Tim Cheadle

timcheadle.comPlan for learning, not certaintyWe spend time planning to avoid time adjusting. But great products emerge from trying things, not gathering requirements.

30 Oct 2025

Starting without a plan feels risky, so we gather requirements. We aim for certainty when we understand the least. Great products are an art of discovery, not perfect planning. What matters most is building and learning quickly. www.timcheadle.com/plan-for-lea...

phaidra.comPhaidra | Your Virtual Plant OperatorPhaidra is an artificial intelligence (AI) virtual plant operator to assist mission critical operations teams. AI controls deployed for the industrial sector help operators reduce risk, improve energy...

This week was wild, but I do have some good news: I'm not gonna go broke! In an act of absolute stars-aligning kismet, I have a new job as ✨VP of Agentic AI✨ at Phaidra.com I'm leading product and engineering, creating autonomous agents to help AI factories run efficiently. I'm so excited.

timcheadle.comLearning to live slowlyLetting go of needing to be productive gave me the space to rediscover myself.

Last year, I stepped away from work for a career break. I thought I needed to fill it with travel, new skills, and big plans. I did almost none of that. And it was exactly what I needed. I wrote about what I learned from slowing down: www.timcheadle.com/learning-to-...

For months, I asked myself if I was wasting this time. Was I failing at my break? It finally hit me that time off isn’t about success or failure or productivity. Letting go of that pressure gave me the space to rediscover myself and to rethink how I want work to fit into my life moving forward.

If you enjoy lessons like this, you might like my newsletter: www.timcheadle.com#/portal/signup

1 Sept 2025

30+ years into programming and I still just wasted an hour using a different library version than the documentation I was reading. Writing code is really just practicing profanity.

31 July 2025

LinkedIn, why does it say Remote Job when there is no Remote Job? I swear to god, one of these days I kick this piece of shit out the window

29 July 2025

Why does your team only seem to hit their stride when everything's on fire? The rush of crisis mode feels like peak performance. Decisions get made quickly. Priorities become crystal clear. People step up. But that clarity is artificial. 🧵

I write about engineering, product, and how to lead with skill and build with soul. No fluff, no hype, just hard-earned lessons, shared every week or two.

timcheadle.comDon't let crisis become a compassCrunch time feels productive. It also reveals problems hiding in plain sight.

29 July 2025

Here's a working link! Hilariously I wrote this thread too fast 🤦‍♂️ www.timcheadle.com/dont-let-cri...

What you're actually seeing is a stress response that temporarily overwhelms the dysfunction that's always been there. Crisis doesn't create great teamwork, it reveals what's been preventing it all along. If urgency is how you get focus, it's time to set a better course.

timcheadle.comtimcheadle.com

29 July 2025

I dove deep into why we get addicted to urgency and how to build sustainable productivity in my new newsletter "Built to Last." Read the full piece and subscribe if you dig it. timcheadle.com/dont…

22 May 2025

At the Anthropic keynote, @mikekrieger.bsky.social made a great point about AI making inefficiencies more obvious. Hours of cross-functional alignment and planning meetings become bottlenecks when building no longer takes weeks.

22 May 2025

In my experience, deep focus is already hard in offices. As companies push RTO while AI makes interruptions more expensive, it'll be interesting to see if office culture adjusts. I doubt it, as a return to office is really more about a sense of control.

5 Apr 2025

Made it to the final round of interviews. Never prepped harder for one. Didn’t get the job I really hoped. It stings and that’s ok to feel. But ya know what? Time to dust off, get up, continue to trust and bet on myself. No reason to start doubting myself now.

simple.orgSimple.orgFast, free software for clinicians to manage patients with hypertension & diabetes.

5 Apr 2025

Also, I wound up prepping a 20 minute talk about the story of building Simple.org It was a lovely walk down memory lane. We solved so many weird and interesting problems, work I’m quite proud of. If you’d like to hear this story, let me know.

19 Feb 2025

Not sure who needs this, but I’m a grown man and I cry all the time. Tears of celebration, love, fear. It’s freeing, leaning into life’s fullness. I once heard that crying is your soul taking a breath. That feels right. ❤️

10 Feb 2025

What I loved most about Kendrick's show is that it wasn't about Drake. It was a Black celebration, a testament to liberation and culture and resistance in spite of America.

10 Feb 2025

The larger story matters. It was for and by Black folks, a reminder of experience and community and power. It told white supremacy: you can lock us up but you can't trap our minds. He also reminds Drake he's a leach, forever an outsider to all of this.

