Category Archives: Finance

“All Models Are Wrong, Some Are Useful.”

“I have a map of the United States … actual size. It says, Scale: 1 mile = 1 mile. I spent last summer folding it. I also have a full-size map of the world. I hardly ever unroll it.” — Stephen Wright (comedian)

Much as we build maps as models of the physical world, we build mathematical models all the time in the business world. For example:

These models can be incredibly useful for planning and forecasting. They are, however, of course, wrong. They’re imperfect at prediction. They ignore important real-world factors in their desire for simplification, often relying on faith in offsetting errors. Reality rarely lands precisely where the model predicted. Which brings to mind this famous quote from the British statistician George Box.

“All models are wrong. Some are useful.” — George Box

It’s one of those quotes that, if you get it, you get it. (And then you fall in love with it.) Today, I’m hoping to bring more people into the enlightened fold by discussing Box’s quote as it pertains to three everyday go-to-market (GTM) models.

First, it’s why we don’t want models to be too precise and/or too complex. They’re not supposed to be exact. They’re not supposed to model everything, they’re supposed to be simplified. They’re just models. They’re supposed to be more useful than exact.

For example, in finance, if we need to make a precise budget that handles full GAAP accounting treatment then we do that. We map every line to a general ledger (GL) account, do GAAP treatment of revenue and expense, model depreciation and allocations, et cetera. It’s a backbreaking exercise. And when you’re done, you can’t really play with it to learn and to understand. It’s precise, but it’s unwieldy — a bit like Stephen Wright’s full-scale map of the US. It’s useful if you need to bring a full-blown budget to the board for approval, but not so useful if you’re trying to understand the interplay between sales productivity, sales ramping, and sales turnover. You’d be far better off looking at a sales bookings capacity model.

To take a different example, it’s why business school teaches you discounted cashflow (DCF) analysis for capital budgeting. DCF basically throws out GAAP and asks, what are the cashflow impacts of this project? The assumption being that if the DCFs work out, then it’s a good investment and that will eventually show up in improved GAAP results. Notably — and I was really confused by this when I first learned capital budgeting — they don’t teach you to build a 20-year detailed GAAP budget with different capital project assumptions and then do scenario analysis. Instead, they strip everything else away and ask, what are the cashflow impacts of this project versus that one?

In the rest of this post, I’ll explore Box’s quote as it relates to the three SaaS GTM models I discussed in the introduction. We’ll see that it applies quite differently to each.

Sales Bookings Capacity Models

These models calculate sales bookings based on sales hiring and staffing (including attrition), sales productivity, and sales ramping (i.e., the productivity curve new sellers follow as they spend their first few quarters at the company). Given those variables and assuming some support resources and ratios (e.g., AE/SDR), they pop out a series of quarterly bookings numbers.

While simple, these models are usually pretty precise and thus can be used for both planning and forecasting (e.g., predicting the bookings number based on actual sales bookings capacity). Thus, these are a lot useful and usually only a little wrong. In fact, some CEOs, including some big name ones I know, walk around with an even simpler version of this model in their heads: new bookings = k * (the number of sellers) where that number might be counted at the start of the year or the end of Q1. (This is what can lead to the sometimes pathological CEO belief that hiring more sellers directly leads to bookings, but hiring anything else does not, or at least only indirectly.)

Marketing Inverted Funnel Models

These models calculate the quarterly demand generation (demandgen) budget given sales booking targets, a series of conversion rates (e.g., MQL to SAL, SAL to SQL, SQL to won), and assumed phase lags between conversion points. They effectively run the sales funnel backwards, saying if we need this many deals, then we need this many SQLs, this many SALs, this many MQLs, and this many leads at various preceding time intervals.

If you’re selling anything other than toothbrushes, these models are wrong. Why? Because SaaS applications, particularly in enterprise, are high-consideration purchases that involve multiple people over sometimes prolonged periods of time. (At Salesforce, we won a massive deal on my product where the overlay rep had been chasing the deal for years, including time at his prior employer.)

These models are wrong because they treat non-linear, over-time behavior as a linear funnel. I liken the reality of the high funnel more to a popcorn machine: you’re never sure which kernel is going to pop, when, but if you add this many kernels and this much heat, then some percentage of them normally pops within N quarters. These models are a lot wrong — from first principles, by not just a little bit — but they are also a lot useful.

