Before you quit to start a company: what to test while employed

Five members of the Product Careers work group, four of whom have founded companies, on what to test before you resign.

Updated October 13, 2026

Use the months before you resign to gather evidence: a customer problem heard firsthand, someone paying for the smallest useful offer, a runway date and a cofounder relationship that has survived a missed deadline.

Listen before you pitch. Sachin Rekhi asks prospects to name their five biggest work problems before he mentions his idea, then to rank his alongside them. For Notejoy, he and his cofounder interviewed in waves of five until the conversations stopped turning up new problems.
Charge for the trial. Ravi Mehta corrected his own example: free mentoring at Scale Higher showed the team could deliver value, not that people would pay. He would run a paid version of the smallest offer and record what each customer paid, whether they finished and what they wanted next.
Set a runway date that ignores unsigned money. Ben Erez ran out of money about a year after leaving a job that paid over $100K. He suggests working out monthly spending, picking the date the cash runs out and leaving fundraising out of it until a term sheet is signed.
Test the cofounder and your own momentum. Hadar Dor suggests a small project with real deadlines before you choose a cofounder. Nikhyl Singhal would look for a time you moved a problem forward without an employer's distribution, engineers and customers.

Group chat with Nikhyl, Sachin, Ravi, Ben, Hadar — the Product Careers work group

Question:

How do you prepare to leave an operating job and start a company?

Sachin RekhiFounder and CEO of Notejoy. Former Head of Product for Sales Solutions at LinkedIn

I left LinkedIn while Sales Navigator was growing and I had a clear path to more senior roles. The decision started with the work itself: I wanted to talk to customers and build product again, while my job had become mostly managing people and reviewing their work. Ada and I chose to start Notejoy together and keep the team to the two of us. We also talked through the downside. I felt I could return to an operating role if the company failed.

Apple Podcasts

For the idea, write down your assumptions before you write code: the specific customer, their problem, and the value you expect to deliver. With Notejoy, we spoke to both likely users and senior leaders who might sponsor the tool. We did interviews in waves of five, revised our mockups or product, and repeated until the conversations stopped revealing new problems. That gives you a practical preparation task while you're still employed: find people outside your own team who have the problem and listen for evidence that your first assumptions need to change.

sachinrekhi

Hadar DorFounding Product Lead for AI Shopping at Instagram. Former founding Product Lead for Ads at Shopify

I’d use the months before leaving to test what kind of work you want to do when no one has assigned you a roadmap. Set aside regular time to speak with potential customers, write down the problem they face, and try to solve one small part of it. Check your employment agreement and keep company data and resources out of that work.

When I left Lyft, I set specific goals for a career hiatus and spent part of it advising founders at five startups. I also coached 40 aspiring or junior PMs. That time taught me about the work and habits I wanted to carry into my next role, even though I ultimately joined Facebook rather than founding a company.

Substack I’d make the decision to resign after you’ve heard a recurring customer problem firsthand and know what you want to test full time.

Ravi MehtaProduct advisor. Former Chief Product Officer at Tinder and VP Consumer Product at TripAdvisor

Before leaving, test whether you can deliver the outcome by hand. When we started Scale Higher with Victoria Young, we offered 1:1 mentoring to students trying to break into tech, with sessions for the first 40 applicants. That gave us a specific group of people and a real service to learn from.

I would use that kind of small test to decide what to build and whether to leave: recruit people with the problem, deliver the service, and ask what they would use again or pay for. We later described Outpace as 1:1 guided sprints combining learning, practice, and feedback in a four-week plan. The practical prep is to define a narrow customer and run a repeatable trial with them before committing to a full company.

Ben ErezCo-founder of Insider Loops. Former PM at Facebook and Lead PM at Attentive

I quit a job paying over $100K to start my first company. I thought I had enough savings, then ran out of money around the one-year mark and had to ask for help. So I’d calculate personal monthly spending, pick a date when the cash runs out, and make sure the plan still works if revenue or funding takes longer than expected.

Medium

Sachin’s interview loop is a good start. I’d add one harder test before resigning: ask prospects to change a real workflow. With my first startup, stores said they would pay us, but the meaningful signal was whether they would integrate their mobile presence, inventory, and customer processes into our software. If you’re a nontechnical founder building software, get specific about who will build it with you. I never found a true technical cofounder, and I consider that my biggest mistake.

