Customer success first, then product work with a PM partner transition · Internal transfer
Enter ed-tech through customer success, then earn a PM seat by bringing classroom-informed research.
Why they left
Left classroom teaching; the essay is written for educators trying to leave for ed-tech during COVID.
Why they moved
She had not heard of product management.
How they moved
Took a customer-success / account-management role in ed-tech, still on a teacher salary.
Orenstein left the classroom for an ed-tech customer-success seat at teacher pay. She had not heard of product management. A PM who took her feedback let her join research, then handed her the work of turning research into shipped product. She later led product management for a digital portfolio used by millions of students, writing the account for other teachers asking how to make the same move.
Outcome
Led product management for a digital product portfolio reaching millions of students.
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Work life
Describes late nights and weekends stretching as a learner after leaving the classroom.
Transferable skill
Educator empathy plus on-the-job research with an internal PM mentor.
~3 months to find an internal seat after the consulting unit dissolved transition · Internal transfer
When a consulting team is winding down, treat an internal PM opening as the transfer, and line up managers who will bet on you.
Why they left
Consulting unit was being dissolved; she had three months to find another internal seat or leave.
Why they moved
When her consulting unit dissolved she had three months to land another internal job.
How they moved
Interviewed for a mobile product-manager role in the company’s B2B space while the consulting group closed.
Choi spent her early career in consulting (organization design, HR strategy, e-book supply chain) with no product-building experience. When her consulting unit dissolved she had three months to land another internal job. A mobile product-manager opening in the same company’s B2B group froze for budget, then came through one week before she would have had to leave. She later accepted an API product-manager role at a growth-equity company in New York.
Outcome
Moved into product internally, then accepted an API Product Manager role at a New York growth-equity company.
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Transferable skill
Getting work done, plus former managers willing to stake their reputation on the hire.
Customer Support Executive, Ansarada→Product Manager
Support → junior PM → senior PM at the same company transition · Internal transfer
Tell the support manager you want product, then volunteer as the release contact so you already sit with the PM team.
Why they moved
Saw the product team’s work from support tickets and wanted that job.
How they moved
Told her manager; he set aside skill-building time and asked the head of product to involve her.
Wayt joined Ansarada in customer support without knowing what a product manager did. After she told her manager she wanted the move, he blocked time for PM skills and worked with the head of product to get her into the product team. She filled support–product gaps, owned a painful release as the support contact, wrote release notes, and sat in product meetings, then became a junior PM and later a senior product manager.
Outcome
Promoted from junior product manager to senior product manager at Ansarada.
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Transferable skill
Customer issues from the support queue, plus owning a broken release end to end.
5 years in data roles before a PM title · ~5 years (2019–2024) transition · Internal transfer
Do PM work under a data-scientist title, then ask for a time-boxed trial when the team cannot fill a PM seat.
Why they left
Day-to-day data science (hours of coding) was not the work she wanted every day.
Why they moved
Stover heard of product management in 2019 as a data analyst at nonprofit MDRC, then did user interviews as a data scientist on Stand Together Foundation’s Customer First team.
How they moved
Told her manager in a 360 that the job had become customer listening and prioritization, then later volunteered to cover PM work for two to three months.
Stover heard of product management in 2019 as a data analyst at nonprofit MDRC, then did user interviews as a data scientist on Stand Together Foundation’s Customer First team. After a 360 review she told her manager the work was already customer listening and prioritization. There was no open PM seat, so she almost took a Yale MBA; after a maternity deferral she asked to cover an unfilled PM need for two to three months, kept the job, declined Yale, and later built data products as a PM at Gallup.
Outcome
Kept the internal PM role, turned down Yale, and later worked as a PM building data products at Gallup.
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Transferable skill
User interviews, shipping LLM-backed features on existing dashboards, and a PM mentor on the team.
Use sales customer access for research, ship product-shaped work in the sales job, and treat each “no” as a resume iteration.
Why they moved
Wanted a product role; sales already showed user pain but the title was not PM.
How they moved
Built two bilingual markets on B2B platforms while still in sales, and learned SQL, Python, and JavaScript.
Pouliot treated a long PM application pipeline like product iteration: every rejection rewrote the resume. While still in SaaS sales he learned SQL, Python, and JavaScript, ran user interviews, and took on product work at the sales job by launching two bilingual B2B markets. In October 2023 he wrote that he had accepted and started a product-manager role.
Outcome
Accepted and started a product-manager role the week of 3 October 2023.
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Transferable skill
Front-line user empathy from sales plus prototypes and user research.
1.3 years as an IBM IT consultant · IBM consulting then Microsoft PM II offer transition · Self taught
Consulting that implements other companies’ software is a path into building the software, not a dead end.
Why they left
Consultants learned a client’s pain and implemented a vendor product, then left without owning what got built.
Why they moved
She wanted to decide how the product itself was built.
How they moved
Left IBM IT consulting after 1.3 years and interviewed into Microsoft product/program management.
Nguyen spent 1.3 years as an IT consultant at IBM implementing enterprise products such as Salesforce, SAP, Workday, and SuccessFactors. Consultants diagnosed a client’s pain and rolled out someone else’s product, then left. She wanted to decide how the product itself was built. In January 2022 she wrote that she had landed Microsoft Program Manager II on Teams.
Outcome
Joined Microsoft as Program Manager II on Teams.
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Transferable skill
Reading a company’s strategy and pain, then mapping it onto a digital solution.
