AI & Sales

A few weeks ago, Tomas Tunguz from Theory Ventures gave an insightful talk on the state of SaaS Go-to-Market. One key takeaway was the explosive growth of AI use among sales teams. This isn’t surprising. Sales teams, by nature, are quick to adopt new tools because they’re profit centers. Anything that works will be adopted quickly because it impacts the top line. AI is helping sales teams in several areas—lead scoring, customer research, training, follow-up automation, competitive intelligence, and price optimization, to name a few.

Sales leaders are reporting lots of efficiency gains thanks to AI, but despite the boost in productivity, AI hasn’t moved the needle when it comes to deal conversions or bookings growth.

The reality today is that AI in sales — as it is in many functions — is really like having a bunch of productive interns. They can handle lots of grunt work, but their output needs to be checked, they’re tough to train, they lack company and situational context, and they’re not equipped to make important decisions. AI can’t yet do what great salespeople do. It can’t build emotional connections, navigate complex negotiations, leverage intuition, adapt in real-time to low-information situations, or respond to subtle cues or nuanced human emotions surrounded in layers of context. In short, AI is really good when it has lots of great training data to work with, which is the polar opposite of what a good salesperson does: they shine and show their real value when they lack data, and the next step is unclear, and they have to jump over hurdles to acquire more information or rely on their emotional intelligence, intuition, instincts, and human connection to make a good decision without it.

That said, I do believe the efficiency gains AI provides will eventually translate into better conversions and growth. But I’m skeptical how high up the chain it can go in terms of high value sales activity.

AI in sales will be a fun one to watch. Sales results are pretty measurable, and teams will quickly adopt what works. We’ll see.

Breaking Down $4.5 Trillion

Healthcare is a $4.5 trillion dollar industry.

I can’t tell you how many startup pitch decks start by stating this fact. Unfortunately, without more details, this number is somewhat meaningless with regard to the vast majority of healthcare companies. Better to break the $4.5t down into parts and talk about the share that your company will seek to impact or how it may shift dollars across categories. Here’s how the $4.5t breaks down at a high level:

• Hospitals and Healthcare Facilities – 31% (~$1.4 trillion)

• Physician and Clinical Services – 20% (~$900 billion)

• Prescription Drugs and Pharmaceuticals – 10% (~$450 billion)

• Health Insurance and Payers – 29% (~$1.3 trillion)

• Medical Equipment and Devices – 6% (~$270 billion)

• Healthcare IT and Digital Health – 4% (~$180 billion)

• Home Healthcare and Long-Term Care Services – 5% (~$225 billion)

Even these categories are way too broad to tell a good story around (as an example, the EHR industry is about $35 billion out of the $180 billion healthcare IT industry; cancer drugs are about $200 billion out of the $450 billion pharma industry).

I love a company story that starts at a high level that everyone can understand and then zooms in deeper and deeper, educating the listener along the way. So it’s a great idea to start with the $4.5t, but that’s just the start of a much more interesting drill down into what you plan to do and how you plan to do it.

Fundraising & Incentive Alignment

There was a really interesting discussion on the “state of venture capital” on the BG2 podcast this week. It's definitely worth listening to the entire episode, but here are three key insights for founders that I thought were worth highlighting, along with some brief commentary:

1/ $100M+ exits are incredibly rare but can be life-changing for founders. Taking 15% of a $100M exit is $15M—not bad at all. But if you've raised $100M in venture capital, a $100M exit is off the table due to the preference stack where VCs get paid first. If you've raised $500M, a $500M exit is off the table. $1bn, etc. Raising more money than you need makes great exits harder and harder to achieve. This is also true of valuations: a high valuation sets a new benchmark for success. There's an important trade-off between driving up valuation (so investors take a smaller portion of your company per dollar invested) and setting expectations so high that even a strong exit may not satisfy investors. I wrote a post a while back about how employees should think about this topic when joining a startup.