I think they work because of offsetting errors theory, which requires the company to be on a relatively steady growth trajectory. Sure, we’re modeling that last quarter’s MQLs are this quarter’s opportunities, and that’s not right (because many are from the quarter before that), but — as long as we’re not growing too fast or, more importantly, changing growth trajectory — that will tend to come out in the wash.

Note that if you wanted to, you could always build a more sophisticated model that took into account MQL aging — or today use an AI tool that does that for you — but you’ll still always be faced with two facts: (1) the trade-offs between model complexity and usefulness and (2) that even the more sophisticated model will still break when the growth trajectory changes or reality otherwise changes out from underneath the model. Thus, I always try to build pretty simple models and then be pretty careful in interpretation of them. Think: what’s going to break this model if it changes?

Marketing Attribution Models

I try not to write much about marketing attribution because it’s quicksand, but I’ll reluctantly dip my toe today. Before proceeding, I encourage you to take a moment to buy a Marketing Attribution is Fake News mug which is a practical, if passive-aggressive, vessel from which to drink your coffee during the next QBR or board meeting.

Marketing attribution is the attempt to assign credit for marketing-generated opportunities (itself another layer of attribution problem) to the marketing channels that generated them. In English, let’s assume we all agree that marketing generated an opportunity. But that opportunity was created at a company where 15 people over the prior 6 quarters had engaged in some marketing program in some way — e.g., clicking an ad, attending a webinar, downloading a white paper, talking to us at a conference, etc.

There are typically two levels of reduction: first, we identify one primary contact from the pool of 15 and second, we identify one marketing program that we decide gets the credit for the opportunity. Typically, people use last-touch attribution, assigning credit to the last program the primary contact engaged with before the opportunity was created. This will overcredit lower-funnel programs (e.g., executive dinners) and undercredit higher-funnel programs (e.g., clicking on an ad). Some people use first-touch attribution, reversing the problem to over-credit higher-funnel programs and under-credit lower-funnel ones. Knowing that both of those problems aren’t great, some send complexity to the rescue, using points-based attribution where each touch by each person scores one or more points, and you add up those points and then allocate credit across channels or programs on a pro rata basis. This is notionally more accurate, but the relative point assignments can be arbitrary and the veil of calculation confusion generally erodes trust in the system.

The correct way, in my humble opinion, to do attribution analysis is to approach it with humility, view it as a triangulation problem, and to make sure people absolutely understand what you’re showing them before you show it (e.g., “we’ll be looking at marketing channel performance using last-touch based attribution on the next slide and before I show it, I want to ensure that everyone understands the limits of interpretation of this approach.”) Then follow any attribution-based performance analysis with some reverse-touch analysis where you show all the touches over the prior two years, deal by deal, for a small set of deals chosen by the CRO in order to demonstrate the messy, ground-level reality of prospect interactions over time. Simply put, it’s the CMO’s job to decide how to allocate resources in this very squishy world, to make those decisions (e.g., do we do tradeshow X and do we spend $Y) in active discussion with the CRO as their partner and with a full understanding of the available data and the limitations on its interpretability. The board or the e-staff simply can’t effectively back-seat drive this process by looking at one table and saying, “OMG, tradeshow oppties cost $25K each, let’s not do any more tradeshows!” If only the optimization problem were that simple.

But, back to the Box quote. How does it apply to attribution? These models are a lot wrong, at best a little useful, and even potentially dangerous. Hence my recommendations about disclaiming the data before showing it, using triangulation to take different bearings on reality, and doing reverse-touch analysis to immediately re-ground anyone floating in a cloud of last-touch-based over-simplification.

Note that the existence of next-generation, full-funnel attribution tools such as Revsure, doesn’t radically change my viewpoint here because we are talking about the fundamental principles of models. They’re always wrong — especially when trying to model something as complex as the interactions of 20 over people at a customer with 5 people and 15 marketing programs at a company, all while those people are talking to their friends and reading blogs and seeing billboards from a vendor. I believe tools like Revsure can take the models from a lot wrong to a little wrong, and ergo improve them from potentially dangerous to useful. But you should still show the reverse-touch analysis to keep people grounded.

And Box’s quote still applies: “All models are wrong. Some are useful.” And what a lovely quote it is.

Why Your CFO Should Be The Customer Testimonial On Your Debt Provider’s Homepage

If you’re VC-backed, you might well have taken some venture debt to top up your last financing round. If you’re PE-backed, it’s probable that your PE sponsor took a material amount of debt — e.g., 1-2x ARR — to help finance the acquisition.

