Put A Stake In The Ground

When you start a new venture — a company, a team, a job, a product, a project — setting goals around its success can be stressful. You don't know how fast things will move and how successful you'll be.

Further, lots of people are afraid of being held accountable, much less being held accountable for something that isn't yet understood.

So there's a temptation to just get started without setting goals and see how things go.

For example, I've seen many startups not set sales goals in the early days because they feel like they don't have enough information.

This is a bad idea.

Setting a goal gets you and your team rallied around a target. If you meet or exceed the target, the team will feel great, and you can celebrate. If you miss, you can surface learnings and insights relative to the goal you set.

If you're hitting or exceeding your goals, surfacing learnings is less important. If you're missing, learning is crucial. A learning that isn't connected to a goal is much less powerful and much less interesting than one that is. This will also create the habit of being held accountable and reporting on failure as much as you report on success.

Put a stake in the ground. Set a goal. If you hit it, great. If you miss it, you'll feel a great deal of pressure to surface high-quality learnings that will get you closer next time.

How To Structure A Commercial Organization

There are several different ways to structure a commercial organization. Markets, products, segments, etc. The model I prefer is to structure the teams around metrics. This does a few things:

1/ It ensures that the organization has a metrics mindset. Sometimes people forget what metric their work moves. Building the org around metrics makes this nearly impossible.

2/ It ensures everyone knows they’re contributing. There’s nothing worse than coming to work each day and doing a bunch of work that doesn’t actually contribute to a business objective.

3/ It helps with prioritization. Teams should prioritize their work based on the impact it’ll have on the metrics. Focus on low effort/high return work, and avoid high effort/low return work. It’s amazing how few people have this mindset.

I separate a commercial org into three buckets. If you’re not directly contributing to one of these three buckets or supporting someone that does then you’re on the wrong team. Commercial orgs only do three things:

1/ They sell stuff.
2/ They implement stuff.
3/ They retain stuff.

Everyone should be impacting at least one of those things. Then assign a set of metrics with targets against each. Here are some examples:

1/ Selling stuff (bookings, upsells, expansions, new logos).
2/ Implementing stuff (speed to go-live, quality of implementation, cost of implementation).
3/ Retaining stuff (retention, renewals, net promoter score, user activity).

I’ve found that structuring the team around these three activities and some set of metrics ensures that everyone has clarity on their role, their value, and how they’re impacting the business in a positive way.

The Rule Of 40: Which Side Are You On?

In the early days, a company with solid product/market fit and a great team will grow extremely fast. Revenue growth can be 1,000+%. But as a company becomes established, things come back to earth. Tripling revenue when you have $50k in revenue is a lot easier than tripling revenue when you have $50MM in revenue. Over time, the company will eat up all the low hanging fruit. Competitors will enter the space and apply pricing pressure and reduce win rates. Scaling becomes even more difficult. Things just start to slow down.

This flattening of growth is nothing to be ashamed of. It's a natural curve for any product or company — even the iPhone's growth has flattened.

 
Apple iPhone worldwide unit sales from 2007 to 2018 (in millions)

Apple iPhone worldwide unit sales from 2007 to 2018 (in millions)

 

The way to break out of this natural flattening is to innovate. As Jeff Jordan says, “to add layers to the cake.” But eventually, even the greatest companies will see their growth rates begin to level off.

To maintain a high valuation despite slowing growth rates, companies will often point their energy towards becoming profitable or increasing profitability. One of the biggest challenges of a maturing company is this: should we step on the gas and continue to grow like crazy, or should we shift our focus to profitability?

The Rule of 40 provides an excellent framework for how to think about this question. The Rule of 40 states that a company's growth rate + profit margin (EBITDA) should exceed 40%. Companies that can stay above 40 will continue to be on the high end of valuations — 10x, 20x, 30x revenue multiples. According to a study done by Bain, software companies that are above 40 have valuations that are double those that fall below the line.

