28 Oct DEEPAK GUPTA GRACKERAI | EXECUTIVE SPOTLIGHT
EXECUTIVE IMPACT: DEEPAK GUPTA SPOTLIGHT
BUILDING THE WORLD’S FIRST AI GTM ENGINE FOR CYBERSECURITY COMPANIES
At Liftoff Enterprises, we highlight visionaries who merge technical mastery with market innovation — leaders building tools that don’t just automate work, but amplify human intelligence. This Executive Impact Spotlight features Deepak Gupta, Founder and CEO of GrackerAI, a company redefining how cybersecurity firms bring their products to market.
GRACKERAI: WHERE AI MEETS GO-TO-MARKET STRATEGY
GrackerAI is building the world’s first AI-powered Go-to-Market (GTM) Engineer, purpose-built for B2B cybersecurity SaaS companies.
Cybersecurity products are inherently complex — zero-trust architectures, identity management platforms, threat intelligence systems — and translating that depth into clear, compelling marketing is one of the industry’s biggest challenges.
“What makes us truly different,” Deepak explains, “is our specialization. We’re not a generic marketing tool trying to fit every industry. We’ve built an AI agent that understands cybersecurity context, compliance frameworks, and technical architectures — and knows how to translate complex features into business value that resonates with CISOs, IT directors, and security engineers.”
In short, GrackerAI gives cybersecurity companies their own AI-powered GTM expert — one that works 24/7, speaks the language of security, and turns deep technical knowledge into market clarity.
THE INSPIRATION: LESSONS FROM LOGINRADIUS
The idea for GrackerAI was born from experience.
Deepak spent years leading LoginRadius, a cybersecurity SaaS company he scaled organically to $8M ARR.
“We had world-class technology — patents, enterprise-grade infrastructure, and top-tier security,” he recalls. “But we spent countless hours trying to explain our value proposition in ways different audiences could understand.”
That communication gap — between what engineers build and what buyers value — inspired Deepak to create GrackerAI.
“When AI reached the point where it could understand both technical detail and marketing strategy, I realized we could solve this problem at scale,” he says. “We’re not just automating SEM or content generation — we’re building an AI GTM Engineer that augments strategic thinking.”
WHO GRACKERAI SERVES
GrackerAI targets B2B cybersecurity SaaS companies with less than $20M in ARR — teams that excel in engineering but struggle with go-to-market clarity.
“These companies have incredible technology,” Deepak explains, “but their messaging often doesn’t connect. Their products are too complex to explain quickly, their audience is highly technical, and they don’t have the budget for a full-scale marketing team.”
GrackerAI bridges that gap — giving smaller cybersecurity firms the ability to compete with industry giants by leveraging AI to craft precise, credible, and conversion-driven GTM strategies.
INNOVATION THROUGH CONTEXTUAL INTELLIGENCE
One of GrackerAI’s biggest breakthroughs lies in contextual understanding.
“We trained our AI to analyze technical documentation, security whitepapers, and competitive landscapes — then automatically generate positioning frameworks that resonate with actual security professionals,” Deepak shares.
Unlike generic marketing AI tools, GrackerAI “gets it.” It speaks the language of security engineers while presenting information in a way that business leaders can act on.
“Cybersecurity marketing isn’t about being flashy,” he says. “It’s about being precise, credible, and accessible.”
AI THAT THINKS LIKE A MARKETER — AND AN ENGINEER
GrackerAI uses AI across three interconnected dimensions:
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Market Intelligence: Continuously analyzing search trends, competitive positioning, and cybersecurity industry signals to uncover opportunities.
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Language Understanding: Using advanced NLP to interpret how security professionals search, like engineers, not consumers.
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Technical Translation: Transforming features such as “SAML 2.0 SSO with adaptive MFA” into tailored messaging for every audience — from a CISO focused on risk reduction to a security engineer focused on implementation.
“This level of contextual adaptation at scale is what drives results — higher-quality leads, shorter sales cycles, and stronger conversion rates,” Deepak explains.
BUILDING WITH VALIDATION, NOT ASSUMPTION
Deepak’s leadership philosophy was forged through what he calls his “successful failures.”
“I built technically impressive products that solved problems too few people had,” he says. “Now I’m obsessed with validation before building. Every feature in GrackerAI exists because cybersecurity companies told us it solved a real pain point.”
That mindset shapes the company’s product culture — iterative, customer-led, and relentlessly focused on solving meaningful problems.
TRUST AS THE FOUNDATION
In cybersecurity and AI, trust isn’t optional — it’s essential.
“Cybersecurity companies are literally in the business of trust,” Deepak notes. “We ask them to let our AI represent their brand in marketing. That’s a huge responsibility.”
GrackerAI’s AI agent works alongside teams — not instead of them. It generates recommendations and insights, while humans maintain full control and approval.
“We’re transparent about everything — from why our AI recommends certain strategies to how it sources competitive intelligence,” he says.
Internally, the same culture of transparency applies.
“We share our roadmap openly, celebrate wins and failures equally, and encourage everyone to challenge assumptions. That’s how we earn trust — inside and out.”
A THIRD PATH FOR CYBERSECURITY MARKETERS
Deepak wants cybersecurity founders to know they have more options than ever before.
“Founders think they must choose between doing marketing poorly themselves or hiring expensive agencies that don’t understand security,” he says. “Now there’s a third path: an AI GTM Engineer that brings specialized cybersecurity expertise at a fraction of the cost.”
With tools like GrackerAI, even seed-stage startups can compete with enterprise marketing teams — using AI to scale credibility, speed, and precision.
THE FUTURE: AI AS THE GREAT TRANSLATOR
“We’re at an inflection point,” Deepak reflects. “For too long, the best cybersecurity products haven’t won because they were the best — they’ve won because they were the easiest to understand and buy.”
GrackerAI is changing that.
“With AI-powered GTM tools, technical excellence and market success don’t have to be at odds. The companies that embrace this shift — that use AI to amplify their go-to-market strategy while staying true to product excellence — will define the next decade of security innovation. That’s the future we’re building.”
Permission granted by Deepak Gupta to feature all quotes, company references, and brand information across Liftoff Enterprises platforms.