Adit Jain & Leena AI: Building the AI-Powered Future of Work
Meet Adit Jain (IIT Delhi, Forbes 30U30), CEO & Co-founder of Leena AI. Explore his journey building a $40M+ funded enterprise AI powerhouse.
Navigating a large company can feel like wading through treacle. Finding the right policy, getting IT help, checking on a reimbursement – simple tasks often become frustrating scavenger hunts across multiple systems and departments. What if there was a single, intelligent assistant that just knew how to get things done? That's the challenge Adit Jain, Co-founder and CEO of Leena AI, decided to tackle head-on.
Adit's journey, from an IIT Delhi hostel room to leading a global Enterprise AI company backed by over $40 million in funding, is a masterclass in pivoting, focusing, and scaling. His story offers deep insights into building a successful B2B SaaS venture targeting the complexities of modern enterprises.
Check out the video of the conversation here or read on for insights.
Early Life & Entrepreneurial Roots 🌱
Born and raised in Delhi, Adit Jain grew up in a typical middle-class household, albeit one with an entrepreneurial influence. His father, an IIT graduate himself, ran his own BPO and IT services business. While Adit initially showed more interest in sports than academics, witnessing his father navigate the challenges of running a business – particularly the thin margins and difficulties with domestic clients – left an impression.
Despite not being academically oriented initially, Adit possessed a love for Math and Science. Encouraged by his parents and inspired by a BBC documentary about IIT, he underwent a transformation in 11th and 12th grade. Dedicating himself to intense study (often 14-16 hours a day), he successfully cracked the highly competitive IIT Joint Entrance Exam (JEE).
The IIT Delhi Experience & Choosing the Startup Path 🎓
Adit pursued Chemical Engineering with a minor in Business Administration and Management at the prestigious Indian Institute of Technology (IIT), Delhi from 2011 to 2015. He describes his time at IIT as profoundly humbling – constantly surrounded by exceptionally talented and passionate individuals excelling in diverse fields, from academics and sports to coding and poker. This exposure broadened his horizons significantly.
True to his earlier self, Adit wasn't solely focused on academics during college. He immersed himself in extracurriculars, including sports, dramatics, and student politics, while admittedly "chilling" when it came to coursework.
Graduating in 2015 coincided with a major boom in the Indian startup ecosystem. Despite securing a coveted job offer from Flipkart and scoring an impressive 99.90 percentile in the CAT exam (for MBA admissions), Adit felt the pull of entrepreneurship. Alongside his IIT Delhi friends and eventual co-founders, Mayank Kukreja and Anand Prajapati, he decided to forgo traditional paths and dive straight into building a startup.
The Entrepreneurial Spark & Early Ventures 🔥
The early days were the quintessential startup struggle. With zero funds, Adit and his co-founders survived on hostel mess food, AWS credits, and even lived illegally on campus for a year post-graduation. They explored ideas in healthcare and education before recalling an AI project on automatic content summarization they had worked on during college.
This led to their first significant venture: Chatteron. Riding the wave of excitement around conversational AI platforms like Facebook Messenger and Telegram opening up for chatbots, they initially built "Zype," a service delivering summarized news via Messenger. While Zype gained traction with around 12,000 users, it generated no revenue.
Recognizing the need for a business model, they pivoted Chatteron into a DIY platform allowing businesses to build their own chatbots for customer support, marketing, and sales across various channels (Messenger, Twitter DMs, websites). Chatteron achieved impressive scale, attracting 30,000 businesses across 150 countries. However, it suffered from poor monetization and a lack of focus.
"In order to build or in order to be everything for everyone, we basically ended up being nothing for nobody."
This period, though challenging, provided invaluable lessons about product-market fit and the dangers of being too broad too early.
The Birth and Growth of Leena AI 🚀
The breakthrough came in late 2017. By meticulously analyzing Chatteron's small base of paying customers (around 12-20), Adit and his team discovered a surprising niche: large enterprises like Coca-Cola and Vodafone were using the supposedly customer-facing platform to build internal HR and IT support bots. Employees were using it to ask about leave balances, company policies, and IT issues.
This insight sparked the crucial pivot to Leena AI.
Strategic Verticalization: Learning directly from the Chatteron experience, they made a conscious, disciplined decision to focus exclusively on solving problems within the HR function initially. The vision was broader, but the strategy was laser-focused: become the best "HR Virtual Assistant" on the market.