So as growth slows, it's useful for executives to ask, what side of the Rule of 40 do we want to be on? That is, are we going to continue to achieve the 40% via revenue growth or do we need to begin focusing on profitability.

The Rule is just a framework; it shouldn’t be taken as gospel. But it provides an extremely useful framing for how to think about one of the most challenging questions high growth companies face.

Slack Connect & The Future Of Business Software

 
slack logo .png
 

Slack recently announced Slack Connect, a product that allows disparate companies to collaborate inside of a Slack channel. They now have more than 40,000 customers using the product.

For those interested in business software, I think there's reason to believe that products like Slack Connect — software that allows users across different companies to collaborate inside the same instance of that software — will lead to a trend that's even more impactful than the shift to the cloud.

Slack Connect users can have a shared Slack channel with their customers, vendors, partners, and prospects. I haven't used the product yet, but I recently collaborated in real-time with a customer to build a presentation using the same instance of Google Slides. It was so much more efficient. Imagine finance teams collaborating on complex invoicing issues inside the same instance of Netsuite. Or project managers at separate companies collaborating inside of SmartSheet. Or a salesperson collaborating with on a customer's buying process inside the same instance of Salesforce.

Moving core, cross-company business activities into a shared workspace will be enormously valuable to the users inside of each company. And even more impactful is the impact on distribution and go-to-market. Suddenly, Netsuite, SmartSheet and Salesforce have native network effects (e.g. their software is more valuable to each user when more users use it). This is why Slack Connect is so interesting. Slack already had network effects inside of a company, but growth was limited to the size of each individual company. Slack Connect enables unlimited network effects.

Don't get me wrong, like the move to the cloud, there are enormous challenges for software vendors that pursue this strategy. There's a reason I don't collaborate on Google Slides with the majority of customers. Most large companies aren't using Google's applications, and thus users don't have a log-in and aren’t authorized to use their personal one for work purposes. There are significant privacy and adoption challenges that need to be overcome.

Slack has an advantage here in that their core customer base is still startups, small businesses, and tech companies (though they’re rapidly moving upmarket). This core allowed Slack to get Connect into market much more quickly than Microsoft could've with its Teams product.

The irony of Microsoft being behind on this is that they own the one asset that could've accelerated the growth and adoption of cross-company messaging — LinkedIn.

LinkedIn already knows most professionals’ "professional social graph." These social graphs are the underlying infrastructure that enable a network to grow. Consider Whatsapp, who built a nice messaging app and then tapped into your phone's address book (your social graph) to seamlessly build out its network. They went from 0 to a billion users in just a few years. They never could’ve done that if they didn’t have access to people’s personal address book. LinkedIn is the world’s professional address book.

LinkedIn messaging could've been a far better and faster-growing version of Slack Connect. But LinkedIn underinvested in its messaging feature to the point that it's almost unusable. The spam is overwhelming, and the poor user experience makes it impossible to use productively.

This miss isn't really a surprise, and I'm not playing Monday morning quarterback. Microsoft hadn't built its initial software around connecting disparate companies. In fact, it was quite the opposite. And turning the tide isn't easy. Also, LinkedIn's core customers are recruiters and marketers; use cases where the value of cross-company collaboration isn't obvious.

So, all of this is to say that there's an enormous opportunity for emerging SaaS companies to build native cross-company collaboration tools into their code, use cases, and culture from the outset. It's hard to predict that any trend is business software will be as impactful as the shift to the cloud, but if there's one out there, this might be it.

Working For Jeff Bezos

I’m reading Amazon’s Management System by Ram Charan and Julia Yang. I absolutely love this excerpt:

As former Amazon executive John Rossman put it: “If you want to succeed in Jeff’s relentless and fiercely competitive world, you cannot:

• Feel sorry for yourself

• Give away your power

• Shy away from change

• Waste energy on things you cannot control

• Worry about pleasing others

• Fear taking calculated risks

• Dwell on the past

• Make the same mistakes over and over

• Resent others’ success

• Give up after failure

• Feel the world owes you anything; or

• Expect immediate results

The most successful are those who can excel in the pressure cooker, week in and week out, shaking off the occasional failure and the subsequent tongue-lashing, put their heads down, and keep on driving.”

