Donna Penick, Product Manager in Los Angeles, CA, United States
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Donna Penick

Verified Expert  in Product Management

Product Manager

Los Angeles, CA, United States
Toptal Member Since
May 24, 2022

Donna is a well-rounded and versatile product and project management leader with industry expertise ranging from aerospace and government to digital media, SaaS, and eCommerce. Her contribution to startups and medium-sized businesses, such as LegalZoom and Napster, has given her hands-on experience with new product development, IT and software development projects, and process improvement. Donna likes challenges and is excited to work with new clients on new projects.

Project Highlights

Prepare Company for S-1 Filing
Enabled the company to produce auditable financials, meeting GAAP requirements to prepare for an IPO.
Develop and Operationalize Subscription Products
Prototyped, iterated, and operationalized subscription products as a major new product offering, working closely with the business owner.
Build SaaS Product for a New Startup
Took over product and project management of an in-house product, partially developed a SaaS application, and brought it to launch as a well-designed, modern application.


Work Experience

IT Manager (Volunteer)

2019 - PRESENT
Church of the Living Word
  • Took over IT functions when the organization separated from the parent organization. The immediate tasks were to find a provider, set up a new Microsoft 365 tenant, and migrate existing users to the new tenant. Managed discovery for legal requests for documents.
  • Investigated file-sharing platforms to determine which best met the needs and implemented the library on With the COVID-19 shutdown, the company needed a platform that could be used for a digital lending library.
  • Investigated tools for converting tapes to MP3 files since a large part of the physical library was still tapes. Oversaw the team that edits audio from current services, converts older sermons, and maintains the library. Set up user support.
  • Collaborated with the leadership during the COVID-19 shutdown to move to Zoom services. Set up support to help users who are computer challenged.
  • Studied, when it was time to return to in-person services, how to do hybrid services so people on Zoom could still participate. Hired an engineer to move and reconfigure existing audio and video equipment and hired an audio engineer for services.
  • Worked with the leadership and a brand consulting company to establish a brand identity and functioned as vendor POC for the implementation. This process was very interactive, with the entire organization providing input at various stages.
  • Collaborated with the business manager on restructuring a local network drive file organization in preparation for the migration to SharePoint but concluded that met the organization's needs better. The migration and user training are in process.
  • Planned to replace an existing out-of-life server with a new server for the domain controller and print server functions. Intended for firewall and network upgrades as funds permitted.
  • Added an IT person to marketing to improve campaign and list management. Advised leadership on improving outbound communication. Work with a brand consulting company for SEO, and search ad/Facebook audience targeting.
  • Set up a private site for members on a faith-based platform.

Project Owner and Project Manager

2020 - 2023
Saasman Solutions, Inc.
  • Joined a friends-and-family startup as a part-time project manager to complete a SaaS application whose prototype was initially built by the client for his use in law practice. The client's first estimate to launch was four to six weeks.
  • Assessed the part-time development team, development process, state of requirements for incomplete and not-yet-started must-have features, and application UI/UX. Made recommendations in all areas and converted team allocation to full-time.
  • Hired a full-time skilled team, including two full-stack developers, a QA engineer, a front-end developer, and a UI/UX designer. Implemented the release process and engaged a DevOps engineer to set up IaC with Terraform for all environments.
  • Acted as a business analyst, product owner, and scrum master, implementing Shortcut (formerly Clubhouse) for project management, writing stories, maintaining the backlog, and leading all scrum ceremonies for the development team.
  • Met with the founder to elicit the undefined requirements for incomplete features and quantify new features considered essential for a launch. Facilitated design meetings with the founder and designer, resulting in an intuitive, modern design.
  • Defined business rules for Stripe integration and documented configuration rules for business owners.
  • Led the development team to identify and correct the technical debt during the initial design phase, including database design: 32 items with a high impact on maintainability were identified and corrected.
  • Took part in the leadership team, providing thought leadership related to process, software, and startups and setting up a Kanban board in Shortcut to help marketing, executive, and support teams structure their work better.

