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

Verified Expert  in Project Management

Project Manager

Los Angeles, CA, United States
Toptal Member Since
June 25, 2019

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

Project Highlights

Revenue Recognition/S-1 Filing
This project enabled the company to produce auditable financials, meeting GAAP requirements to prepare for an IPO.
Develop and Operationalize Subscription Products
Worked with the business owner to prototype, iterate, and operationalize subscription products as a major new product offering.
Engineering Process Transformation
Instituted standard software development, testing, and release processes in a fast-growing, seven-year-old startup.


Work Experience

IT Manager

2020 - PRESENT
  • Participated with stakeholders and a PR company in a "catalyst" process to identify the organization's current voice and personality.
  • Worked with the internal team and a PR firm to create a new logo. Gathered input from stakeholders and worked collaboratively with the PR firm to create options. Presented survey to the members for selection of the winner.
  • Worked with the PR firm and internal team to approve the design and write content for the new website concurrent with the logo design. Managed testing in prep for rollout. Launched the new site.
  • Collaborated with a PR firm to develop initial rounds of Facebook posts; identified members to take over writing and publishing posts and documented the process.
  • Worked with a PR firm on identifying and optimizing Google search terms to drive traffic to the website.
  • Managed vendor migration of users to new Microsoft 365 account. Selected and engaged a different vendor for ongoing support.
  • Analyzed usage and migrated files from a local server to the cloud.
  • Researched tools to meet various needs and acquired nonprofit licenses if available.

Project Owner and Project Manager

2020 - PRESENT
Saasman Solutions, Inc.
  • Joined this "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 his law practice. The client's first estimate to launch was four to six weeks.
  • Assessed the part-time development team, the development process, the state of requirements for incomplete and not-yet-started "must-have" features, and the application UI/UX. Made recommendations in all areas and was converted 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 (Terraform) for all environments.
  • Functioned as a business analyst, product owner, and scrum master. Implemented Shortcut (Clubhouse) for project management. Wrote stories, maintained the backlog, and led 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.
  • Tasked the development team with identifying and correcting technical debt during the initial design phase, including database design. Thirty-two items with a high impact on maintainability were identified and corrected.
  • Participated in the leadership team throughout the engagement. Provided thought leadership related to process, software and startups. Set up a Kanban board in Shortcut for the marketing, executive, and support teams to better structure their work.

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

2016 - 2018
US Small Business Administration
  • Led the transition of the development team within OCIO from Waterfall to Agile and introduced the use of Jira. Mentored the contractor scrum master, developers, and junior business analysts. Educated career Federal IT employees on Agile practices.
  • Mentored junior business analysts to work with internal customers to capture the workflow behind a work request and to think through the process from a user perspective. This resulted in less wasted developer time and increased customer satisfaction.
  • Participated in writing the 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 each department to clean up their sites. Completed the project in seven months (a previous failed attempt took 15 months).
  • Spearheaded the project to upgrade and migrate all custom SharePoint applications from SharePoint 2010 on local servers to SharePoint 2016 in Azure (IaaS). This was SBA's first success in moving all locally hosted applications to Azure.
  • Functioned 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 UAT.


2015 - 2015
  • Performed discovery for a small nonprofit 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 store (WordPress/WooCommerce) with the accounting system (Sage) and other manual internal legacy processes.
  • Researched and recommended plug-ins to support various desired new features.

Director, 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 in a way that complied with GAAP revenue recognition requirements and provided auditable financials to support an S-1 filing.
  • Served as business process owner for Operations and Finance during prototyping and development of subscription products. Subscription products accounted for 50% of the revenue growth that supported a $5 billion valuation at IPO.
  • Successfully 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 functioned as product owner for the internal applications team. Tools included 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.
  • Functioned as a technical project manager on the Salesforce implementation for Customer Care, including API development, object architecture, interface design, and data migration from RightNow to Salesforce.
  • 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 fulfilled manually.
  • Developed trusted relationships with stakeholders in Operations, all business lines, and corporate departments. They were willing partners in the multiple UAT rounds necessary for major initiatives.
  • Worked closely 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, ensuring all business and usability requirements were met.
  • Managed major releases, including coordinating resources from geographically distributed groups.
  • Researched and selected internationalization and localization vendor, completed projects to prepare the database and web app to handle double-byte character sets, and localized the service for launch in Germany and Japan.
  • Managed 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.
  • Directly 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 technical writing consultants, including screening, interviewing, and hiring.
  • Interviewed engineers for each system module. Asked in-depth questions that required them to think about the interfaces with other modules that they had not considered. Created diagrams to help visualize the missing pieces.
  • Wrote interface control documents, architecture documents, functional and design specifications, release notes, and installation guides for headend components and subsystems for 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 to complete 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%.
  • Proposed and led the delivery of "just enough" documentation set for two prototype projects for the US Marine Corps.
  • Led project 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/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 embed tags to correctly apply the 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.