Software Engineer, Meta (Toronto)→3 years later→Returned to Meta as Senior Software Engineer
About 3 years around Meta, a startup, and Amazon · ~3 years after the layoff transition · Career break
A layoff need not close the door; he returned to write models, not just tune them.
Why they left
Meta laid him off after about four and a half months in Toronto.
Why they moved
He wanted to build foundational AI models himself, not only implement and fine-tune them at Amazon.
How they moved
Took a Meta recruiter’s rehire outreach three years later and compared it with other AI offers.
Sharma joined Meta in Toronto in 2022, was laid off after about 4.5 months, then worked at a startup and Amazon. A Meta recruiter brought him back as a senior AI engineer in Menlo Park; he chose Meta over other AI offers to write foundation models rather than only fine-tune them.
Outcome
Rejoined Meta in Menlo Park as a senior software engineer on AI models.
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Transferable skill
Report ties the change to themes like Meta, Amazon, AI.
Principal Engineer, Amazon→4 years later→Returned to Amazon as Senior Principal Engineer
11+ years at Amazon then 4 at Google · ~4 years at Google transition · Career break
Leave to learn what you actually miss; he came back for Amazon’s bar and intensity.
Why they left
He was restless by 2019 and wanted to break inertia by joining an entirely different culture.
Why they moved
He wanted Leadership Principles, a high writing bar, and Amazonian urgency back in his work.
How they moved
Rejoined Amazon in 2024 after four years as a senior staff engineer at Google.
Arguelles left Amazon in 2020 after 11-plus years, restless and wanting a different culture at Google. After four years he boomeranged back, saying he missed Leadership Principles, Amazon’s writing bar, and the intensity he had taken for granted.
Outcome
Returned as a senior principal engineer, knowing the messy parts and still choosing Amazon as home.
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Transferable skill
Report ties the change to themes like Amazon, Google, principal engineer.
Engineer, Replit→1.5 years later→Returned to Replit as software engineer (IC)
About 3 years including the first Replit stint · ~15 months away transition · Career break
If the leave thesis was wrong, going back as an IC can be the correction.
Why they left
He thought Replit would fail or take a ten-year slog, and the Remi manager seat did not fit.
Why they moved
He wanted to build large-scale systems again once Replit’s path looked like a real SaaS giant.
How they moved
Came back on October 29, 2025, almost four years after his first Replit start date.
Bergeson left Replit thinking the company might fail or take a decade to matter, then managed engineering at Remi. About 15 months later he returned as an IC on distributed systems, saying his reasons for leaving had been wrong.
Outcome
Returned to the team he left, happiest as an IC rather than an engineering manager.
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Transferable skill
Report ties the change to themes like Replit, IC, distributed systems.
Software Engineer, Microsoft Azure Firewall→2 years later→Returned to Microsoft as Software Engineer
3 years at Microsoft before the smaller-company stint · ~2 years at a smaller company transition · Career break
A smaller company can teach you that you missed the people and culture, not the logo.
Why they left
After three years she wanted to see what the tech world outside Microsoft looked like.
Why they moved
She missed managers who challenged her and Microsoft’s people and culture.
How they moved
Told former manager Murali Sangubhatla she was open to returning; he placed her on a sister team.
Leong left Microsoft after three years to see tech outside a big company. After two years elsewhere she missed managers who pushed her and Microsoft’s culture, and a former teammate brought her onto a sister Azure team.
Outcome
Rejoined Microsoft on an Azure sister team after about two years away.
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Transferable skill
Report ties the change to themes like Microsoft, Azure, culture.
Engineer, Microsoft (~13 years)→7 years later→Returned to Microsoft as Partner Director of Engineering
13 years at Microsoft before leaving in 2009 · ~7 years away transition · Career break
A culture change plus old colleagues can make a burned-out exit reversible.
Why they left
He was burned out by Microsoft’s culture and breakneck product-launch pace.
Why they moved
Former colleagues described a reinvigorated Microsoft under Satya Nadella.
How they moved
Took vetting conversations after late-2016 emails and joined as partner director of engineering in January 2017.
Lester left Microsoft at the end of 2009 burned out by the culture and launch pace, later standing up Qualcomm’s Redmond engineering center. Former colleagues pulled him back in 2017 to lead mixed-reality and HoloLens engineering under Nadella’s culture shift.
Outcome
Returned to lead mixed-reality and HoloLens engineering groups.
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Transferable skill
Report ties the change to themes like Microsoft, HoloLens, engineering director.
Development Lead, SQL Server, Microsoft→12 years later→Returned to Microsoft on 3D and AR engineering
Left 2005, returned March 2017 transition · Career break
Come back when the company’s product inflection matches the work you want to shape.
Why they left
By 2005 Microsoft felt like it was treading water and still had no foothold in mobile or social.
Why they moved
He wanted to help shape an early 3D and augmented-reality space after Surface, Azure, and HoloLens.
How they moved
Returned in March 2017 to work on 3D and AR technology.
Sundaresan left Microsoft’s SQL Server team in 2005, watching the company tread water while he worked at Amazon, Yahoo, and Roku. Surface, Azure, and HoloLens changed his view; he came back in 2017 to help shape 3D and augmented-reality work.
Outcome
Rejoined Microsoft after Amazon, Yahoo, and Roku to work on emerging 3D/AR products.
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Transferable skill
Report ties the change to themes like Microsoft, SQL Server, AR.