Katie Derr

As a CFO, I’ve participated in board meetings that meaningfully moved the company forward and others that fell short of their potential. The difference is rarely the quality of the board itself; it’s how management prepares for and uses the meeting. In this article, I outline practical ways leadership teams at venture-backed companies can turn board meetings into a real operating advantage accelerating decision making, sharpening strategic alignment, and elevating the overall board experience.

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The Jekyll and Hyde CFO: Paranoia and Optimism in One Role....A great CFO lives in constant tension. On one side, you’re a true believer in “only the paranoid survive.” You assume forecasts are wrong, risks are underestimated, and capital is never as available as it looks on a spreadsheet. You’re always running downside scenarios and asking, what breaks first? On the other side, you’re expected to project confidence. You stand next to the CEO and say the growth plan is real, the BAHGs are achievable, and the team should lean in. That contradiction isn’t a bug. It is the job. The mistake isn’t holding two opposing views. The mistake is sharing them poorly. Who Gets Which Message? C-suite: full realism. This is where paranoia belongs—scenario planning, tradeoffs, and hard constraints. Board: structured truth. Risks framed as managed, with clear decision points and options. Team and org: consistency and belief. Not blind optimism, but confidence grounded in reality. Different audiences, same facts. What changes is emphasis, not truth. The Balancing Rules 1️⃣ Be consistent with messaging. One reality. One narrative. If people hear different stories, trust evaporates. 2️⃣ Acknowledge the challenge, lean into the opportunity. Smart people know when things are hard. Say it out loud—then explain why it’s still worth pushing. 3️⃣ Make the offramps clear and precise. “If X doesn’t happen by Y, we adjust like this.” Clear offramps turn ambition into a managed bet instead of reckless hope. Paranoia should inform the plan, not paralyze it. Your role isn’t just to protect the downside—it’s to help the organization commit fully while staying ready to adapt. Listen to the data. Listen to the market. Listen to your people. Adjust when reality changes. People don’t follow perfect plans. They follow leaders they trust. That’s the Jekyll and Hyde of a great CFO.

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I recently joined Colin Hewitt for his podcast, The New F*Word, which explores how Fractional CFOs are reshaping cash flow, financial strategy, and business growth. A Fractional CFO doesn’t need to have all the answers on day one. As I mentioned to Colin, "The biggest mistake I see is jumping straight to solutions before fully understanding the business. The approach I rely on is simple: listen first, create alignment, then deliver. That means understanding the people, the numbers, and the real problems before trying to fix anything. Once there’s alignment on what matters, execution becomes much easier." In this episode, we touch on a variety of other topics, including: * How to decide between a fractional CFO and a full-time hire * Why a company's financial narrative must pass the one-sentence test * The importance of alignment across every stakeholder * How to balance long-term vision with tactical flexibility * Why scenario analysis is a critical complement to point forecasts Please see the links below for the full podcast. I value your insights and look forward to your feedback... Apple: https://bit.ly/4aH65e0 Spotify: https://bit.ly/4qNfozk YouTube: https://lnkd.in/egaZEuFu #TheNewF*Word #FractionalCFO #CFOResponsibilities

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Financial reporting has stayed stubbornly manual even as the rest of the finance stack modernized. That’s why we’re leading Inscope’s $14.5M Series A. Inscope is built for the teams doing the work (and the firms reviewing it): it links statements to source data, automates 60%+ of prep, and keeps trust + auditability at the center. The platform was founded by operators who lived the problem, Mary Antony and Kelsey Gootnick, CPA, both CPAs and former controllers. The early adoption has been strong since its 2024 launch: 5x+ customer growth and 30x+ ARR growth. Looking forward to partnering with Mary, Kelsey, Jared Tibshraeny, Ankit Arya, and the broader team as it sets a new standard for how reporting gets done: faster cycles, higher confidence, and a workflow built for scale. Why Sean Jacobsohn and I invested: https://norwest.co/inscope

