when growth_stage = 'pupa'
What organisms teach us about organizations
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HubSpot is currently going through a metamorphosis.
We’re figuring out RevOps, tipping past the $1B mark, transitioning leadership, and so much more. Things feel optimistic, exciting—but also unsure, unstructured. We need to break down old structures in order to build new ones, and that requires trust and patience.
The growth of a company from startup to enterprise has a lot in common with the growth of a caterpillar into a butterfly. And those parallels are especially meaningful when you’re in the goopy, amorphous pupa phase.
It can be disorienting to go from a stage where the emphasis is on quick execution for immediate results to a stage where ideas take longer to incubate and impact is measured in years, not days.
Agility still matters, but individual effort doesn’t scale alone—new structures provide leverage that amplifies individual efforts, breaking linear growth.
This essay has two goals:
For members of organizations at any stage to leverage these insights to develop your opinion on what strategies, structures, and specializations are most relevant to your organization
For members of an organization in the pupal stage to be assured that uncertainty is a necessary part of the process, and to be wise to signs that the transition isn’t going well so that you can right the course or jump ship
This essay will go deep into each phase, then “organisms & organizations” summarizes the big ideas and “when order != ‘lepidoptera’” discusses other patterns of growth that don’t fit the caterpillar metaphor.
growth_stage = ‘caterpillar’
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growth focus
Caterpillars are simple organisms. They are quite literally designed to eat. Everything that a caterpillar does is to this end. Avoding predators is necessary, but not a purpose in and of itself—caterpillars avoid predators so that they can eat and grow.
Similarly, startups will need to navigate a competitive landscape and adapt, but the primary function of all of these activities is growth.
shedding skins
As caterpillars grow, their skin can only stretch so far. Inevitably, it splits under the pressure, revealing a new skin layer that does the job until the caterpillar outgrows it too.
Likewise, startups go through stages where processes and systems stretch, break, and must be remade.
This breaking can feel discouraging—unless you understand that it’s exactly how a caterpillar is designed to grow. Savvy leaders can sense the skin tightening and get new systems/processes lined up, smoothing the transition. Prepare too early and you risk missing important growth opportunities.
flexibility > structure
Here’s an interesting thing about caterpillars. Caterpillars are insects and have only six true legs, at the front of their bodies. These are the legs that will eventually become the butterfly’s legs (if all goes well for the caterpillar).
Their hind “legs” are actually muscular structures called pro-legs. If the caterpillar’s body weren’t so soft and flexible, such pro-legs wouldn’t work.
Likewise, caterpillar-stage organizations are flexible, relying more on internal muscle (i.e. individual effort) than external structure to get to where it needs to go. People adapt into roles as needed, often extending beyond their job description (just as body tissue extends to form a pro-leg).
This flexibility and simplicity come with trade-offs. Without the hard exoskeleton of a mature insect, caterpillars are vulnerable to predators and other environmental dangers. Likewise, a particularly aggressive competitor or sudden shift in market conditions can spell disaster for an early-stage startup, even when a more mature organization could weather the storm.
So, just like caterpillars, startups take a “numbers” approach. Many caterpillars hatch from their eggs, but only a small percentage eventually become butterflies. Likewise, a broad array of startups test the market, but only about 10% succeed.
adaptations & luck
Different species of caterpillars have specialized adaptations. Some are brightly colored and poisonous to predators, others camouflage into the leaves around them. Some have even become carnivorous.
Likewise, some startups have neutralizers and differentiators. Some will be particularly good with data, while others will have excellent operational processes or best-in-class customer service, etcetera. But none of the startups will be good at all of these things, because they must reserve energy for raw growth.
A caterpillar’s success depends on how well their adaptations match their current environment (call it product-market fit) and a healthy dose of luck.
To put a sharp point on it, a lot of things that can feel like problems to a cautious, analytical person (people flexing into unfamiliar roles, lack of external structure, high risk of failure, vulnerability to unexpected events, lack of robust systems) are actually adaptive1 for an early-stage startup.
