We’re looking for a Chief Technology Officer to lead the combined engineering organization through a period of ambitious growth and technological transformation. This is not a maintenance role. It’s a mandate to retool how an entire organization builds software, to mentor a talented team through that transition, and to ensure that what we’re building today is designed for the world our users will inhabit tomorrow.
The right person is energized by a set of hard questions: Which parts of our platform are durable advantages, and which will be commoditized by AI? How should we build for an agentic user who discovers and transacts through AI intermediaries rather than browsing a website? Where are we underinvested? What does a world-class engineering team look like when AI fundamentally changes how software is written?
Reporting directly to the CEO, you’ll own the full technology function: engineering, infrastructure, and technical architecture. You’ll be the company’s eyes on the technology frontier, constantly scanning what’s emerging, and pressure-testing our assumptions about what’s feasible. As a key member of the senior leadership team, you’ll surface information and opportunities to help shape company direction and make the best possible strategic decisions.
Just as importantly, you’ll be a mentor and teacher to the entire organization. The transition to AI-augmented workflows isn’t just a tooling change, it’s a cultural one. We need a leader who can bring the team along, raise everyone’s capabilities, and create an environment where engineers, product managers, designers, and business operators are all fluent in what’s now possible.
Retool How We Build
Lead the adoption of AI-augmented development workflows across the engineering organization, fundamentally increasing what the team can ship and how fast they can ship it
Mentor engineers, product managers, designers, and business operators in new ways of working, making AI fluency a core competency across the org, not just a tooling layer for a few
Build on the team’s existing foundation of modern tooling, agile practices, and continuous delivery to foster a culture of continuous experimentation where the team is always testing what’s newly possible and incorporating it into how they work
Establish the org as an industry reference point for how modern technology teams operate at the intersection of AI and product development
Build for Tomorrow
Assess which elements of our platform represent durable competitive advantages and which are at risk of being commoditized or disrupted by AI
In close partnership with the CPO, develop a technical strategy for the agentic future: how our platform should work when users discover, research, and transact through AI agents and intermediaries rather than traditional interfaces
Qualification
You bias toward speedLocationFamiliarity with the art world
Required
You've led engineering organizations through periods of significant change: post-acquisition integration, rapid scaling, or fundamental retooling, and you have the judgment that comes from having done it, not just studied it
You bias toward speed. You know how to set an aggressive tempo, clear the obstacles that slow teams down, and create a culture where shipping is the default, not the exception
You think critically about moats and defensibility, and you connect engineering investments to business outcomes. You're comfortable in conversations about revenue, margin, and growth
You take security and infrastructure seriously, particularly as AI introduces new categories of risk across development and product surfaces
Location: New York or London; or East Coast Remote
Preferred
Experience with two-sided marketplace platforms, particularly those serving both B2B and B2C audiences
Familiarity with the art world, luxury goods, or cultural industries
Background as a technical cofounder or early-stage CTO who has built and shipped product with small, high-output teams