10 Feb 2025

Black excellence is the American dream. Happy Black History Month ✊

In case you’re wondering what it’s like to text your 8 year old daughter 🫠

(No, my 8 year old doesn't have a phone. She uses her iPad)

Alright, here are my Severance theories. - There is no Dieter. In the woods, Kier discarded the gentle part of himself he hated. This lead to the idea of severance - What is Lumon doing? Severance is the product. A cure for mankind, "Remedium hominibus" 1/2

- Mark *is* Cold Harbor. He's the experiment. (Maybe the test is severing deep emotional bonds, e.g. his wife) - The other MDR folks are variables in the experiment. The work is a red herring - They're raising goats for animal testing 2/2

30 Jan 2025

Worst smells in the kitchen when you have kids: - Ketchup on the plate they left out - The lunchbox from last week - Old yogurt - The dishwasher you forgot to run last night - Half eaten bowl of cereal

Last summer I took a career break. Focusing on myself and loved ones restored my sense of optimism and serenity. Now I'm ready to get back to work. I'm looking to join a company making things that matter for people who value them. Learn more about me and how I might help: 🧵

I’m passionate about music and food. I play piano, drums, and I’ve been a DJ since I was in high school. I love traveling the world and meeting its people and cuisine. I love to exercise and read. I will happily geek out about basketball, sneakers, or hip hop.

timcheadle.comHow to work with meAs a part of onboarding at Binti, new hires are expected to work on a "user guide", a short document that offers guidance on how each person likes to work. It includes things like communication styles...

Thanks for reading! I appreciate anyone who shares this for reach. I really look forward to finding ways to work together. Shout out to @fayecheadle.com, @kvlly.com, @engineeringbae.bsky.social, @fabrary.net, @rosew.bsky.social, and everyone else I lean on to be a better person every day. ❤️

I'm an extrovert who values cultivating relationships, building what's important, and changing as we learn. I'm looking to join a company with a positive outlook, solid foundations, and appreciation for its workers. Learn more about working with me: www.timcheadle.com/how-to-work-...

I have two amazing kids and every day I learn about the huge overlap between parenting and management. There's something to be said for letting your kids (and team) make mistakes and being there to lift them back up.

We're a good fit if you're looking for someone who can make decisions quickly, get in the details when needed, and trust to hit the milestones that matter for your customers. You're not afraid to iterate quickly, and you're open to new ideas.

timcheadle.comWhat I value in a jobEvery time I've looked for a job or helped others do so, one question always rises to the top. What am I looking for?

You're trustworthy and build trust in others. You'll advocate for my team, give us focus, show appreciation for good work and guidance when we fall short. You're a partner who will help me grow and challenge me with support. Read more about what I value: www.timcheadle.com/what-i-value...

So what am I looking for? I’m looking for outcomes. I want to help teams with strategy, planning, and technical expertise. I want to help engineers become their best selves and learn from them as well. I want to ship code that’s simple, flexible, and delivers timely value.

simple.orgSimple.orgFast, free software for clinicians to manage patients with hypertension & diabetes.

At some companies, that role may be VP or Director. At others, those outcomes may require a Principal or Senior Staff engineer. I'm also open to product management roles, or as an advisor to VC portfolio companies. I want to find a place where I can make an impact.

In 2018, I joined @dburka.bsky.social to co-found Simple.org, an open source app to prevent heart disease. Our app is used by thousands of nurses every day, supporting over 5 million patients in India, Bangladesh, Ethiopia, and Sri Lanka. It’s the work I’m most proud of.

Most recently I served as VP of Eng at Binti.com, a startup improving child welfare, and led the Shipping team at Shopify. As a senior lead and exec, I helped our teams understand each other's needs, learn from customers, and make pragmatic decisions that met business goals.

For my first decade, I worked in network ops and streaming at AOL and as an early SRE at @Google. Supporting the world's busiest websites honed my tech chops and ability to build at scale. It was super exciting, but I found myself wanting an impact closer to customers.

I left Google and started an agency, helping companies focus on growth instead of tech. I guided product strategy, built Rails apps, and learned sales and marketing. I loved the mix of tech, design, and business, learning what matters most: adding value to people’s lives.

Over 25 years I’ve done everything from CSS to DNS. I've been a founder, an exec, led teams at Google and Shopify, and grown startups. I’ve been fortunate to build products that touched millions of lives. See linkedin.com/in/timcheadle to read more about what I’ve accomplished.

Happy lunar new year! 🧧

27 Jan 2025

If you see this, post a fictional artist/band you would love to see live.

Shana V. White (she/her)@shanavwhite.blacksky.app

If you see this, post a fictional artist/band you would love to see live.

26 Jan 2025

Best game of the season from my Hornets 💪 #NBASky

25 Jan 2025

Woozy after today’s workout, I called the mountain climber movement “meat grinders”. Accurate. That’s what they’re called now.

24 Jan 2025

Honestly all I want to do is eat chocolate hazelnut uncrustables and binge watch Rescue 911

21 Jan 2025

Of all the bullshit on LinkedIn, showing me videos of that asshole and not providing any means of moderating it is the worst. What’s the opposite of engagement hacking?

20 Jan 2025

Today I’m choosing to ignore the conflagration and celebrate resistance, giving thanks to the heroes of liberation. #MLKDay

20 Jan 2025

Maggie Walker: Disabled rights activist, first Black woman to charter a bank Harriet Tubman: Spy, Suffragist, Liberator, Demon Slayer Bayard Rustin: Civil and gay rights activist, organized the March on Washington Hiram Revels: First Black senator Mary Jackson: NASA’s first Black woman engineer

19 Jan 2025

I’m having sleepovers with my kids, playing video games, and eating uncrustables. Find your joy.