Pick Your Trail - Technical Program Manageer

About Pickyourtrail:

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!

PickYourTrail is a technology-driven travel company building personalized, end-to-end travel experiences. Our platform powers dynamic itinerary creation, real-time pricing, booking orchestration, and post-booking workflows at scale. We operate in a high-throughput, real-time environment where backend systems are critical to business success.

What are we looking for?:

You are enthusiastic about developing highly scalable, foolproof, end-to-end quality software. You have worked on api integrations, have a good understanding of api docs, SOAP, REST, rate limiter and caching. You are very passionate about data structures and algorithms. You are flexible in working with multidisciplinary teams and you push your teammates to their limits & ensure that the work is done. You consider AI as your friend and use them in all facets to augment your work, as your pair programmer, code reviewer and design philosopher. If you feel we are talking about you, contact us asap.

Role Summary:

The Technical Program Manager (TPM) owns end-to-end delivery across all technology and product teams Chennai and Madurai acting as the operating backbone between Functional Leads, Tech Leads, and the business. This person takes the wheel on sprint execution, builds the framework that governs how work enters the system, and is personally accountable for predictable, on-time delivery with zero unannounced misses.

Key Responsibilities:

• Own sprint planning, daily standups, and weekly headcount planning across all tech teams.
• Track daily/weekly task completion and proactively flag at-risk items 35 days in advance.
• Run a live, transparent sprint dashboard (commitments, completion %, blockers, next steps) and communicate every missed deadline or feature go-live before it becomes a surprise.
• Design and run the Product/TechBusiness Prioritisation Framework how requests are raised, scored, and scheduled so no ad-hoc work enters a sprint without a documented trade-off decision.
• Build trusted working relationships with all Functional Leads (HR, Revenue, Tech, Product, MDD, Marketing, Fintech, Finance, Design, Co-founder) and all Tech Leads across Chennai and Madurai, including on-site time with the Madurai Fluid team.
• Enforce a 2-week rule: no sprint item exceeds two weeks without being broken into sub-tasks. Fix scope problems before they enter a sprint, protecting both predictability and velocity.
• Run structured reviews (45-day mid-point, full-quarter retro) and produce a 90-day report on delivery hit rate, ad-hoc reduction, sprint health by team, and a Q2 governance proposal.

What Success Looks Like (North Stars):

• 95% on-time delivery
• All sprint items broken down to 2 weeks in scope
• Zero unannounced misses every slip flagged before it lands, every time.

Ideal Candidate:

• 6+ years running technical programs or engineering delivery across multiple teams, ideally spanning more than one site/geography.
• Demonstrated ability to build or operate a prioritisation / intake framework that arbitrates competing business and engineering demands.
• Comfortable running daily standups and sprint mechanics directly this is a hands-on delivery role, not purely a coordination role.
• Strong stakeholder communication; instinct to over-communicate risk early rather than explain a miss after the fact.
• Structured, data-driven operator: comfortable building dashboards, tracking hit rates, and presenting retros to leadership.
• Willing to travel regularly to Madurai and work directly with distributed tech teams.

Youd be a Sooper Trooper if you have:

• Experience building consumer-facing, high-traffic platforms
• High ownership and accountability
• The ability to balance speed vs. quality
• Bias towards solving real customer and business problems
• The Mindset to most often than not think AI First