Medium+1

Sachin RekhiFounder and CEO of Notejoy. Former Head of Product for Sales Solutions at LinkedIn

One way to make those pre-resignation customer interviews useful: ask each person to name their five biggest work problems before you mention your idea. Then add your proposed problem to the list and ask them to rank all six. If yours consistently lands near the bottom, you have a weak reason to ask someone to switch tools, even if they politely say they would use yours. I use that sequence to reduce the confirmation bias that comes with pitching an idea first.

Apple Podcasts

Hadar DorFounding Product Lead for AI Shopping at Instagram. Former founding Product Lead for Ads at Shopify

Before choosing a cofounder, work together on a small project with real deadlines. Pay attention to how you make a hard decision, give each other feedback, and handle a week when the plan stops working. I’ve found that working closely with someone I trust, who trusts me back, has a huge effect on my career choices. Working with Archie Abrams again was a major reason I joined Shopify.

Substack I’d want that working relationship tested before tying a new company to it.

Nikhyl SinghalFounder of Skip. Former VP of Product at Meta and Chief Product Officer at Credit Karma

The readiness test I would add is whether you can create momentum without your employer's distribution, engineers, and existing customers. In my conversation with Shreyas Doshi, I pointed out that starting a new product inside a large company can feel like founding while drawing on a great deal of support. Look back for a time when you identified a problem, chose a direction, and got people moving before anyone gave you a plan. If you cannot find one, create that experience on a small scale before you resign.

YouTube

I would ask why I want to do this now, and whether I want to spend years working on the problem. Shreyas urged founders in that same conversation to plan psychologically for a ten-year journey. That changes the discussion with family and prospective cofounders: everyone should understand the time commitment alongside the cash risk Ben described.

YouTube

Ben ErezCo-founder of Insider Loops. Former PM at Facebook and Lead PM at Attentive

I’d keep fundraising conversations out of the runway calculation until there’s a signed term sheet. With my first startup, we raised an initial friends-and-family round quickly and assumed a second $250K round would follow once we had a prototype. We overestimated how easy that would be. Investor dinners felt promising too, but I learned that serious interest takes a concrete commitment. Put a separate date on your calendar for when you will cut spending, seek income, or stop if that second check never arrives.

Medium

Ravi MehtaProduct advisor. Former Chief Product Officer at Tinder and VP Consumer Product at TripAdvisor

One correction to my earlier example: free mentoring can test whether you can deliver value, but it cannot tell you whether people will pay. At Scale Higher, we learned that willingness to pay depends on how people experience the offer, so you have to charge to get a clear signal for a paid product. We also tried to shorten the time between each hypothesis and what we learned from customers.

Before resigning, I would run a paid version of the smallest useful offer and record three things for each customer: what they paid, whether they completed it, and what they sought next. Those observations give you a stronger decision than a list of people who say they like the idea.

Ben ErezCo-founder of Insider Loops. Former PM at Facebook and Lead PM at Attentive

Hadar’s small project test would have saved me some pain. I started my first company with friends, then found that slow progress made hard personnel decisions emotionally difficult. Later I moved to Gainesville to recruit developers while my cofounders stayed in South Florida; the distance made it harder for them to stay involved in daily product decisions, and the team shrank.

Medium

I’d use that trial project to agree on who makes product and hiring calls, how often you work together, and what happens if one person needs to step away. Then see how those agreements hold up during a missed deadline.

Sachin RekhiFounder and CEO of Notejoy. Former Head of Product for Sales Solutions at LinkedIn

Ben's point about who builds the product is worth making explicit before you resign. I kept my development skills current with a small side project even while working in product and, later, a GM-like role at LinkedIn. When we started Notejoy, I spent time getting back into the technology stack and built the web, desktop, and iOS apps myself. If your plan assumes a tiny team, list the actual work needed for the first product and identify who can do each part before you commit to that plan.

sachinrekhi

Hadar DorFounding Product Lead for AI Shopping at Instagram. Former founding Product Lead for Ads at Shopify

I’d do some market homework alongside the customer interviews. Make a list of the companies already serving the same customer, ask how customers solve the problem today, and write down why your approach might earn a place in their workflow. When I began angel investing, researching companies and their markets and speaking with founders taught me a lot about the kinds of businesses people were actually building.

Substack That exercise is useful before quitting too, because a promising customer conversation still leaves open how you’ll reach enough similar customers.

Nikhyl SinghalFounder of Skip. Former VP of Product at Meta and Chief Product Officer at Credit Karma

Sachin's ranking exercise and Ravi's small trial should lead to one more question: do the same customers want the same product? At Cast Iron, we had paying customers and thought we had found product-market fit. By the tenth customer, the engineers were handling different feature requests because the first customer's problem differed from the second's. I would track the request and the work needed to serve each prospect, then look for a repeatable sale before hiring around the early wins.

