Freelance Product Managers in: Enterprises

In this mini-series, we’ll look at utilization of freelance product managers in different environments; when it makes sense, and — yes, also when it makes less sense. 

This week: Enterprise-size companies (i.e. 1000+ employees).

But they don’t need to be sitting in the same room, of course. Photo by Alex Kotliarskyi on Unsplash

Freelancing in Enterprises — A Big Challenge

Given that enterprise-size companies are large and powerful, but also slow and inert operations, freelancers are quite frequently brought in for various purposes — and at various levels, be it building/reshaping a line of business’ entire product strategy/organization, or bringing in an interim product manager to get delivery work done.

Unfortunately seems like Unsplash was fresh out of images of “Get Sh*t Done” mugs, so this will need to do. Photo by Kyle Glenn on Unsplash

So, are freelancers the backbone of the enterprise economy? 

No, employees are.

Freelancers are the back massage tool that loosens your stiff back.

Also, a good amount of massage therapists are actually freelancers. Photo by Toa Heftiba on Unsplash

A Complex Environment

At companies that employ a four- to six-digit amount of people, put simply  a lot of stuff happens, constantly. And it’s usually highly intertwined.

“So, here’s a chart of our reporting structure…” Photo by Paul Teysen on Unsplash

This also includes people joining, people leaving, people getting promoted, people switching departments — and especially with usually rather slow hiring processes, freelancers are frequently the only way for enterprises to fill gaps.

Drivers for Innovation 

But this isn’t the only potential purpose freelancers may serve in enterprises; their superpower is innovation.

Oof. Photo by Riccardo Annandale on Unsplash

Are you saying employees can’t be innovative?

Don’t cancel me just yet (please):

Of course, on-staff people can also have great ideas, and may push for innovation.

But — as counterintuitive as this may sound, innovative ideas (sometimes the exact same ones) are usually better received by “someone external”.

The reason’s rather basic communication psychology, and is similar to why people need mediators, and psychiatrists, and scrum masters: the sender-message-channel-receiver model.

With enterprises resembling the populations of small to mid-sized cities, that population — although usually less diverse in comparison — has a huge range of social intricacies:

  • Some people…just don’t like each other.
  • Some like each other too much to be impartial in situations where they need to be.
  • Some are jealous.
  • Some are disrespectful.
  • Some are protective.
  • And most of them stick to their cohort, meaning that they associate most closely with similar peers.
Gang gang. Photo by JAYAKODY ANTHANAS on Unsplash

As an on-staff product manager, it’s important to procure and introduce to innovative ideas. And it’s even more important to actually put those ideas into action — but if some decider doesn’t like you, or you don’t belong to an influencer’s close peers, you’re out of luck.

Too bad — try again. Photo by Mahdi Bafande on Unsplash

On the other hand, very tightly-knit groups have a tendency to reject outside opinions — which include those of consultants and freelancers.

Both extremes are unhealthy behavior. As a freelance product manager, it’s important to 

  • use the former situation to support the on-staff team in overcoming the divide they’re facing, 
  • and in the latter one, it’s the uphill battle of needing to prove one’s self and thus not only gaining staff approval, but also breaking the habit of being closed off.

In It for the Long Haul

With all that I’ve described, you might be thinking –

“All of this sounds like it takes a while…”

And if you are — you’re definitely right.

And if you didn’t — kinda proving my point, so thanks! Photo by Elena Koycheva on Unsplash

Throw in being onboarded into the complex structure of that mid-sized city enterprise, and you’re usually talking months — nothing under 3, but usually more like 6–12, sometimes approaching 18.

So kicking off a project only makes sense if both parties are positively sure about investing a longer period of time. 

As an Enterprise, why should I hire Freelancers?

  • Fast scaling of human resources (usually without the actual HR department, lol — try getting people on board as fast through your company’s HR process, I dare you!).
  • Encourages more efficient planning and steering.
  • Helpful outside opinions.
  • Despite the usual tune of “freelancers are (much) more expensive than employees”, they’re actually cheaper in some cases (we wrote about this a few weeks back):

A Cost-Conscious Case For Hiring Freelance Product Managers
Think you’ll be saving money with employees? Consider this!medium.freelanceproductmanager.com

As a Freelancer, why should I work with an Enterprise?

  • Some of the big names have really large, impactful and interesting projects going on! It’s rather easy to understand why one would be interested in contributing.
  • Depending on where you’re coming from, working in a highly regulated and “processualized” environment can be inspiring, actually.
  • Usually more stable contract situation (which is a question of preference and may constantly shift — but especially for freelancers seeking a bit more routine or reliability (looking to found a family?), this is a perk)

So, how about it?

As freelancers, do you have enterprises in your client list? Do you prefer working with enterprises? If you work for an enterprise, what’s your experience with working with freelancers? We’d love to hear from you, please leave us a comment below!👇

Interested in more stories around freelancing in Product Management? We publish regularly to our Freelance Product Manager publication & would appreciate a follow! 👆

And as always,

Thanks so much for reading!

We acknowledge that with the 5 minutes, you could’ve literally done anything else, and we’re very honored that you decided to dedicate them to our piece! ❤️

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