This is a near perfect description of the best people I’ve worked with over the years.

Hiring Your First Head Of Sales

By far, the most frequent question I get from founders is this: How do I go about hiring a Head of Sales? I've literally received this question four times in the last six or seven weeks.

Hiring a Head of Sales at a startup is a very difficult, important, and scary thing for a founder. Making a mistake on this hire can set the company back several quarters. I try to avoid making declarative statements to founders because context is so important and each situation is unique. That said, here are a few things that will help reduce the risk associated with hiring a Head of Sales for the first time:

1/ Ensure the candidate has been an ultra-successful individual contributor. I know, I know, the best salespeople aren’t necessarily the best managers. You don't need the best salesperson in the world, but you do need someone who has done it before. In startup sales, you can't lead the calvary if you can't sit in the saddle. Strong sales capabilities (both to sell direct and to sell salespeople on joining the company) are crucial in this role. If this candidate can't sell, they likely can't recruit. It’s not worth that risk.

2/ Ensure the candidate has sold into (roughly) similar-sized organizations in the past. If you're selling to large enterprises, don't hire an SMB expert, and vice-versa. It's not impossible to make the transition, but it's relatively unlikely that it will be successful. Often, the things that make people good at SMB sales make them bad at enterprise sales. Also, do consider the candidate's experience with the vertical you're selling into. Ideally, you will be able to find someone who has sold into that vertical in the past. I wouldn't make this a requirement in every situation. The importance of this is industry dependent. But if the industry has a steep learning curve, optimize around that set of experience.

3/ If you have the capital, hire a headhunter to help. Doing this search right requires an expertise and time investment that most founders can't afford. This is a good opportunity to outsource.

4/ Hire a “stretch VP.” A stretch VP is a rising star (generally Director level) that needs to level-up a bit to become a sales leader at a larger organization. This type of candidate will generally lean towards execution but will have the potential to recruit and run a team. This is a good hedge. If the candidate levels-up and can run the whole sales organization, that's great. If they can't, it'll be easier to “level” them with a more senior candidate. If you hire someone too senior, you run the risk that they won't be execution-focused, and it will be difficult/impossible to level the candidate if things don't work out. A stretch VP is a good way to reduce risk.

5/ Overinvest in intrinsics. This candidate is going to be accepting a very difficult job. Make sure they have the intrinsics that will make them successful in a high-pressure startup environment — grit, humility, adaptability, and curiosity. More on that here. Also, this is hard to do, but make sure the candidate is someone that is at a stage in their life and career they simply aren’t willing to fail. Some call this “personal exceptionalism” — more on that here.

Things That Don't Scale

I recently started using Superhuman, the popular $30 per month email application, that's getting lots of buzz. It's a wonderful product. It solved my email overload problem.

I would've started using it sooner, but before they would grant me access, I had to complete a thirty-minute consultation with one of their staff members to configure my email and learn how to use the product most effectively. That seemed unnecessary to me, so I passed.

I eventually got desperate and agreed to the consultation. I now see why they force this — they go deep on how you use email, do some real-time customizations, and make sure you know how to use the product. All of this makes users much less likely to churn.

That said, it's surprising that Superhuman, an application with thousands and thousands of users, would make this kind of investment in onboarding new users. For a $30 per month consumer email application, this seems like the definition of something that won't scale.

I recently came across an interview with Superhuman's co-founder, Rahul Vohra, where he talked about the importance of these consultations and was asked if he thinks they can scale. He responded by saying that organizations need to identify the things they do that won't scale and decide which of them they should keep on doing. These are things that, from the outside, may seem small and wasteful but are actually core differentiators consistent with the heart of the organization's strategy and competitive advantage.