That being said, caterpillars don’t eat and grow forever. (Unlike, for example, lobsters.)
Sufficient consumption or a shift in the seasons triggers the caterpillar’s next stage: pupa.
growth_stage = ‘pupa’
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a protective barrier
Moths spin silk cocoons for themselves, whereas butterfly caterpillars form hard chrysalises. Either way, the transition involves one last shedding of skin. This skin doesn’t tear—it hardens around the larva, forming a protective barrier for the pupal stage.
Similarly, companies might double-down on existing processes to buy time for higher-level strategic thinking. For example: suspending new feature requests for an outdated system in order to invest in creating a new system that will scale better in the future.
“Slowing down to speed up” and “slow is smooth and smooth is fast” resonant with more and more of the organization.
Certain vulnerabilities in the company must be deliberately protected (think: GDPR, SOX, etc) and leaders might increasingly talk about “guardrails” and “guided autonomy”.
outside-in structure
The pupa is more than just protection. It also represents how a company in transition will look externally, to their customers, to determine what structures they need for the next phase. It is this external mission, this customer focus, that gives an organization the confidence to break down existing internal structures.
At HubSpot, the goopy, transitional insides of the company are held together by dedication to the customer. We can all align towards this goal and use it as our structure and guiding direction, even with a lot of other uncertainty.
We’ve always been customer-first, but as a caterpillar, we relied on flexibility and muscle (individual effort) to delight our customers. Now that we have over 100,000 customers, we need to develop new structures that amplify individual effort. These structures take time, energy, intention, and strategy to develop. So right now, we’re in the pupa phase.
primordial soup
After the caterpillar’s final shed skin becomes a protective shell, something absolutely fascinating happens within the pupa.
The caterpillar melts.
What structures did exist—the prolegs, the central muscles, fuzz, stingers, etc—turn to goop.
Some vague structures remain, or their growth is easy to envision. The caterpillar’s stubby true legs will become the long, elegant legs of the butterfly. Their head, eyes, and main neurons will remain in a relatively similar configuration.
But the caterpillar’s soft abdomen must become the slender exoskeleton of the butterfly, and the wings must develop from nothing into complex structures capable of flight.
It can be difficult to imagine how such a transition is even possible, let alone be a driving force in making it happen.
And this is essential:
Teams feeling the strain of growth are looking for structure and certainty. But in order to transform, the organization temporarily enters a stage of less structure and less certainty.
an organism in transition
To me, this is exactly what HubSpot feels like right now.
We have a clear, uniting purpose that provides us structure and security—help millions of organizations grow better.
But within that mission, there are so many questions. How should we arrange ourselves? What structures will serve us in the long run? Who should our leaders be, and what should we ask of them? How do we get data people to report to data people, but still be embedded in orgs? What do our career pathways look like? Is RevOps really a cost center or is it R&D? How do we keep our remarkable culture?
There’s even more change and transition than usual. We’re ramping up new folks and wishing old friends well on their next adventures.
Some folks’ transitions are easy to understand, like the development of the caterpillar’s tiny legs into long ones.
Others are finding that their roles no longer exist, or there’s less flexibility than there was before.
Some new ideas and structures are full of so much promise and absolutely dazzling to think about, like the butterfly’s developing wings. But it’s impossible to know if those wings are well-formed until the pupa opens, so there’s a lot of asking for trust, a lot of cautious optimism, and a lot of preparing for the first big test.
In some ways, we have no idea what we’re doing—we’re in the soup.
In other ways, we know exactly what we’re doing—this soup is adaptive, the iteration and uncertainty are essential to the organization’s continued growth. We are listening, learning, adapting, and growing.
There’s a lot of excitement, possibility, transformation, optimism—but the rubber hasn’t quite hit the road yet. We’re stacking our chips, making good bets, and waiting for the ball to settle.
