Job Description

aiola is looking for a CTO to own the company's technology vision, technical strategy, architecture, and engineering organization, and to serve as a key technology partner to the CEO and business. This is a hands-on executive leadership role for someone who is comfortable operating at both the strategic and technical level — someone who can set the direction while stepping into the details when it matters.

You will lead a team of ~15 engineers, own the technical roadmap across our voice AI and agent orchestration stack, and ensure that technology directly supports the company's product and business objectives. You will work closely with Sales and customers, including joining customer calls to run technical demos and answer deep, complex technical questions from Fortune 500 prospects.

Requirements

• Proven experience as a CTO, VP R&D, Head of Engineering, or similar senior technical leadership role.
• Track record of leading and scaling engineering teams (~15+ people).
• Strong hands-on technical background — able to go deep on architecture and implementation, not just manage from a distance.
• Experience with data quality / imperfect-data challenges in production ML systems.
• Experience building or scaling multi-agent AI systems / agent orchestration.
• Track record building enterprise-grade, high-reliability systems at scale for Fortune 500 / enterprise customers.
• Excellent communication skills, with experience in customer-facing technical settings (demos, technical sales support, POCs).
• Comfortable working closely and frequently with Sales, Product, and other business functions.
• Experience in a startup / scale-up environment, with the ability to balance long-term technology strategy with hands-on execution.

Responsibilities

• Own aiola's overall technology vision, strategy, architecture, and technical roadmap, aligned with the company's business and product goals.
• Lead, grow, and mentor an R&D team of ~15 people across voice AI, agent orchestration, and Salesforce/CRM integration.
• Set the technical direction for a platform that must perform reliably in noisy, real-world field conditions — movement, background noise, varied accents, and imperfect data.
• Drive the architecture and scaling of intelligent agent orchestration — the 'squad of specialized sales agents' behind each field rep's personal AI agent.
• Ensure the platform delivers enterprise-grade performance, reliability, security, and scalability for Fortune 500 customers, in production — not just in demos.
• Partner closely with the CEO, Product, Sales, and executive leadership on technology decisions, priorities, trade-offs, and execution.
• Represent technology in customer-facing engagements: deliver live product demos and serve as the senior technical authority in customer conversations.
• Translate complex technical concepts into clear, credible answers for enterprise prospects, including tough technical objections around accuracy, security, reliability, and integration depth.
• Drive engineering best practices, architecture decisions, development standards, and delivery quality across the organization.
• Build a strong engineering culture focused on ownership, speed, quality, and pragmatic execution in a startup / scale-up environment.
• Be hands-on when needed — reviewing code and architecture, challenging technical decisions, or diving into a hard technical problem alongside the team.

Big Pluses

• Background in enterprise sales enablement or CRM-connected platforms, including Salesforce integrations at an architectural level.
• Experience with voice AI / speech technology (ASR, voice interfaces) in real-world, noisy conditions — movement, background noise, and accents.
• Familiarity with data quality / imperfect-data challenges in production ML systems