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Ben ErezCo-founder of Insider Loops. Former PM at Facebook and Lead PM at Attentive

If the first product needs an engineer you have yet to recruit, make the work concrete before you ask someone to join. I taught myself to create clickable mockups for my first startup, and within weeks two developers were working with me on a prototype. I also took a basic iOS class so I could discuss specs with them more clearly. That preparation gave prospective collaborators an actual product flow to react to, even though I could not build the software myself.

Medium

Question:

Ravi, Nikhyl asks whether a founder can create momentum without an employer’s customers or engineers. For your first 40 mentoring applicants, what would you have checked before resigning to know the service could keep attracting customers on its own? Please cite your public account.

Ravi MehtaProduct advisor. Former Chief Product Officer at Tinder and VP Consumer Product at TripAdvisor

For those first 40 mentoring applicants, I would have recorded where each person heard about us and whether they applied because of a channel we could use again. Then I would have offered the smallest paid version and tracked how many applicants paid and completed it. We offered those first sessions free, so applications alone could not answer the willingness-to-pay question.

I learned at Scale Higher that you have to charge for a paid product to get a useful signal, and shorten the time from a hypothesis to what customers actually do. Before resigning, I would have repeated the recruitment and paid offer with a second group through the same channel. That would tell me more about independent customer acquisition than a single burst of interest.

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Frequently Asked Questions

How do you decide what role to take next?
Name what the role has to give you, then check the offer against evidence: the actual weekly work, whether the company is growing and whether there is a real opening at the next level.
Is a bigger title at a smaller company worth it?
When it comes with real decisions, a growing business and someone to learn from. Otherwise a smaller role at a stronger company, with harder work and better coaching, can lead to more scope.
When should you switch career tracks?
When a bounded trial shows the new work suits you better and a real role exists for it. If the ceiling is your company rather than the work, look for better scope and sponsorship and stay in your craft.
How do you know when to leave a job?
Make one specific request first, with a date to revisit it. Leave if the company cannot create the work you want, or its paths keep pulling you away from it.
How do PM, designer and engineer roles differ now?
One split is by decision: the PM decides what ships, the designer how people use it and the engineer how it works. Before product-market fit the founder may make the PM's call.
How do you move into product management?
Most reliably from an adjacent role at your own company. Otherwise lean on your domain or a side project with real users, and show product judgment in the interview.
Which tech jobs will hold up as AI spreads?
Members would bet on roles that own the economics, rules or evaluation of AI products, leaders who can choose among competing prototypes, and skills like customer intuition.
How do you build product analytics skills?
Write precise metric definitions, read your own product's dashboards every day, log predictions before launches and learn to read the SQL that AI tools write for you.
How should you prepare for a performance review?
Start months ahead: ask for specific feedback, keep a log of your work, find likely objections before calibration and keep the self-review to two pages.
How do you get promoted to the next level?
Show next-level work over time, built on decisions you drove, and check that the team needs someone at that level. If it has no room, a growing team may offer a clearer case.
What should you do in your first 90 days in a new role?
Agree on why you were hired, study customers and product data, hold off on people and strategy decisions, and share a written plan by day 90.
What should early employees know about startup equity?
Your ownership percentage, how investors get paid before employees in a sale, the cash it takes to exercise, and whether the salary works if the equity pays nothing.

All career growth questions →

Frequently Asked Questions

Before you quit to start a company: what to test while employed

Product Careers

Frequently Asked Questions

How do you decide what role to take next?

Is a bigger title at a smaller company worth it?

When should you switch career tracks?

How do you know when to leave a job?

How do PM, designer and engineer roles differ now?

How do you move into product management?

Which tech jobs will hold up as AI spreads?

How do you build product analytics skills?

How should you prepare for a performance review?

How do you get promoted to the next level?

What should you do in your first 90 days in a new role?

What should early employees know about startup equity?

Your ideas, super powered.

Before you quit to start a company: what to test while employed

Product Careers

Frequently Asked Questions

How do you decide what role to take next?

Is a bigger title at a smaller company worth it?

When should you switch career tracks?

How do you know when to leave a job?

How do PM, designer and engineer roles differ now?

How do you move into product management?

Which tech jobs will hold up as AI spreads?

How do you build product analytics skills?

How should you prepare for a performance review?

How do you get promoted to the next level?

What should you do in your first 90 days in a new role?

What should early employees know about startup equity?

Your ideas, super powered.