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Every hire, product feature, and GTM experiment is a capital allocation decision, most teams just don’t call it that. I’m kicking off a 3-part series on capital allocation for founders, operators, and finance leaders with a simple question: ➡️ Will the next $1 you deploy become worth more than $1? Series overview Part 1: defines the core concept + the math Part 2: where capital goes + how to measure whether it’s working Part 3: AIMS framework for communicating allocation decisions to management teams and your board Part 1 (attached here) lays the practical foundation: 🔹 The $1 invested test and ROIIC vs. hurdle rates (scoreboard vs. decision lens) 🔹 A lightweight “investment brief” to evaluate bets (GROW / BUILD / BUY) 🔹 The small metric toolkit that translates finance into operating decisions (NPV / payback / ROIIC / incremental margin) 🔹 Early-stage proxies when DCF inputs are unknowable (burn multiple + revenue quality) 🔹 Operator “vital signs” to spot drift early (profit engine, leverage, cash conversion, optics) Series Roadmap ✔️ This series (Parts 1–3): breadth-first. shared, lightweight framework to define value creation, choose decision-grade metrics, and communicate tradeoffs clearly ✔️ Next series: depth-first. momentum drivers + operational decisions that need near real-time measurement to spot drift early and course-correct fast Read Part 1 here and Part 2 and 3 on substack. Next Series will be out next week. 💰 What’s one bet you’re funding right now, and how will you prove it’s working?

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As founders scale, financial leadership needs evolve just as fast as product or team strategy. In this article, Jason Anglin does a great job outlining when a startup needs a fractional Director of Finance vs. a fractional CFO. And why getting that choice right can save both time and capital. Worth a read for founders approaching their next growth stage.

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Before you push for rapid growth, make sure your systems are ready. If your business isn't optimized, small inefficiencies can become big, expensive problems as you scale. Even something as simple as shortening your cash flow cycle by seven days can free up a significant amount of working capital. Growth is exciting—but smart, strategic growth is what builds lasting success. #Abunden #BusinessGrowth #CFO #FinancialManagement #CashFlow

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Hiring and compensation have a huge impact on your growth plans. It’s critical to have a real strategy, and not a “best effort” or piecemeal approach. That was the focus of yesterday’s CFO Roundtable, which I and York IE had the pleasure of co-hosting with Kristen Craft from Fidelity Private Shares. When it comes to hiring, we discussed how important it is to step back and look at the big picture. Regularly reviewing your org chart ensures your structure is evolving with the business, not just reacting when a new need pops up. Designing roles around the company’s goals, rather than individual preferences, is hard but crucial if you want to scale in a healthy way. On compensation, we talked about creating a clear philosophy that aligns with your strategy and stage. Are you paying at the top of the market as a recruiting advantage, or taking a role-based approach? How do you leverage base, bonus, and equity to create aligned incentives that motivate and retain your teams? And thank you to Michaela Goodwin, Eduardo Arreaga, Megan Dunn, CPA, and Rick Darer for sharing their experiences, and to all the finance leaders who joined the discussion. These conversations always remind me how much there is to learn from this community.

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Running a fractional CFO firm means managing multiple clients at once, all with different needs, deadlines, and reporting cycles. This is the stack we built to make sure nothing falls through the cracks: 1. HubSpot: full visibility into every prospect and client relationship. Nothing slips. 2. Anchor: automated proposals, agreements, invoices, and payments that sync straight into QuickBooks. 3. Claude + ChatGPT: research, drafting and sanity-checking work that used to take hours. 4. Fireflies.ai: every call transcribed and summarized automatically. I walk out of every meeting with a clean action item list. 5. ClickUp: client engagement lives here. Onboarding phases, recurring deliverables, automated task flows and AI Agents handling the routine so we stay focused on the work that actually matters. Founders hire us to bring order to their financial chaos. You can't do that if your own house isn't in order. #FractionalCFO #QuantusAdvisors #AI #FounderTools #FinancialLeadership

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5 Signs Your Business Needs a Fractional CFO: 1. Cash flow feels tight despite growing revenue Your business is generating more sales, but day-to-day liquidity is under pressure. 2. Reporting exists but does not drive decisions Numbers are being tracked, but leadership lacks actionable insights. 3. Fundraising conversations are approaching You need credible forecasts, clear narratives, and investor-ready financials. 4. The finance function is stretched or unstructured Roles, responsibilities, and processes are not aligned with your growth ambitions. 5. Leadership needs financial challenge and clarity Founders and executives require strategic guidance rather than operational focus alone. A fractional CFO brings board-level insight, sharper forecasting, and strategic guidance without the cost of a full-time hire. Find out how ConnexionCFO can support your growth at connexioncfo.com. #fractional #cfo #fractionalcfo #financialleadership #businessgrowth

