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The Sales Playbook: Hard-Won Lessons From Over Two Decades In Sales

By Jason Flagg, Vice President of Sales at Irish Titan

As someone who's spent a good chunk of my career navigating the highs and lows of sales, I've picked up a few lessons along the way—some learned through the grind, and others gifted by mentors and peers. Today, I'm pulling back the curtain to share a playbook of insights that I wish I had when I was just starting out or a few years into the game. Whether you're a rookie or a seasoned vet, these nuggets of wisdom are designed to elevate your sales game and inspire your strategies. __1. Ride with the Winners __The company you keep can lift you up or weigh you down. Surround yourself with top sellers and watch your own success skyrocket.

2. Build Your Army Networking isn’t just about collecting business cards; it’s about building an army of people rooting for your success. The more, the merrier.

3. Patience Pays Off Good news: Consistency compounds. Bad news: It’s a marathon, not a sprint. Brace yourself for the long haul.

4. Family First Work won't remember your overtime like your family wil remember your absence. Prioritize accordingly.

5. Embrace the Opportunity Every challenge is an opportunity. Swap out "have to" for "get to" and watch your attitude—and your altitude—change.

6. Teamwork Triumphs Solo wins might fill your wallet, but shared victories build your career. And remember, losing alone just stings without the team.

7. Lessons in Loss The deals that slip through your fingers often teach you more than the ones you seal. Don’t fear failure; learn from it.

8. Play the Long Game Success in sales isn’t about hitting this quarter's target—it’s about the ongoing quest to be better.

9. Sweat the Stress Away Daily exercise isn’t just good for the body; it keeps your stress levels in check and your mind sharp.

10. Stack Your Skills The more skills you stack, the higher your stack of wins. Broaden your abilities to broaden your opportunities.

11. Run Your Own Race Focus on your path, not your peers’. Your journey is about your growth and your goals.

12. One More Call You’ll never regret making one more call or prepping a little more for that meeting. The extra mile is less crowded.

13. Preparation Creates Separation The gap between good and great? It’s all in the preparation. Be thorough, be ready.

14. Integrity Over Everything Choose commissions that don’t compromise your character. Integrity lasts longer than instant gains.

15. Time Blocking Guard your time like it’s treasure. Focus on what’s important, not just what’s urgent.

16. Trust Your Gut Make decisions confidently and seek buy-in where needed. Trust leads to trustworthiness.

17. Appreciate Your Solution Engineer Thank them daily. No one wins alone, especially in sales.

18. Be Fully There Whether you’re at home, with friends, or at work—be present. Your full attention is the best gift you can give.

19. Thrive on Competition Find a rival, a teammate, anyone who pushes you to up your game. Healthy competition keeps you sharp and speeds up your growth.

20. Self-Reflection is Key Always evaluate your own performance before looking outward. Make sure you’re set up for success in every deal.

21. Value Experience The deep insights come after the honeymoon phase. Stick around, dig deeper.

22. Never Stop Learning Continuously refine your methods and mindset. Growth is a lifelong project.

23. Be proactive in your check-ins Come prepared, stay organized, and you’ll stand out for all the right reasons.

There you have it—sales lessons served straight, no chaser. I hope these lessons not only resonate with you but also encourage you to push boundaries and redefine your own strategies. Remember, the path to sales mastery is continual—there’s always room to tweak, refine, and reinvent your approach. Stay curious, stay driven, and most importantly, stay true to what fires you up in this game. Let’s make these insights our stepping stones to greater successes together. Now, get out there and sell like a Titan!

By Jason Flagg, Vice President of Sales at Irish Tita

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