2/ Raising too much can lead to a loss of focus, spreading talent too thinly across initiatives. Companies often say they won’t use all the capital they raise, but that’s tough to avoid in practice. If you’re an entrepreneur with a bank full of funds and a head full of ideas, you’re likely going to pursue those ideas. The discipline to keep the money in the bank is inconsistent with the mindset of a creative, ambitious, high-growth leader. And early on, focus is everything, and it’s one of the major advantages a startup has. You only have a small team of top performers that can create outsized value, so spreading them too thin can significantly reduce their impact.

3/ The incentive structure in venture capital has shifted a bit, impacting the alignment between VCs and founders. The venture model, traditionally known as "2 and 20," means firms typically charge a 2% management fee and take a 20% carry (their share of profits when a portfolio company exits). In the past, venture capital was sort of a boutique asset class, with a few players managing smaller funds and relying heavily on that 20% carry to make a profit. Today, due to companies going public later and seeing more value creation in the private markets and the fact that starting a company has become much easier, venture capital has become a far larger asset class with more capital, more investments, and lower margins. As a result, that 2% management fee can become a substantial source of income — 2% of a $1 billion fund is $20 million per year. This structure incentivizes VCs to deploy capital more quickly as they don’t earn that management fee until the money is deployed. It's not a huge deal, but this can lead to some incentive misalignment between a VC and founder, so it’s worth being aware of.

Writing

“I’ve seen many people shy away from writing because it doesn’t come naturally to them. What they overlook is that writing is more than a vehicle for communicating—it’s a tool for learning. Writing exposes gaps in your knowledge and logic. It pushes you to articulate assumptions and consider counterarguments. Unclear writing is a sign of unclear thinking.”

-Adam Grant, Hidden Potential: The Science of Achieving Greater Things

Why Is It So Hard To Sell To Health Systems?

As a seller, you want to sell to an organization with a single decision-maker who’s free from regulatory constraints, has high margins, a risk-taking mindset, plenty of cash, and no legacy systems in place to slow things down. This is the exact opposite of a typical health system.

Many salespeople claim their market segment is the toughest. But those who sell to health systems might just take the prize. Health systems are notoriously challenging to sell into. To sell to these organizations more effectively, it’s helpful to consider why that is.

1. Complex Organizational Structure

Health systems have very complex ownership and decision-making structures. There are multiple layers of authority, often with competing interests, incentives, and priorities: executive leadership, service line leadership (orthopedics, cardiology, nephrology, etc.), procurement leadership, and technology leadership, all of whom can veto a decision. Clinical needs can also quickly shift priorities, sometimes sidelining other initiatives. And then there’s the troublesome “innovation” team, often connected to a venture investment fund with its own set of disjointed incentives. Selling a product to a health system often requires buy-in, alignment, and approval from all of these stakeholders. A key part of the job for a salesperson is to help the buyer navigate their own internal processes to enable a purchase.

2. Regulatory and Compliance Constraints

Health systems face numerous layers of regulatory oversight that can significantly slow down procurements. Requirements include HIPAA, accreditation standards, state licensing, anti-kickback laws, and CMS guidelines, to name a few. On the technology side alone, there are the HITECH Act, EHR incentive programs, FDA software regulations, FISMA, and interoperability standards. Vendors must undergo rigorous vetting and compliance processes, which can radically slow and often end a sales cycle. It’s crucial that sellers have a deep understanding of the regulatory and compliance issues that overlap with their products.

3. The Dominance of the EHR

Few industries have a software vendor that wields as much influence over internal decision-making as EHR vendors do in healthcare. These are giant, long-term contracts, and depending on where a health system is in its EHR implementation, dozens to hundreds of EHR employees can be embedded within the health system. Often, if you’re selling a software product, someone in the health system will consult their EHR vendor before even considering a conversation. These EHR vendors frequently have ancillary or directly competing products, and there’s a saying among health tech salespeople that the large EHR Account Managers are trained to respond to any new software procurement by saying, “We already do that.” And often, once you get approval to move ahead, a lengthy integration conversation must be waded through, both in terms of feasibility and timing.