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The CFO stack has long been underserved by tech, but now it’s front and center in the AI transformation. With every tool claiming to be their AI savior, finance leaders are overwhelmed. It’s hard to separate buzz from reality. Yesterday we brought together 25 top CFOs and 4 cutting-edge startups to cut through the hype and see what’s actually working. And it wasn’t just talk, we saw it in action with live demos! Big thanks to the founders who joined us to share what they’re building: 🚀 Campfire – For the first time, finance teams don’t have to choose between overstaying their welcome on QuickBooks or suffering through a year-long NetSuite implementation to only be disappointed. Why add bandaids on top when you can fix the foundation? Modern + AI GL makes the switch worth the pain. John Glasgow 🚀 Inscope – Turns out financial reporting doesn’t have to be painful. Inscope automates the work behind audit-ready statements so teams stop chasing errors and wrangling formatting. Mary Antony 🚀 Anrok – The demo took us through an actual tax audit! Sales tax is confusing and global regulations change fast. Anrok takes the manual work (and stress) out of staying compliant, wherever you do business. Michelle Valentine 🚀 Abacum – Planning and forecasting shouldn’t mean late nights in spreadsheets. Abacum has struck the perfect balance between robust functionality, flexibility, and ease of use. Julio Martínez Thanks to the finance leaders who joined us and didn’t shy away from tough questions on where products stand today and what’s missing. That kind of honest, back-and-forth with the CFO community is what makes these sessions so valuable. We’re enthusiastic about what’s unfolding in the CFO stack – it’s one of the rare corners of tech that’s both primed for AI innovation and packed with leverage for teams. At Scale, we’ve been lucky to work with standouts like BILL, Monto, Klarity, Papaya Global, and Abacum, companies transforming everything from AP, AR, Payroll, Accounting, and FP&A. Major thanks go out to our amazing Exec in Residence, M.G. Thibaut, and her team at Coterie CFO for putting this together. Plus shout out to our other cohosts - the crew at PwC Charlise Hyatt, MBA, Joseph Niedringhaus who hosted us in their awesome SF space, Michelle Schwartz, Jeff Davis at Vaco and Josh Dorsey, Weston Rice at Stifel Bank. If you’re working on something in the CFO stack, reach out, we’d love to chat. For any finance leaders that want to be part of this community, click the link in the comments!

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Ok, I said I was going to talk about my approach to startup compensation vs market compensation this week so here we go: As we all know startups are risky and can't afford anything. I have had many many conversations with folks that are confused as to why they're not being offered the same cash compensation they imagine they can get at Meta or Google... because anyone can get a job there. (be nice Ian) So if you're not being offered your full board, what are you being offered? Usually enough cash to barely make rent and an option grant that will someday be worth more than all the money your parents made ever. So how do you know you got enough options/equity? Here's my napkin math: Step 1: Market Comp: 140k Your actual Comp: 105k Difference: 35k: (yikes) Step 2: How long are you going to take this affront on your worth? Lets say 3 years Step 3: What kind of return do I need to get on that cash i gave up? You're working at a company that's pretty risky. What kind of return do you need for that kind of risk? This is debatable but let's go with 20% (this is my floor for this stage of business but we're not going deep on cost of capital today.) Step 4: What is the value of the compensation I've not taken? If we do a present value calculation (picture below), the deferred compensation is roughly $74k. Cool.... so what does that mean? It means you need to get an equity grant worth about this much. If you want to learn how to value the options, the internet has got some tools for you. If you got a grant of restricted shares, congratulations that's a bit more complicated. The upshot is that this method will help you think through what you're giving up and framing it as an investment, because it kinda is. All investments have some element of risk. As risk goes up, the required return goes up. Because I'm a nerd, i tend to do this analysis for my friends when they get equity grants to either tell them to leave Whinesville or hold out for better. Do I recommend you do this kind of negotiation yourself? If you're feeling that brave, have at it. If not, call a friend that does startup finance and they can probably help, maybe with beer.