Patience pays off at this stage of development.
depleting reserves
Not every chrysalis becomes a butterfly.
Caterpillars can’t take in new energy during the pupal stage. Those that haven’t stored up enough energy in the growth phase may still instinctively enter the pupal stage, but if they run out of energy during development, they can starve mid-transformation and never emerge as a butterfly.
An organization needs to store up sufficient trust, cultural, and monetary capital before it enters the pupal stage if it’s going to make it out the other side as a mature organization.
For example, HubSpot leadership started hiring managers with a data focus and taking concepts like analytics engineering seriously before entering what I identify as the pupal stage.
We still don’t have a cohesive analytics engineering career ladder or certainty of where the RevOps org structure will land, but we have a collection of good enough adaptations (re-leveling & promotion of individuals who negotiate for it, basic career ladder frameworks as a starting point, a culture that values autonomy and respect, strong stock performance bolstering RSU compensation, initiatives to battle burnout, a commitment to transparency).
These interim solutions demonstrate that people care, and built up trust for this transitional phase. We can pull from this energy store while we figure out what our long-term solutions look like.
Without such interim solutions, when the pupal stage introduces even more uncertainty and even less structure, savvy employees realize they may be better off elsewhere. If a critical mass of folks leaves, finding effective structures within the primordial soup of the pupal organization is much slower, if not impossible. And the slower it is, the more stored energy the transition consumes, and the less likely the transition will be successful.
a healthy pupa
How to determine if an organization is likely to make it out the other side? These questions help:
Is there a unifying mission or goal in the company that allows distributed teams to determine how they, individually, need to evolve to contribute to the next phase of the organization?
Can leadership support iteration and uncertainty as valid states? Or is there pressure to present impossible results?
Does this organization have sufficient momentum (revenue, growth, goodwill from customers, good culture) going into the time of transition? Without this, the pupa will die before it can emerge as a butterfly.
Are the structures and guardrails needed during the transition strong enough to hold in the soupy bits? If not, breaking down existing structures may result in mass attrition, failure to meet the company’s commitments, or both.
growth_stage = ‘butterfly’
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Becoming more complex does not necessarily mean becoming slower.
A butterfly moves faster and farther than a caterpillar, even migrating across continents to follow favorable conditions.
Butterflies have complex, specialized structures (wings, eyes, proboscises, exoskeleton, legs) that add leverage to their muscle, allowing them to do things that caterpillars cannot.
Similarly, a mature organization has effective processes that increase the leverage of individual efforts.
Once good processes and structures are in place, the fundamentals won’t need much change (a wing is a wing) but can adapt to a variety of conditions.
specialization and neurons
All large organisms include highly specialized structures. Similarly, mature organizations include specialized roles. Sales orgs split into more granular segments, data teams peel apart analytics engineering from machine learning engineering from data analysis, etc.
This leads some people to the false conclusion that large organizations only need specialists. This misconception is a mortal danger for a maturing organization.
Connective tissues and neurons are equally important to specialized structures. A leg cannot function without its connection to the abdomen, and neurons are essential to coordinating the entire organism.
The specialized structures are usually easier to see and understand. These are roles like sales reps, product managers, machine learning engineers, statisticians, recruiters.
The connective tissue function is enabled by multi-specialists. Sometimes, this looks like folks in separate orgs meeting in the middle, such as a sales VP that collaborates closely with a marketing VP. Other times these roles stand on their own, like a separate project management org.
The neurons can be hard to spot at first. These generalists are your purple people. These skilled communicators and translators focus on problems to be solved over any individual specialization or function. Their work often defies boundaries between job titles, departments, and disciplines—which is essential to being a good neuron!
These generalists provide essential connection points between specialized departments. This looks like effective triage of unexpected problems, creative cross-functional problem solving, identifying areas where the activities of one department counteract another, etc.
Instead of worrying that connective tissue and neuron type roles “break” the organization design, appreciate that they are essential to the organism design.
