Chief Technology Officer

Location: Boston (Hybrid, 2 days in office)

The CTO will play a pivotal role in redefining the future of revenue enablement by unifying Showpad’s multi-product portfolio into a modern, scalable platform used by sellers and marketers around the world. This leader will be central to shaping the technical strategy that brings together Showpad and Big Tin Can ’s combined assets, modernizing to a unified platform, and accelerating the company’s shift toward AI‑powered enablement.

As a key member of the senior team, the CTO will be instrumental in building a high‑performing global engineering organization, establishing architectural clarity across 17+ products, and positioning Showpad for its next stage of profitable growth. This is a rare opportunity to lead a complex technology transformation at scale while helping define the next generation of an industry‑leading platform.

• Lead and transform Showpad’s global engineering organization, ensuring teams are aligned, high‑performing, and executing consistently across geographies.
• Drive the unification and modernization of Showpad’s multi‑product estate (17+ products), consolidating legacy Showpad and Big Tin Can  systems into a single, scalable, cloud‑first, AI‑enabled platform.
• Establish and execute the architectural strategy required to migrate long‑tail acquired products toward a modern core platform, balancing near‑term customer commitments with long‑term simplification.
• Implement disciplined engineering processes, KPIs, and operating mechanisms to increase development velocity, improve quality, and materially reduce cost across global teams.
• Strengthen the global delivery model with a particular focus on scaling Pune as a major engineering hub while maintaining Belgium as a center of excellence and Boston as the leadership anchor.
• Partner closely with Product to translate the commercial strategy into a clear, focused engineering roadmap, ensuring faster innovation around AI, content intelligence, coaching, and buyer engagement workflows.
• Engage directly with enterprise customers and strategic partners, representing technical credibility and helping shape the evolution of the next‑gen Enablement OS.
• Develop leadership depth and organizational cohesion across distributed teams, mentoring senior engineering leaders and instilling a culture of accountability, transparency, and technical excellence.
• Support the CEO and investors in future M&A diligence and integration, including tech evaluation, consolidation planning, and organizational integration.
• Report regularly to the CEO and PE sponsors on engineering performance, platform progress, risk management, and milestones tied to EBITDA improvement and value‑creation goals.

• Extensive experience leading globally distributed engineering organizations (150–500+ engineers), ideally across multiple hubs such as the U.S., India, Eastern Europe, and Western Europe.
• Proven success in unifying and modernizing multi‑product SaaS portfolios, particularly in environments with differing tech stacks, mixed architectures, or multiple acquired codebases.
• Demonstrated ability to drive engineering transformation in a PE‑backed or financially disciplined environment, improving velocity, quality, and cost efficiency while supporting EBITDA expansion.
• Hands‑on technical depth across modern cloud architectures, data platforms, and AI/ML‑powered product capabilities.
• Strong customer‑facing presence with credibility in enterprise SaaS, capable of representing engineering to strategic customers, partners, and executive stakeholders.
• Track record of aligning engineering strategy with business outcomes, including platform simplification, customer experience improvements, predictable delivery, and scalable global execution.
• Experience building leadership depth in global teams and driving cultural cohesion across geographically dispersed engineering organizations.
• Comfort operating in complex, high‑change environments with multiple stakeholders, legacy constraints, and a need for architectural clarity and decisive prioritization.

• The CTO must have the…