Carson V. Heady

Carson V. Heady is Managing Director for Microsoft Elevate, a bestselling author, top sales influencer, and podcast host who has built a career helping people and organizations win through technology, authenticity, and servant leadership.

With over 25 years in sales and leadership roles across Microsoft, AT&T, Verizon, and T-Mobile, Carson has mastered the art of selling in complex environments. At Microsoft, he leads the Americas Nonprofit team supporting over 400 named nonprofit organizations, delivering transformative outcomes by aligning customer missions with Microsoft’s cloud, AI, and security solutions. He has also created a replicable demand generation social selling model that has generated $1 billion+ in revenue that he has trained in 11 countries and presented to Microsoft CEO Satya Nadella and his leadership team. Carson's success is driven by a philosophy that fuses heart, hustle, and human connection.

Carson is the author of 6 books, including the "Birth of a Salesman" series and his latest releases "The Show Must Go On" and "UNBEATABLE" — modern sales playbooks for navigating reinvention, resilience, and growth in an evolving landscape. His books blend storytelling with strategic insights and are used by sales professionals, leaders, and organizations as practical guides to career advancement.

He is also the host of two successful podcasts: *Mastering Modern Selling* and *Connected Teamwork*, where he interviews top industry voices and explores topics like AI in sales, personal branding, emotional intelligence, and nonprofit digital transformation. His guests have included CEOs, bestselling authors, comedians, Microsoft executives, and healthcare experts.

Carson is an 8-time CEO/President’s Club winner, a frequent keynote speaker, and a recognized LinkedIn Top Voice in sales and leadership. He’s known for his high-energy delivery, candid storytelling, and tactical advice that inspires sellers to take bold action while staying grounded in purpose.

Rooted in Cape Girardeau, Missouri, and now based in St. Louis, Carson is a proud husband and father of three daughters. He believes success isn’t just about quota — it’s about showing up, staying true, and making a difference.

Co-host of The Crocodile School Podcast

We are capable of so much more than our small but powerful reptilian brain want us to believe. How do we access our true potential and transform the parts of us that keep us small? Join leadership coach & award-winning author Hylke Faber and best-selling author & Microsoft #1 Social Seller Carson V. Heady for this monthly podcast in which they explore how we can use every challenge as an opportunity to get to know more of our best self and share that with others. Carson will bring live case examples and leadership lessons and Hylke will bring coaching insights leveraging his Taming Your Crocodiles approach and the truth that is available in this moment.

I’m going to say something most people in sales won’t admit publicly:  AI has made my prospecting—and getting executive meetings— almost too easy.


I've been doing this for 24 years, and yet I'm operating at the top of my game because of AI in real-world practice.

I use Copilot to research an entire organization in seconds—website, annual report, press releases, and leadership priorities.

Copilot analyzes tone, writing style, and leadership preferences straight from executives’ LinkedIn activity.

It surfaces their challenges, opportunities, data trends, and the language they use to talk about them.

Then with the right prompts, I generate a 2-sentence hook so compelling it practically forces an open.

Followed by a brief but surgical email—written in their style, tied to their mission, rooted in their work.

And I maximize my well of potential executives to engage with Sales Navigator to reach the right people based on title, keywords and any other relevant variable.

My probability of landing an executive meeting in any organization is virtually 100%.

Not because I’m special.

Because AI lets me add value in seconds that used to take considerably longer to compile and construct.

AI didn’t replace the work.

It amplified the craft.

It made me sharper.

It made me faster.

If you’re in sales and you’re not using AI like this yet…  you’re leaving opportunity on the table every single day.

Here are the prompts that power 80% of my day:

 “Analyze this executive’s website, mission, annual report, AND LinkedIn tone. Draft a 2-sentence hook and a value-focused outreach message written in their style.”

This one prompt gets me meetings I used to think were impossible.

