Treasurer × Tech / SaaS: How the Conversation Is Moving

BullishJack speaks with clear confidence about Harri's growth, launching new products, and his priorities for the next 12 months, framing them as intellectually rewarding challenges rather than worries.

Cfo Thought Leader — 1214: The CFO Checklist Keeps Growing | Jack Gordon, CFO, Harri · Sep 2026

MixedShe frames the next 12 months as balancing AI costs/ROI, industry disruption, and 'we don't really know what's going to happen with customers or competitors,' signaling cautious, mixed confidence rather than clear optimism.

Cfo Thought Leader — 1190: Fixing What Growth Tries to Hide | Jaylene Kunze, LegitScript · Jun 2026

BullishShe notes 'a lot of capital... sitting on the sidelines,' strong buyback/M&A activity, and a receptive IPO market, framing broader capital conditions as favorable though not the main focus.

All-In with Chamath, Jason, Sacks & Friedberg — OpenAI CFO Sarah Friar: IPO, AI Rivalries, New Device, and Spending $100B+ on Compute · Jun 2026

MixedHe recalls a 'really bad market' in 2022-23 and a 'really tough' NYC commercial real estate market, but frames it as something they successfully navigated—mixed/hedged view of external conditions.

Cfo Thought Leader — 1204: When Capital Conviction Matters More Than Market Timing | Andrew Korn, CFO, EliseAI · Aug 2026

SkepticalHe recalls the 2023 fundraising environment as 'one of the toughest SaaS funding environments in the last decade' with daily asset repricing and a failed deal before finally closing—mostly negative in retrospect.

Cfo Thought Leader — 1214: The CFO Checklist Keeps Growing | Jack Gordon, CFO, Harri · Sep 2026

BullishHe describes hospitality as a historically laggard but now rapidly adopting industry with a huge $15B TAM and Harri positioned to 'own the economic relationship with an entire industry,' reflecting strong optimism.

Cfo Thought Leader — 1214: The CFO Checklist Keeps Growing | Jack Gordon, CFO, Harri · Sep 2026

MixedDiscussion of the CFO profession's evolution (broadcaster vs. team captain, long-term vs. quarterly investor mismatch) is balanced/analytical rather than clearly optimistic or pessimistic about where the finance/CFO field is heading.

Run the Numbers (CJ Gustafson) — The CFO Who Was “Ill Equipped” to Save Lehman Brothers · Jul 2026

SkepticalShe calls it 'a weird time to be in software' with AI-driven disruption making customer/competitor dynamics unpredictable, shifting planning horizons from 3 years to 3 months—concerned more than hopeful.

Cfo Thought Leader — 1190: Fixing What Growth Tries to Hide | Jaylene Kunze, LegitScript · Jun 2026

BullishExtensive enthusiasm for AI-driven scheduling and agentic tools delivering measurable ROI (98% accuracy, 93% time reduction), tempered by candid acknowledgment of data-readiness struggles and unresolved AI pricing models.

Cfo Thought Leader — 1214: The CFO Checklist Keeps Growing | Jack Gordon, CFO, Harri · Sep 2026

MixedBalanced view: AI is called a 'key enabler' for growth and operating leverage, but he also flags unresolved pricing challenges and risks like hallucination/embellishment, landing on a mixed 'powerful but complicated' stance.

Cfo Thought Leader — 1213: When Constructive Tension Yields Sharper Decisions | Martin Uhrik, CFO, Third Bridge · Sep 2026

SkepticalDan Bats argues LLMs make people 'sound convincing' but 'hand-wavy,' warning that reliance on AI risks a generation not truly understanding the underlying work — a skeptical take on AI's downside.

Run the Numbers (CJ Gustafson) — The CFO Who Was “Ill Equipped” to Save Lehman Brothers · Jul 2026

BullishHe frames Harri as 'the innovative disruptor' pushing a slow-adopting industry forward, and personally embraces systems-thinking and continuous incremental improvement (citing Atomic Habits) as core to his approach.

Cfo Thought Leader — 1214: The CFO Checklist Keeps Growing | Jack Gordon, CFO, Harri · Sep 2026

MixedBalanced view via the procurement anecdote: build and understand process manually before buying new software, cautioning against over-indexing on tech without process clarity.

Run the Numbers (CJ Gustafson) — How to Hire for Finance: Athletes First, Experts When Obvious · Apr 2026