Technical Product Manager

Trek Travel provides global cycling, hiking, and walking vacations of a lifetime with the goal of helping more people actively explore and experience the world. This is Trek Travel's first dedicated product management seat, owning the website and every other digital product across the business — the guest portal, booking and reservation flows, email infrastructure, campaign landing pages, CRM and data analytics, dashboards, and internal tooling. 

This is a hands-on role that combines building the product operating model with running it day to day, across a delivery team of internal staff, fractional specialists, and agency partners. You'll bring product instincts, customer understanding, and marketing fluency to everything you spec, coordinate, and ship, with real autonomy to shape how product gets built. This is your opportunity to join the Trek Travel team and leave your mark on our company, on the active travel industry, and on the world at large. 

POSITION RESPONSIBILITIES INCLUDE, BUT NOT LIMITED TO:

Product Strategy & Roadmap

• Own the roadmap for the website, guest portal, and all other digital products 
• Run quarterly product strategy reviews and monthly roadmap reviews with leadership 
• Stand up the product development lifecycle end to end: idea intake, sizing and prioritization, PRDs, spec documents, and release readiness 

Delivery & Team Management 

• Run the delivery cadence across teams: sprint planning, grooming, stand-ups, retros, and dependency tracking 
• Plan team availability and capacity, aligning people's hours against company priorities and the annual marketing and business initiatives calendars 
• Manage a mixed delivery team of internal staff, fractional specialists, and agency partners 

Marketing & Campaign Support 

• Support and coordinate digital ads, organic and paid social, digital campaigns, and email — bringing strategy, creative, copy, build, and deployment together through to launch 
  Support SEO/GEO and business development with the digital and technical work they depend on: landing pages, tracking, campaign infrastructure, and site health 

Technical Execution 

• Write PRDs and translate approved designs into build-ready specs that engineering partners can execute without back-and-forth 
• Anticipate downstream effects of changes across backend, frontend, and data, and prevent scope creep before it lands in a sprint 

CRM & Analytics 

• Own CRM and marketing data analytics: HubSpot, campaign tracking, dashboards, GA4, segmentation, and lifecycle data 
• Monitor product and business health daily: conversion, funnel drop-offs, feature usage, and campaign performance 
• Report on metrics leadership can act on 

Cross-Functional Coordination 

• Coordinate across sales, marketing, guest services, guest experience, forecasting, field, logistics, and the trip product and design teams to turn feedback into prioritized product work 
• Use AI to improve workflows, both for personal productivity and across the functions you coordinate — including drafting PRDs, scoring and sizing intake, and running AI-accelerated, spec-driven development with engineering 

The top priority in this role is the end-to-end customer funnel: ads that run efficiently and carry awareness, retargeting, and re-engagement for new and repeat guests; an email program with meaningful segmentation that improves over time; and a website that converts on both. CRM and analytics support all three, and building a product process the team can run inside is central to the job.

WHAT ELSE WE'D LIKE TO SEE FROM YOU:

• 5+ years in product management, including experience as a technical product manager or product owner working directly with engineers 
• A track record shipping software products end to end, from problem definition through PRD, spec, build, QA, and release 
• Strong product instincts and taste, with the judgment to hold the bar on what ships 
• Understanding of marketing and product marketing deep enough to coordinate ads, campaigns, and email across the functions that produce them 
• Working fluency in agile practice — experience running sprints, grooming, and retros, and judgment on when to adapt the process 
• A technical foundation strong enough to read a spec, discuss architecture trade-offs with engineers, and judge build cost and complexity 
• Systems thinking, with the ability to see how the pieces connect and build workflows that hold up as things change 
• Hands-on experience with delivery tooling (ClickUp, Jira, Asana, or similar), GA4, and CRM tooling (HubSpot, Salesforce, Close, or similar) 
• CRM and lifecycle marketing experience: segmentation, campaign data, and email platforms (Iterable, Clay.com, Smartlead.ai, or similar) 
• Experience managing mixed teams of agencies, contractors, and internal staff, including planning their hours and availability against shared priorities 
• Daily, practical use of AI tools in your product workflow 
• Clear, unambiguous writing — PRDs and specs that keep projects from stalling 

NICE TO HAVE:

• Experience standing up a product function from scratch at a startup or small company 
• E-commerce, booking-flow, or conversion-focused product experience 
• Background in travel, hospitality, outdoor, or another operationally heavy consumer business 
• A relationship with cycling, or genuine curiosity about why people fly across the world to ride bikes 
• You believe in the importance of hospitality and customer service, recognizing that customers are all around. 
• You rock a positive, solution-oriented attitude and always ask “how can I help?” 
• You exude fun and flexibility while contributing to the overall success of your Team.

TREK TRAVEL OFFERS:

• A fast pace, casual, fun, and flexible company culture where initiative and pro-activity are highly valued 
• Competitive health care 
• Dental and vision insurance 
• Flexible Spending Accounts (FSA) 
• Short Term/Long Term Disability 
• Life Insurance 
• 401(k) with company match 
• Competitive Paid Time Off and Volunteer Time Off package 
• Paid Holidays 
• Flexible schedules 
• Reward program for sustainable commuting to the office 
• Employee discounts and outdoor industry discounts 

At Trek Travel, we think outside the box, continuously improve, encourage feedback, and give it all we got, all the time, no exceptions. This is a full-time exempt position and is eligible for Trek Travel's competitive benefits package. This position is based in Madison, Wisconsin, and reports to the Head of Growth. Interest in the active travel industry is beneficial but not required.