From Startups to Fortune100: Some Lessons

Let’s face it, I’m a startup gal.


I always do things the “quick and dirty” way, I have a strong bias for action, I can’t stand “processes” if they slow me down, and I am not used to having more than half of my work hours spent on “stakeholder management.”

But here we are, folks. Kristin (Stannard) Kent, startup gal, has been working at HP - yes, the Hewlett Packard - for almost a year. 50,000 employees, $50B in revenue, offices in over 170 countries. 

We can get into the reasons for the switch a different day, but for now, I wanted to talk about some of the biggest lessons I’ve learned as I’ve transitioned from working for small scrappy companies to this household-name behemoth.

yellow flag if someone interviews for a startup and thinks they can handle it no problem because their previous job “was like a startup within a big company.”

When at startups, I’ve always wondered how much truth was behind the statement “but it was like a startup within a big company” when I’ve interviewed someone coming from a bigger company. I have found that every company has its share of chaos (big companies as much as small ones), so it’s true that big companies can still be figuring out processes for something new. But that’s where the similarities end for me. Big companies often have hourlong trainings on product patents, regularly recurring sessions on cybersecurity, ethics, privacy, and foreign policy, and sometimes people in roles due to tenure rather than fit. There are specialized teams for market research, competitive research, and user research. For anyone used to big co life, moving to a startup can be a shock - it requires a complete mindset shift and adaptation to a different organizational culture. Honestly, 80% of the people I saw transition from a big company to a startup didn't last more than six months.

Working at a big company doesn’t necessarily mean it will be a “cush” job.

You can take the girl out of the startup, but you can’t take the startup out of the girl. (Should I be saying “woman?” I’m 36 and still find it odd to refer to myself as that.) Anywho, I’ve realized after each job where I’ve “burnt out” that it’s me, hi, I’m the problem it’s me. I am certain many people at big companies enjoy a strong work-life balance. I have not yet figured out how to do this for myself as I am slightly obsessive and also have not consistently focused my obsessive behavior toward anything outside of work or family. 

“Executive” is an incredibly vague term that means this person is generally on the upper echelon of seniority but could be doing any range of roles.

I realize this is obvious to anyone who has grown up in the corporate world. But to me, before joining HP, I’d see someone introduce themselves as an “executive” and repeat the Office Space quote in my head “so…what would you say you do here?’ So now I know what it means and I can tell you. It is generally a Director level person or higher at big cos. As mentioned above they are probably in meetings all day long and doing a lot of stakeholder management. I’m technically an executive at HP. Thank you for being impressed, I will indeed “go on” with my bad self.

You may regularly be presenting to hundreds of people.

I’m used to 10 - 500 person companies. This means that the teams are obviously smaller and there is no regular need to talk to more than 30 people in any kind of town hall at a time. But at big companies, teams are huge, and lots of “town halls” are needed to keep the communication lines a-flowin. Though I generally consider myself somewhat charismatic, I am still battling nerves most of the time I’m getting on that Teams video and presenting to such huge teams.

“governance” is a common term - and it means that There are processes to create new processes, and then probably also processes to create those ones too.

Honestly the biggest challenge for me during this transition is the truth behind the idea of “red tape.” I see a new software platform come out that everyone’s talking about that is making teams more productive (especially in the “AI this, AI that” world we’re living in today) and I want to try it and get my team using it. Unfortunately, at big companies, it doesn’t work like that. For good reasons, but still something to adapt to. (If everyone thought like me and wanted to introduce a new software every 3 months, well you can see how that would quickly become unmanageable.) Internal “governance committees” are formed to outline the general strategy and rules for when we can consider introducing new software or not, and then there are forms to submit and many live reviews/demos to go through to convince all of the different stakeholders that this software will be worth it. Then a new senior exec may start in your org and you have to kick off the convincing all over again. ;)

Microsoft office is not Google suite.

Oh wait, I forgot about the actual biggest challenge for me. Many big companies use Microsoft Office. After using the Google Suite for 10+ years, this has been incredibly difficult to transition to. Why can’t you add 2 different hyperlinks in a single Microsoft Excel cell? Why does Microsoft Outlook search never find what I need it to? Why can’t you type on the same line that someone else has their cursor on when you are collaborating in Microsoft Word? Please send help.

The perks are 100% real.

I realize that I’m taking advantage of probably 10% of the actual perks that HP offers, but the truth of the matter is, people stay at big companies for life sometimes because the perks are so good. Perks include the ability to switch jobs and level up and learn about a new part of the business, as well as free financial advisors or significant fertility coverage. The amount of emails I get from our HR team just asking about how satisfied I am with different services makes me realize how much companies like HP actually care / how much time they’re spending to ensure it remains an amazing place to work that retains talent.

Previous
Previous

2025: Big Goals, Big Baby, and Balancing It All

Next
Next

Mat Leave Round 2 Thoughts