Agentic Adoption: From Pilots to Production

CTOs compared notes on what changes when agentic systems move from experimentation to production. The consensus was that engineering is shifting from writing code to designing systems, reviewing agent output, and investing more heavily in security and evaluation. Many also noted new tensions emerging between engineering and product teams as workflows evolve.

The discussion converged on a simple principle for non-engineers using AI-generated code: bring problems or prototypes, not code. Participants also highlighted the challenge of managing board expectations, which often outpace organizational readiness. When it came to measurement, token counts were largely dismissed in favor of metrics such as human override rates and user adoption. Across the board, teams are building resilience through tiered model strategies, local model transitions (Gemma, Llama, and others), and provider-agnostic architectures.

AI Adoption in Practice: What's Working, What's Not

A second sitting of the March conversation for a new group of CTOs. How the development lifecycle has actually changed, code contributions from non-engineers (PMs, designers, even executives), pressure from CEOs and boards to reorganize or move faster, and what leaders are measuring beyond speed, including contingencies if models degrade or become cost-prohibitive.

AI Adoption and Impact in Your Organization

Ninety minutes with fellow CTOs on navigating AI adoption in practice. Each leader framed where their organization stands today, then the group dug into lifecycle change, the democratization of code contribution, managing investor pressure, and the one bet each CTO is most confident in (or most nervous about) a year out.

AI Adoption Fundamentals: Getting the Foundation Right

A back-to-basics session for leaders at every stage of adoption. With so many organizations pilot-rich but transformation-poor, the group worked through the fundamentals that separate durable adoption from stalled experiments: where to start, what to standardize, and how to build the organizational muscle before scaling the tooling.

Navigating AI Team Pushback

The adoption conversation nobody puts in the board deck: what to do when your own engineers resist. Leaders compared notes on the sources of pushback (craft identity, quality concerns, job security, tool fatigue), what distinguishes legitimate resistance worth listening to from change aversion, and the approaches that actually moved skeptical teams.

The AI Bandwagon: What CTOs Are Actually Seeing

Everyone was on the bandwagon; this session asked what the view looked like from on board. Leaders cut through the hype to compare what they were genuinely observing in their organizations: how teams were changing the way they build software, which gains were real versus claimed, and where the gap between AI's promise and daily practice still sat.

Tech Roadmap Strategy Under CEO and Board Pressure

How do you hold a coherent technology roadmap when the CEO and board want AI everywhere, faster? Leaders discussed defending long-horizon technical investments against short-cycle pressure, translating roadmap tradeoffs into board language, and when to bend the roadmap versus when to hold the line.

Innovation, the CPTO Question, and Building Second Lieutenants

A wide-ranging session on balancing innovation against maintaining and scaling existing systems, the steepest learning curves for leaders bridging the engineering-product divide in CPTO roles, the ethical considerations AI is forcing into product decisions, and how leaders build the layer of "second lieutenants" that lets them step back from the day-to-day.

What Does the Board Want From a CTO?

Most CTOs hear from their board quarterly and guess at the rest. This session unpacked what directors actually expect from the technical seat: a technology strategy that maps to the business plan, a credible story on scaling, a roadmap that survives contact with reality, and fiscal discipline in how engineering spends. The throughline: boards don't want more technical detail, they want confidence that the technology bets and the business bets are the same bets.

Market Shifts, Cost Reductions, and Team Impact

With the market reset in full effect, leaders compared notes on managing through cost reduction: where to cut without breaking the organization, how budget pressure was reshaping team structures and priorities, and how to keep the best people engaged when growth stories had turned into efficiency stories.

Managing Up: Working With a Non-Technical CEO

The skill most technical leaders never got taught. This session focused on managing up to a CEO or any non-technical executive: translating engineering reality into business language, earning trust without dumbing things down, and handling the moments when your CEO's instincts and your technical judgment point in different directions.

Leading Through the Efficiency Era

Against an industry-wide reset of headcount and expectations, leaders discussed doing more with flatter budgets, protecting culture and momentum through difficult cycles, and leading teams whose sense of stability had been shaken by the broader market.

Org Design, Measurement, and Operating Into a Downturn

Two sessions built entirely from leader-submitted questions: effecting change beyond your direct influence, team topologies for data science and international R&D, monitoring organizational health beyond quarterly surveys, optimizing R&D spend, growing people in a low-growth company, and the perennial question of how to benchmark what "good" looks like for an engineering organization.

From Great Resignation to Great Recession

Two sittings on the hiring climate's whiplash: whether the market was shifting from an engineer's market to an employer's, transitioning from product-centric to platform-centric companies, navigating team pushback on top-down roadmap mandates, and the org design challenges growth had created.

Closing Out 2021: Measurement, Managing Up, and Scaling

The final sessions of the year, with engineering leaders from growth-stage companies across fintech, health, and SaaS. How to measure engineering success and accountability going into 2022 (OKRs, delivery goals, DORA), the challenges of managing up to the CEO, and the hiring strategies that actually worked in that year's market.

Retention, Remote, and the Road to 2022

The summer session tackled retaining and growing teams in a white-hot hiring market, how companies were navigating distributed vs. hybrid vs. return-to-office, and what those decisions were doing to culture and growth.

The First Table: Leading and Scaling Engineering Organizations

Where it started: an intimate session of five engineering leaders on how their roles had evolved with growth, organizational design at scale, culture change, Covid's impact on productivity and culture, and strategies for expanding teams in a brutal market for engineers.

CTO Summit: Leading Through Covid

A gathering of CTOs five months into the pandemic, on leading organizations through a disruption nobody had planned for: keeping suddenly-remote teams productive and connected, making technology decisions under deep uncertainty, and holding a culture together over video.

CTO & Security Summit: The Many Hats of the Startup CTO

An in-person discussion on security and the reality that startup CTOs rarely get to be just one thing. The role demands technology leader, security leader, and DevOps leader all at once, and the group dug into how to carry that load: where to invest personally, what to delegate, and how to keep security from being the hat that falls off first.

Where It Began: The CTO Coaching Panel

The first gathering: a group discussion with technology leaders on CTO coaching and the value of a sounding board. The conversation that night, about how isolating the CTO seat can be and how much leaders gain from candid peer exchange, became the premise for everything that followed.