CTO Roundtables
Where senior technology leaders talk, off the record.
Hoola Hoop convenes CTOs, CPTOs, and engineering leaders for candid, invitation-only conversations about the problems they can't discuss anywhere else: AI adoption, board pressure, org design, and the changing shape of the role itself.
CTO: Off The Record
Our flagship roundtable brings together a small, curated group of CTOs, CPTOs, and VPs of Engineering. No vendors, no pitches, no recordings. Just peers comparing notes on what's actually working and what isn't.
We've been convening this table since 2019. The topics change; the candor doesn't.
Each session focuses on a single topic shaping engineering leadership right now. Topics are drawn directly from our coaching work, so they reflect what CTOs are wrestling with this quarter, not last year. Sessions are hosted and facilitated by Leigh Newsome, at times joined by a Hoola Hoop colleague who has also held the CTO seat.
- 015 to 8 leaders, curated for peer fit
- 02Chatham House rules. Insights leave the room, attribution doesn't
- 0390 minutes, structured discussion with room for what's on your mind
- 04Every six weeks, in New York and virtually
Next at the table
Agentic Adoption: From Pilots to Production
Agents and AI tooling are moving from experiment to everyday use. How has your development lifecycle actually changed? How are you handling non-engineer commits, managing board pressure to move faster, and measuring impact beyond speed? And what's your contingency if models degrade, get restricted, or become cost-prohibitive?
Agentic Adoption: From Pilots to Production
An evening session of the same conversation, timed for East and West Coast leaders. Candid peer discussion on how agentic systems are reshaping the development lifecycle, the org chart, and the board conversation.
Seven years at the table
Every session's questions come from our coaching and advisory work, so the archive doubles as a record of what engineering leaders were actually wrestling with, year by year. Discussions themselves are off the record.
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.
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.
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.
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.
The roundtable is where the conversation starts.
Many leaders come to a session with one question and leave with a clearer view of the larger challenge behind it. When that happens, the next step is usually a one-on-one conversation with a former operator who has scaled through the same transitions you're navigating.
Join the next session
Tell us a little about yourself and we'll be in touch about the next roundtable.
Attendance is by invitation to keep every conversation genuinely peer to peer. We typically respond within two business days.