Plan roles for neurons and connective tissue, recognizing that the unique work of these skilled collaborators and translators is its own kind of specialization. Your org chart can be clear and your organization can remain agile. Big and fast.
The sluggish, siloed, frustrating experience of many large organizations (Comcast is a great example) is not an inevitable symptom of size, but rather a dysfunction of neurons and connective tissue.
Ignoring or undermining cross-functional coordination is like snipping a nerve—it will paralyze your entire organization.
organizations & organisms
To pull it all together:
Startups and caterpillars are (and should be) focused upon growth above all else. Flexibility matters more than structure, and a lot gets done through internal muscle (i.e. individual effort). In a few key areas related to product-market fit, specialists ensure that the organization’s main differentiators are solid, but otherwise, generalists flex to cover the needs.
As the organization grows, it goes through cycles of stretching and breaking. While the breaking is essential to rapid growth, strategic operators line up new structures just in time for them to replace the old structures.
At a certain point, sometimes because the organization is ready and sometimes because something in the environment or leadership forces it, the organization enters a significant transitional phase.
This transition feels different than the stretching and breaking from before. Perhaps for the first time, the company leans into guardrails and guidance. A unifying goal or mission provides a sense of external structure, and there are big plans for improvements, but day-to-day operations may feel soupy and uncertain. The business takes a longer-term view than they ever had, and invests in projects that will take years, not months, to pay off. This is a phase of optimism, uncertainty, and patience.
This can be a challenging time for ops folks because while they’ve been begging for more structure and certainty, the organization temporarily enters a phase of less structure and less certainty. If the organization hasn’t stored up sufficient trust capital, cultural capital, and monetary capital, it can starve in this stage and fail to emerge as a mature organization.
During a successful pupal phase, existing structures are broken down while new, more intentional structures are formed. Some structures are replaced with better versions of themselves (legs), some structures are no longer needed and are eliminated (prolegs) and some structures seemingly must be constructed from nothing (wings).
The emerging organization is mature, leveraging structure to extend the impact of individual efforts, as long as the connective tissues and neurons of the organization are also well-developed. Mature organizations need specialists, cross-team collaborators (connective tissues), and problem-focused generalists (neurons). A deficiency in any one area will lead to organization-wide dysfunction.
when order != ‘Lepidoptera’
Not every organization is a butterfly. Some of these other patterns to watch out for may help you gain insights on what’s adaptive and what isn’t for the organization you’re in.
If the mature stage of your organization is more bulletproof than bullet-dodging, then a beetle may be a more relatable metaphor. The larval and pupal stages are similar, but the mature beetle invests more in its exoskeleton than its wings.
Continuous stretch & break growth is common in crustaceans, like lobsters, which can grow from microscopic larvae to 50 lb monstrosities without any major changes in their structures. If a company invests early in structures that turn out to be adaptive for the environment, then metamorphosis is not required, and the company may grow for quite a long time in more or less the same shape.
Gradual metamorphosis without a pupal stage is possible, and means you might relate more to a frog’s development than a butterfly’s. This type of metamorphosis will feel more gradual, with clearer interim steps. Some prior functions are still eliminated (like the tadpole losing its tail), but there is more of a sense of expanding existing functions (spine branching out into legs, then fingers) than rebuilding existing functions.
Extended incubation periods, such as those that parent companies can provide, allow an organization to have already developed mature structures by the time it sets out “on its own”. In those cases, mammals and birds may provide helpful lessons.
So, is your company a butterfly, a lobster, or something else?
If you’re in the caterpillar stage, can you embrace the stretch-and-break growth?
If you’re in the pupal stage, can you find comfort in the company’s core mission & goal even while the insides feel like soup?
And if you’re in a mature organization, do you provide equal and appropriate attention to specialists, cross-functional coordinators, and problem-solvers that transcend org charts? Or are silos paralyzing your org?
I’d love to hear your thoughts, counterpoints, and extrapolations in the comments or on twitter @compilerqueen ☺