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What a good Fractional CFO actually does (and doesn’t do). There’s often confusion about what a Fractional CFO is meant to be. It’s not a part-time Finance Director who produces prettier reports. And it’s not a temporary stand-in until you “hire someone proper”. A good Fractional CFO focuses on decisions. Scenario planning. Cash visibility. Margin mechanics. Investor narrative. The work sits at the intersection of finance and strategy. A Fractional CFO isn't in the business all the time. Well duh.... . But because of this they focus in on the stuff that matters. What's the cash runway? What metrics does the business need to guide and direct? What information are investors looking for right now? They don't have the time to pay too much attention to matters like chasing invoices, reconciling accounts or firefighting basic processes. Yes these are important and it matters that your Fractional CFO understands what the processes are. But if these processes are broken in some way, the structure underneath probably needs attention. Fractional works because it concentrates senior thinking where it has the most leverage. You get experience applied to the moments that matter — hiring, fundraising, pricing, sequencing — without that full-time overhead. It's about getting someone experienced who can take that helicopter view of your business and apply a fresh professional perspective on your business. It’s not about doing less finance. It’s about doing the right finance at the right level. #FractionalCFO #SaaS #AIEnabled

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Proud moment for our team at Robyn Consulting Group (RCG Financial), we’ve officially launched our newest white paper, a strategic roadmap for exit-minded SaaS founders and CEOs. This guide is the result of months of research, financial analysis, and insight gathering. Huge thank you to our RCG team for the diligence and expertise poured into this project — and to our clients and community who participated in our founder survey and shared their real-world experiences on scaling and exit readiness. Inside the guide, we uncover the four key metrics private equity firms scrutinize — and how you can optimize each one to position your company for a 10x valuation multiple. 👉 Get your copy here: https://lnkd.in/eyhz83kk

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Brad Wolfe | Operational CFO Series The CHRO & CFO Partnership in PE-Backed SaaS The CHRO and the CFO. The most underestimated partnership in PE-backed SaaS. Most think of the CHRO as a support function. In a PE-backed company under $1B, that's a costly misread. Headcount is 60–75% of the total cost structure in SaaS. Comp, benefits, equity, and severance are the largest discretionary levers management controls. The CFO who treats the CHRO as administrative leaves money — and real risk — on the table. Eight Places Where It Matters Most 1. Headcount planning — joint discipline, not negotiation. Stop letting the budget become the CHRO advocating for hiring while the CFO defends EBITDA. Work from the same workforce model — role design and capacity on one side, revenue-per-employee benchmarks and covenant constraints on the other. 2. Compensation architecture and EBITDA integrity. A commission plan raising OTE 10% across a 50-person sales team is a seven-figure P&L event. A bonus structure misaligned with financial targets is a governance failure. Design it together — or own the consequences separately. 3. The management incentive plan. The CFO builds the model. The CHRO owns the narrative. If the CHRO can't explain the MIP to the VP of Engineering fielding three competing offers, the plan has failed — at exactly the moment the company needs it most. 4. Workforce data as a financial signal. CS turnover is a churn signal. Time-to-fill in engineering is a product risk. Manager flight risk is organizational fragility. A CFO who treats HR data as compliance output is missing the most predictive signals in the business. 5. Restructuring and workforce reductions. The CHRO owns legal mechanics. The CFO owns the model. Miss severance obligations and you'll mis-state the cost. Don't understand the financial rationale and you can't hold the line when managers push back. One plan. Two owners. 6. Benefits and total rewards. In a 200-person SaaS company, benefits run $3–5M annually. Redesign without modeling EBITDA impact and you have a budget problem. Cut unilaterally to hit a target and you have a retention problem. Design the envelope together. 7. People due diligence in M&A. HR liabilities are routinely underestimated. The bigger risk is organizational — can the acquired team execute? Are key people retained? Only the CHRO can answer with real depth. Skip it and the deal surprises you six months post-close. 8. The people narrative to the board. CS attrition costs X in recruiting, Y in ramp, Z in churn risk. When the CHRO and CFO present people data through a financial lens together, both gain credibility with the sponsor. What PE Sponsors Watch For Comp decisions that weren't modeled. Restructurings that overran projections. MIP participants who don't understand their economics. Retention problems that hit the financials before they reach the board. wolfepacks.com

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Last week, I had the opportunity to speak about the impact of Anthropic's Claude CoWork feature for Finance leaders in the Elevation Capital portfolio companies. The Zoom session had 100 registrations, 85%+ attendence and almost 95% sit-through rate where attendees sat through the whole session and asked questions. The demand for AI in Finance is very very high! VC investors are incredibly conservative about what they show their portfolio and what they don't, for good reason, they have millions of dollars on the line riding on the success of these start-ups. In this context, I want to take a moment to appreciate the forward thinking nature of Elevation's team to have folks like Vartika Bansal, Harsh Agrawal and Pankaj Ghai do sessions like these for their portfolio. It will help make both Elevation and the portfolio companies AI-native. In this post Vartika Bansal summarises the key take-aways from the session. But if you are a Finance leader still looking at YouTube, LinkedIn and other places and thinking, I will use AI when I have the time, it might be too late. The time to start is now, install it, pay for it and get to work. It is now or never, if you have questions or get stuck feel free to DM me!