I've been thinking about this a lot lately. As an organization scales, the things that aren't scaling start to become really obvious. And smart companies find ways to outsource, automate or completely stop doing them.

The hard part of all of this is identifying those things that, on the surface, seem like they obviously won't scale but actually drive big value.

At the Ritz-Carlton, every single employee (even the maintenance folks) has a budget of $2,000 per guest to make things right. On the spot, without asking.

Zocdoc, the medical appointment booking service, sends a $10 Amazon gift card to users every time a doctor reschedules an appointment.

Zappos maintains a 24/7 call center, posts their phone number on every page of their website, and doesn’t have a phone tree.

In the early days, most startups will tend to overinvest in high-touch and high-cost activities. They have to do this because they're forcing their way into a market. They can't cut corners and scale isn't an issue.

One-on-one product training. High-touch recruiting and employee onboarding. Ultra-fast customer service response times. Even small things like sending hand-written holiday cards to every customer. These are obvious and easy to do in the early days. But many of them won't scale and there’ll be pressure to stop doing them over time.

The easy part is dropping things that don’t scale. The hard part is continuing to do them.

How Silicon Valley Became Silicon Valley (And Why Boston Came In Second)

When I was a kid growing up in central Massachusetts, I remember that a bunch of my friends' parents worked for super high growth tech companies like Digital Equipment Corporation (DEC), Data General, and Prime. While some people reading this may not have heard these names, these companies were behemoths. In the late eighties DEC alone was one of the largest companies in the world and employed more than 120,000 people. These companies were booming at the time in an area known as the “Route 128 Corridor”. Route 128 is a highway that runs south to north about 10 miles to the west of Boston. The area was a hub for technology companies — mostly focused on semiconductors, microprocessors, and minicomputers. It seemed like almost all my friends' parents worked at one of these companies or a company that provided support to these companies.

I also remember the bust that came in the early nineties when many of these companies downsized and thousands of people lost their jobs. It was a rough time for many people in the area.

What I didn't know at the time was that there were a set of competitors based in Santa Clara County, California, in the area now known as Silicon Valley, viciously competing with the Route 128 companies. Companies like Hewlett Packard, Intel, and Apple.

Most people now know that the Silicon Valley companies came out on top and that the tech scene in the area outpaced eastern Massachusetts significantly. Massachusetts remains one of the top 3 tech hubs in the U.S., dominates biotechnology, and is well on its way to becoming the country’s Digital tech hub. But outside of healthcare, the Silicon Valley area is far ahead and sees about 3x the number of startups and venture funding than the entire state of Massachusetts.

That said, back in the mid-1980s, you would've had no idea which region was going to come out on top. It could’ve gone either way.

AnnaLee Saxenian wrote a phenomenal book about all of this titled, Regional Advantage: Culture and Competition in Silicon Valley and Route 128 that examines the differences between the two regions.

Having lived in and worked in both areas, here are some of the key differences between the regions that I think allowed Silicon Valley to outperform. Certainly some of the takeaways are isolated to these regions at that point in time. But as lots of cities across the country try to increase the number of tech startups launched in their communities, many of the lessons from the battle between Silicon Valley and Route 128 can be applied by policymakers and tech leaders today.

