A working CEO and COO definition: Jenny Lawton of Bolster

Ask for a CEO and COO definition and you usually get an org chart. Jenny Lawton gives a functional one: the COO is in service to the CEO, and what that means changes with every CEO you serve.

Lawton is executive vice president at Bolster, the on-demand executive talent marketplace connecting companies with vetted executives for interim, fractional, advisory, project and board roles. Before that she was chief strategy officer and then CEO at MakerBot, the desktop 3D printing company acquired by Stratasys for over $400 million. She was COO of littleBits, the STEM learning division of Sphero, and COO and chief innovation officer at Techstars. She was inducted into the Connecticut Women's Hall of Fame in 2014.

A teenager who outsourced babysitting

Long before any of that, Lawton ran a babysitting business, notably as the person arranging the work rather than doing it. She also ran children's birthday parties, did calligraphy, and at around fifteen decided she could be a graphic artist and started producing business cards and corporate logos.

Her explanation is that her mother told her from a very early age that she could do whatever she wanted, and that she took it seriously enough to throw it back regularly. Both her parents taught at community college, and she says she was an enigma to them.

Her filter for work now is consistent with that. Something interesting, something that teaches her, something that makes a dent. Not the same thing each time, which her career confirms, but always something she wakes up glad to be doing.

Order out of chaos, and why process is freedom

Lawton describes her core skill as walking into an ambiguous situation and putting order to it. Pattern matching, working out where you are, where the destination is, and the efficient path between them.

She traces it partly to a degree in applied mathematics. What she loved was knowing there was an answer even when the middle of the problem looked impossible.

Her advice for operators is deliberately unglamorous. You cannot know where you are going without knowing where you are, an idea she borrows from a Peloton instructor and restates as the observation that a car cannot collect you if you do not say where you are standing.

From there, put in place the simplest operating system that gets you from here to there, and be willing to change it as you grow. She means this literally. It might be nothing more than a cadence of meetings and an agreed way of tracking communication.

The argument for why that matters is the best part. If you do not tell people how things work and what the basic process is for making something happen, they arrive each day wondering how anything gets done. Give them a framework and they get more done, and are usually more creative inside it, because the framework absorbs the questions that would otherwise consume them.

Her analogy is Montessori. A very large box that people feel completely free inside, defined by a rigorous set of rules.

She is direct about the objection. People associate process with bureaucracy and pointless paperwork. She sees it as liberating, because knowing how something operates tells you the space you get to work in.

Michael raises the observation that a striking number of well-known founders came through Montessori. Lawton has not studied it, but her read is about the misunderstanding. People do not associate rigor with Montessori because it is open and mixes ages and lets children choose. What they miss is that inside that choice there is a defined order of operations. Logic and order alongside flexibility, with little hierarchy but real rules.

What a COO is actually in service of

Lawton has held nearly every seat: CEO of a technology startup in the 1990s, owner of two bookstores and coffee shops for about a decade, and COO several times. Bolster is the first role in a long time that is neither.

She was worried about that. What does it mean when the buck does not stop with you. Her answer, having done it, is that it has been good, because she can work as part of a team while still leading her own effort.

Her self-diagnosis explains the rest. She thinks like a CEO internally, and that is precisely why she views the COO job as service to the CEO. Knowing how a CEO thinks makes you a better partner to one. At this stage she has no need to be the CEO, and finds real satisfaction in supporting first-time CEOs learning the job.

Asked what the COO is in service of, she refuses a single answer, and the reasoning is the useful part.

There is one thing a CEO cannot delegate: being the leader of the business and setting its tone and culture. Beyond that, it varies completely. Some CEOs want to be entirely outward-facing and touch nothing day to day. Others want the day to day and no part of the outward, future-facing work. The job is understanding what this specific CEO wants to do, what they are good at, and which gaps need filling. She calls it a dance and a relationship.

What is common is the skill set. A COO has to understand how every element of the business works and how the pieces fit together. She notes the role is increasingly being redefined as something closer to a chief of staff, and reaches for an image from writing about political chiefs of staff, who empty a briefcase containing something for every possible problem.

Her concrete standard: read the financials and hold a real conversation with the CFO. Know enough to tell a salesperson when they are talking nonsense. Talk to marketing. Talk to engineers. High-level fluency across every function.

The MakerBot lesson about values that cannot scale

Lawton joined MakerBot just after a $10 million round from Foundry Group. The acquisition came a little over 18 months later, arriving in the middle of a roughly $50 million raise they had begun, not because the first round was spent but because their plans were ambitious enough to need more.

The lesson she takes from that period has nothing to do with the sale.

