Co-founder · Strategy + Execution Coach
Rob Simons
Rob is a strategic coach, facilitator, and co-founder of Coach.Win who helps founders and leadership teams turn quarterly chaos into clear strategy, sharper execution, and real results.
Stay in
the loop.
Stay current. Stay sharp.
Practical insights on AI and automation, strategy and execution, and leadership and team development — curated for leaders who are serious about winning and staying ahead.
01 The People Behind Coach.Win
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coaches.
Most of what we publish — the stuff that doesn't fit in a newsletter — goes up on LinkedIn. Follow Rob and John there for the in-between thinking.
Co-founder · B2B Sales + Leadership Coach
John Lund
John is a serial entrepreneur, B2B sales coach, and co-founder of Coach.Win with decades of experience helping leadership teams close the gap between big strategy and real results.
Coach.Win on LinkedIn
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Programs, news, and what we're publishing — all in one feed.
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02 The Monthly
One email.
Once a month.
Winning Ideas, Impact Plays, and News & Events — packed with what's working for real leadership teams right now. No filler. Just the stuff worth your time.
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What's inside
W
Winning Ideas
What the best teams are doing right now to lead better and execute faster.
I
Impact Plays
One move your team can make this month that actually shifts performance.
N
News & Events
What's happening at Coach.Win and what's coming up for you.
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The Meeting Excellence Guide
A 28-page framework for running every recommended company meeting that actually moves the needle — delivered to your inbox the moment you subscribe.
03 Twice-Weekly Video Series
Take 10. Take 20.
Take 30.
Curated videos in your inbox twice a week. Pick the levels you want. Subscribe to one, two, or all three.
Tue & Thu
10
Take 10 to Win
One curated YouTube video every Tuesday and Thursday. Practical skills you can apply the same day.
Leadership Execution Coaching
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Free · 2× a weekTue · Thu
Tue & Thu
20
Take 20 to Win
Two videos per email focused on Microsoft 365, Copilot, and AI. Built for users who want to stay ahead.
Microsoft 365 Copilot AI for work
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Free · 2× a weekTue · Thu
Mon & Wed
30
Take 30 to Win
One Claude and Cowork video every Monday and Wednesday. Real AI workflows you can put to work immediately.
Claude Cowork AI workflows
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Free · 2× a weekMon · Wed
04 The Coach.Win Podcast + YouTube
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The Coach.Win Podcast
Plays the latest episode first.
Where to listen + subscribe
YouTube
Watch the podcast · @coachdotwin
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Spotify
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New episodes auto-update everywhere you subscribe.
05 Take the next step
Ready to execute?
Content is a start. A conversation with Coach.Win gets you moving. Tell us where you're stuck and we'll tell you whether we can help.
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