Revenue Recognition/S-1 Filing

This project enabled the company to produce auditable financials, meeting GAAP requirements to prepare for an IPO.

LegalZoom wanted to prepare for the IPO, but the state of order and financial data could not support 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. Because everything was so tightly coupled, most of the project had to be deployed simultaneously, with extensive data migration and a hard deadline.

We outsourced all but the website work 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 that 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 of 2021, with a valuation of $7.5 billion.

Develop and Operationalize Subscription Products

Worked with the business owner to prototype, iterate, and operationalize subscription products as a major new product offering.

The executive team wanted to bundle legal subscription services with the legal documents already part of the product suite. It was no problem to offer variations of subscription services on the website; the challenge was to effect those changes into the fulfillment system so customers got what they had purchased and would lose access to features if the subscription lapsed.

It was not feasible to modify all downstream processes for each iteration of the product offering, so initially, most services were fulfilled manually; a few could be configured for a certain block of time via the product catalog. Until the subscription features were firmly defined, each cohort of purchasers had to be tracked throughout their subscription life to ensure access.

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

Subscriptions now account for 50% of revenue and result in a $5 billion valuation at IPO.

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 next steps in growth. There were many challenges: minimal QA and no dev/test/staging environments, no auditable release process, and source control was used inconsistently. The developer mindset was process-averse, thinking that the process would hinder rather than help.

We 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 built 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 versions of SharePoint and Windows Server. The 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 of the 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 identify what to keep, archive, or delete. We could archive/delete about half of the 1.5 TB of data.

The department had not yet transitioned to Agile, but I used a modified Agile approach, grouping the sites into "sprints" for migration and test by the dev team, with 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 7 months.

Upgrade SharePoint Applications and Move to Azure

Led the upgrade/migration of custom SharePoint applications from SharePoint 2010 on premises to SharePoint 2016 in Azure.

A software upgrade had been pending for several years with no forward progress, and new OCIO management wanted to move all local data center servers to Azure (IaaS). Challenges were due to limited resources, lack of access to servers, lack of expertise, and frequent interruptions for production support. My main tasks were to convince management that others should step up and learn how to do production support, to obtain training and support from Microsoft for the resources working on the project, to help the primary resource think through technical issues, and to get permission from operations for the primary resource to have extended server access while he was learning how to set up and configure the server farm. The farms were successfully built in the on-premise data center, and the applications were upgraded and run locally until the Azure environment was ready. This was the first success in moving internal customer-facing applications to Azure.

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, 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)


Microsoft Word, Visio, Balsamiq Mockups, Google Docs, Jira, Pivotal Tracker, Salesforce, Confluence, Slack


User Acceptance Testing (UAT), Waterfall Delivery, Agile Software Development, Scrum, Agile, Kanban, Agile Project Management, Requirements Analysis

Industry Expertise

Digital Media, Nonprofits


SharePoint, WordPress, Amazon Web Services (AWS), Azure


IT Project Management, Project Discovery, Software Development Management, Project Management, Business Analysis, Remote Work, Startups, Product Ownership, Business Requirements, User Requirements, Web Applications, Requirements, Stakeholder Interviews, Cross-functional Collaboration, Software Development, Distributed Team Management, Project Scoping, Agile Sprints, Process Documentation, Operational Workflow, Technical Writing, Project Coordination, eCommerce, Process Improvement, Data Migration, Software Integration, Scrum Master, Clubhouse, New Product Development, Functional Requirements, Business Process Analysis, Websites, Documentation, Client Presentations, Vendor Selection, Stakeholder Engagement, Product Management, SaaS Design, SaaS Product Management, Cross-functional Team Leadership, Sprint Planning, Sprint Ceremonies, Sprint Retrospectives, User Stories, Backlog Grooming, Feature Backlog Prioritization, API Integration, Stripe, Legacy Software, Waterfall Methodology, Lucidchart, Software as a Service (SaaS), SaaS, Stakeholder Management, New Product Rollout, Process Flows, Discovery Workshops, Product Development, Project Planning, Customer Relationship Management (CRM), Risk Management, Cloud Migration, IT Infrastructure, Business Process Flow (BPF), Technical Project Management, Operations, Service Design, Cross-departmental Collaboration, Product Launch, Localization, Vendor Management, WordPress eCommerce, WordPress Plugins, Sales Tax, Release Management, QA Leadership, A/B Testing, Financials, Internationalization, Engineering Best Practices, Stripe API, Startup Consulting, User Experience (UX), User Interface (UI), Web UI, IT Helpdesk, Branding

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