MakerBot began as an open hardware and open software company, a group of makers democratizing 3D printing. That was the mission the core employees came for. Open and shared.

Taking venture capital changed the objective. Her framing is blunt and correct. Once you accept that money, you are obliged to return it at a multiple, which means the company has to do specific things to make that happen. So MakerBot was in conflict with its own culture from the moment it became venture-backed, because leadership now had to drive sales to build value for shareholders while employees had joined for something else.

The generalizable insight: when you set values and culture, make sure they can grow with the company. If they only carry you so far, and something forces them to change, you have a serious internal problem.

Michael notes the parallel with Catherine Stewart's account of Automattic's shift toward monetization, which produced the same friction.

Lawton's resolution was transparency and business education. Honest conversations explaining that salaries, bonuses, benefits and everything else are funded by selling the product, and that this is how a business works.

She is equally honest about the limit. Once you change a mission element, there is very little you can do. MakerBot lost people when it closed part of the software and began patenting hardware designs, because that was not why they were there. The remaining responsibility is to say so plainly: this is not going to change, and it is going to move further from where you want it, so let us work out how you want to handle that.

Running Techstars as three businesses

Lawton's description of Techstars operations is the most concrete account of accelerator mechanics I have come across.

The scale changed enormously during her tenure, from roughly 15 accelerators to 55 across 15 countries. Doing that meant not only iterating the operating system but hardening it, running each accelerator off a common playbook with a formulaic approach to budgets.

Underneath sat real accounting complexity, covering both actual funds and synthetic fund management, with cap tables behind each fund that she describes as extremely complicated.

The structural insight is that Techstars is not one company. There is an investing business and an operating business, which have different financials, different economic models and different ways of working. They were separate, and merged during her time, which she calls interesting, complicated and messy. And there was effectively a third: city accelerators and corporate accelerators ran on different operating models funded from different pools.

Geographic expansion combined research with opportunism. They studied entrepreneurial communities to understand maturity and therefore how many accelerators a city could support, and asked equally whether they should exit places they were already in. In parallel they mapped which industries they had corporate partners in and which they wanted. Then partners and cities approached them with their own proposals.

Give first, and flipping the failure rate

Techstars is known for its mentor network and the principle of Give First. Lawton's version: lean in and do something for someone without wondering what comes next, with the caveat that something does come back, unpredictably.

She frames it as a balance, where giving builds a reserve that lets you ask for help comfortably later, because you know you have contributed.

The statistic she cites about accelerators is the striking one. Startup failure rates are famously high, and her rough numbers are that going through an accelerator and joining a supportive network inverts them, taking something like an 80% failure rate to an 80% success rate.

Her thesis at Bolster extends that logic one stage further. If a scaling CEO keeps working with someone who already knows how to scale a business, learning while doing, the trajectory should keep improving and value should reach investors sooner.

She also notes that Techstars bets on teams able to pivot rather than teams likely to deliver the idea they arrived with. Sphero is the example, a small robotic ball before Disney's accelerator turned it into something else entirely.

The margin of error, and the twelve-year pull-through

Michael quotes Lawton's own earlier words: the acceptable margin of error for women is lower, and a direct, all-guns-blazing approach reads as positive in men and negative in women.

Her update is measured. There is more awareness and more conversation, and there is still a great deal of unconscious bias, which does not disappear because people want it to.

Her evidence comes from an unusual vantage point. She left the workforce for nearly a decade to run bookstores and a coffee shop, so she has two clean before-and-after snapshots. Between leaving and returning she was struck by how many more women had seats at the table, how much larger their voices were, and how much of middle and senior management they occupied. And she notes the smaller signals, like no longer needing to wear a suit and heels to be taken seriously.

The bias she still sees clearly is in fundraising. She had spent the previous day coaching a female CEO on the fact that she would be evaluated on what she has already delivered, while the men pitching would be evaluated on potential. Her view is that this runs deep in entrepreneurship, and considerably deeper for people of color.

Her prescription is patient and specific. Distinguish inclusion, meaning a seat and a voice, from diversity. Be willing to spend the time both require. And listen for your own excuses as they arrive, the ones about how there simply are not any qualified women with enough experience. Lean into potential instead. It takes work and it feels awkward, like anything new.

The frame she uses for all of it is the same one she used with frustrated MakerBot employees: innovation takes decades, and you have to look at it longitudinally.

Her example is the twelve-year adoption cycle she was chasing at MakerBot. Put a 3D printer in front of a child in kindergarten and by the time they reach the workplace they will ask where theirs is, the way a calculator became assumed. She saw it beginning while she was there, with colleges calling to ask what to do with the printers students were bringing with them.