4. Low Risk Tolerance

Given the life-and-death nature of their work, inherent low margins, litigious concerns, mostly not-for-profit structures, and heavy regulatory burdens, health systems rightfully prioritize avoiding mistakes over taking risks. This makes selling a new, unproven product quite challenging. They want free trials, extensive case studies, flexible contract terms, and numerous customer references. Their ROI standards are stringent, and they rely heavily on evidence-based data before making a decision. Also consultants are often brought into the process as well to help reduce risk and add rigor, adding further scrutiny and potentially misaligned incentives. A healthy cautiousness is a key part of the culture of a health system.

5. Health Systems Are (Mostly) Local

Over time, most industries will consolidate down to a few national or global players. This isn’t true in healthcare. There are 2 to 4 dominant health systems in each large metropolitan area in the country. There is some overlap via large regional players or national health systems, but not a ton; it’s a highly fragmented space. There are a bunch of very large health systems businesses scattered across the US. There are 5 US airlines whose annual revenue exceeds $5 billion. There are nearly 10 times as many US health systems that meet that threshold. These factors make selling more difficult for a variety of reasons. You don't have a consistent set of priorities across markets to sell into. There's often allegiance to local or regional vendors. It's hard to leverage competition because a New York health system doesn’t care much about that big account you won in Houston. More broadly, the lack of scale in these local health systems trims margins and makes budgets much tighter than they might be on a national scale. 

6. Supply & Demand Mismatch

Over the last decade, more than $100 billion in venture capital has poured into health tech startups, creating a vast supply of vendors that need to show a return on that capital by selling their products to health systems. The supply of products far exceeds the demand, leading to vendor overload for health systems. There’s a lot of noise out there that buyers are forced to wade through. Many health systems have responded by launching innovation teams, some with venture funds attached, which attract vendors to test products using health system staff and provide the fund with deal flow. These innovation teams often wield outsized influence, creating incentive misalignment and internal conflict. Even when these aren't in place, you can bet that the health system you're selling to is pretty sophisticated at sidestepping salespeople.

Starting Up & Scaling Up: Turning Duct Tape Into Steel

I heard a great metaphor for building companies the other day.

When you start a company, you're scrambling, trying to find your way, and building lots of new things. You find that when things work, the company is held together with duct tape. A large part of the job in making it into a great company is turning that duct tape into steel so that it can sustain itself without requiring superhero levels of daily effort. It's worth stepping back to understand this metaphor and how the priorities of an organization change over time.

The Duct Tape Days

The "duct tape" days are tough. You have to tackle a bunch of new and challenging things: raise money, convince great people to join you, figure out how to build something new, find product/market fit, implement it, and make customers happy—along with dozens of other little things you need to do to get a company off the ground.

The hardest part of this phase is that you're breaking ground on something new. All along the way, you know in the back of your mind that it might not actually work. This is stressful and hard to manage. However, the best part of this phase is the high level of alignment with your team. You probably don't have many customers (if any), you don't have a lot of employees, and everyone is mostly rowing in the same direction. The highest priority for any given employee at this stage is the same (or very close to the same) as the highest priority for the company. That's a great thing.

When you get past this initial phase and find that you have something that works and that people want, you quickly start to encounter a new set of problems. Your problems shift from building something new to scaling it. And the better the company performs, the more problems you will have. If you talk to people at startups, most (actually, all) will tell you it's a sh*t show. The faster the growth, the bigger the sh*t show.

The reason is that a company takes on more commitments as it grows—commitments to customers, investors, governments, auditors, partners, vendors, and one another via cross-functional teams. In the early days of scaling, these commitments grow linearly with the company. All of these commitments are new, and the workflows to manage them must be built from scratch. You probably expected some of them, but you'll also discover commitments you never imagined at the outset due to the compounding complexity that comes with scale.

Scaling Up

To manage these commitments effectively, the company will soon start to split into teams and add managers, new job titles, and levels. This structure becomes necessary because specialized groups can more effectively focus on specific areas, make faster decisions, enhance accountability, communicate more efficiently, and take ownership of the new workflows built around the growing set of commitments.

Pretty soon, you have a structure and a long list of commitments and priorities that looks something like this:

• Finance: Budget management, financial reporting, cash flow management, compliance and audits

• Sales: Revenue targets, customer acquisition, CRM management, territory or account management

• Operations: Customer onboarding, process optimization, logistics and fulfillment, vendor management

• Product: Product roadmap, feature development, quality assurance, user feedback integration

• Marketing: Brand management, lead generation, content creation, market research

• HR: Talent acquisition, employee onboarding, performance management, employee development

That's a lot of duct tape.