"Write a 2 paragraph e-mail to this executive that will maximize my probability they will take a meeting with me using themes from their company mission and LinkedIn page, with a subject line that maximizes open rate."


What’s one real-world AI workflow you’ve used that genuinely changed how you operate?


LinkedIn for Sales Humantic AI Mastering Modern Selling Salesman on Fire LLC Salesman on Fire

Best-Selling Author | Managing Director, Americas @ Microsoft Elevate Nonprofit | Sales Hall of Fame | Podcast Host | Award-Winning Sales Leader

This week marks 500 days without alcohol—a personal milestone in a journey that has transformed my mindset, energy, and focus.


With 25 years in sales, I often believed that a drink could help take the edge off, unwind, or fit into the social fabric of the job. 

Reflecting on this, I see now that it was largely a habit that wasn't serving me.

The past few years have been incredibly challenging, and I won’t sugarcoat that. 

However, through this process, I’ve discovered clarity and discipline, realizing that I am better off without alcohol.

Now, instead of reaching for a drink, I choose a book or music. 

Instead of numbing my feelings, I engage in breathwork and practice being present. 

Instead of masking stress, I confront it with a clear mind and full awareness.

Each day brings its own challenges and opportunities, but the significant change is that I face them feeling my best.

For anyone on a similar journey or re-evaluating habits, remember that you are not alone. 

The greatest investment we can make is in ourselves.

I would love to hear from others—what habit have you replaced that has made a significant difference?

Laid off. 1,628 job applications. One life-changing lesson. If you think a great resume is all it takes, this story might change everything you believe about standing out and getting hired.

I thought my resume would open every door. I was wrong.

I've had my job eliminated three times in my career—completely out of the blue.

I had second-level director experience and a "sparkling" resume. I truly believed I’d walk into another job quickly.

Instead, I spent over a year unemployed.

- I applied to over 1,000 jobs.
- I only got a handful of interviews and was told I was overqualified, or they offered 1/3 of what I made the prior year.
- I finally landed a role making half of what I earned before.

What got me noticed and led to an interview from the 300+ applicants?

I wrote a book.

During my time out of work, I channeled my energy into something no one could take from me: my voice.

That painful chapter taught me a truth I now share with everyone:

- Be the overwhelming choice for what you want next.
- Lead with your superpowers—your unique skills, stories, and perspective.
- Relationships will open more doors than résumés ever will.

Even if you are the perfect fit, you still might not get the job. Sometimes it goes to a friend of the hiring manager. Sometimes you're overqualified or just not what they're looking for.

But you have something they don’t: resilience.

So write the book. Do the thing that makes your unique superpowers stand out from the crowd when the odds are against you. 

- Tell your story.
- Build relationships. You have to de-risk your next hiring manager's decision to hire you.
- Stay in the game and bet on yourself.

Because what differentiates you—not just what’s on paper—is what changes everything.

Are you relying on your resume… or are you building a reputation no layoff can take away?

Today’s professionals face volatile job security, generational shifts in values, low engagement, and technological disruption like never before.


Roles are being automated. Departments are being merged. Entire business models are evaporating under the pressure of AI, cloud economics, and shareholder impatience. 

Careers are no longer ladders — they’re obstacle courses.

If your sense of worth, identity, or security is tied to a title, a company logo, or a job description, you’re standing on quicksand.

Your only real job security now is relevance.

People aren’t disengaged because they don’t care.

They’re disengaged because they cared too much for too long and watched the rules change anyway.

They optimized for loyalty and were replaced by algorithms.

They hit numbers and still got restructured.

They delivered miracles and were told to “do more with less.”

If you are still protecting your comfort zone, still clinging to the way things used to be done, still telling yourself you’re “not technical,” you are training your own replacement.

Here’s what I’ve learned the hard way — bleeding behind the scenes while everyone expected me to perform.

1. Control the controllables.
You cannot control restructures, markets, or AI roadmaps.
You can control your preparation, your discipline, and your relationships.