Early Traction & Y Combinator: This focused approach quickly yielded results. Leena AI secured around 20 enterprise customers within six months and was accepted into the prestigious Y Combinator accelerator program (Summer 2018 batch). YC provided critical global validation, access to networks, and helped refine their pitch (Adit famously practiced his 120-second Demo Day pitch over 100 times).
Funding Milestones: Leena AI's focused strategy and market potential attracted significant investor interest:
Seed Round (2018): $2 million raised post-YC, validating the global potential.
Series A (Nov 2020): $8 million led by Greycroft, fueled by the increased need for remote employee support during the pandemic.
Series B (2021): $30 million co-led by Bessemer Venture Partners and B Capital Group (co-founded by Facebook's Eduardo Saverin), aimed at product expansion beyond HR and aggressive global scaling.
Total Funding: Over $40 million.
Leena AI Today: Vision, Product, and Impact 📊
Leena AI's mission is ambitious: to build the "Jarvis for the Enterprise." The goal is to create a single, intelligent Autonomous Agent that acts as the primary interface for employees interacting with various enterprise functions, effectively becoming the AI-powered future of work.
Product Evolution: From its initial HR focus, Leena AI has expanded its capabilities significantly. Its platform now offers modules for:
HR Service Delivery: Policy answers, document generation, onboarding, etc.
IT Service Management (ITSM): Password resets, software access, troubleshooting, ticket deflection.
Admin & Procurement: Request handling, vendor queries.
Finance: Reimbursement status, payroll queries.
ERP & CRM: Information retrieval, task updates (e.g., updating Salesforce via chat).
Leena AI uses proprietary NLP models tailored for each function and emphasizes deep integrations with core enterprise systems (like Workday, SAP, ServiceNow, Microsoft Active Directory) as a key differentiator. They also offer their own integrated case management system for issues requiring human intervention.
Core Value Proposition: Leena AI aims to drastically improve employee experience by providing instant answers and automating workflows, while simultaneously delivering significant cost savings to enterprises. Adit speaks of aiming to automate 60-70% of support tickets, potentially allowing companies to significantly reduce the size of their internal support teams. The focus is on preventing tickets by resolving issues instantly through AI.
Global Reach & Customer Base: Leena AI serves over 500 enterprise customers across 90+ countries. Notable clients include Nestlé, Puma, Coca-Cola, Sony, and Etihad Airways.
Business Metrics & Goals: While specific revenue figures are private, Adit indicated an ARR likely exceeding $20 million (as of the podcast recording) and a clear goal to reach $100 million ARR within the next three years. They achieve this through a per-employee per-month subscription model, with pricing varying by geography and modules purchased. They boast near-zero customer churn over the last three years, attributing it to a strong focus on driving end-user adoption.
Adit Jain: The Leader & Investor 👨💼
Now based in New York City to spearhead global growth (particularly sales, which he heads), Adit Jain embodies the intensity and learning mindset often seen in successful founders.
Leadership & Approach: He emphasizes a relentless focus on value selling – understanding customer business problems and quantifying ROI. He's candid about past mistakes (like hiring too quickly post-Series B without adequate competency checks) and stresses the importance of continuous learning and adaptation. His approach to driving product adoption involves treating internal employees like consumers who need to be "sold" on using the tool.
Vision & Ambition: Adit is less focused on achieving "unicorn" status and more on building a "very large, sustainable, fast-growing business with global impact." He sees Leena AI as a direct challenger to the massive $500 billion ITSM market dominated by incumbents like ServiceNow and BMC.
Recognition: His achievements have been recognized, notably being named to the Forbes 30 Under 30 US list in 2020. He is also a member of the Forbes Technology Council.
Angel Investing: Beyond Leena AI, Adit is an active angel investor, backing other technology startups like GalaxEye Space, Neuranics Lab, Enpass Technologies, and SKILLEDGE.
The Future of Work, Powered by AI
Adit Jain's journey with Leena AI exemplifies the challenging but rewarding path of building a category-defining enterprise SaaS company. From early struggles and critical pivots to mastering global sales and building deep AI capabilities, his story underscores the importance of focus, resilience, and an unwavering commitment to solving customer problems.
As enterprises worldwide grapple with complexity and strive to improve employee productivity and experience, solutions like Leena AI are poised to play an increasingly central role. Adit Jain and his team are not just building a company; they are actively shaping the future of how work gets done.
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Until the next founder's thesis📕,
Your host, AD