If making a career switch feels scary right now, you're not alone
Re tech uncertainties, first in-person event (!!) and weekly jobs
You’ll always find reasons to not make a big career move.
However, the job market now feels more uncertain than ever. Layoffs and recession headlines dominate the news. If you’re thinking about switching into tech, or growing your career here like I am, the headwinds can feel even stronger. Layoffs and fears of AI reshaping entire industries make it feel like now might be the worst possible time.
I get it. When I switched industries in 2020, the job market felt equally bleak. The pandemic had hit, companies were freezing hires, and no one knew what the next few months would bring…let alone the next few years.
But here’s what I’ve learned: there’s never a perfect time to pivot. There’s always going to be noise. And under that noise, the fundamentals haven’t changed: tech is still one of the best places for generalists to accelerate their careers, learn quickly, and build skills that compound over time.
Here’s why I still think now is a good time, but also a few things to watch out for:
✅ Exposure to emerging technologies. Tech is at the center of AI and automation trends. Being in the room where these tools are being built, or quickly adopted, keeps you relevant and learning skills that will matter in every industry. It forces you to keep up.
✅ Faster career growth. Startups and smaller tech companies often give you more responsibility earlier than more traditional companies. You can wear multiple hats, build cross-functional skills, and grow your scope faster.
✅ Tech is broad. Healthcare, education, consumer products…tech touches every sector. You don’t have to work at an AI startup to build a future-proof career.
✅ Long-term skill compounding. Even in a tough market, you’ll develop skills, like product thinking, data literacy, and AI fluency, that pay dividends no matter where you go next.
But…
❌ Don’t do it just for a quick win or the brand name. The big comp packages and IPO hype aren’t as common now. Big Tech isn’t the comfortable place it once was, and layoffs and restructuring are still happening. Startups can be messy, and equity might be worth less than you think. Focus on roles where you’ll actually build skills and make an impact.
❌ Understand it’s not always easy. The bar is higher now. Companies are more selective. It takes strategy, networking, and patience to make the pivot successfully.
Even in a tougher market, the best companies are still hiring, just more selectively. The messy times are when new ideas and business models are born. And if you’re thinking about where you want to be in 2, 5, or 10 years, now is the time to invest in yourself, skills that make you adaptable, strategic, and indispensable.
If you’re waiting for certainty, you’ll be waiting forever.
If you’re considering a move, I’m cheering you on. And if you want to talk through your next steps, I’d love to help.
Breaking into Startups: Join me in NYC (June 17)
I’m co-hosting my first in-person event in NYC (with Draper Startup House)!!!!
This is for aspiring and current operators on what it really takes to work at a startup. You’ll get to meet each other and hear from a panel with a founder, investor, and operators (I’m still putting finishing touches on the panel!)
Spots are limited, and I’ll be personally reviewing every registration to make sure we have a thoughtful group.
Tech Jobs I'd Apply to This Week
Curated US roles (mostly) for generalists and career changers with ~2+ years of experience.
Typically includes: Strategy & Ops / BizOps / GM, Chief of Staff, GTM, Program/Project Manager, Product & Product Marketing, etc.
Deployment Strategist – Kaizen Labs (Civic Tech, Seed, NYC)
Operations Manager, Central operations – Commure + Athelas (Healthcare, Series E, Mountain View)
Growth Lead – Conversion (Fintech, Series B, SF)
Strategy & Operations – Tandem (Health Tech, Seed, NYC)
Partnerships Manager – Carry (Fintech, Series A, Brooklyn, NY)
Product Partnerships Senior Manager – CVS Health (Healthcare, Public, Woonsocket, RI and NYC)
Business Operations Lead – Outsmart (EdTech, Seed, Los Angeles, CA)
Director of GTM Operations (Chief of Staff Track) – Shelf (AI, Series B, NYC)
Manager of Business Strategy – Sensor Tower (Analytics, Series B, NYC)
Product Operations Manager – Uber (Transportation, Public, NYC)
Manager, Strategic Initiatives – OpenTable (Hospitality, Public, NYC)
Associate, Strategy and Business Operations – Cohere (AI, Series D, NYC/London)
Project Manager – Etsy (E-commerce, Public, Brooklyn, NY)
Strategy Manager – Hearst (Media, Private, NYC and Chicago, IL)
Senior Operations Manager, Commercial Strategy – Squarespace (Website Builder, Public, NYC)
GTM Operations – AirOps (Ecommerce, Series A, NYC/SF/Remote)
Commercial Strategy Manager – Thumbtack (Marketplace, Series D, Remote)
Manager, Product Launch Sales Strategy – Comcast (Telecommunications, Public, Philadelphia/NYC)
Senior GTM Financial Analyst – Intercom (Customer service, Series D+, SF)
Partner Operations Manager – YouTube (Tech, Public, NYC)
Chief of Staff - Floodbase (Climate Tech, NYC), shared by Martina
Program Manager - Schoolhouse.world (Edtech, Remote)
This is NOT meant to be "every tech generalist job under the sun", just roles on my radar that I want to share with you!
What I’m reading this week
Ways to stand out when you apply for a startup
The job isn’t just the job - what kind of work will win even with AI
In case you missed it…
📖 Free Guide (18 pages): Breaking into Tech
My path from Finance to Tech
The 3 best jobs for generalists in tech?
Should you pick the right company, or the right job?
Why I pivoted to tech (even in a bad job market)
If you find this newsletter helpful, share it with a fellow nonlinear techie!
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