Quickly, the distance between the highest priority for any individual employee starts to diverge from the highest priority for the company, and that distance only continues to grow over time. You start to have lots of competing priorities and people rowing in different directions.

Competing priorities naturally lead to confusion and miscommunication among team members, resulting in unclear roles and conflicting work. This misalignment often causes inefficiencies and duplication of efforts, as teams may unknowingly work on similar tasks independently. Frustration can build, decreasing morale and motivation among employees who feel their efforts are not well aligned with company goals. Decisions get delayed, and things might feel like they’re standing still, leading to missed opportunities and slowed progress.

Tech people like to lovingly refer to this as "thrash."

Ultimately, this thrash can lead to poor performance and poor culture.

Turning Duct Tape Into Steel

Companies need to get ahead of all of this natural and inherent side effect of growth. They need to start turning the duct tape into steel by putting goals, processes, metrics, and communication systems in place to ensure a high-performance standard against all of these new commitments. They also need to align the work being done with the company’s strategy and financial objectives. Tools like vision and mission statements, OKRs, company values, cultural principles, financial targets, team offsites, company-wide meetings, cross-functional meetings, accountability and reporting systems, and management processes need to be implemented to solidify strong systems and prioritization around the company’s commitments.

There are multiple frameworks and playbooks on how to do this well. However, every company is different, and each should publish and regularly communicate its systems to their teams. Doing this well can become an enormous competitive advantage over time. I’ll write more over time about some of the things I’ve seen work well.

The Cadence

One of the most common and dangerous areas of misalignment in this phase—particularly for b2b companies—is between product, marketing, and sales. In consumer-focused companies, a natural glue pulls these teams together. Often, there’s no sales team, and large parts of marketing are embedded within the product (algorithm-based merchandising, social sharing features, cart abandonment targeting, etc.). This glue doesn’t exist or is far less sticky inside a b2b company. In b2b, these teams are often separated under different leaders but are the commercial lifeblood of the company. The product team builds things that create TAM, the marketing team builds a pipeline out of that TAM, and the sales team closes that pipeline pipeline. Without tight alignment between these three teams, things can quickly fall apart.

To help manage this, one framework I love and highly recommend borrowing and wanted to highlight today is "The Cadence: How to Operate a SaaS Startup" as described by David Sacks in his somewhat dated but enormously valuable Medium post.

In it, Sacks recommends putting sales and finance on a shared cadence and calendar and product and marketing on another shared cadence and calendar.

From the post on the sales and finance cadence:

"Every company runs on a fiscal year as an accounting requirement. This finance calendar should be synchronized with the sales calendar for reporting reasons. When the books close on a fiscal quarter, the numbers should reflect a complete quarter’s sales activity, not an incomplete mid-quarter picture. The leadership and board will have a much better sense of what’s happening in the business if sales plans are snapped to fiscal quarters."

And on the marketing and product cadence:

"When rapidly scaling startups don’t have effective product management, one of two things happens. First, they just ship sand. They polish and fix bugs and usability issues, but they don’t ship tentpole features, new products, and major releases. Or when they do, they end up going wildly over schedule. A product that was supposed to take one quarter will still be in development multiple quarters later. ‘V2s’ that were supposed to take a couple of quarters end up being years late and paralyze the company. This happens because the product was never scoped correctly. The quarterly discipline ensures that you do big stuff—rocks, not just sand—while scoping correctly."

"None of this is to say that code can’t be shipped weekly or even daily for code management reasons, but PM planning should revolve around quarterly or seasonal releases. Now that you know there will be a major quarterly product release, you can plan marketing around that. This is why marketing and product are on the same calendar. Startups are product-driven, and most news that the company puts out will feed off of new product releases."

While I’m a huge fan of this approach, the brilliance isn’t necessarily in the details but in two very important concepts:

1. The notion of internal teams making solid commitments to one another and

2. Tying that commitment to a calendar and firm timeline.

Getting teams to hold one another accountable and rely on each other with specific timelines is a giant step in turning duct tape into steel.

