It’s been more than a year since I decided to step down as CFO of Harvard University to become the CFO of Onshape. In a blog post last spring, I explored the counterintuitive similarities between a world-famous institution and a relatively unknown startup. I shared my excitement for joining a company determined to change the design and manufacturing world and my initial impressions of the Onshape workplace.

Time flies, particularly at a company like Onshape, and I just crossed the one-year point in my tenure here. To mark the milestone, I thought it would be interesting to share a few candid observations about life on the ground in an early-stage startup.

In addition to lacking a CAD background when I walked in the door at Onshape, I also had no experience with startups – so I had no biases as to what a startup should look or feel like. But I have some now, albeit based on a sample size of one.

Here are a few lessons I’ve learned about startup culture and how to keep moving forward in uncharted territory.

1. You should seek out a permanent state of controlled chaos.

There is a nearly constant undercurrent of tension at Onshape – between the forces of creativity that push the boundaries of what’s possible, and the forces of process and control that enable product to be put in the hands of customers. As early as we may be in our journey, we still need to give our customers a product with an incredibly high degree of reliability, and to provide a steady stream of improvements that must be developed, compiled, tested, and put into production. We have to mix the cold, calculating eyes of what is practical with the more rose-colored perspective of what just might be possible. Not just once, but every three weeks! Rinse and repeat...

2. Seek out an acceptable level of messiness.

“Perfect is the enemy of the good” is a somewhat tired workplace cliché – I heard it often at Harvard from people whose actions said otherwise – until you find yourself in an environment where moving too slow might well mean death. Onshape won’t suffer death by starvation any time soon because we just raised a whole lot of money. The real danger is death by abandonment or, even worse, indifference. If we aren’t able to innovate and give users a meaningfully different and better experience compared to their existing CAD systems, customers will say “thanks, but no thanks.”

This means the next enhancements for users must be days away, not months or years away. For us, the goal is straightforward: Get a reasonably good enhancement out the door and keep moving. In place of perfection, we’re striving for an “acceptable level of messiness.” Most of what startups need to deliver, and what their customers want to see, is “good enough” to get the job done for most people – with added value that can be readily understood and appreciated, and with accompanying communication channels that allow those customers to help shape further improvements.

The journey from good to great involves hundreds of small improvements originating from thousands of voices, and along the way we will tolerate messiness – both behind and in front of the curtain. Messiness results in time saved within Onshape from forgone navel gazing, and reallocated to higher use. As CEO John McEleney advised me one night, “If things are too clean too soon, then you probably aren’t focusing enough on what is important.” I think about that remark a lot.

3. Capital goes to its highest and best use – and stays away from everything else.

Onshape raised $80 million in September, but you wouldn’t know it by snooping around our kitchen, where the coffee maker is about as no-frills as it gets. And we didn’t celebrate our new funding round over a beer in our lounge because no such lounge exists. I imagine this might turn off some potential employees who want to see more creature comforts in a startup. But those employees wouldn’t fit into our culture anyway.

Our culture is about deploying our resources – financial, human and otherwise – toward the business priorities that are likeliest to produce successful customer outcomes. That doesn’t mean that Onshape is “anti-fun.” We laugh with each other – and at each other! And in between the laughter, we empower each other, challenge each other, and acknowledge each other’s achievements – all in service of benefiting our customers. That’s why if you took a tour of our office, you would have a hard time guessing whether we have $8 million or $80 million in the bank. We’re less show and more tell – and we like it that way.

I imagine this might sound self-serving or holier-than-thou. All I can say in response is that I wish “Thou” worked here so he or she could help me when it’s my week for kitchen clean-up duty.

4. Do your job.

Being based in Boston, many of us Onshapers are New England Patriots fans, though we grudgingly welcome supporters of other NFL teams as well. Patriots coach Bill Belichick may never visit our office – you have an open invite, Bill! – but the operating philosophy he uses with his 53-player roster is highly relevant to life at Onshape and, I would think, to life at nearly any startup. How so?

Coach Belichick’s mantra is “Do Your Job,” a simple directive that plays out here in several ways. The most obvious relates to the character traits we especially value at Onshape:

  • Versatility – Many employees can step into multiple roles, and all employees are willing to learn new roles quickly if needed.
  • Adaptability – It is important to have the right skills to do the expected. But it is even more important to have the ability to respond quickly and effectively to the unexpected. As they say (or at least as Mike Tyson says), everybody has a plan until they get punched in the mouth.
  • Unflappability – This is about keeping calm in the face of just about everything. It is about understanding the difference between passion (highly encouraged) and drama (highly discouraged).
  • Relentlessness – Working at a disruptive startup has much in common with pushing a big rock up a very steep hill. Success is less about strength than persistence. Every night comes with a reminder of everything that remains to be done; and every morning is an opportunity to dust yourself off and start over again, with a renewed energy. And oh yeah, the stakes get higher with every inch of progress because hard-fought gains can disappear in the blink of an eye.

These are very difficult competencies to master. As a result, Onshape’s leadership team has the important responsibility of doing the many large and small things that encourage development on these dimensions, and otherwise enable a high-performance environment. Bill Belichick tells his team to do their job, but then he and his coaches work to put each player in the best possible position to succeed.

Each of us ends up highly dependent on everyone else performing at their peak level based on what is asked of them, and when everything is working as it should, the pieces blend together seamlessly – which is the essence of team.

Like I said earlier, I don’t really know what life is like at any other startup so perhaps my observations have no broader applicability. And make no mistake, I know this is not Lake Wobegon – individually and collectively, we have occasional down days at Onshape. With that said, at my one-year mark, I am incredibly proud of what we are building at Onshape, and even more proud of how we are going about it.


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