Below is a selection of professional projects I’ve led. Some specific details and metrics have been intentionally left out for company privacy.
Operational Planning:
Streamlining Complex Annual Planning Process
A nonprofit organization needed a streamlined systematic approach to its annual operation and budget planning cycle that aligned with its affiliate organization’s planning cycle.
With two separate entities and a set of newly written bylaws requiring coordination in planning, the organizations needed to ensure that all requirements were met and the correct parties were involved and consulted during the process which had overlapping timelines.
To address this, I used the waterfall project approach and developed a detailed timeline using Workfront to outline a transparent roadmap with key milestones, required lag times, and deadlines for presentations and reporting to stakeholders including public and board members. I worked with leadership to formalize a steering committee, outlined a stakeholder management plan and communications plan to ensure the right parties were included in discussions at the right times and that the decision makers were clear.
As a result, the process ran smoothly and successfully by meeting all deadlines, increasing public engagement, and providing a solid foundation for the process to run well the following year. By establishing a clear and transparent process and creating a new governance structure, the organization was better prepared to monitor risks and address larger issues that may arise in the future.
Strategic Project:
Implementing an Organization Wide Policy Change
A healthcare nonprofit organization needed to implement a state level policy change requiring healthcare providers to enable patient access to behavioral healthcare at the primary care level.
The project would entail changes to multiple IT systems and require extensive changes to provider contracts. I set up this project with a hybrid approach to ensure flexibility in addressing the IT changes in iterations and managing the overall project with a hard deadline in a more waterfall approach.
Working with many cross-functional teams including IT, contract managers, finance, and clinical providers in a remote environment proved challenging. With the added complexity of rapid changes in procedures, technical capabilities and human resources that came with implementing this project during the COVID pandemic, I held several check-ins with smaller workgroups and a weekly larger all team leads check-in where we could address overlapping issues and discuss developing risks.
Given the unforeseen delays partly due to COVID and other priority shifts, the project began to veer off track and extend beyond the original deadline. To address this, I brought key issues to the steering committee along with options for how we could address them and move the project to a closed status with transition to operational mode. This ultimately helped get the project back on track and stay in scope with only minor adjustments to the overall timeline. The work moved to operational status and the targeted healthcare providers were successfully able to allow patients access to behavioral healthcare.
Process Improvement:
Process Mapping for Improved Client and Staff Satisfaction
A nonprofit healthcare organization was missing opportunities to establish value based payment structures with providers and creating re-work for staff due to a complicated and unclear process that crossed many teams and departments. This was causing an increase in provider complaints as well as an increase in the amount of time staff were utilizing to try to resolve the complaints.
I established a team with representatives from each of the departments that touched any part of the process and interviewed each team member to identify their pieces of the process puzzle, then presented a pieced together version of the entire process where the team together identified areas of discrepancy and pain points or problem areas. With a visual outline of the entire process beginning to end, this helped the team to identify areas that were working well and hone in on areas that were causing trouble, whether it was an unclear role or handoff or a need for a specific tool that was lacking.
Through this process, I facilitated team workshops to help identify and rank prioritized solutions. This included a short term need for clear roles to be defined for reviewers and decision makers, and also a longer term document tracking system implementation to replace the use of Excel sheets on individual hard drives, which were no longer sufficient for the interdependent process. I worked with the team to implement the low effort, high impact improvements including creating a shared RACI model to clearly identify each team and individual’s role in the process and a visual process map with key decision points and team handoffs for all teams to reference. This saved staff time on re-work and reduced provider complaints by improving communication and process transparency. The longer term priority of implementing a document tracking system was also approved for a project of its own.
Grant Program Management:
Overseeing a Transitioning Grant Program to Completion
A global advocacy nonprofit had been awarded an extended grant to provide 8 sub-recipients funding to implement community (Internet) network projects in cities throughout the southeastern US. The challenge I was presented, was that an unforeseen budget issue had resulted in having to transition the large body of prior grant work and next round of funding work from an external consultant to a very small in-house team going forward, presenting a significant resourcing risk. Additionally, a key in-house expert that had been assigned to provide technical guidance to the sub-recipients was also leaving the organization, which presented not only a resourcing risk to the success of the program, but also concern from both the grantor and the fund recipients.
The organization was concerned about several items in transition; oversight of the grant budget, execution of contracts for the portfolio of projects, and being able to track deliverables once work started. Taking these concerns into consideration, I started the transition by meeting with the contractor to understand the high-level goals of the grant work and to outline the key players, risks and issues, and tasks in progress. To address the budget concerns and loss of a required resource, I set up a steering committee to help guide decisions that could impact the grant funder and/or organization such as budget oversight, loss of resources and changes to scope of each sub-recipient project. I set up a timeline that mapped high level program and individual milestones required of each project and tracked the overall health of the portfolio as well as each sub-recipient’s work. Because projects from the first round of funding were still in progress and also had to be monitored to ensure funds were being spent appropriately, I included these in an overall timeline with key milestones to monitor and report on bi-weekly.
There were many challenges for each sub-recipient including lingering issues from COVID such as supply chain issues, loss of human resources, leadership changes as well as being unable to travel and problem solve or collaborate in person when needed. I worked with each team, bringing in internal expertise where needed to help brainstorm and problem solve to keep their projects moving forward and solicit information that would fulfill our funder’s needs. The many sub-recipient delays resulted in a delay to the overall grant timeline. However, all projects was completed to satisfaction or progressing as expected by the end of the funding contract except one which was unexpectedly cancelled leaving a significant amount of funding left unspent. Since the funder was pleased with the progress and communication transparency we achieved, they agreed to allow use of the remaining funds to hold a very successful in-person training/educational event for the fund recipients to share insights and discuss future funding and collaborations. In all, the $1.5m in funding was spent within the scope of the grant funder’s expectations and produced successful stories for public communication.
Agile Team Leadership:
Leading a Small Dispersed Team to a Successful Fundraising Proposal
A nonprofit organization was struggling with meeting fundraising goals for the year to meet its public support test. There had been a successful first phase project that gained popularity and the organization saw an opportunity to develop a fundraising effort around this success with a goal of raising a significant portion of its annual target.
The challenge was that to gain approval to move forward with a fundraising effort, leadership determined they would need a strong fundraising strategy proposal on a very tight two week turnaround. I led a team of 5 representatives from various departments including Fundraising, Grant Management, Marketing and Communications, and Engagement to create the proposal for presentation to leadership. The all-remote team spanned several different time zones making synchronous problem solving and brainstorming a challenge. With a short kick off with all team members, I communicated the agile framework we would use including Kanban style task management and sometimes asynchronous ‘stand-up’ meetings to report progress and roadblocks. This involved a live Zoom call that was recorded for those team members unable to attend and a virtual whiteboard to report their thoughts after they had a chance to review the recording. I helped the group identify tasks that would need to be completed, take ownership of specific tasks, handoff when needed, and report back in a virtual asynchronous manner that enabled the team to keep moving forward despite the time zone differences.
The team ultimately met the challenge, completing a very thorough proposal ahead of the deadline. To gain approval, I created an asynchronous presentation opportunity for leadership where the team provided a detailed overview of the plan via video and employed a Slack Q&A to address any concerns before leadership approved the plan to move forward. Although the overall fundraising goal was unfortunately not met, I led a reflection process to help the team identify what went well and what could be improved for future proposals and fundraising efforts that leadership could reference in the future. Through this process, the group identified that more advanced strategic planning and more opportunities for synchronous work would help increase creativity, reduce burnout and improve cross-team coordination throughout the organization that could lead to greater success.
Jessica A. Castillo 