Summary
Overview
Work History
Education
Skills
Timeline
Generic

Jessica Milewski

San Diego,CA

Summary

B2B/B2B2C/B2C SaaS professional with 15+ years of Technical Product Management experience. Payments/FinTech: 10+ years of expertise in implementing and reviewing API payment service integrations, as well as forging partnerships to identify opportunities for optimization and growth. Regularly attending conferences, webinars, podcasts, etc. to stay abreast of FinTech industry innovation and compliance changes. Successfully launched 0-1 and 1-N products. Experience supporting up to $750M+ products. Strong understanding of how to leverage Generative AI to enhance product portfolio development and elevate customer engagement initiatives.

Overview

28
28
years of professional experience

Work History

Senior Manager, Global Head of Payments/Group Product Manager, Payments and Finance Systems

Fuze Health (Truepill)
10.2024 - 09.2025
  • Company Overview: Truepill is a digital health platform that offers pharmacy software, fulfillment, and patient support.
  • Owned the end-to-end payments strategy for Truepill and Fuze Health initiatives, serving as the subject matter expert and primary liaison for internal and external stakeholders. Defined and tracked key performance indicators, driving targeted strategies for performance improvement.
  • Spearheaded the development of a strategic plan for payment and billing operations, enhancing user experience, reducing costs, and enabling seamless integration across financial platforms for a $750M portfolio serving 6M+ patients.
  • Developed a payment risk management strategy across Fuze Health brands that reduces fraud, improves dispute win rates, and uncovered cost-saving opportunities exceeding $200K in fees.
  • Led a high visibility Finance team data initiative to speed up the time to revenue flash by 2 days.
  • Managed team of Product Managers through product development lifecycle. Mentored junior PMs, fostering professional growth and enhancing team capabilities.

Payments and Product Management Consultant

Self Employed
04.2024 - 10.2024
  • Conducted in-depth research and documentation on U.S. payment systems for FinDoc (Salesforce payments ISV). Performed vendor analysis for purchase card integration into MarginEdge (restaurant management). Provided strategic payment advisory for Truepill prior to transitioning to a full-time role.

Head of Product

Chargent (by AppFrontier)
04.2023 - 01.2024
  • Company Overview: Chargent is a payment processing solution that integrates with Salesforce.
  • Led a team of payments PMs, in a player-coach role, supporting subscription billing, automated collections, and telephonic solutions to deliver feature functionality for Chargent’s merchants.
  • Supported sales initiatives for customer acquisition and retention by delivering innovative product solutions, contributing to a 99% AppExchange rating. Contributed to 2024 strategic planning.
  • Supported top 5 high-touch accounts on their Salesforce and Chargent implementations and launches.
  • Led initiative to migrate customers to the latest Chargent version, boosting customer satisfaction and reducing maintenance costs by retiring older software versions.

Senior Product Manager, Payment Services

Salesforce
09.2018 - 03.2023
  • Company Overview: Salesforce is a cloud-based software company that helps businesses manage customer relationships.
  • Directed strategy and roadmap of Salesforce’s 0-1+ in-house payments product offering, Elevate Payments API/ SDK, growing product portfolio to seven gateway / wallet payment offerings.
  • Responsible for ensuring millions of seamless transactions with B2B/B2B2C payments through secure checkout, notifications, product integration, and self-service for managing recurring billing.
  • Drove discovery and strategy sessions with enterprise customers leading to net-new logos that produced over 80% of volume. Led early adopter / beta program retaining all participating customers.
  • Spearheaded all aspects of integration partner engagements in collaboration with legal and cybersecurity teams; streamlined development with technology readiness scorecard leading to 20% faster time to market, and created Tableau rev-share attribution report to ensure profit optimization.

Senior Product Manager, FinTech – Global Payment Services

Blackbaud
02.2014 - 02.2018
  • Company Overview: Blackbaud provides cloud-based solutions for nonprofits and education.
  • Optimized PayFac Services and FinTech products, processes, and feature set including secure checkout.
  • Directed collection and management of sensitive KYC (Know Your Customer) / AML (Anti Money Laundering) data to comply with regulations and enhance customer experience.
  • Delivered enhancements to advance Finance and Compliance initiatives by leading discovery and design efforts with internal stakeholder and client teams. Led A/B testing and tracked conversion rates.

Various Roles

Various SaaS Companies
01.1998 - 01.2014
  • Excelled in multiple roles, including Project/Program/Account Management, Scrum Master, QA, and Business Analysis, while supporting spouse's service in the Navy.

Education

Engineering Leadership - Certificate Program

California State University, Chico
2022

Women’s Leadership Program -

Salesforce
2021

Transformative Leadership - Certificate Program

San Francisco State University
2000

Bachelor of Science - Marketing

University of Arizona
1995

Skills

  • Data Driven: Performing market research and analyzing qualitative and quantitative product data to uncover opportunities for optimization and innovation, while maintaining dashboards for consistent reporting and visibility Experience with Looker, Snowflake, and Tableau
  • Product Strategy: Developing multi-year roadmaps, gaining leadership buy-in, client/partner advisory boards, and other key events Leading the definition, prioritization, and reporting of OKRs and KPIs
  • Team Leadership: Leading globally geographically distributed product and engineering teams to quickly resolve issues and deliver features in timely releases Providing mentorship, guidance, and support to junior PMs to foster their professional growth Organizing team-building activities to enhance cultural engagement and strengthen collaboration across diverse teams
  • Cross-functional Leadership: Partnered with Scrum teams, sales/growth, marketing, operations, customer success, compliance, and external stakeholders to align on and drive towards a unified vision
  • Customer Focus: Focusing on customer needs by creating feedback loops and gathering insights from customer interactions, developing personas, jobs-to-be-done, user stories, and feature requirements/acceptance criteria to ensure a clear understanding of desired business outcomes
  • Communication: Communicating complex ideas clearly with technical/non-technical audiences to manage dependencies across teams and stakeholders

Timeline

Senior Manager, Global Head of Payments/Group Product Manager, Payments and Finance Systems

Fuze Health (Truepill)
10.2024 - 09.2025

Payments and Product Management Consultant

Self Employed
04.2024 - 10.2024

Head of Product

Chargent (by AppFrontier)
04.2023 - 01.2024

Senior Product Manager, Payment Services

Salesforce
09.2018 - 03.2023

Senior Product Manager, FinTech – Global Payment Services

Blackbaud
02.2014 - 02.2018

Various Roles

Various SaaS Companies
01.1998 - 01.2014

Transformative Leadership - Certificate Program

San Francisco State University

Engineering Leadership - Certificate Program

California State University, Chico

Women’s Leadership Program -

Salesforce

Bachelor of Science - Marketing

University of Arizona

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