Job Title

About Pickyourtrail Pickyourtrail was founded with the vision of making travel seamless through technology. Our platform empowers travelers to effortlessly customize their vacations end-to-end — with tech driving everything from planning to on-trip support. With offices in Chennai, Madurai, Gurgaon, and Jaipur, and a 450+ member team, we are actively hiring passionate young talent to join us in building India’s largest leisure travel brand. We are backed by marquee investors and founders such as Girish Mathrubootham (Freshworks), Sridhar Vembu (Zoho), and Kunal Shah CRED Job Description: Designation: Assistant Manager - Founder's office Location: Chennai Why This Role Exists: Pickyourtrail is scaling hard and fast. We need high-agency talent who can cut through chaos, connect the dots across marketing, product, and partnerships , and move top-of-funnel metrics without hand-holding. If you just walked out of B-school and are itching to skip the corporate conveyor belt, this is your breakout chapter. Who We're Looking For: 3–4 Years of Relevant Experience : Exposure to roles in corporate strategy, business operations, project management, or a founder’s office—preferably in a fast-paced startup or dynamic environment. Strategic & Operational Thinking: Ability to support cross-functional initiatives, optimize internal processes, and coordinate with teams to meet business objectives. Stakeholder Collaboration: Experience working with senior leadership, department heads, or founders to manage high-impact projects and align on priorities. Project Execution Skills: Comfort with managing multiple priorities, creating structured workflows, and ensuring timely delivery of key initiatives. Financial & Analytical Acumen: Strong understanding of business data, financial metrics, and strategic implications to support decision-making. Day-to-Day Responsibilities: Experimentation: Design, test, and analyse growth levers across GTM, partnerships, SEO, product funnels, and CRM—often simultaneously. AI Leverage: Prototype ways to multiply output with AI—think faster research, automated workflows, smarter attribution. Problem Solving: Break ambiguous growth problems into first-principles hypotheses, then pressure-test with data and own P&Ls Non Negotiables: Systems Thinker: You see GTM, product, and partnerships as one connected stack—not silos. 0 → 1 Energy: You get excited by blank slates and undefined problems; you create structure, not request it Mode Switching: Comfortable toggling between “do the work” and “decide what work matters.” Bias for Action + Communication: You’d rather ship a 70 % V1 today than a perfect V2 next quarter High Ownership: You run toward accountability, not away from it