Expert Consultant | Project Manager, Product Owner, Business Analyst, Change Agent

2016 - 2018
US Small Business Administration
  • Led the transition of the OCIO development team from Waterfall to Agile and introduced Jira.
  • Mentored the contractor scrum master, developers, and junior business analysts and educated the career Federal IT employees on Agile practices.
  • Contributed to writing the request for proposal (RFP) for the subsequent development services contract to specify Agile instead of Waterfall as the project management methodology. Reviewed all proposals and participated in the selection process.
  • Drove the project to move all SharePoint team sites from local SharePoint 2007 to SharePoint Online. Engaged stakeholders from all departments to clean up their sites and completed the project in seven months, after a prior 15-month failed attempt.
  • Spearheaded the project to upgrade and migrate all custom SharePoint applications from SharePoint 2010 on local servers to SharePoint 2016 in Azure. It was the company's first success in moving all locally hosted applications to Azure.
  • Acted as the product owner to rewrite and launch two legacy ColdFusion applications into SharePoint. Gathered requirements, created wireframes, worked with developers and stakeholders, and performed user acceptance testing (UAT).


2015 - 2015
  • Performed discovery for a small nonprofit company in preparation for building a new online store. Documented the as-is condition for all internal processes and proposed the to-be-desired end state.
  • Formulated recommendations on integrating the new WooCommerce store built in WordPress with Sage accounting system and other manual internal legacy processes.
  • Researched and recommended plug-ins to support various desired new features.

Director of Process and Technology | Project Manager, Product Owner, Business Analyst

2007 - 2015
LegalZoom, Inc.
  • Conceived and delivered a year-long project to rebuild the ordering system for compliance with generally accepted accounting principles (GAAP) revenue recognition requirements and provided auditable financials to support an S-1 filing.
  • Served as the business process owner for operations and finance during the prototyping and development of subscription products contributing to 50% of the revenue growth that supported a $5 billion valuation at the initial product offering (IPO).
  • Delivered two major new internal .NET applications supporting Customer Care and Finance. Wrote requirements and provided wireframes for an internal rules engine that would enable API interaction with the website.
  • Championed the transition from Waterfall to Agile and acted as the product owner for the internal applications team using Jira and Confluence.
  • Transformed engineering processes by setting up development, testing, and staging environments, enforcing the use of source control, creating a QA team, and implementing a formal release process.
  • Acted as the technical project manager on Salesforce implementation for Customer Care, including API development, object and interface design, and data migration.
  • Instituted an intake process to provide a single channel for triaging new work requests.
  • Drove to completion a stalled project to automate fulfillment in the FileNet workflow system for all products still being manually fulfilled.
  • Developed trusted relationships with stakeholders in all business lines, operations, and corporate departments, taking part in the multiple UAT rounds necessary for major initiatives.
  • Collaborated with an offshore team in Thailand for the internal application and back-end development.

Program Manager, Software Development | Project Manager, Business Analyst, Technical Writer, Tester

1999 - 2007
Universal Music Group/Napster
  • Facilitated all requirements, design, status, and launch-readiness meetings for four iterations of digital music services that eventually became the legal version of Napster. Created data maps, process flow diagrams, and other documentation.
  • Performed ad-hoc testing on the desktop application and met all business and usability requirements.
  • Managed major releases and coordinated resources from geographically distributed groups.
  • Researched and selected internationalization and localization vendors, completed projects to prepare the database and web app for handling double-byte character sets, and localized the service to be launched in Germany and Japan.
  • Spearheaded the integration of XM Radio Online into Napster and the integration of Napster with Sonos.
  • Filed as a joint patent holder for the silent-license delivery and renewal system, Microsoft Digital Rights Management, used before the company moved to unencrypted MP3s.
  • Supported the CTO by monitoring and assessing progress and risk on all tech team efforts and managing exploratory projects, such as prototyping a new content search provider.

Technical Writer

1998 - 1998
  • Supervised, screened, interviewed, and hired technical writing consultants.
  • Interviewed engineers for each system module. Asked in-depth questions that required them to think about the interfaces with other modules they had not considered and created diagrams to help visualize the missing pieces.
  • Wrote interface control and architecture documents, functional and design specifications, release notes, and installation guides for headend components and subsystems within an early effort to launch an interactive TV system.
  • Remained fully engaged after extensive layoffs to stay and complete the documentation for all subsystems for handoff to a vendor to complete the project. Received a double bonus for diligence in completing the project.