That said, I’ve historically found that product teams can sometimes be reluctant to commit to firm timelines, as they’re described in this framework. Product development processes from companies like Google or Spotify often prioritize agility and rapid iteration to respond to changing user preferences and market trends. This can cause them to favor less rigid timelines, which makes a shared calendar with the marketing team challenging to operationalize.

Conversely, companies like Oracle or SAP, which deal with large customer expectations, integration requirements, buying cycles, budget cycles, and program cycles, require fixed timelines and have more structured environments. You can almost view Google and Oracle as two sides of a spectrum.

The right approach to this spectrum isn’t to be philosophical (e.g., is Google better than Oracle?) but should be based on the unique characteristics and attributes of the buyer and the way the product is bought, sold, and implemented. Before adopting this approach, I’d encourage all commercially focused teams to dive deep on this point.

Ultimately, every company is built on a foundation of duct tape in the beginning—it’s messy, thrashy, and fragile, and it feels like it could fall apart at any moment. It’s important to understand how and why this happens so you can get ahead of its pitfalls. The companies that succeed are the ones that learn to replace duct tape with steel methodically and with intention. Time-based, cross-functional accountability is an incredibly valuable tool and tactic to manage through this crucial transition.

Asking Great Questions

Pushing oneself to ask great questions is extremely important. It forces you to think critically, accelerates your learning, improves decision-making, and helps build trusting relationships. Here are some things that have helped me ask better questions:

Tell yourself a story and use questions to fill in the gaps.

When I'm interviewing someone, being interviewed, or just having a conversation with a colleague or founder about a business problem, I typically take what the other person is saying and try to tell a story that makes sense in my mind. If someone is explaining a new company they'd like to start, I'm listening, but as I hear them talk, questions pop into my head about things I want to know more about or inconsistencies with my preconceptions. This is the trigger for most of the questions I ask, and it’s a useful way to generate dozens of questions in a single conversation.

Of course, you have to temper your questions and prioritize the most important ones so you don't sound like a nut. But forcing yourself to tell your own story based on what you're hearing—and fitting it into your worldview, or using it to learn something new and adjust your worldview—is a great way to ensure you're asking high-value questions.

Be ruthlessly authentic and ask “dumb” questions.

Have you ever noticed that whenever you ask a “dumb” question, it often turns out to be a great one? Dumb questions are wonderful. They typically simplify the topic, challenge assumptions, align the conversation at a high level, and enhance inclusivity. The trick is having the humility and courage to risk showing that you don’t know something that others do. This is definitely a risk worth taking. Try to never hesitate to do this. Be authentic. The best questions are about the things you really want to know. As someone once said, “Not knowing is not ignorance; not seeking to know is.”

Ask what people think, feel, or would do—not what they know.

I almost always find that opinions based on facts are way more interesting than simple facts. Instead of asking a job candidate, “What is our competitor's product strategy?” try asking, “What do you think of our competitor's product strategy?” Similarly, don’t ask your real estate broker, “How can I get a better price?” Instead, ask, “How would you go about getting a better price?”

This tactic encourages the person to really think about the answer and provides you with genuine insights rather than just reciting what they know. Also, give them time to think and express their full answer. Rushing them only leads to less interesting responses.

Tradeoffs

Over the years, I've found that leaders (and people in general) are often resistant to facing the tradeoffs that come with the difficult decisions they make.

You see this a lot with public policy. A simple example is governments mandating that tech companies implement encryption to protect user data and sensitive information. On the surface, this is a great thing. However, several tradeoffs come with encrypted data, the most noteworthy being that law enforcement can't access information related to criminal activities by users or the company itself. So regulators will also ask companies to encrypt their data and provide a back door so it can be accessed when required by law. But, of course, you don't have encryption if you have a back door. Regulators are often unwilling to face the natural tradeoffs associated with the regulations they create.