2. Become a student again.
Every reinvention I’ve survived began with humility. Learn. Ask. Adapt.

3. Build a personal brand, not a résumé.
Your résumé tells people where you’ve been.
Your brand tells them why they should follow you anywhere.

4. Create your own serendipity.
Opportunity doesn’t knock anymore. You have to go hunt it.

5. Leave a legacy, not just a footprint.
Your kids, your colleagues, your customers — they’re watching how you respond to pressure.

You still matter. Because someone is watching you right now trying to figure out if they can survive this too.

Because someone needs your courage more than your credentials.

Because the world doesn’t need another polished professional — it needs someone willing to bleed quietly and still stand back up.

Today’s professionals face volatile job security, generational shifts in values, low engagement, and technological disruption like never before. The M

Open article: The Professional Survival Guide for 2026: The Show Must Go On in the Age of AI, Anxiety, and Reinvention by Carson V. Heady • 3 min read

The Professional Survival Guide for 2026: The Show Must Go On in the Age of AI, Anxiety, and Reinvention

My 7th book drops this week.



This one is about stacking the odds in your favor.

📘 *Moneyball Sales* is built on 24 years in the arena and over **$1B in revenue**—using LinkedIn, AI, discipline, and relationships the right way.

It’s for sellers who are:
• Working hard but seeing stalled pipelines
• Tired of guessing instead of knowing
• Ready to replace hope with probability

This book shows how to:
• Earn executive access (without pitching)
• Use AI to amplify judgment—not replace it
• Build momentum that compounds over time

No gimmicks.
No shortcuts.
Just a repeatable system that actually works.

It's disheartening to hear sellers say, "I'm doing just as well as everybody else; nobody's hitting goal, so it's not that big of a deal." This mindset is misguided. 

To truly excel, one must compete against themselves and their own potential. 

I could never accept a number next to my name that doesn't reflect my absolute best. 

I am committed to leaving no stone unturned in my pursuit of excellence, and I will go down swinging every time.

Focusing on relationships and resources ensures that results will follow. 

I've missed my goal once in my life, and while I could point to two uncontrollable factors, that’s irrelevant. I took the time to analyze what worked and what didn’t, returning stronger and more prepared.

Your aim shouldn't be to blend in with the crowd; it's about becoming the best version of yourself. 

Use your unique skills, passions, and superpowers to uplift those around you and deliver wins to every customer you engage with.

If your goal is simply a paycheck and benefits, that's understandable. 

However, remember that there are countless individuals eager to take your place. 

To be the best, you need that special drive, a commitment to continuous learning, and a relentless pursuit of your own potential. 

Are you truly leaving it all on the field?

Hope is the most dangerous drug in sales.
It makes you feel busy while your pipeline quietly dies.


“I hope they reply.”

“I hope this closes.”

“I hope next quarter is better.”

Hope delays hard conversations.

Hope avoids real prospecting.

Hope keeps bad deals alive and good habits dormant.

Top performers don’t hope.

They act.

✔️ They follow up when it’s uncomfortable
✔️ They ask the tough questions
✔️ They disqualify fast
✔️ They create new pipeline instead of babysitting old dreams

Hope is passive.

Process is power.

Where are you hoping… instead of doing?

What if the key to your greatest success in 2026 isn’t about working harder—but mastering your unique strengths, building unshakable trust, and turning challenges into opportunities? 


Here are my 10 Tips for Success in 2026:


- Embrace Your Superpowers: Lean into what makes you unique. Focus on your strengths—they are your greatest assets in delivering value to your team and customers.

- Never Settle for Average: Good is not enough. Dare to push beyond what others think is possible, and you'll discover extraordinary opportunities.

- Be Data-Driven: Numbers tell a story—listen to them. Consistent execution, paired with data insights, is your ticket to sustained success. Use data to perfect your process.

- Master Your Schedule: Discipline your time. Start your day with purpose and protect the moments that fuel your energy and creativity.

