Product Manager

Product Manager (AI-First) - Job Description

About Pickyourtrail (PYT)

Pickyourtrail (PYT) is an expert co-creator of super hit customised holidays. We are the perfect partner to the designated travel planner/s of every group - big or small. Our service, customisation and expertise help us deliver super hit holidays and make the planner the hero of the holiday.

The mission is simple: to make customized international travel easy, reliable, and uniquely memorable. Candidates are invited to join the team in shaping the future of global exploration!

Why work with Pickyourtrail

Pickyourtrail is one of the very few travel startups that has not only survived the pandemic but have significantly expanded, increasing our product portfolio to now include domestic staycations and global markets in addition to our India outbound market.

Despite the tough circumstances surrounding the pandemic, we have managed to maintain and, in fact, grow our Glassdoor rating to 4.2 out of 5.

Key benefits:

• High Impact Opportunity

Leisure travel is on a major uptick, much like online meetings were in February 2020. This presents a unique opportunity to utilize your experience to accelerate the organization's growth and achieve desired objectives.

• Growth:

Work alongside seasoned travel entrepreneurs and marketers, gaining invaluable experience in a high-growth sector

• Autonomy & Ownership:

We empower our team members to take full ownership. You are responsible for the full, end-to-end execution of all strategies and the delivery of measurable result

Role Overview

Pickyourtrail is seeking a Product Manager to drive product development and optimization across our core platformsmobile app, custom CRM (Plato), and itinerary building tool. This role serves as the critical bridge between business teams (Customer Experience, Finance, Sales, Marketing) and technology, owning the end-to-end product lifecycle from discovery to delivery for internal tools and customer-facing features.

This role requires an AI-first approach to product problem-solving. The ideal candidate must actively leverage AI tools (LLMs, copilots, automation agents, analytics assistants) in their daily workflow to build strong points of view before engaging stakeholders. Every initiativewhether wireframing, creating working prototypes, performing data analysis, or building financial modelsshould begin with AI-assisted exploration and synthesis.

Key Responsibilities

Product Management & Strategy

• Write comprehensive Product Requirement Documents (PRDs) across App, Plato CRM, and itinerary platform.
• Prioritize feature requests based on impact and outcome analysis.
• Define success metrics early; partner with Data Analytics to measure performance.
• Own roadmap execution for dashboards, customer features, and platform improvements.
• Collaborate with designers (Figma) to translate requirements into user-centered solutions.
• Conduct minimal UAT and sign-off testing before releases.

Platform & Dashboard Ownership (Plato CRM)

• Build and maintain task-based dashboards for CX sub-teams.
• Troubleshoot costsheet discrepancies, voucher uploads, and invoice management.
• Address refund challenges through system fixes and training materials.
• Automate manual workflows where possible (e.g., quote generation).

Cross-Functional Stakeholder Management

• Serve as primary product contact for CX, Finance, and Sales teams.
• Mediate customer-reported bugs between business and engineering.
• Capture and evaluate feature requests to reduce manual effort.
• Resolve cost/payment discrepancies and mediate operational constraints.

Engineering Collaboration & Delivery

• Partner with engineering teams to oversee execution.
• Work with Scrum Master for sprint planning and backlog prioritization.
• Create release notes and demo videos for launches.
• Monitor adoption metrics and address post-launch feedback.

AI-First Product Mindset (Mandatory)

• Demonstrated hands-on experience working with AI tools such as LLMs for structured thinking and prototyping.
• Experience integrating LLM APIs or building AI-powered workflows (preferred).
• Use AI to generate wireframes, prototypes, data analysis, financial models, and structured PRDs.
• Strong understanding of prompt engineering and iterative refinement.
• Working knowledge of agentic AI workflows and multi-step reasoning systems.
• Expected to arrive at stakeholder discussions with structured hypotheses, AI-generated alternatives, and working artifacts.

Required Qualifications

Experience

• 2-4 years of product management experience in B2C tech, travel, or consumer internet.
• Experience building internal tools, CRMs, or dashboards.
• Proven stakeholder management across cross-functional teams.
• Experience in high-growth startup environments.
• Evidence of AI-first working style (candidates may demonstrate this during interviews).

Technical Skills

• Strong proficiency in PRD writing, user story creation, and backlog management.
• Hands-on experience with Figma.
• Familiarity with data analytics platforms.
• Working knowledge of Google Sheets.
• Ability to quickly learn and master internal platforms.
• Strong working knowledge of databases and APIs

Core Competencies

• Exceptional communication skills across technical and non-technical stakeholders.
• AI-native problem solving: uses AI tools to structure ambiguity before engaging teams.
• Outcome-oriented prioritization and trade-off decision making.
• Self-starter mentality with end-to-end ownership.
• Strong mediation and facilitation skills.

What Success Looks Like

In this role, you will collaborate with multiple stakeholders across Customer Experience, Finance, Sales, Marketing, and Engineering. However, the success of your work will ultimately be measured by its impact on key business metrics such as improving conversion rates across web and app journeys, increasing gross margins through better cost visibility and system accuracy, improving Brand Loyalty Score (BLS) by enhancing customer and operational experiences, and driving internal operational efficiency through automation and product improvements. The expectation is that you proactively identify opportunities where product enhancements, process improvements, or AI-assisted workflows can meaningfully move these metrics.