Completing a Successful Reorganization within a Well-Established Company

Jason De Oliveira



Organizational Challenges in a Well-Established Organization

I worked on organizational changes with a previous company, such as replatforming, aligning, and introducing agility into the organization. As the CTO, I had around 160 collaborators, as the organization was large and well-established. These collaborators were split into four divisions: product, engineering, innovation, and IT. As a company, our goal was to provide cybersecurity and data security tools to consumers. This meant that we needed the latest algorithms and methods to secure data and ensure restricted access. Having teams dedicated to specific departments was meant to streamline the process, although its functionality was questionable.

When I arrived, these teams were already formed and were trying to implement agile. However, both the engineering and product teams had just made important changes in the prior years, slowing the success of agile. The organization was using an external consulting company, running audits, and implementing a new organization involving agile teams that changed multiple times per month. In my opinion, these changes were too much, and the structure lacked stability, decreasing teams’ motivation and happiness.

Completing the Reorganization

Running an Audit:

My first step of the project was to do an audit to understand the company’s situation. The corporation had over 20 years of existence with multiple organizations, skills, and large growth. When the company had around 50 people on its teams, I learned that a straightforward scrum system performed their needs. As they grew to 160 individuals, the concerns of coordination, roadmap planning, and the organization became increasingly important. If a single team missed a deadline, it could completely impact the roadmap for the rest of the company.

Platform Approach and Product Execution:

Some of the organization’s projects were autonomous. However, our goal was to provide a fully implemented platform approach. For me, this was an essential step in terms of organization. With multiple products linked to our company, if multiple teams worked independently and siloed, these products would become siloed as well. I had to address the connection between the organization, and the way products were delivered.

Alignment for New Teams:

The company had recently acquired other companies to increase our challenges, and those teams were not fully integrated. One of my goals was to amalgamate these teams into the global organization so that everything was clear. To do this, I aligned job descriptions and responsibilities between our company and those that we acquired, ensuring that each role was cohesive in our organization.

Collaborating with Leadership and Teams:

At this point, I began working together with each team and each manager, putting in place the heads of each department. It was vital to come to each conversation with an open mind and not bring my solution to the table. Working together with managers and teams, we created an organizational structure that was much more aligned with the company as a whole.

Seeing that I was only six months into this company, I didn’t have a great rapport with teams and managers as others did. Because of this, I put in place a recruitment process for managers, giving everybody in the company the ability to pick the best candidate. With these new managers, we worked to instill the new organization.

Once the key players were in place, our team looked back at the history of our company. We looked through the previous structures of our company and what worked well and what did not. From there, we created a list of the topics we needed to address with our new organization. Our list included addressing teams working collaboratively rather than in silos.

After leadership was in alignment, I scheduled a town hall meeting, discussing the reorganization. Topics of conversation included: expectations of specific roles, soft skills needed, and any other concerns brought to our attention. Our company held bottom-up workshops, where individuals brainstormed topics that needed changing and proposed topics to increase efficiency.

Following Up:

After beginning this reorganization, I put in place KPIs that allowed me to follow up with my team. When I found individuals were underperforming or lacked motivation, I increased my interest and tried to help my team members forward. After following through, I always remembered to accompany this help with a follow-up message a week or so later, simply asking if everything was still going well. With large teams, middle managers allowed me the clarity to see the challenges of my team.

Keys for a Successful Reorganization

  • When completing a reorganization, it’s not just about the hierarchy but also the processes, objectives, and pains you want to address. Keeping the focus on these key points will focus the reorganization on the true purpose.
  • It is vital to train the key stakeholders involved in the reorganization about what language to use. Change is frightening for many individuals, and hearing the words reorganization can strike nerves with certain team members. Learning how to deescalate situations and provide empathy to these conversations will streamline the process.

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Jason De Oliveira


CommunicationOrganizational StrategyEngineering ManagementLeadership RolesCTOAgile, Scrum & Kanban

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