Technical Chief of Staff to the CTO

Technical Chief of Staff to the CTO at Ladders

Our client, a leader in the Information Technology space, is seeking a Technical Chief of Staff to the CTO. This pivotal role offers a unique opportunity to deliver significant outcomes for customers and stakeholders, collaborate cross-functionally, and take ownership of key priorities, providing substantial visibility, growth, and impact.

Location: Remote (US-based candidates only, no visa sponsorship available)Compensation: $167,000 – $313,000 annually.

Responsibilities

• Lead execution of the CTO's 3-year technical vision by aligning engineering and product strategy
• Drive technical content for board materials and investor presentations, including competitive intelligence
• Document and evolve the CTO's operating model within the company handbook
• Oversee company's internal AI transformation and facilitate rigorous testing of AI capabilities
• Implement standardized R&D metrics frameworks to improve engineering outcomes
• Collaborate with Finance on budget stewardship and infrastructure optimization
• Define and monitor organizational health metrics, aligned with company's values and mission

Qualifications

• 12+ years of experience in executive operations, including 3+ years as a direct partner to an executive
• Track record of drafting Board of Directors materials and influencing long-range technical roadmaps
• Experience leading large technical programs impacting 1,000+ engineers across multiple departments
• Previous role as a Director of Engineering or Principal TPM with high-availability system oversight
• Expertise with DORA or SPACE metrics to enhance developer productivity and system reliability
• Experience in organizational design and talent strategy for budgets over $50M
• Exceptional communication skills to synthesize complex technical information into concise briefs

Benefits

• Health, finance, and well-being support
• Flexible Paid Time Off (PTO)
• Participation in Team Member Resource Groups
• Equity compensation and Employee Stock Purchase Plan
• Growth and Development Fund
• Parental leave support
• Home office financial assistance

Our client is an equal opportunity employer. We encourage you to apply even if you don’t meet every qualification—your background could be exactly what this team needs.

Key skills/competency

• Technical Vision
• Executive Leadership
• Engineering Strategy
• Product Alignment
• AI Transformation
• R&D Metrics
• Budget Stewardship
• Organizational Design
• Stakeholder Management
• Board Communication