Winning Strategy

Something shifted in how we lead products and projects.

If you're like me, you stepped into leadership wanting to build amazing things and guide teams to success. But somewhere along the way, the landscape changed dramatically.

Today, leadership has become a never-ending firefight. Metrics and deadlines often overshadow people and purpose. And let’s be honest—navigating the politics, uncertainty, and constant change can leave even the best leaders questioning — “what are we doing here?”

I've been there.

It doesn’t have to be this way.

Over the last 18 years, I have advanced from being a Software Developer in 2005 to the role of CIO in 2022, gaining hands-on experience at Twitter, Amazon, and several of North America’s largest corporate banks. I’ve led teams through chaos, learned hard lessons, and found ways to not just survive—but thrive—in dynamic, high-pressure environments.

I've learned that surviving - and thriving - requires more than just technical skills or management theories.

It requires real, battle-tested experience. The kind that only comes from:

1. Navigating through impossible deadlines

2. Building high-performing teams in uncertain environments

3. Making tough decisions when there's no clear playbook

My mission? To help you do the same.

This newsletter is for leaders like you who want to stand out in their professional journey. It’s packed with practical guides, real stories, and case studies from the frontlines.

But more than that, it’s about:

1. Building Products with Agility

2. Building resilient and high-performing teams, and

3. Building a career that can sustain tough times

If this resonates with you, you’re in the right place. Let’s face the chaos together and come out stronger on the other side.

Join the community and start your journey here:

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Free subscribers get:

• One issue every month.

Paid subscribers also get full access to:

• Two issues every week on Thursdays and Sundays.

• 180+ guides including 14 different Agile frameworks, How to Calculate Team Capacity for the Upcoming Sprint + Capacity Template, 1 Year Training Plan for Scrum and Agile Teams + Template

• In-depth, training-ready decks

• Handy templates to make things easier

• Access to future video and written offerings

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Here’s what people are saying about Winning Strategy

They inspire me to keep moving.

Check out some of my best posts

Here are some of my most viewed posts:

1. What To Do When - Your Team Ignores Your Suggestions?

2. Observation As a Skill.

3. How Great Scrum Masters Handle Process Resistance

4. Leadership Glitch

5. How to facilitate impediment resolution?

If you’ve made it this far, subscribe below and connect with me on LinkedIn.

See you soon,

Vibhor