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I just watched a startup make a seemingly innocuous hiring decision during exit planning that will likely cost them real money in the future sale process. The mistake ... they created and filled a new role called Director of Delinquent Accounts. Now, you might think, "but Jason, how does improving cash collections and reducing bad debt expense hurt a sale?" It doesn't. What the startup actually did was create a glaring signal that something is structurally wrong. Here's what happens in diligence. A buyer will request an organizational census early in the process. That title is a yellow flag (maybe red) that immediately prompts deep investigation. Is the sales team overselling the product? Is your product failing to retain customers? Do you have weak collection controls? Are you extending credit instead of requiring payment upfront on credit card? But the real damage runs much deeper. By creating a permanent, full-time Director role, the startup has inadvertently signaled something far worse than the current problem; they believe this delinquency issue is structural and permanent. You don't hire a Director to fix a six-month problem. You hire a Director because you expect the problem to persist indefinitely. A sophisticated buyer will read that organizational decision exactly as intended, not the way management hoped. PLEASE REMEMBER, every hiring decision, organizational change, and strategic action you take in the 12-24 months before an exit will be heavily scrutinized and interpreted through a buyer's lens. When making decisions during that exit-prep window, ask yourself the hard question "how could an external party view this negatively?" Also, be aware that most CFOs advising on exits have only worked the sell-side. You'll benefit far more from an advisor who has also worked the buy-side (e.g., Corporate Development, Investment Banking, or Private Equity). They can help apply the buyer's lens during the run-up to an exit.

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Shit in = shit out 💩 (are we allowed to swear on here?!) Sorry to be the one to say it, but if your bookkeeper isn’t thinking about how you’ll use your financial data strategically… you are 100% going to end up in a mess. I know this because every single founder who has come to me for help preparing for investment has had their financial records in complete disarray. And you know what this does: ➡️ It costs you MORE money to fix. Yup more money. ➡️ It slows you down b/c you have to spend time fixing things before you can get any value from your accounts to talk strategy. ➡️ If you don't find errors, the investor's analyst will and this will slow you down even further and worse, could become bargaining power when it comes to negotiation. Bookkeeping is by far one of the most important jobs in your finance department because it is the foundation on which you: 💰 Determine whether your business is financially viable 💰 Make decisions about driving sales or hiring a new team member 💰 Decide whether you launch in a new geographical location 💰 Raise investment, apply for grants or apply for bank funding The list can go on and on. I'm honestly just frustrated with the quality of bookkeeping in general and I'm sorry founders have to go through such a painful process. The best advice I can give to every single founder out there is this: 🚨 When you hire a bookkeeper, or outsource to an agency, ask them one question: ''Do you understand how accurate accounting connects to financial strategy and raising investment?'' Because most bookkeepers are focused on compliance. Tax returns. GST. BAS. And yes that's fine but it's NOT enough. If this is a pain point for you, reach out. I'd love to help.

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Your valuation is shaped before diligence starts. Founders who can show protected know-how, repeatable revenue logic, and clean operating leverage walk into fundraising with more control. Investors are not just pricing today’s ARR. They are pricing defensibility, margin expansion, and how hard you are to copy. That is why patents, licensing rights, and fractional executive depth matter more than most decks admit. They change the risk story. And when the risk story improves, leverage usually follows. Too many startups treat moats as branding. I think moats should show up in valuation math—do you agree?Your valuation is shaped before diligence starts. Founders who can show protected know-how, repeatable revenue logic, and clean operating leverage walk into fundraising with more control. Investors are not just pricing today’s ARR. They are pricing defensibility, margin expansion, and how hard you are to copy. That is why patents, licensing rights, and fractional executive depth matter more than most decks admit. They change the risk story. And when the risk story improves, leverage usually follows. Too many startups treat moats as branding. I think moats should show up in valuation math—do you agree?

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