ILS Project Leader | Project Leader, Technical Writer

1989 - 1998
LItton Data Systems
  • Led department modernization from DOS-based word processors to the Unix-based Interleaf publishing system.
  • Proposed and implemented a conditional text system that significantly reduced errors and cut the time required to incorporate review comments by 45%.
  • Oversaw and led the delivery of a documentation set for two prototype projects for the US Marine Corps.
  • Led the project team to document all operating procedures for a client information services group.

Engineering Writer Specialist | Technical Writer, Project Leader

1985 - 1989
Northrop Aircraft, Ventura Division
  • Collaborated and iterated with IBM SCRIPT/VS developers to create a conditional text system that significantly decreased errors and reduced by 75% the time required to incorporate changes into test and maintenance procedures.
  • Worked with SCRIPT/VS developers to create an automated text formatting system that used embedded tags to correctly apply rules for multiple Mil-Specs to the same set of files, significantly reducing errors and time for incorporating changes.
  • Managed all customer reviews and post-review cycles to incorporate and verify review comments.
  • Received commendations from field engineering, flight operations, and customers for the caliber of work and attention to detail.

Prepare Company for S-1 Filing

Enabled the company to produce auditable financials, meeting GAAP requirements to prepare for an IPO.

LegalZoom wanted to prepare for an initial public offering (IPO), but the state of order and financial data could not support generally accepted accounting principles (GAAP) requirements. This project required broad changes to the SQL database structures, internal customer care, fulfillment processes, and the eCommerce website. Payment processing had to change. New .NET applications were needed to support customer care and provide an auditable record of new products and price changes. As everything was so tightly coupled, most of the project had to be deployed simultaneously, with extensive data migration and a hard deadline.

Everything but the website work was outsourced to an offshore company whose owner was an architect and worked in our office for the project's duration. We identified product owners for the new applications and key stakeholders in each fulfillment team and hired a technical PM. We prioritized everything we could roll out before the main launch and got that done. Detailed deployment planning ensured the rollout went smoothly, and we met our deadline, giving finance the necessary window to prepare the S-1 filing.

The company delayed its IPO twice and went public in June 2021 with a
$7.5-billion valuation.

Develop and Operationalize Subscription Products

Prototyped, iterated, and operationalized subscription products as a major new product offering, working closely with the business owner.

The executive team wanted to bundle legal subscription services with the legal documents already part of the product suite. Since this affected both Fulfillment operations and Finance, it was more than a matter of simply testing conversion on the website. For each offer tested, the cohort of purchasers had to be specially handled to ensure they received the services paid for and expedited the order if that was part of the offer. The cohort had to be clearly marked so Finance could perform the financial analysis for each offer tested and correctly determine the revenue recognition schedule.

As soon as subscriptions seemed viable, the FileNet fulfillment workflow was extended to include subscription features. The website also was modified to ensure the features available via My Account were accessible with an active subscription and not accessible if the subscription ended.

Personalities were a challenge in this project, but eventually, the business owner for this product line became my favorite business owner to work with.

Subscription products were responsible for 50% of the revenue growth that provided the company with a $5 billion valuation at IPO.

Build SaaS Product for a New Startup

Took over product and project management of an in-house product, partially developed a SaaS application, and brought it to launch as a well-designed, modern application.

This knowledge management application was conceived by a lawyer who built a working prototype for his own use. He had assembled a part-time development team to move it to AWS and complete the development for launch as a SaaS product.

I was hired as a project manager because the lead developer could no longer manage the work. However, it was immediately apparent that the real need was for a product owner. No single feature was complete or even fully articulated. There were no documented requirements. The UI was grid-based and outdated.

My approach was three-pronged: 1) work with the owner to help him get clarity in this thinking about each feature and capture the requirements as user stories; 2) hire a skilled team that could build the application; 3) apply rigor by implementing Agile processes.

The team was built over time, starting with one senior developer. The team grew to three developers, a QA engineer, and finally a designer, who completely redesigned the application. As soon as full-time developers were on board, we switched to complete Agile.

We supported the virtual American Bar Tech show in March 2021 with a soft launch. Completed the remaining phase-1 features during Q3 2021.

Engineering Process Transformation

Instituted standard software development, testing, and release processes in a fast-growing, seven-year-old startup.

