VP of Engineering

📋 Description

• Transform how our flat engineering organization scales with agents. Maintain and enhance high talent density. Drive operational efficiency by utilizing AI. Establish a forward-looking technical vision that aligns with business objectives.

• Influence the way Counterpart develops software in an AI-driven environment. Collaborate with the CEO, engineering leaders, and technical product managers to refine our development practices, operational strategies, and output optimization.

• Oversee Engineering as a function that allocates personnel and agents across competing initiatives. Take ownership of allocation decisions, engineering standards, delivery quality, and the frameworks that ensure project teams uphold technical coherence while working autonomously.

• Manage the infrastructure that facilitates AI-native engineering: developer experience, AI and data platforms, and system infrastructure.

• Lead hiring, performance management, compensation, and talent development for the engineering team. Collaborate with the Head of People and the Chief of Staff to ensure the Engineering staff model and operations are in sync with the company’s operational rhythm.

• Ensure our systems uphold high standards for reliability, observability, and security, adhering to compliance requirements such as SOC 2, HIPAA, and NYC Cybersecurity regulations.

• Represent Counterpart's technological capabilities both internally and externally, aligning with leadership, partners, and investors to convey vision and execution.

⛳️ Requirements

• More than 12 years of engineering leadership experience, having guided engineering organizations through various stages of company evolution. You have engaged regularly with the board, investors, and executive leadership, and understand what exceptional engineering organizations look like at different stages, as well as which structures become ineffective as the company scales.

• A well-defined perspective on what AI-native engineering entails. This goes beyond merely utilizing AI tools; you have deeply considered how AI transforms the role of engineers, the configuration of engineering organizations, and the economics of software delivery. You are well-versed in industry trends and can substantiate your viewpoints, while also recognizing where industry hype diverges from reality.

• Profound technical knowledge that enables you to form strong opinions on system architecture, AI and data infrastructure, and deployment pipelines.

• Strong customer empathy and product intuition. You view business and technology as interconnected, and always seek ways to empower the business through technology: developing new capabilities while enhancing the underlying systems. You avoid refactoring for its own sake and refrain from launching features that cannot be supported by the underlying architecture.

• Proven experience in leading fully distributed teams characterized by high trust and accountability.

• Experience in regulated sectors (insurance, fintech, healthcare, or similar) is a significant advantage. You recognize that compliance (SOC 2, HIPAA, state cybersecurity regulations) is an integral aspect of system architecture, not an afterthought.

🏝️ Benefits

• Fully remote workplace

• Unlimited Vacation: We provide flexible time off, allowing you to take time as needed.

• Work from Anywhere: Counterpart operates as a fully distributed company, meaning there is no central office. Employees are free to work from wherever they are most productive, with opportunities for in-person team meetings a couple of times each year.

• Stock Options

• Health, Dental, and Vision Coverage

• 401(k) Retirement Plan

• Parental Leave

• Home Office Allowance: To help you set up your home office with essential equipment and accessories.

• Wellness Stipend

• Book stipend

• Professional Development Reimbursement

• No working birthdays: Enjoy your birthday off, allowing you to relax, celebrate your special day, and spend time with loved ones.

• Charitable Contribution Matching