Similarly, I recently talked with a small group about Chapter 11 bankruptcy (the legal process that allows a business to reorganize its debts while continuing to operate). Some were arguing that it shouldn't be allowed. If someone is going to run their company into the ground, they shouldn't be allowed to have a court step in and save them. At first glance, this also makes sense. So perhaps we should do away with Chapter 11 bankruptcy? Maybe, but only as long as we're willing to face the painful tradeoffs.

With Chapter 11, a business leader is incentivized to raise their hand and ask for help before they become completely insolvent and run out of cash so that debtholders can salvage at least some of their money. Without it, if a leader knows there's no way out, they'll keep the company going until it’s down to its last dollar, hoping to survive somehow, meaning debtholders get nothing. Ironically, Chapter 11 protects debtholders. Further, what would happen to innovation in America if founders of companies knew that if they failed, they were done for good? What would that do to the amount of risk entrepreneurs take? How many companies never would've been founded? There's a reason you see a lot more innovation come out of countries that provide some form of protection to risk-taking inventors. 

Of course, one of the most common tradeoffs in business is deciding how much to invest in growth versus how much to expand profit margins. If a leader asks their board, the advice is very often to do both. Said differently, ignore the tradeoffs.

A large part of leadership is making difficult decisions, which are typically just a set of tradeoffs that must be managed. Great leaders know that it’s not just about what you gain; it’s also about surfacing and dealing with downstream consequences and what you’re willing to lose.

A Finance Deep Dive

A couple of weeks ago, I completed a Finance for Senior Executives course at Harvard Business School. I took the course because, while I feel like I have a pretty good grasp of finance from business school and work experience, I wanted to refresh my brain on the fundamentals and go a bit deeper than I've been able to over the last several years. The course was excellent, and I highly recommend it for operating executives who find themselves in a similar spot. The content was designed for senior executives who don't work directly in the finance function. The course had a virtual portion followed by four days of in-person living and studying on the HBS campus. The class was grounded in the case study method, with 13 real-life case studies (including a great one where we had to try to rationalize Peloton's stock price in the Summer of 2019...). The class was filled with an incredible group of intelligent, thoughtful, energetic, and self-motivated students who were really fun and inspiring to get to know — 89 students from 21 countries. Just a great group. The syllabus covered six primary topics:

• Measuring Performance and Financial Ratios

• Discounted Cash Flow 

• Valuation

• Capital Structure and Leverage

• Mergers, Distress, and Recapitalizations

• Capital Allocation and Pursuing Margin and Growth

As we went through the coursework, I made a note of some of the more insightful reminders, ideas, concepts, and topics that stuck with me. I thought I'd share some of them here:

1/ The primary job of finance is to ensure that the company doesn't run out of cash and makes good financial investments. Watching working capital (current assets - current liabilities) closely is crucial — lots of very profitable companies run out of cash. I’ve seen this quickly become an issue for tech companies that don’t hold inventory and have taken their eye off working capital, as well as tech enabled healthcare service companies that have a revenue cycle lag.

2/ Terminal value of a company (its value in perpetuity) should be used carefully, as there's never really a company that runs forever. That said, over the long term, the discount rate will balance this and make the calculation more reasonable. The terminal value of a company should be calculated after growth and margin have stabilized.

3/ Net present value measures the dollar value an investment adds or subtracts by comparing the present value of cash inflows and outflows. Internal rate of return calculates the percentage rate of return that makes net present value zero.

4/ There's really no such thing as a "good" growth rate or margin or financial ratio. It all depends on the context and the particular situation. It's sort of like a size 10 shoe. Does it fit? Well, it depends. 

5/ You should care a lot more about the market value of a company than the book value of a company as that’s the value that investors will pay assign to the firm, though the latter is a lot easier to calculate and make sense of.

6/ Bad economics in an industry almost always beats great management over the long term. 

7/ Don't discount the fact that your debtholders are important stakeholders and investors. While interest payments cap their upside, they are the first investors to get paid in a liquidation, and returning their capital and providing them with interest payments drives substantial value. Too often, we only consider equity holders when we think about enterprise value creation.