Either way, if you’re an enterprise software startup, there’s a good chance there is some debt on your balance sheet.

Debt providers typically aren’t very attention demanding. They don’t require board seats and they usually don’t ask for board observer rights. Sure, they want detailed monthly financial reporting, but your company is producing those reports anyway and it’s easy to add them to the distribution list. So debt providers don’t necessarily get a lot of mindshare from the executive team and board.

If you have debt, here’s my simple advice on managing it:

  • Ensure covenant compliance tests are on featured prominently on your one-page key metrics dashboard that accompanies every draft operating plan and is presented at every QBR. This keeps covenants top-of-mind, where they need to be. Covenants are, simply put, existential.
  • Try to use debt providers who already work with your investors. This will provide your investors with some leverage if things get dicey. Think: “if you call this loan, you will never do business with our portfolio again.” While such words are more impactful from a relatively big customer, they are also not by any means some kind of invincibility shield.
  • Call when you’re in the yellow zone. Don’t wait until you trip covenants to have a conversation with your debt provider. There are a lot of other options besides calling the loan (e.g., refinancing) and it’s best to discuss them while you’re on the warning track, not against the wall.
  • Build a relationship with your debt provider. As the saying goes, “build relationships before you need them, because by the time you do, it’s too late.” Return their calls quickly. Check in when not strictly necessary. Offer to do reference calls on new deals. Or, speak at their executive dinners. Say yes to the invitation to their baseball box. Appear as a guest on their podcast. Show them the respect you should show someone who just might be in a position one day to bankrupt your company. Because they are.

When having conversations with your debt provider, think of covenants in two ways:

  • In the literal sense, they are part of the contract that you made for your debt. If you break one, you’re in breach of that contract, and they can take whatever remedies the contract provides.
  • The intent of most covenants is to ensure the lender gets paid back. They serve as an early warning system to alert the lender of potential trouble. So, e.g., if you had a big deal slip from 9/30 to 10/05 and that threw off your required Q3 liquidity ratios, then you’ve already corrected the problem within two weeks. Hopefully, that calms repayment concerns.

Remember the lender is not only trying to see if you can honor your word, but more importantly, to see if there’s any incremental repayment risk.

Finally, remember that while covenants are black-and-white tests, what to do when they’re breached is not. The debt provider has a lot of different cards to play, and the vast majority of debt providers are not in the “loan to own” business, so they have no desire to take control of your company. The cards they choose to play will be not only a function of the business situation, but of existing relationships and people.

Which is why I always say that your CFO should be the customer testimonial on your debt provider’s homepage. Who wants to call that loan?

(Thanks to Ian Charles for teaching me this principle back in the day.)

Back to Finance: Why I’m Joining the Board of Vic.ai

You can’t run a financial planning company for six years and not develop a certain affection for working with the office of the CFO. It doesn’t hurt when, despite your exterior marketing shell, there’s an inner finance person down there underneath.

Since selling Host Analytics five years ago, I’ve tried to stay in touch with my finance roots. I’ve done some advisory work on the FP&A side of the house (e.g., advising the rocketship that is Pigment) and kept in touch with up-and-comers like Mosaic and Causal. I’ve worked with CPQ disruptor CacheFlow. I’ve kept an eye on next-gen spreadsheets like Rows and invested in a sense-maker called Decipad. But, other than being lucky enough to make an investment in FloQast, I’ve not done much on the other side of the house: the land of accounting and controllers. Until now, that is.

I’m pleased to announce that I’m joining the board of directors of Vic.ai, a company focused on bringing the benefits of AI to the accounting department, selling solutions used by hundreds of firms worldwide. Vic.ai has raised over $110M in VC financing from top-tier investors including Cowboy Ventures, Notable Capital, and Iconiq Growth.

Here are some of these reasons why I’ve decided to join the board:

  • Founder/CEO chemistry. The independent director role is all about working with the CEO on the challenges of building and scaling a company. In the past few months, I’ve spent quite a bit of time with Alex and am certain that we’ll enjoy working together to accomplish great things.
  • Working with Alex is like teaching the 301 class, not the 101 class. He’s already a successful entrepreneur, having built and sold his first company in 2014 after nearly a decade’s work. So it’s a more challenging and demanding job than usual. He keeps me on my toes.
  • I like marketing and selling to finance teams. They’re busy people. They’re not the most experienced buyers (unlike marketing or IT they don’t buy a lot of stuff). They’re a staff function so priorities can change overnight. They don’t like fluff. Finance is the show-me state of corporate functions. That makes marketing and sales somewhat more challenging, but more rewarding once you nail it.
  • I like what Vic.ai does. The product solves practical problems for busy people who know they need to be experimenting with and learning about how AI can help them improve operational efficiency. I think the product-market fit is outstanding.
  • The benefits are real and tangible. With due respect to my Future of Work friends, we’re not selling intangibles like stronger culture or improved collaboration. We’re selling improved cash flow, time saved, money saved, and errors reduced. Hard benefits. Yum.
  • The VC investors are great. It’s been great to meet Ted and Will from Iconiq, Jeff from Notable, and Jillian from Cowboy. While I have worked with some of their partners in the past, I’ve not yet worked with them and am super excited to do so. It’s also great to reconnect with Greg from Costanoa with whom I worked closely for years at Alation.

I don’t know the whole team executive well yet, but have been psyched to meet the CMO Mark and the CRO Ben, and any Kellblog reader will know I have one message for them: sales & marketing is a three-legged race, so let’s perfect the art of working together.

Finally, I also look forward to working with cofounder Kristoffer and to helping him and Alex take Vic.ai to the next level.

A Friendly Reminder to Cost-Cutters: Keep the Company a Great Place to Work for Survivors

It’s been a tough year. We’re currently in peak planning season for 2024. With capital scarce and expensive, with companies increasingly trapped in Schrödinger’s startup paradox, and with more startups than ever focused on positive cashflow and The Rule of 40, it’s safe to say that Silicon Valley is still very much in a cost-cutting mood.

I’ve done a lot of cost cutting over the course of my career so I thought I’d share one key rule that sometimes gets overlooked when you’re in the thick of this process. Here’s the rule: no matter what you do, no matter how deep the cuts have to be, keep the company a great place to work for those who still work there (aka, the survivors).

Why do we forget this? As we struggle to hit top-down targets through rounds of cost-cutting, we cut here and squeeze there so much that we can develop a certain myopia. While we eventually congratulate ourselves for building a plan that finally achieves the financial targets, we often forget to sanity check that plan in two ways:

  • Achievability. Is the resultant plan even do-able? Or have incoherent cuts across departments left us close to attaining financial targets, but out of balance across functions? Are the revenue (and ergo cash collection) targets realistic? If not, the consequence is missing those targets, triggering another painful round of cuts. Always make a plan that you can beat.
  • Quality of life. What will it be like to work at the company we just created? Will the people we hope to retain want to keep working for us? Are there still free drinks in the frig? An annual company kickoff? A bonus program with non-zero expected value? More subtly, have we teed up both failure and internal warfare by overcutting marketing relative to sales? Or product relative to engineering? More simply, do we still have travel budget? Do people feel like they have the resources they need to succeed?

While this may sound basic, lots of companies mess it up. Why? Because it’s so hard to build a budget that hits the new targets in the first place, the last thing the executive team wants to do is sanity check that budget and find more problems.

In addition, the management team is likely still wedged in an incremental rather than absolute mentality — meaning that while a given function had $5M last year and needs to cut to “only” $4.5M this year (and yes, that’s after absorbing some naturally inflating costs), that $4.5M is still a heck of a lot of money and, for that matter, a lot more function budget than we had three years ago when we were in the earlier stages of building the company. To solve the latter problem, the executive team needs to first heal itself (by reframing their own thinking) and then get the rest of the management team on board with absolute rather than incremental, year-over-year thinking.

But back to quality of life. Let’s make this concrete by giving several real examples of what people get wrong:

  • No raise policy. You’re better off cutting more people in order to make room for merit increases and promotions — that is, if you really care about keeping the company a great place to work for the survivors.
  • No backfill policy. A mindless policy that basically says the C-suite can’t be bothered with headcount resource allocation and will effectively leave it to chance. And create perverse incentives to not terminate weak employees in the process.
  • Little or no travel budget. I recently spoke with a product leader with a team of about 8 PMs, none of whom were allowed to travel anymore. They’d be better off with 6 PMs and some travel budget. If you believe PMs need to meet customers to do their jobs, that is. Ditto for product marketers. Double ditto for sellers. It’s not about the travel budget per se. It’s about making the people who stay feel they can be successful.
  • Bonus targets in excess of plan targets. This is the old, “well we cut the plan but we didn’t change the bonus targets” trick and it’s simply not credible. In the end, what matters is the expected value of the bonus program to employees, and if that plan has unrealistic targets, that value quickly drops to zero. If that’s 20% of someone’s total compensation, that’s a material pay cut — and that’s certainly not keeping the company a great place for those who stay.
  • Workflation. This is the opposite of shrinkflation (e.g., the constant price for an ever-shrinking candy bar). This is where you get the same pay, but for a much bigger job. For example, if you replace managers with player-coach team leads, or if you blow up your success team and ask sellers to take on post-sales account management.
  • Killing internal events. Like it or not, wiping out the annual company kickoff or the president’s club reduces the expected value of working at the company to the employees. My advice is to cut these back, but don’t kill them.
  • Cutting supporting resources. Whether you’re cutting marketing relative to sales (and thus potentially creating a “baby robin” problem) or cutting SDRs relative to sales (putting more work on sales), or creating an imbalance by cutting product relative to engineering, you must remember that a healthy organization is a dynamic system, with interacting functions and checks and balances. Cut holistically. Instead of reducing SDR and SC support ratios across Europe, cut direct operations in a few smaller countries.

So, when you started reading this post, I’m guessing you were thinking, “oh no, we’d never do that at my company” and by the time you finished the above list you were thinking, “oh no, we did — in like three areas.” That’s why I made the list.

You can use the list to sanity check your plan or you can just derive directly from the core principle. Whenever you are cutting, always, always keep the company a great place to work for those who are going to still work there.

The alternative, frankly, is bleak. Your employees will do the last round of cuts for you — and you may not like what they decide.

“The Board Brought Me In” Telltale

There’s only one executive who should ever say, “the board brought me in,” and that is the chief executive officer (CEO).  Yet, you’d be surprised how often you hear other executives — chief revenue officers (CROs), chief marketing officers (CMOs), chief product officers (CPOs), and most often chief financial officers (CFOs) — say, “the board brought me in.”

It usually comes up in an interview, with a candidate running through their background.

“Well, I was at XYZ-Co, and things were going great, but at PDQ-Co they needed some help, so the board brought me in to help get things back on track.”

A+ on storytelling, but (usually a) C- on reality attachment.  “And where,” methinks, “was the CEO during all this board bringing in and such?”

(And if things really were going so well at XYZ-Co, tell me why’d you jump ship to do a fixer-upper at PDQ-Co again?)

I always view “the board brought me in” language as a telltale.  Of what, I’m not entirely sure, but it’s usually one of these things:

  • Self-aggrandizement.  Sometimes, it’s just the candidate trying to sound larger-than-life and they think it sounds good to say, “the board brought me in.”  In this case, the candidate’s judgement and credibility come into question.
  • Innocent miscommunication.  Perhaps the candidate knew an existing board member and was referred into the position by them.  OK, I suppose technically they could think, “the board brought me in,” but didn’t the CEO interview them and make the final call?  Did the board really bring them in — as in, against the CEO’s wishes?  Maybe it’s just old-fashioned communications confusion.  Maybe.
  • Genuine confusion.  Or, perhaps the candidate is under the illusion that they somehow work for the board and not the CEO.  This can happen with CFOs in particular because, unlike all other CXOs, there is something of a special relationship between the board and the CFO.  But in tech startups, in my humble opinion, the CFO works for the CEO, period — not for the board.  They may have a special relationship with the board, they may meet with the board without the CEO being present (e.g., audit committees).  But they work for the CEO.  If you feel differently, great.  If you feel like I do — best to use this as a telltale of a potentially huge problem downstream.
  • A placeholder CEO.  There is always some chance the CEO is somehow a placeholder (e.g., a founder who’s lost all but positional power in the organization and acting in some lame duck capacity).  In this case, the CXO in question might just be saying the truth — perhaps the board really did bring them in.  But then the candidate’s going to need to explain why they jumped into such a mess [1].

I’m sure there are other possibilities as well.  But the main point of this post is to say that your ears should perk up every time you hear a CXO [2] candidate say, “the board brought me in.”  Mine do.

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Notes

[1] And I suspect the most common answer will be, “and they were planning to make me CEO in X months once they worked on the transition.”  In which case, I’d want to understand why the candidate is so trusting (or naïve), what written assurances were given, and why they would take a CXO job with a dubious call option on CEO as opposed to taking a straight-up CEO job.  (To which the best, but still somewhat unfortunate, answer is — it was the only available path I had at the time.)

[2] For all values of X != E.