She applies the same mechanism to representation. A girl who sees her mother working as an executive, or a woman as a senator, without anyone remarking on it, simply expects that to be how the world works. Which is why her concern about rights being eroded sits alongside genuine optimism: there is a generation coming that will have a problem with that problem.

The advice she gives children

It is her mother's advice, unchanged. You can do whatever you want to do. It is your life and your decisions to make. If you do not ask, you do not find out, and the worst outcome is that someone says no, at which point it is still your decision what to do with that answer.

She is self-aware about the risk, noting she has caught herself effectively telling children to buck their parents, which is not the intent. What she wants them to have is a strong core, and her point is that if you cannot find it where you are, you go and find it, starting with yourself.

The thing she did not expect

Michael's standing question produced an answer about life rather than work, which Lawton flags herself.

Approaching 60, with four children, she now finds herself caring for her mother. Her observation is that she now understands why people step back from full-time work, because life acquires more weight. She likes the idea that this stage is when you have a large accumulated store of knowledge to share, and she was genuinely surprised by how much the caregiving component returns.

Her closing thought is generational. She sees people earlier in their careers being far more deliberate about balance, more willing to say they will work from Portugal for a month and expect it to be accommodated, and more convinced they can have a meaningful working life and a life. She calls that an enlightened viewpoint, and connects it back to pull-through: those people become the leaders and politicians later, and she is glad about it.

The 5 things I took away from this conversation

1. Process is the framework that makes freedom usable. The Montessori framing, a very large box defined by rigorous rules, is the best defense of operating process I have heard. Without it, people spend their day working out how things happen rather than making things happen.

2. Set values that can survive your own growth. MakerBot's culture was incompatible with venture-backed obligations from the day the money arrived, and nobody had checked. If your stated values only work at your current stage, you have scheduled a crisis for the moment you change stages.

3. There is no fixed COO definition, only a fixed skill set. What the job contains depends entirely on what the CEO wants to keep. What does not vary is needing to read financials, challenge a sales forecast, talk to marketing and understand engineering. Fluency everywhere, ownership of whatever the CEO leaves.

4. Start by baselining where you actually are. It sounds obvious and almost nobody does it. Lawton's point is that scaling plans routinely describe a destination without an honest starting position, which makes the path between them fiction.

5. Judge change on a twelve to twenty year clock. Whether it is 3D printers reaching classrooms or women reaching boardrooms, the mechanism is pull-through, and it is slow enough to be invisible day to day. That is both a reason for patience and an argument for starting now.

FAQ

What is a practical CEO and COO definition? Lawton's version is that the COO is in service to the CEO. The CEO cannot delegate leadership of the business or its tone and culture. Everything else is negotiable and varies by CEO, so the COO's remit is defined by what that particular CEO wants to do, what they are good at, and where the gaps are.

What are the core COO role responsibilities regardless of company? Understanding how every part of the business works and how the parts interact. Lawton's concrete test is being able to read the financials and engage the CFO, challenge a salesperson credibly, hold a real conversation with marketing, and talk to engineers. She notes the role increasingly resembles a chief of staff.

What does a simple operational plan example look like? It can be as basic as an agreed meeting cadence and a defined way of tracking communication. Lawton's approach is to establish where the company actually is, define where it needs to get to, and install the simplest system that connects the two, then iterate as the company grows.

How do you handle a culture conflict caused by taking investment? Transparency about the why, and honest conversations about how a business funds salaries and benefits. Lawton is also clear that some people will leave, because a change in mission cannot be argued away. The responsibility is to tell them plainly that the direction is not reverting, so they can decide.

How do accelerators change startup outcomes? Lawton's rough figures are that the typical failure-heavy distribution flips, with a majority of accelerator companies succeeding rather than failing, largely through the supporting network rather than the capital. Her thesis at Bolster is that pairing scaling CEOs with people who have already scaled extends that effect further.

Also mentioned

• Bolster, the executive talent marketplace, co-founded by Matt Blumberg of Return Path
• MakerBot, acquired by Stratasys, and its open hardware origins
• littleBits and Sphero, including the Disney accelerator that produced BB-8
• Techstars and the Give First principle
• Foundry Group and Brad Feld, the connection behind several of these relationships
• Montessori education, Lawton's model for structure that creates freedom
• The Connecticut Women's Hall of Fame, which inducted Lawton in 2014
• Jenny Lawton at jenny@oldschoolventure.com

Listen to the full episode

Jenny Lawton on Between Two COO's

Between Two COO's is hosted by Michael Koenig. Subscribe on Apple Podcasts, Spotify, or wherever you listen.