Cultural differences

Massachusetts had a much more traditional, risk-averse approach compared to the Valley. A big reason for this comes from the parochial and puritanical cultural history of Massachusetts. But, more practically, it also comes from the fact that most people that worked in Silicon Valley weren’t from California. They were from the east coast or the midwest. You can’t underestimate the impact this has on a region. People aren’t spending time with their high school friends or church friends or summer camp friends. They’re spending time with the people they work with. And what do they talk and think about during that social time? Work. They’re bound together by their work. And they're much less worried about trying something new and failing at it because their friends and family back home may not even know about it. An executive that worked on both coasts described it this way in the book:

“On the East Coast, everybody’s family goes back generations. Roots and stability are far more important out here. If you fail in Silicon Valley, your family won’t know and your neighbors won’t care. Out here, everybody would be worried. It’s hard to face your grandparents after you’ve failed.” —William Foster, Stratus Computer

This meant that people in the Valley were much more willing to take risks, start companies and jump from job to job. As they jumped from job to job and made friends with people at work, they created networks centered around their work across several companies in the region. It was common for an engineer to quit their job on a Thursday and show up at another startup on Monday. These new experiences led to more friendships and led to a ton of collaboration between companies and an openness to sharing with one another for the greater good. It was common for Silicon Valley competitors to call one another for help with technical problems. This kind of collaboration created a rising tide for everyone in the area. The power of this kind of environment is enormous.

By contrast, in Massachusetts, most of the people working in tech were from New England. From the book:

”The social world of most New England engineers, by contrast, centered on the extended family, the church, local schools, tennis clubs, and other civic and neighborhood institutions. Their experiences did little to cultivate the strong regional or industry-based loyalties that unified the members of Silicon Valley’s technical community. Most were from New England, many had attended local educational institutions, and their identities were already defined by familial and ethnic ties.”

There was a separation between work and social life for Route 128 workers. For workers in the Valley, it was much more of a grey area. Workers in Route 128 tech often went right home after work and immersed themselves in their local towns, where they had ties that went back generations. Workers in the Valley didn’t have these ties. Instead of driving several miles back to their town, they were more likely to go out to dinner or to a bar in the area to talk about technologies and markets.

Job hopping

As mentioned above, workers in the Valley would jump from job to job growing their network and gaining new experiences. Route 128 had a much different culture where loyalty was highly valued and if you left you could never come back. Workers often stayed at their jobs for 10+ years. This was unheard of in the Valley. Workers felt that they were working for the Valley — the community — rather than for an individual firm. If they decided they wanted to come back they were often welcomed with open arms. As I've written in the past, this impact is felt today as California has banned the use of employee non-compete agreements while Massachusetts has allowed them to persist.

Collaboration with universities

Stanford actively promoted startups by offering professors up to help with product development and created several funding mechanisms for new ideas. MIT took a far more conservative approach and was very reluctant to invest dollars or time into things that were too risky. This created artificial walls between the best tech companies and the best technical research. Many of the east coast companies claimed they had better working relationships with Stanford and Berkeley than they did with MIT and Harvard.

Dependence on government contracts

Because of its proximity to Washington, Route 128 companies had lots of reliance on government contracts that had long term obligations that restricted innovation. It also (appropriately) led to a secretive culture that stalled collaboration with associations, competitors, partners, and other organizations in the local ecosystem. By contrast, by the early seventies, Silicon Valley companies were receiving far more financing from venture capital investors than they were from government contracts. The east coast's dependence on government contracts made widespread collaboration nearly impossible.

Geography

Silicon Valley companies started around Stanford and expanded to cities like Mountain View and Santa Clara but couldn’t go too far as they were locked in by the Santa Cruz mountains to the west and the San Francisco Bay to the east. This led to a very dense community of tech companies. By contrast, the Route 128 companies were spread far and wide. DEC, the largest of the companies in the eighties, was based in Maynard, with more than 20 miles of forest separating them from the hub of Route 128.

Organizational structure

Related to the dependency on defense contracts and its proximity to established political and financial institutions, Massachusetts companies were more formal and created organizational structures that had a strong resemblance to the military. This kind of organizational design can slow innovation as the lower rungs of the ladder are less reluctant to offer new ideas and there's far less cross-functional learning. Executives had their own parking spaces and executive dining rooms. Stock options were only offered to those at the highest levels of the organization. This even applied to work attire — the uniform for 128 companies was a jacket and a tie, in the Valley it was jeans and a t-shirt.

