically the phrase about being there "every step of the way," as the real measure of whether personalization survived scale [1].
• Reading customer reviews is a deliberate practice for reconnecting with the mission, and he singles out non-traditional students such as a 43-year-old mother of five returning to school [2].
• Y Combinator rejected the founding team as unable to build the product and set a three-week deadline to find a CTO; the hire was won by a photo of the first cohort's Central Park graduation [1].
• His passion for creating career mobility for workers originated at Uber and Handy and now drives Stepful's focus on the healthcare skills gap [4][6].