podcast ·Jan 08, 2026

How to Win with Content, Consistency, and AI with Keith Kakadia

by Drewbie Wilson

In this episode of Call The Damn Leads, I sit down with Keith Kakadia, the founder and CEO of Socially In, one of the top social media agencies in the country. With more than 14 years in sales and digital marketing, Keith's built a powerhouse team that helps brands dominate online — all while staying true to the fundamentals of human connection.

We dig deep into what really works in modern sales and social media. From losing a $60,000 deal over one extra page in a proposal to mastering AI tools and automations that streamline client relationships, Keith shares the hard lessons and smart systems that every sales professional needs to know.

If you've been trying to do "all the things" online or wondering how to blend sales, marketing, and automation without losing the personal touch — this conversation is for you.

Episode Highlights

💥 A $60K Lesson in Attention to Detail: Keith shares the story of losing a massive deal over a one-page mistake — and how it reshaped his sales process forever.
💻 Social Media Strategy Simplified: Why you don't need to be everywhere — and how focusing on LinkedIn and X (Twitter) can 10x your B2B pipeline.
🧠 The Power of the ICP: How to define your Ideal Client Profile and create content that speaks directly to the decision makers you actually want to sell to.
🎥 Content that Converts in 2025: Educational + personal = unstoppable. Keith reveals why posting about your hobbies, travel, or even your wedding can be the secret to attracting business.
🤖 AI-Incorporated Sales: How Socially In uses custom GPTs, automation, and AI note-takers to boost efficiency — without losing the human touch.
🔄 Seamless Sales-to-Service Handoff: Why salespeople should stay involved in onboarding to improve retention, referrals, and long-term revenue.
📋 The Personal CRM Advantage: Build your own "Rolodex" outside of the company CRM to maintain your relationships for life.
⚙️ Automation Meets Authenticity: How AI tools can prep your calendar, research your prospects, and keep your schedule tight — so you can focus on real conversations.

Key Takeaways

Details Matter: The smallest mistake can cost the biggest deal. Slow down and double-check everything.
Less Is More in Marketing: Focus on one or two platforms, master them, and show up consistently.
Engagement > Posting: Don't just post — connect. Comment, DM, and engage to build real relationships.
Be Human: Mix personal stories with professional insight. People buy from people they relate to.
Play the Long Game: Social selling takes time. Consistency compounds results — stay patient.
AI Is a Tool, Not a Replacement: Use it to automate the boring stuff, not replace the conversations that close deals.
Sales Never Ends at the Close: Stay involved after the deal to build trust, drive referrals, and grow lifetime value.
Protect Your Network: Build a personal CRM and treat your connections like gold. Relationships are currency.

How to Connect with Keith Kakadia

📱 LinkedIn, Instagram, X, Facebook: @KeithKakadia
🌐 Website: www.sociallyin.com
💼 Company: Socially In – Full-service social media agency specializing in B2B marketing and content strategy. Keith's an open book and always happy to talk sales, marketing, or AI strategy — don't hesitate to reach out!

🎯 Call to Action

Call The Damn Leads

"By sales professionals, for sales professionals - Tales of your wildest sales stories and tactics to succeed in your sales career across various industries."

Join Drewbie Wilson, a sales veteran with over 20 years of experience, as he brings you insider stories, humor, and actionable strategies to excel in your sales journey.

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Wild Sales Stories: Engaging tales of real-life sales adventures.
Proven Tactics: Actionable strategies to boost your sales game.
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Don't miss out on the insights, humor, and strategies that can take your sales career to new heights! Sales professionals, entrepreneurs, and small business owners striving to enhance their sales, marketing, and personal growth to achieve financial success and time freedom.

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