Chief of Staff to the CTO

Validity•Boston, MA

2d•$250,000 - $285,000•Hybrid

About The Position

Validity is seeking an experienced Chief of Staff (COS) to amplify the contributions of our CTO as he leads 100+ engineers, product managers, and specialists during one of the most exciting times in our company's history. This is not an executive assistant, project manager, or operational administrator role. The COS is someone who thinks and makes decisions like a CTO/CPO, communicates with board-level fluency, and earns credibility with senior leaders through insights, preparation, follow-through, and speed to quality results. The COS understands the cost and missed opportunity resulting from misallocating the CTO's time and extends the CTO’s presence strategically across multiple competing priorities, ensuring none lose momentum. The COS will be incredibly strategically positioned within the company as a result of their proximity to the decisions and relationships that matter most.

Requirements

10-15 years’ experience in a Chief of Staff role of at least the VP level operating across engineering, product, and business functions.
Deep product management and technical fluency - enough to earn the respect of principal engineers, architects, and senior product managers.
Exemplary written communication skills. Experience creating materials CEOs, boards, or major customers have relied on. You know how to craft a technology narrative that resonates and is compelling.
Experience acting on an executive’s behalf. Comfortable leveraging the CTO’s authority in his absence and clear about when to act versus when to escalate
Track record of operating effectively in ambiguity; drive to clarity, and hold multiple workstreams without losing track of what matters most.
You are organizationally savvy - you build trust broadly, read organizational dynamics accurately, and use both to remove obstacles and drive important work forward.
You have experience-informed perspectives about how engineering and product organizations should run at scale, and you can apply those opinions constructively.

Responsibilities

Amplify the CTO’s contributions by representing him in cross-functional executive conversations, steering committees, and strategic working sessions - not as a note-taker, but as a proxy who can make judgment calls, commit resources, and hold peers accountable.
Invest time developing deep synchronization with the CTO. Learn how he makes decisions, observe what factors and dependencies he considers, and develop an understanding of how he makes trade-offs to achieve overall goals.
Own the operating rhythm of the CTO’s organization: leadership reviews, planning cycles, key performance conversations, and strategic offsites - ensuring these are high-quality and lead to decisions, not just discussion.
Lead high-priority strategic initiatives on the CTO’s behalf, from framing the problem through driving to resolution, with little supervision. Ensure the CTO’s priorities are understood and acted upon consistently across a distributed, global organization.
Build trusted relationships with the CTO’s direct reports and other senior leadership. Leverage these relationships to accelerate communications and assess where the organization is healthy and where opportunities for improvement exist.
Develop a clear point of view on any organizational issues, tensions, and opportunities and surface them along with recommendations to the CTO before they become problems.
Where functional leads need the CTO’s authority to unlock progress, act as that authority with judgment, consistency, and appropriate escalation.
Write and edit at a C-suite level: board materials, external thought leadership, internal communications, and strategic documents. Ensure the technology narrative is coherent, compelling, and credible and reflects the CTO’s voice and vision with precision.
Serve as an active thought partner to the CTO regarding Validity’s AI innovations. Track the external landscape in AI, synthesizing competitor moves, emerging capabilities, and customer signals into inputs the CTO can act on.
Coordinate across Engineering, Product, and Data Strategy to ensure the AI roadmap is coherent, resourced, and on schedule - including creation of collateral and GTM materials.
Ensure that AI innovation work maintains organizational priority and velocity.
Ensure that when the CTO makes a commitment - to the CEO, the board, a customer, or his team - there is a system behind it that ensures follow-through