- Leverage Social Selling: Relationships matter. Platforms like LinkedIn aren’t just for networking—they’re game-changers for building trust and landing deals.

- Understand Customer Risk: Decisions are driven by the fear of failure, not just FOMO. Help your customers feel secure, and you’ll win their trust.

- Build a Personal Brand: Your reputation is your currency. Cultivate it by showing up authentically and sharing your value with the world.

- Communicate Transparently: Clarity builds confidence. Keep your customers informed and aligned to foster stronger partnerships.

- Lead with Value, Not Products: It’s not about selling—it’s about solving. Focus on how you can empower your customers to achieve their mission.

- Turn Challenges into Opportunities: Every obstacle hides an opportunity. Find it, and you’ll create lasting impact for your team and customers.

What's your superpower, and how will you use it to best serve others in 2026?

I’m inspired by how technology is transforming live basketball! 🏀 Check out how we’re using data and innovation to elevate the game. https://msft.it/6041Qy7kx


Microsoft
National Basketball Association (NBA)

I just discovered a powerful LinkedIn feature that helps recruiters find you faster—if you’re open to work, don’t miss this tip! https://msft.it/6042QEbBw 

It’s a simple switch that could change your career path.

Open article: If You Aren’t Using This LinkedIn Job Search Feature, You Should Be by msft.it

If You Aren’t Using This LinkedIn Job Search Feature, You Should Be

Most people say they want feedback. Very few actually want the kind that changes them.


I didn’t grow the most during the highlight reels of my career.

I grew during the moments I was sure everything was falling apart.

The layoff I didn’t see coming.

The only performance plan of my life.

The seasons where confidence was low and uncertainty was loud.

In those moments, I had two choices:

Protect my ego… or rebuild my future.

So I sought out intentional mentors and told them:
👉 “Be straight with me.”
👉 “Tell me what I don’t see.”
👉 “Tell me where I’m the problem.”

And they did.

Sometimes it stung.

Sometimes I disagreed at first.

Sometimes I had to sit with it for days before I could admit they were right.

But every time I leaned into that discomfort instead of defending myself, I improved faster than I ever had when things were going well.

🔹 Growth rarely comes from praise
🔹 Blind spots don’t disappear on their own
🔹 Your next level is usually hiding behind a hard truth
🔹 The mentors who challenge you are the ones who change you

The people who helped me most weren’t the ones who told me I was doing great.

They were the ones who cared enough to risk the awkward conversation.

The ones who told me where I was playing small.

The ones who pointed out habits, patterns, and mindset gaps I couldn’t see from the inside.

I would not be where I am today without those voices.

Not because they made me feel good.

But because they made me better.

If you’re serious about leveling up your career, your leadership, or your life, here’s a question worth asking someone you trust:

“What’s one thing I’m doing that’s holding me back — that I might not see?”

Then don’t argue.

Don’t explain.

Don’t defend.

Just listen. Reflect. Adjust.

That’s where real growth begins.

Who’s someone in your life that tells you the truth, even when it’s uncomfortable?

New AI features from LinkedIn will soon help jobseekers find positions that best suit them without the need for exact keyword matches or specific job titles.

#msftadvocate #microsoft #technology #artificialintelligence #innovation #humanresources #careers

Open article: LinkedIn's new AI tools help job seekers find smarter career fits by msft.it

LinkedIn's new AI tools help job seekers find smarter career fits

Exciting news! LinkedIn is using AI to make finding the right people easier than ever. This update helps professionals connect faster and smarter.  https://lnkd.in/gqWy5FZd

Kathleen Hogan, our chief strategy and transformation officer here at Microsoft, shares how we’re embracing AI to transform how we work and lead. Companies of any size can follow our lead.

Open article: Microsoft Is Transforming Itself Into an AI Company and You Can Too by msft.it

Microsoft Is Transforming Itself Into an AI Company and You Can Too

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