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Lead, Finance Analytics & Enablement Ai/Ml

hopper

Remoto Boston - Remote
AI

Job Score

100 pts
Remote model (+90) AI (+10)

About the Role

Hopper is looking for a Lead, Finance Analytics & Enablement AI/ML to own our data warehouse, business intelligence, GCP/AI optimization, and Finance AI enablement strategy. You will be a key business partner across the organization, managing partner relationships across a broad range of commercial arrangements, reporting directly to the Chief Financial Officer.

What would your day-to-day look like:

  • Provide actionable insights to drive business decisions based on finance and data analytics

  • Own the data warehouse strategy, governance and execution of the finance ledger

  • Build and lead a Center of Excellence for reporting including owning infrastructure and metrics across finance and the business units

  • Create, own, implement and track success of the Finance AI automation roadmap in partnership with FP&A, accounting and data

  • Establish data pipeline and AI model foundation

  • Understand and optimize our GCP infrastructure costs in partnership with engineering and Financial Operations

  • Establish Finance as the single source of truth for financial and business performance and create self-service analytics for key stakeholders

  • Manage a team of 4 engineers and 1 finance and strategy manager

  • Establish internal controls and support external audits related to data governance

An ideal candidate has:

  • Work experience 15+ years in travel and/or SaaS

  • Bachelor's Degree, with a strong preference for a Master's degree or equivalent experience

  • Engineering background preferred

  • Fluency in SQL, Python, GCP and Data Science, hands on coding ability

  • Understanding of LLM-based systems, prompt design, and AI model evaluation frameworks

  • Familiarity with automation frameworks and observability tools (Amplitude, Datadog, Looker) to assess reliability and performance

  • Strong data reconciliation skills across large, multi-source datasets

  • A bias toward first-principles thinking — questioning assumptions, stress-testing processes, and always asking why something works the way it does

  • Clear communicator with senior leadership and external partners

  • “Comfort with ambiguity and ground-zero building

Nice to Have

  • Background at a high-growth technology or marketplace company

  • Experience working cross-functionally with data engineering or warehouse teams

  • Perks and benefits of working with us:

    • Well-funded and proven startup with large ambitions, competitive salary and the upsides of pre-IPO equity packages.

    • Unlimited PTO.

    • Carrot Cash travel stipend.

    • Access to co-working space on demand through FlexDesk AND Work-from-home stipend.

    • Please ask us about our very generous parental leave, much above industry standards!.

    • Entrepreneurial culture where pushing limits and taking risks is everyday business.

    • Open communication with management and company leadership.

    • Small, dynamic teams = massive impact.

    • 100% employer paid Medical, Dental and Vision coverage for employees.

    • Access to Disability & Life insurance.

    • Health Reimbursement Account (HRA).

    • DCA/ FSA and access to 401k plan.


    More about Hopper

    At Hopper, we are on a mission to become the leading travel platform globally – powering Hopper’s mobile app, website and our B2B business, HTS (Hopper Technology Solutions). By leveraging massive amounts of data and advanced machine learning algorithms, Hopper combines its world-class travel agency offering with proprietary fintech products to bring transparency, flexibility and savings to travelers globally. We have developed several unique fintech solutions that address everything from pricing volatility to trip disruptions – helping people travel better and save more on their trips.

     

    The Hopper platform serves hundreds of millions of travelers globally and continues to capture market share around the world. he Hopper app has been downloaded over 120 million times and has become largely popular among younger travelers – with 70% of its users being Gen Z and millennials.

     

    While everyone knows us as the Gen Z and Millennial travel app, Hopper has evolved to become much more than that. In recent years, we’ve grown into a travel fintech provider, commerce platform, and global travel agency that powers some of the world’s largest brands.

     

    Through HTS, our B2B division, the company supercharges its partners’ direct channels by integrating our fintech products on their sites or powering end-to-end travel portals. Today, our partners include leading travel brands like Capital One, Nubank, Air Canada, and many more.

     

    Here are just a few stats that demonstrate the company’s recent growth:

    • Billions of dollars worth of travel and travel fintech are sold through Hopper and HTS’ channels every year.