LegalZoom needed to mature its IT processes to take the following steps in growth. There were many challenges, including minimal QA and no development, testing, and staging environments, no release process, and inconsistent use of source control. The developer mindset was process-averse, thinking that the process would hinder rather than help.

I performed a deep-dive discovery to inventory all servers and their contents that comprised the platform and to identify stakeholders and the workflows in each fulfillment team. We then built and tested the environments, enlisting these stakeholders as core team members for testing. We also formed a QA team and created a SharePoint workflow for managing releases.

The developer mindset changed gradually via multiple discussions and some notable failures. Still, persistence paid off, and the result was a more mature process that could support the next step of preparing for IPO.

SharePoint Sites Migration from On-premise to Cloud

Moved all SharePoint sites to SharePoint Online and decommissioned local servers.

The agency's SharePoint team sites were running on obsolete SharePoint and Windows Server versions. Sites were large and stale, and the OCIO had no relationship with the program office stakeholders to engage in the cleanup. A previous failed attempt to build an on-premise server farm and upgrade the team sites had taken 15 months as a waterfall project. Even though moving to SharePoint Online was a far better solution than building new servers on-premises, some management perceived the move to the cloud to be high risk.

The first step was to get executive buy-in to move to SharePoint Online. Next was to identify stakeholders in each program office who could help determine what to keep, archive, or delete. We could archive and delete about half of the 1.5 terabytes of data.

The department had not yet transitioned to Agile. Still, I used a modified Agile approach, grouping the sites into sprints for migration and test by the development team, with user acceptance testing (UAT) and go-live in subsequent sprints. The SharePoint contractor team was energized and excited to be going to the cloud, and we completed the project in seven months.

Website and Database Internationalization and Localization

Led a project to localize Napster's platform for launch in Germany and Japan.

Researched and selected the vendor, then led the project to internationalize the Oracle PHP platform to handle double-byte characters. Managed the follow-on efforts to localize into German and then Japanese. Worked with the vendor and local and in-country resources to support successful launches in both countries.
1973 - 1974

Bachelor's Degree in Education

University of Tennessee - Knoxville, Tennessee, USA

1969 - 1973

Bachelor's Degree in Liberal Arts

University of Tennessee - Knoxville, Tennessee, USA

APRIL 2015 - APRIL 2017

Certified Scrum Master

Scrum Alliance

MARCH 2005 - MARCH 2008

Project Management Professional (PMP)

Project Management Institute (PMI)


Zoom, Visio, Balsamiq Mockups, Slack, Jira, Pivotal Tracker, Confluence


Requirements Analysis, Scrum, Agile, Agile Software Development, Kanban, Agile Project Management, Software Testing


SharePoint, Azure


Product Owner, Product Ownership, Business Analysis, Discovery, Project Management, Requirements, Business Requirements, User Requirements, Software Development Management, Project Discovery, Remote Work, Business Process Analysis, Web Applications, Stakeholder Interviews, Cross-functional Collaboration, Microsoft, Delivery, Flowcharts, Technical Documentation, Technical Requirements, Flow Diagrams, Technical Writing, User Flows, Stakeholder Analysis, Stakeholder Engagement, Scrum Master, Startups, Sprint Planning, Clubhouse, Functional Requirements, Remote Team Leadership, Cross-functional Team Leadership, SaaS, User Stories, Sprint Retrospectives, API Integration, Collaboration, Systems Analysis, Process Improvement, IT Project Management, IT Projects, Release Management, New Product Rollout, New Product Development, Stakeholder Management, eCommerce, Software Integration, Data Migration, Lucidchart, Websites, Documentation, Client Presentations, SaaS Product Management, Backlog Grooming, Feature Backlog Prioritization, Stripe API, Legacy Software, Software as a Service (SaaS), Agile Sprints, Google, Backlog Management, Business to Consumer (B2C), Subscriptions, IT Business Analysis, Communication, Customer Support, Project Tracking, COTS, A/B Testing, Vendor Selection, Internationalization, Localization, Salesforce, WordPress Plugins, WordPress eCommerce, Digital Media, Vendor Management, WordPress, Engineering Best Practices, Amazon Web Services (AWS), Social Media, Education

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