8/ A good formula to memorize is valuing a company using its free cash flow projections. As I've written here many times, the value of a company is the present value of the discounted free cash flow you can take out of it. Free cash flow can be calculated using the balance sheet and income statement with the following calculation: EBIAT (earnings before interest after taxes) + depreciation - cap expenditures - change in working capital. It's not about memorizing the formula; it's about understanding how the balance sheet and income statement interact and how to use them to calculate the cash flows a company will generate.

9/ Debt is a government-subsidized form of capital. The tax deduction on interest is the major value in financing an investment with debt over equity. This is really meaningful. Obviously, it is less relevant for startups that still need to produce profits. 

10/ The "irrelevance hypothesis" says that in an ideal world with no market imperfections, the dividend policy of a company is irrelevant to its overall valuation because shareholders can create their own homemade dividends by selling their shares. Of course, real-life market imperfections always need to be logically applied when creating a dividend policy. 

11/ Operating leverage is an important metric to watch over the long term. High operating leverage means that small changes in sales lead to disproportionate increases in operating profit because fixed costs remain constant while revenue increases. 

12/ Businesses can be placed on a spectrum from "high tech," which are high growth/low profit, to "cigar butt" businesses which are low to no growth/high profit (companies that only have a few puffs left). There’s nothing thing wrong with a company that isn’t growing but is throwing off cash and not all companies need to stay in business forever. It's important to understand where a company is on this spectrum to guide where to place capital — invest in growth, return to shareholders, or pay down debt. 

13/ Dividend payments are effectively the same as a corresponding investment in growth when the dollars generated and value creation are the same (the only relevant difference is that in one scenario, the money is in the investor's pocket versus the company's pocket). But the value is the same. This is a good reframing, similar to the importance of returning capital to debtholders. Capital is capital regardless of whether the investor holds it in your company or puts it in an index fund.

14/ Generally, markets value growth increases over margin increases because growth compounds on itself. The exception is low-margin businesses. You'll get more upside there from growth. All should be calculated through discounted cash flow analysis.

15/ High discount rates favor high-margin businesses, and low discount rates favor high-growth businesses. 

16/ Detailed discounted cash flow rates often aren’t used on a practical basis inside of companies. The reason, generally, is that there are often more ideas that exceed the discount rate hurdle than can be executed. That said, it’s crucial that all leaders understand discounted cash flow, NPV, and IRR.

I'm really glad I took the class. I'll look into other courses like this to deepen my knowledge in areas where I haven’t gone as deep as I’d like in recent years.

Salesforce’s Pivot & The AI Business Model

Back in October, I wrote a post titled Selling Software vs. Selling Work, in which I noted that AI may begin to disrupt the traditional SaaS business model. As a reminder, the traditional SaaS business model allows software companies to sell their software as an ongoing service with annual recurring payments. Typically, the software is billed on a "per-seat" or "per-employee" basis. Pioneered by companies like Salesforce, this model has been enormously lucrative for large SaaS companies because they can grow as they sign up new logos, but they can also grow organically and naturally as their customers hire more employees (more seats). This has been a boom for the SaaS industry as most customers have grown headcount substantially over the last 10 to 15 years.

However, a large part of AI's promise is that it will likely eliminate a huge number of white-collar jobs, such that productive companies might start materially reducing headcount in the aggregate, posing a fundamental challenge to the per-seat SaaS model.

This is starting to become a lot more real. A couple of weeks ago, at their annual Dreamforce conference, Salesforce's CEO Mark Benioff announced a major pivot, at least in their AI product strategy. They are moving away from a per-seat model to a per-conversation model where the company will charge $2 for each customer service or sales conversation held by one of their AI assistants. This shift, in theory, will allow them to continue to thrive as companies begin cutting headcount and amping up investments in AI. For those who have read Clayton Christensen's Innovator's Dilemma, this is a pretty big deal and a brave move for Salesforce.

From the Innovator’s Dilemma:

"In essence, the dilemma is that successful companies often focus on improving existing products or services to meet the demands of their most profitable customers. This focus leads them to overlook or dismiss disruptive innovations, which typically start as lower-quality or niche products but eventually improve and take over the market. By the time the established company recognizes the threat, it is often too late to adapt."

Benioff must have read the book.

