About

Jonathan Rappaport

Business leader and technology strategist. Fifteen years building scalable marketplace infrastructure and AI ecosystems where commercial strategy meets technical execution. I close the gap between strategic intent and operational reality — transforming environments where progress was measured in quarters into systems that operate with the pace and precision of modern product cycles.

Previously: Principal PM, enterprise freight marketplace · Group PM, 40-person org, regulated marketplace at scale · Founder, live event loyalty platform · PM, ticketing and live entertainment.

Los Angeles, CA Harvard Business School · CS50 · University of Utah, BS Business LinkedIn →
$1.2M
Customer savings, AI-powered anomaly detection system
136%
Retention increase, shipment reliability platform
GMV lift, personalized marketplace discovery engine
480%
Ticket conversion lift, scalable content platform
$1.5B
GMV, personalized marketplace discovery engine
$12M
Client revenue generated, CRO-focused growth agency
$375M
Ticket revenue attributed to product, 2.5-year engagement
60%
NPS improvement from continuous feedback program
Career Overview

At a Glance

Portfolio

Selected Work

Resume

Experience & Impact

Mothership Principal Product Manager Oct 2022 – Present
  • Directed product strategy for company-wide core marketplace, API, and EDI ecosystems, optimizing the end-to-end lifecycle across checkout, trust, and fulfillment funnels while expanding external API and EDI capabilities.
  • Led the 0 to 1 incubation of Galaxy, a next-generation AI-powered evolution of the carrier API and EDI platform, defining the roadmap for automated partner integrations and agentic workflows to enable scalable adoption.
  • Strategized and launched Mothership Intelligence, an AI-powered validation and compliance system using ML models for anomaly detection — $1.2M in customer savings and a 136% increase in retention through improved shipment reliability.
  • Partnered with Finance, Engineering, and Legal to design a scalable prepay and checkout system, simplifying cross-border purchasing while reducing manual reconciliation and customer friction.
  • Developed and launched behavior-driven pricing and incentive strategies, balancing customer adoption with margin efficiency during a volatile market cycle.
  • Collaborated with Data Science on ML models for classification and anomaly detection, improving platform accuracy, reliability, and downstream user experience.
  • Collaborated with Data Science and Engineering to modernize event-driven data infrastructure and ML classification models, improving platform accuracy and experimentation velocity for high-volume logistics data.
  • Built a continuous customer feedback and experimentation program, driving 35+ product improvements and a 60% lift in NPS.
  • Championed a culture of ownership and high-velocity execution by mentoring and leveling up Product Managers & Engineers, ensuring alignment between technical requirements and long-term commercial goals.
Weedmaps Group Product Manager Jan 2020 – Oct 2022
  • Promoted to Group PM from Senior PM and led a 40+ member team across B2B and B2C product verticals, including three direct PM reports.
  • Implemented and executed a dynamic product strategy for WM Orders that resulted in a 5x increase in GMV year-over-year. These strategic initiatives markedly improved product-market fit, cementing its position as the most influential product within the company's portfolio, ultimately contributing to its IPO in 2021.
  • Partnered with CEO, Legal, and auxiliary executive collaborators to address outstanding pre-IPO compliance issues and risks in a highly regulated industry.
  • Launched department-wide user testing programs to create a culture of data-informed decision making.
  • Strategized and launched WM Insights, the first B2B subscription data product for the company, reducing client churn by 60%. This product created new business insights for 1,500+ businesses and is one of my favorite product achievements to date — fueling my drive to build products based on customer insights that lead to uncovering new opportunities for my customers' growth and ultimate success.
Cro Metrics Senior Growth Product Manager Dec 2018 – Jan 2020

As a Senior Growth Product Manager, I served as a strategic lead for global brands including Uber, Teachers Pay Teachers, and Sierra Club, embedding within their product organizations to scale their experimentation capabilities. I managed the end-to-end lifecycle of these relationships, from initial hypothesis ideation to executive reporting and contract renewals. By delivering over 12 million dollars in incremental revenue through disciplined A/B testing, I demonstrated the tangible ROI of a growth-led product culture. This performance directly resulted in the expansion of experimentation programs across my client portfolio and solidified product optimization as a primary revenue engine for these organizations.

Season Share / Attend Co-Founder & Product Sept 2015 – Jan 2020

As Co-Founder, I spearheaded the product vision for a season ticket sharing platform, evolving a conceptual MVP into a market-validated solution. By securing placements in the Techstars Innovation and SXSW accelerators, I established product-market fit across native and web platforms. I successfully navigated the company through a strategic pivot from a consumer marketplace to a B2B SaaS model, a move that secured additional funding and diversified our revenue streams. Upon completing these milestones in 2020, I transitioned out of the organization, having proven the scalability of the model and established a foundation that extended the company's runway and ensured its long-term operational viability.

Live Nation Entertainment Product Manager, Search & Content Oct 2013 – Sept 2016

I owned the product roadmap for Live Nation's consumer-facing content platforms across various web properties such as Ticketmaster, House of Blues, Ticketweb, and Boomrat, focusing on audience development and technical SEO. Through the execution of cross-channel campaigns and platform optimizations, I drove a 340 percent increase in site traffic. More importantly, these efforts led to a 480 percent increase in conversion metrics, successfully turning content engagement into measurable ticket sales at a global scale.

Axis41 Manager, Web Marketing Sept 2011 – Aug 2015

I managed a team of three strategists to deploy sophisticated paid media campaigns across search, social, and display channels. Using Adobe and Google Analytics to build custom reporting frameworks, we identified and captured untapped growth segments for our clients. These initiatives delivered significant results, including a 145 percent increase in organic site traffic, a 95 percent boost in demo requests, and a 68 percent reduction in cost per conversion year over year.