CFOs heading into 2026 are facing a familiar challenge with new constraints. Growth is still a priority, but capital is cautious, fundraising cycles are longer, and expectations for readiness are higher than ever.
AI-driven cost structures, heightened diligence standards, and tighter margin scrutiny are reshaping how finance leaders plan, invest, and scale. What once lived in silos now collides across budgets, tooling decisions, and capital efficiency.
These pressures were at the center of a recent CFO Leadership Council webinar, Preparing for 2026: Inside the Strategic Mindset of Today’s CFOs, sponsored by Fidelity Private Shares. The conversation featured:
- Matt Derda, Director of Product Marketing, Fidelity Private Shares
- Michelle Hipwood, CFO & Co-Founder, EnFi
- Dan Lindberg, CFO, SCATR
What emerged was a clear pattern. CFOs are no longer preparing for isolated milestones like fundraising or audits. They are redesigning how finance operates so their companies can stay ready — regardless of timing, market conditions, or growth stage.
How CFOs Are Rethinking Planning for 2026
Cost management is no longer about pulling back across the board. For today’s CFOs, it’s about preserving runway while keeping the organization positioned to move quickly when the right opportunity emerges.
Dan Lindberg framed the tension with this question: “How do we protect the cash position while we’re waiting for the whale?”
For many companies, revenue timing has become harder to predict, particularly when growth depends on a small number of large deals or long sales cycles. Wins can be meaningful, but they may arrive later than planned or cluster unevenly across quarters, making forecasting and cash planning more complex.
Michelle Hipwood pointed to how growth itself can introduce new pressure: “Every time you grow, you generate your variable cost with AI costs.”
This combination of timing uncertainty and variable cost growth forces CFOs to think differently about expansion. Growth is no longer just about increasing top line. It’s about pacing investment against runway, margin impact, and the reality that revenue may not arrive on a clean or predictable schedule.
In that environment, how finance leaders communicate performance and priorities can also build trust and attract capital over time.
>> Actionable takeaway for CFOs: Shift from blunt cost cutting to disciplined investment. Evaluate spend based on whether it preserves optionality and supports faster decision-making when opportunities arise.
When AI Turns Fixed Budgets Into Variable Cost Models
Efficiency is no longer measured by how fast tasks get done, but by whether finance processes can keep up with increasingly dynamic cost structures. As AI becomes embedded across products and operations, costs are often tied directly to usage, features, and volume — making traditional, static budgeting models insufficient.
With cost variability now flowing directly through the P&L, CFOs are narrowing their definition of efficiency. The focus has shifted away from speed for its own sake and toward eliminating work that doesn’t materially improve visibility or decision-making.
Hipwood underscored that shift simply: “Efficiency is also about focus.”
That focus requires granular cost visibility that links financial performance directly to how products are built and used. Without that visibility, finance teams are forced to react to margin erosion after the fact rather than anticipate it. The same discipline applies to maintaining accurate ownership data, particularly as valuation assumptions and equity compensation come under closer scrutiny.
Lindberg described how misaligned systems amplify chaos and cost during pivots:“Startups create chaos by nature. When you pivot — and you often have to pivot hard — the tools and systems you’re set up with are usually configured for a different direction. That misalignment creates friction for the teams doing the work and leads to future costs.”
In response, CFOs are recognizing that static, periodic approaches to cost review can’t keep pace with this level of change. When cost structures shift alongside product direction, finance needs earlier visibility into where friction and margin pressure are building — not after the fact.
>> Actionable takeaway for CFOs: If finance can’t trace costs back to product usage or feature-level decisions, efficiency won’t scale. Implement tracking and tagging systems that link usage directly to financial models and collaborate closely with technical teams to understand cost drivers before they impact margins.
Scaling Finance Without Adding Friction or Headcount
As cost models become more dynamic, efficiency is less about cutting expenses and more about preventing downstream drag. CFOs pointed to tool sprawl, process rework, and misaligned expectations across functions as some of the most expensive, and least visible, sources of inefficiency as companies scale.
Technology decisions have become strategic finance decisions, shaping how confidently CFOs can operate as complexity increases. When tools and workflows fall out of sync with strategy, friction compounds quickly — showing up later as rework, delays, or unnecessary headcount growth.
Hipwood shared how automation helps her scale finance without adding complexity: “I lean heavily into automation — from virtual cards that enforce spending controls to pre-generated reporting templates. It reduces manual oversight and speeds up our monthly close so finance can focus on analysis instead of assembly.”
Rather than staffing ahead of growth, CFOs are prioritizing workflow automation and AI tools to extend the capacity of existing teams. By implementing automation before hiring, finance leaders can optimize resources, maintain control, and preserve insight as complexity increases.
>> Actionable takeaway for CFOs: Eliminate friction early by aligning tools and workflows with current strategy. Automate repetitive processes before adding headcount, and invest in flexible systems that reduce manual effort while scaling seamlessly with the business.
Always-On Investor Readiness Starts With Equity Visibility
Investor readiness is no longer something CFOs prepare for on a timeline. It is an operating posture that should be built into the business.
That expectation for readiness came through clearly in Hipwood’s experience: “Day one, if someone asks for diligence, we can turn it on.”
Investor expectations have shifted toward immediacy. Requests increasingly arrive outside of active fundraising periods, and speed and accuracy in responding to diligence requests may now signal credibility and confidence.
To support always-on readiness, CFOs are ensuring:
- Audit-ready financials
- Clean cap tables and accurate ownership data
- Organized governance documentation and data rooms
Equity visibility plays a central role in this posture. Clean, accurate equity data supports fundraising, board governance, and employee trust, while manual or inaccurate systems can introduce legal risk, delay deals, and create internal confusion.
This kind of readiness increasingly looks like day-to-day due diligence when scaling your business — not a scramble triggered by a specific event.
CFOs emphasized that real-time equity visibility can strengthen stakeholder confidence and that treating ownership data as a strategic asset, rather than a back-office task, can improve decision-making across teams.
Scenario planning completes the picture. CFOs are increasingly running multiple scenarios to evaluate:
- Dilution and ownership changes
- Funding timing, runway, and capital needs
This is also where many teams pressure-test assumptions before they prepare for their next equity financing.
>> Actionable takeaway for CFOs: Build readiness into daily operations. Keep financials and equity data clean at all times, maintain an organized data room, and use scenario planning to anticipate ownership and capital outcomes before investors ask.
The CFO Priorities That May Define 2026
As CFOs look toward 2026, one message from the conversation was clear: readiness is no longer optional. Finance leaders can’t rely on point-in-time preparation or backward-looking performance. The ability to respond quickly, clearly, and confidently is now a defining leadership signal.
To meet that bar, CFOs are building finance operations that are:
- Forward-looking, with scenario modeling that anticipates change rather than reacts to it
- Operationally integrated, connecting finance, product, and leadership around shared data and decisions
- Ready for investor and audit scrutiny, with clean records, strong governance, and rapid responsiveness
In this environment, success isn’t measured solely by what a company has already achieved. It’s defined by preparation, clarity, and the ability to act when conditions change. CFOs who invest early in scalable systems and always-on readiness give their organizations a meaningful advantage heading into 2026.
Connect with Fidelity Private Shares to put these strategies into practice — with tools that support audit-ready equity data, faster diligence responses, and more confident planning.
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