VP of Engineering

Sigma Squared • Cambridge, MA

75d

About The Position

We’re looking for a VP of Engineering to join the team here at Sigma Squared and own the intersection of product development and technical execution. In this role, you’ll be responsible for shaping our technology initiatives and scaling the engineering organization as we bring a world-class talent insights & analytics platform to market. Reporting directly to the CEO, you’ll manage the engineering team directly and collaborate with the executive leadership team to define and build innovative features that drive customer value. This role blends deep technical leadership with product-first thinking and startup agility.

Requirements

• Proven experience as a Technical leader in early/growth stage companies.
• Strong technical background with deep expertise in cloud-native architectures, data platforms, APIs, and machine learning systems.
• Demonstrated success leading product-driven development efforts, ideally in a B2B SaaS organization.
• Experience managing and scaling technical teams in fast-paced, dynamic environments.
• Strong understanding of security, privacy, and compliance requirements in SaaS.
• Entrepreneurial mindset with a bias for action and experimentation.

Responsibilities

• Partner with Product and Design to translate business goals into scalable technical solutions.
• Drive continuous feature development, leveraging AI, LLM’s, and data science to enhance platform capabilities.
• Ensure scalability, reliability, and performance of the platform as we grow.
• Oversee devops, infrastructure, and cloud management (e.g., AWS).
• Follow best practices in security, data privacy, uptime, and scalability.
• Push the boundaries of our tech stack, tools, infrastructure, and security protocols through adoption, modernization, or experimentation.
• Champion agile methodologies and rapid iteration cycles to accelerate innovation and delivery.
• Lead, mentor and scale a high-performing engineering team.
• Foster a collaborative, inclusive, and execution-oriented culture.

Benefits

• A uniquely compelling opportunity to advance our mission with world-class colleagues, a tremendous amount of responsibility and autonomy, and access to all the information you need to succeed.
• Competitive salary, bonus plan and equity package.
• Comprehensive health, dental, vision, and FSA/HSA benefits.
• 401(k) with employer match.
• Flexible PTO and all the usual holidays.
• Employer-paid life and disability insurance.
• Educational assistance and training reimbursement.
• Employee assistance with no-cost counseling, referrals, and resources.
• Financial well-being support with no-cost consultations, personalized assessments, and coaching.
• Adoption assistance, free legal support, and more.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Number of Employees: 11-50 employees