Executive Assistant to MD and CEO Full Time NEW

Executive Assistant to MD and CEO

A high-trust strategic operator role at the center of one of India’s most loved retail brands.

About Crossword

Crossword is India’s largest organized books and stationery retail chain with 135+ stores across 40+ cities and one international store in Dubai. What started as a single bookstore has grown into a beloved brand that brings the joy of reading, learning, and discovery to millions of Indians every year. About Crossword We are a passionate, family-run business with an ambitious growth plan to expand to 300+ stores over the next three years, taking the Crossword experience to every corner of the country. Our product mix spans books, premium stationery, educational toys, and gifting. But at our heart, we are an experiential retail brand where customers come not just to buy, but to browse, discover, and fall in love with the written word.

Three outcomes that defines this role

1) Become the trusted extension of the CEO’s office, driving accountability and follow-through across the organisation.

You build a deep understanding of Crossword’s business, people, and priorities, enough that when you follow up on the CEO’s behalf, your interventions carry weight. You work with senior leaders and their teams to ensure that the CEO’s commitments and decisions translate into completed work, not lingering items.

• Follow up with senior leaders, function heads, and their teams on every priority that has been set, ensuring deadlines are met and commitments are honoured.
• Drive follow-through across cross-functional teams with professionalism, persistence, and the maturity to hold senior people accountable without friction.
• Build deep context on the business, key relationships, and internal dynamics so that your interventions are informed and credible.
• Handle select external communications such as vendor coordination, recruiter interactions, and routine business correspondence on behalf of the CEO’s office. 

2) Translate strategic priorities into executed reality, and over time, become a project driver in your own right.

You are the force that keeps the CEO’s strategic priorities moving forward. Quarterly goals, recurring rituals, and cross-functional initiatives. Through disciplined tracking and structured execution, you ensure that ambitious plans don’t lose momentum. As trust and context grow, you take on projects directly and become a genuine multiplier inside the CEO’s office.

• Track and drive the CEO’s strategic commitments, quarterly goals, recurring business reviews, store visits, and cross-functional projects.
• Build simple, effective tracking systems that give the CEO clear visibility on progress across the organisation.
• Over time, independently own discrete projects such as research, analysis, vendor negotiations, competitive intelligence, and strategic communications.
• Apply a sharp sense for numbers in vendor conversations and cost reviews, contributing directly to commercial outcomes.

3) Architect the CEO’s personal operating system, so every day, every hour, and every interaction counts. 

The CEO’s time is the company’s most valuable resource, and you architect how it gets spent. Drawing on sharp personal organisation, modern productivity frameworks, and AI-powered tools, you build and continuously improve the systems that keep the CEO’s office running at peak output.

• Manage the CEO’s email and messaging channels, prioritising, drafting, and handling routine correspondence so the CEO’s attention goes only to what matters most.
• Architect and protect the CEO’s calendar, ensuring every day is structured for impact, with prep and context ready before every interaction.
• Run a tight task management system, tracking every commitment and ensuring nothing slips. Leverage AI tools, automation, and the Google Workspace ecosystem to continuously raise the bar on how the CEO’s office operates.

What you’ve done? ( Experience )

• Graduate or postgraduate in any discipline.
• 5 to 8 years of experience as an EA, Chief of Staff, or Business Associate to a CEO, MD, Director, or Founder of a high-growth or mid-sized business.
• Track record of managing complex calendars, multiple inboxes, and high volume coordination across senior stakeholders.
• Experience driving follow-ups across distributed teams and senior people you do not directly manage.
• Experience owning projects end-to-end (not only supporting them) such as research, presentations, vendor coordination, and negotiations.
• Comfort with numbers and simple commercial analysis.
• Fluent in English and Hindi, able to write professional business communications on behalf of the CEO.
• Fluent with the Google Workspace ecosystem (Gmail, Calendar, Drive, Sheets), WhatsApp Business, and modern AI and productivity tools (ChatGPT, Claude, Notion, or equivalent). 

Who you are? ( Skills & Attributes )

• Highly logical, structured, and truth-seeking. You think in steps, you like systems, and you are uncomfortable when things are disorganized.
• A meticulous tracker. Following up consistently, documenting commitments, and never letting things slip is second nature to you.
• Mature and street-smart. You know how to get work done from senior people without burning bridges.
• Highly loyal and intensely confidential. You hold sensitive information with discipline and maintain professional distance at work.
• Tech-forward. You actively seek out AI tools, automation, and smarter ways to work. You build systems, not just execute tasks.
• Hungry and growth-oriented. You want to build a career, not clock hours.
• You are excited by responsibility, not intimidated by it.
• Comfortable operating in a high-velocity, founder-led environment where pace and ambition are constant.
• Flexible with working hours and energy. You understand this is not a strict 9 to 6 role.

What’s in it for you? 

• A seat at the centre of one of India’s most loved retail brands, with visibility into every function and every decision. 
• Direct mentorship from the MD and CEO of a 130+ store retail business at an inflection point. 
• A clear career path. Two to three years in this role, followed by a move into a larger business role or function leadership within Crossword.
• Early exposure to every part of running a multi-city retail business including operations, expansion, HR, marketing, finance, technology, and international. 
• A culture that values structured thinking, ownership, and growth. 
• Compensation that is competitive and aligned to experience, capability, and quality of fit.