More broadly, as we consider an industry shift in this direction, it raises several important questions:

1/ Does it work? Can the AI fully replace a human or is it more of an assistant? Surely, for basic tasks, it will, but how far up the stack of human intelligence will this go?

2/ Given the low cost of supplying this kind of AI once it's built, will customers be willing to pay a price that preserves the revenue and profits generated from the per-seat model, or will SaaS companies take a significant hit? In many ways, this will come down to competition and the proprietary nature of the software. Companies like Salesforce have thrived via their scale and the fact that there wasn't a better place to go. Is AI a real, novel, differentiated technology that can't be recreated, or will it be easy to copy and will margins quickly contract?

3/There's an old saying in software that you can turn any task that you do in Microsoft Excel into a SaaS company (expense reports, project management, budgeting, sales pipeline management, etc.). What's the corollary for AI? Will thousands of point solution AI companies be built around LLMs?

4/ What does this do to white-collar employment? We've seen over the course of history that new technologies disrupt employment in the short term. Though in the long term, the shifts from the agriculture age to the industrial age to the services age to the information age, have led to long term increases in wages and employment. Is it different this time? Will AI get so high on the totem pole of human intelligence that the work humans do is materially reduced? A nice proxy for this might also be the spreadsheet. Prior to the invention of spreadsheet software (VisiCalc in 1979), there were large buildings full of white-collar analysts doing the calculator work that Excel does for us today. That shift only created more analyst jobs because high-quality analysis could be done more cheaply. When something gets cheaper, we typically do more of it.

Just when I thought b2b software was getting kind of stale…here we go again…it seems AI is going to be driving a new platform shift, and it's impossible to know where it all lands. But it's great to see companies like Salesforce protecting their shareholders by resisting the innovator's dilemma and getting out in front of what could be a massive new chapter for b2b tech.

Growth Without Capital

In the early days, startups are very capital-intensive. They don't have a product generating positive cash flow, so they often rely on some outside capital (debt or equity) to grow their top line. This is a necessary evil in the early days to get a company up and running. With the need for capital underscoring the financing strategy for most startups, it's easy to forget that the best companies are companies that don't need capital to grow. An excellent example of this is a franchise like Subway that leverages franchisees' capital to open new stores and expand its footprint. In addition to a franchise model, there are lots of other business models that companies can use to grow without capital:

1/ Preselling or securing customer deposits: getting a customer to pay in advance or fund the development of a product. 

2/ Joint ventures and strategic partnerships where a partner provides the capital to grow. 

3/ Government grants and contracts.

4/ Revenue sharing and licensing agreements. Getting your own sales team to sell other people's stuff.

5/ Supplier financing. Getting very favorable payment terms from your vendors such that they can use funds elsewhere for some period of time.

6/ Revenue from Licensing Technology or IP: Companies can license their technology or intellectual property to other firms, generating revenue without direct investment.

7/ Network effects. Building a product that’s more valuable as more people use it, so there’s a built-in incentive for customers to market it for you.

Early-stage companies will be inclined to rely on organic growth as they get off the ground. But it's important to incorporate — or at least be thinking about — less capital-intensive growth strategies and business models as the company matures. Again, the best companies out there are those that can achieve high growth rates without a corresponding need for capital investment.

Complexity As A Moat

Judy Faulkner, founder and CEO of Epic, had a good blog post the other day titled More Complex Than Rocket Science where she talks about the complexity involved in healthcare IT. From the post:

"My favorite t-shirt says, “Healthcare IT is more complex than rocket science.” The three Epic employees who used to work in rocket science agree."

Healthcare IT is absolutely super complex. And that complexity creates a ton of challenges for founders trying to get their idea into market. But that complexity is also an advantage in that it creates a moat around a business where it's very difficult for a copycat to come along and recreate what the company is doing. For example, if you're doing automated care management for cystic fibrosis (CF), you need to wrap your head (and your product) around specific nutrition insights, medications, lung function testing, infection management, psychological support, financial aspects of CF care, and then roll that into a service with some technology wrapped around it. And that's just to build a useful product, never mind the challenges associated with taking it to market.

The upside of the pain in taking a healthcare product to market is that often the product/market fit you’ve found is its own moat.