    • Our fintech products – including Cancel for Any Reason and Flight Disruption Assistance – have exceptionally strong CSAT because the terms are always clear, and customers receive instant, no-questions-asked resolutions.

    • Almost 30% of our app customers purchase at least one fintech product when making a booking; and consumers are 1.6x more likely to repurchase if they add fintech to their booking vs if they booked just travel.

       

    Given the success of its fintech products, Hopper launched a B2B initiative, HTS (Hopper Technology Solutions), which represents more than 75% of the business.

    Through HTS, any travel provider (airlines, hotels, banks, travel agencies, etc.) can integrate and seamlessly distribute Hopper’s fintech or travel inventory on their direct channels. As its first HTS partnership, the company partnered with Capital One to co-develop Capital One Travel, a new travel portal designed specifically for cardholders. Other HTS partners include Air Canada, Uber, CommBank, Nubank, Flair Airlines and many more.

    Hopper has been named the #1 most innovative company in travel by Fast Company Hopper has been downloaded over 120 million times and continues to have millions of new installs each month. Hopper is now the #3 largest online travel agencies in North America and 70% of our app customers are Gen-Z and millennials travelers.

    Hopper has raised over $750 million USD of private capital and is backed by some of the largest institutional investors and banks in the world. HTS is primed to continue its growth as the leading travel ecommerce provider in a $1 trillion online shopping category. The Hopper app and website will also continue to be the preferred travel provider for Gen Z and Millennials..

     

    Come take off with us!


    #LI-REMOTE

About Artificial Intelligence

Artificial Intelligence is currently the fastest-growing field in the technology market. The revolution in generative models (GPT, Claude, Gemini) has created massive demand for AI-specialized professionals.

Key areas of practice include Machine Learning Engineering, MLOps, Prompt Engineering, AI Research, and Applied AI. Python, TensorFlow, PyTorch, and LLM knowledge are essential skills.

AI salaries are the highest in the technology sector, with many remote work opportunities at international companies.

Discover Other Areas

Understand the scope of work, key skills, and tools used in different career areas.

About Scrum Master

The Scrum Master is the professional responsible for facilitating the adoption of Scrum and agile practices within development teams. They act as servant leaders, removing impediments, promoting continuous improvement, and ensuring Scrum events and ceremonies happen in the best possible way.

Key skills include event facilitation (sprint planning, daily, review, retrospective), backlog management, team coaching, conflict resolution, and agile metrics (velocity, burndown, cycle time). Knowledge of Jira, Trello, Azure DevOps, and frameworks like Kanban, XP, and SAFe is a differentiator.

Scrum Masters in technology companies are highly valued, especially those who can promote team autonomy, create psychologically safe environments, and lead agile transformations at scale. The field offers opportunities from junior scrum master to agile coach, head of agile, and director of agile transformation.

About Project Management

Project Management is essential to ensure strategic initiatives are delivered on time, within scope, and with quality. PM professionals coordinate teams, manage risks, and communicate with stakeholders.

Key methodologies include PMBOK, PRINCE2, Scrum, and Kanban. Tools like Jira, Asana, Monday, and MS Project are widely used in daily work.

Certifications like PMP and PgMP are important differentiators in the market, with growing demand in technology and consulting companies.

About Customer Success

Customer Success is the area responsible for ensuring clients achieve their goals when using the product or service. It is a strategic function for retention, expansion, and customer satisfaction.

Key skills include account management, churn analysis, NPS, onboarding, upsell, and cross-sell. Knowledge of CS tools like Gainsight, Totango, and ChurnZero is a differentiator.

CS is becoming increasingly strategic in SaaS companies, with professionals directly contributing to recurring revenue growth (MRR/ARR).

About Web Designer

The Web Designer is the professional responsible for creating visual interfaces for websites, web applications, and landing pages, combining aesthetics, usability, and user experience. They transform business needs into functional and responsive layouts that communicate brand identity.

Key skills include UI design, responsive design, prototyping (Figma, Sketch, Adobe XD), wireframing, design systems, accessibility (WCAG), information architecture, and basic HTML/CSS knowledge. Knowledge of UX design, motion design, and front-end is a differentiator.

