Chief Technology Officer

Location: Boston (Hybrid, 2 days in office)

Opportunity for Impact

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 BigTinCan’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.

Role & Responsibilities

• 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 BigTinCan 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.

Professional Qualifications

• 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.

Personal Characteristics 

• The CTO must have the business acumen, commercial orientation, and overall leadership style to be a key member on a highly collaborative and experienced senior leadership team.
• Humble and Authentic - Lacks ego and engages colleagues in a transparent and “real” fashion.
• Results-Oriented - Focused on achieving success and holding others accountable.
• Strategic - Ability to understand the big picture and operationalize it.
• People-oriented - Thinks about how people will be affected and skilled at dealing with others.
• Communication - Exceptional EQ and knows how to communicate effectively with all levels of the company.
• Intellectual Curiosity - Demonstrates the ability to learn quickly and has a high mental capacity.
• Decisive - Clearly defines a path forward and is comfortable taking action to achieve a goal.

Company Highlights: 

Welcome to the new era of revenue effectiveness. The merger of Showpad and Bigtincan is creating the first AI-powered platform to strengthen the entire field selling motion. 

By unifying two industry-acclaimed solutions for content, readiness, engagement, and intelligence into a single operating system, we are delivering unrivaled scale and accelerated growth for our 2,000+ combined customers worldwide, including leaders in manufacturing (Dow, Dupont), healthcare (Fujifilm, Kaiser Permanente, Johnson&Johnson), CPG (Smucker’s, Mitsubishi, Stanley Black & Decker), and enterprise tech (HID, CultureAmp, LastPass). 

Acclaimed by analysts and adored by customers, we’re recognized as a Leader in the Forrester Wave™ Revenue Enablement Platforms, honored by Gartner as a Customers’ Choice in Revenue Enablement Platforms, and, together, endorsed by nearly 3,000 5-star customer reviews on G2. 

United, we’re focused on powering the next generation of field selling success through a more holistic engine that creates lasting value for our customers and a new vision for our category.

Discover the revenue team outcomes we’re driving together at showpad.com.

What you can expect from Showpad

We welcome every voice and are committed to building a truly inclusive environment where your differences are not just welcomed, they are celebrated. We’re building a best-in-class experience for our employees and are always identifying opportunities to encourage our team to be their authentic selves. Whether that’s paid parental leave, paid holidays (including Juneteenth and paid time off to vote), paid time off to volunteer at non-profit organizations, personal development opportunities or professional stretch assignments, you can expect Showpad to support you. 

We are committed to creating a diverse and inclusive organization and are proud to be an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, pregnancy, disability, age, veteran status, or other dimensions of identity.

DISCLAIMER: For this search, we collaborate with an external executive search partner: true. Your application will be reviewed by their team. Only the retained candidates will hear from their consultants and be invited for a first screening call.

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