Today, something like 75% of all venture capital funding goes to three states -- Massachusetts, California and New York. As governments and entrepreneurs across the country try to expand the number of tech companies that emerge and grow in their communities, it’s important to remember that ecosystems create a lot more jobs than companies. The key is less about funding and micro-incentives and more about creating the complicated environment that allows an entire ecosystem to thrive.

Quick Decisions

Whenever I interview someone that recently worked at a startup that went out of business I ask them why it failed. How analytically someone answers this question says a lot about them. But the truth is that I'm mostly asking because I'm curious. I want to know what to look out for.

More often than not, the answer comes down to one thing: dysfunctional leadership. More specifically, for some reason, leadership didn't communicate well and couldn't make quick decisions. 

Tomas Tunguz had a great blog post on this topic recently, titled the Challenge of Uncertainty. From the post:

The management team of a company is a decision-making and productivity chokepoint. Critical decisions flow through them. If the management team ruminates on most decisions, the company’s progress stalls. In a 100 person startup, five slow-to-decide executives limit the productivity of 95 employees. In a 1000 person startup, the ratio might be 10:990. There’s enormous leverage in a hierarchical organization if the leadership moves quickly. The converse is equally true. Sluggish decision-making halts all progress.

The cost of deciding slowly seems small. Just a day or a week of more research; one more experiment. But a day’s delay in a 1000 person organization costs the company more than $400k in lost productivity.

Slow decision-making can be paralyzing for a company.

Management teams should check themselves occasionally on the speed and quality of their decision-making. It will almost always deteriorate over time. There are dozens of little things that can weigh down management and cause them to slow the pace -- too many direct reports, too many meetings, not enough meetings, new personalities, fear of telling the truth, personal issues, different communication styles, poor prioritization and on and on. All of these things will come up at some point. How well a leadership team weeds through this stuff and finds a way to continue to make good, speedy decisions might make the difference.

Personal Exceptionalism

Harry Stebbins had a great interview with venture capitalist Michael Dearing on the 20 Minute VC Podcast a couple weeks ago. Michael talked about a trait that he looks for in founders and startup teams that he refers to as "personal exceptionalism". This is the idea that a person believes that they are special and that their outcomes are going to be "outside the bounds of normal". They’re not arrogant, they just strongly believe that they can produce results far greater than the mean.

This idea really resonated with me; not as an investor but as a person that hires a lot of people and builds teams and is constantly trying to scour through candidates to find the best of the best. The notion of personal exceptionalism really captures what I look for. Rather than try to explain the concept myself I've transcribed Michael's comments on it below. Spot on.

I think my radar for personal exceptionalism has evolved over time but I think the constant is that I’m looking for people who have broken out of the bounds of normal for their peer group. Now that does not [necessarily] mean in business or as technicians or technical talent. It just means that whatever the circumstances were in their lives, that that was not the determining factor. They were able to break out either because they took some crazy personal risk, they took some very sharp left-hand turn, they ended up accomplishing more and seeing more and building a much better experience base because of that risk-taking. So that personal exceptionalism that says that they are special that they are destined for really unique outcomes relative to their peer group. I think that shows up early in somebody’s life and it’s quite independent of pedigree or brand name work experience. In fact, sometimes those things are negatively correlated. But the distinction you make between arrogance and personal exceptionalism is an important one. Personal exceptionalism just means that they see themselves as special and their outcomes are going to be outside of the bounds of normal. I think that they a lot of times are some of the most self-critical people I know and they beat themselves up when they do miss a goal or they fail in a venture they beat themselves up far harder than any third party could so the arrogance piece is easy to suss out. You see it in the form of the people they attract around them and the kinds of networks that they build how much are they are a taker versus a giver in those networks. So I actually have found over the years it’s relatively easy to separate the sheep from the goats.