Web Designers in technology companies are highly valued, especially those who master design systems, design tokens, and can create interfaces that convert and engage. The field offers opportunities from junior web designer to product designer and design lead.

About Data

The Data field has undergone a radical transformation with the rise of Generative AI. Data professionals are fundamental for evidence-based decision-making across all industries.

Key specializations include Data Engineering, Data Science, Business Intelligence, Machine Learning Engineering, and Analytics. Tools like SQL, Python, Spark, dbt, and cloud platforms (AWS, GCP, Azure) are essential.

The data market continues with high demand and salaries among the most competitive in the technology sector, with many remote work opportunities.

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Expert Tip

Generative Design and AI as a Co-pilot

If the last decade in digital design was defined by mobile standardization and UX/UI becoming the core of product development, 2026 marks the dawn of a new era. We are no longer designing just for flat glass screens; we are building intelligent ecosystems, three-dimensional environments, and autonomous algorithms.

For designers looking to stand out and secure the best six-figure remote opportunities in the US tech market, understanding where the industry is heading is no longer a "nice-to-have" differential—it's a matter of professional survival. Below, we break down the four major trends that will dictate hiring and compensation in the 2026 design landscape.

1. Generative Design and AI as a Co-pilot (Not a Replacement)

The fear of Artificial Intelligence replacing designers is officially in the past. In 2026, generative AI is deeply and natively integrated into industry-standard tools like Figma, Adobe, and Framer. The most valued skill by top-tier tech companies is no longer speed in aligning components, but rather algorithmic art direction and prompt design.

  • UI Automation: Wireframing, component variations, and complex design systems can now be generated with a few text prompts.
  • The Designer's New Role: Professionals are shifting from operational executors to curators and strategists, ensuring that AI-generated outputs align with user psychology and core business objectives.

2. Spatial Design and Spatial Computing

With the maturation of mixed reality devices (such as the Apple Vision Pro and Meta's advanced lineups), Spatial Design has evolved from an experimental niche to a mandatory department in Big Tech and forward-thinking startups.

Designing for spatial computing requires a complete paradigm shift: designers must understand Z-axis depth, visual ergonomics, spatial audio, and interactions based on eye-tracking and hand gestures. Roles like AR/VR Product Designer and 3D Interaction Designer are seeing an exponential jump in job listings, often paired with premium compensation packages.

3. Conversation Design and Invisible Interfaces (Zero-UI)

Driven by the omnipresence of Large Language Models (LLMs), the way users interact with systems has fundamentally changed. In 2026, many of the best interfaces don't rely on buttons or hamburger menus; they are conversational. UX Writing and Conversation Design have taken center stage.

  • The Challenge: How do you design the "personality" and flow of a virtual assistant so it feels natural, empathetic, and on-brand, rather than like a rigid robot?
  • The Opportunity: Designers who know how to map complex decision trees, create logical flows for voice and text, and train the empathy of AI models are being heavily scouted by top US startups.

4. Digital Sustainability and Eco-Design

The ESG (Environmental, Social, and Governance) agenda has finally reached the product design tables. The internet consumes a massive amount of energy, and in 2026, tech companies are being strictly held accountable for their digital carbon footprint.

Enter the demand for Digital Eco-Design. This involves creating lighter interfaces, optimizing user flows to reduce screen time (saving battery life and server processing power), and adopting color palettes and assets (like SVGs instead of heavy raster images) that require less energy to render. Being a sustainable designer has become a powerful B2B selling point for agencies and freelancers alike.

Conclusion: The Evolution of Talent

The 2026 design market is highly rewarding for those who embrace complexity. The barrier to entry for making "pretty screens" has dropped significantly, but the demand for professionals who can solve intricate business problems through empathy, strategy, and the mastery of new technologies has never been higher.

If you want to stay ahead of the curve and get direct access to the remote jobs that are actively looking for these specific skills, make sure to follow Mondywork's daily curation. The future of design is hybrid, remote, and full of opportunities.