The Challenge

A fast-growing data intelligence and visualization software company faced a critical juncture in its journey. Its legacy platform, while functional, was outdated and unable to meet the demands of a rapidly evolving market and acquiring enterprise clients. To remain competitive and scale effectively, the company needed to transition to a modern, Cloud-based SaaS model. This transformation was essential not only for operational scalability but also to align with market expectations and investor priorities.

However, the company’s small engineering team was stretched thin, tasked with balancing the maintenance of the legacy platform while also building the new SaaS product. The complexity of this dual challenge made it difficult to prioritize resources and maintain team morale.

At the same time, the company was preparing to secure a significant investment to accelerate its growth. This required not only a solid modernization strategy but also a compelling narrative that demonstrated scalability, innovation, and ROI potential to investors. The newly appointed CTO, while highly skilled, needed guidance to navigate these challenges and articulate the company’s vision in a way that would inspire investor confidence.

The Approach

Steven stepped in as a Strategic Advisor to provide leadership, operational clarity, and hands-on coaching to the new CTO. The goal was twofold: to create a clear and actionable plan for the company’s SaaS transformation and to position the company as a compelling investment opportunity. His approach was carefully structured to address both the technical and business aspects of the challenge.

Assessing the Current State and Defining Priorities

• Conducted a comprehensive review of the company’s technology stack, engineering processes, and product roadmap. This assessment identified gaps in scalability, inefficiencies in legacy platform support, and areas where the team was stretched too thin.
• Collaborated with the CTO to prioritize immediate needs versus long-term goals, ensuring the team’s focus was aligned with the company’s broader vision.

Crafting a Technology Modernization Strategy

• Developed a phased, 3-year roadmap to transition from the legacy platform to a Cloud-native SaaS solution.
  
  Phase 1: Stabilize and optimize the legacy platform to reduce the burden on the engineering team.
  
  Phase 2: Build foundational SaaS features, focusing on scalability, security, and modularity.
  
  Phase 3: Fully transition to a Cloud-native SaaS model, integrating advanced capabilities like analytics and data visualization enhancements.
• Ensured the roadmap balanced innovation with risk management, allowing the company to maintain operational continuity while progressively modernizing.

Strengthening the Engineering Organization

• Identified resource gaps within the engineering team and implemented strategies to address them.
• Introduced new workflows and tools to improve team efficiency and resource allocation.
• Coached the CTO on leadership practices to empower and motivate the team, fostering a culture of collaboration and innovation.
• Designed a plan to strategically grow the engineering team, bringing in specialists where necessary while upskilling existing members to meet the demands of the SaaS transition.

Aligning Technology with Business Goals

• Established technical KPIs that directly aligned with the company’s business objectives, such as scalability, customer retention, and operational efficiency. These KPIs provided measurable milestones for both internal progress and investor reporting.
• Introduced governance and Agile practices to ensure timely and high-quality delivery of SaaS features.

Preparing for Investor Success

• Worked closely with the CTO and leadership team to craft a compelling narrative for investor pitches.
• Highlighted the strategic vision and roadmap for the SaaS transformation, showcasing how the new platform would enable market expansion, scalability, and significant ROI.
• Emphasized the company’s ability to manage the legacy platform while innovating, ensuring operational continuity during the transition.
  Presented clear, data-driven projections for growth, backed by the technical KPIs and phased roadmap.
• Provided coaching and feedback to the CTO to ensure a confident, polished delivery during investor presentations.