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Freelance Product Managers in: SMEs

Freelance Product Managers in: SMEs

The typical “pretty well-off tech SME” office, don’t we all know it. Photo by Austin Distel on Unsplash

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: Small and Medium-sized Enterprises!

Had to google it, but yes, this is actually a bank for small & mid-sized companies. Photo by aiman baseron Unsplash

Freelancing in SMEs — Maneuvering a Crossroads

SMEs are generally defined as companies with more than 10 and less than 250 employees (with numbers varying by territory), the key distinction between SMEs and startups being that SMEs are usually:

  • Operating on an existing (or established) business model (vs. trying to establish or grow into one)
  • Generating revenue early on, without (major) external investments (vs. funding the above thru VC etc.)
  • Focused on organic and sustainable business growth (vs. trying to 🚀 to become a 🦄)
Couldn’t spare you the quick trip to Cringeville, sorry. Photo by Ashley West Edwards on Unsplash

Accordingly, these companies have a) either avoided or surpassed a “startup stage”, and b) haven’t grown into an enterprise-size operation (yet). So, in an ideal setup, where the firm’s business, revenue and staff would be largely stable, there wouldn’t be any imminent need for freelance product management support….right?

Photo by Andrea De Santis on Unsplash


Photo by Kind and Curious on Unsplash

Having worked with SMEs, let me outline their achilles heel:

While generally a good thing, companies that don’t aspire to shoot for the moon (startups) or dominate the market (enterprises), will by default attract exactly that type of talent — i.e. people who:

  • prefer work-life-balance over a 60+hr/week– startup hustle
  • prefer knowing all their coworkers (and liking some of them) over the prestige of working for a household name
  • prefer a stable work environment over pressure to perform and to adapt quickly, facing job loss upon failure
  • prefer a laid-back conduct over complex and demanding org structures of enterprises

Again, none of these are bad things, or bad choices. 

But — let me be blunt:

SMEs are prone to attracting underachievers.

Now, before you cancel me, hear me out:

 Please. Photo by Franco Antonio Giovanella on Unsplash

I’m not saying that SMEs are mostly staffed with underachievers, just that they run the risk of attracting them. I’ve attached my favorite exemplary SMEs that defy this logic at the end of the post, so bear with me!

In the war for talent, SMEs think of this as their competitive edge — “Come work for us, we pay less than enterprises and have less crazy fun stuff to work on than startups, but we’ve got work-life-balance, and we’re all chill & friendly!”

Sounds nice, sure. But — what if someone thinks “Ah, sounds like the perfect coasting job”? 

What if this is their idea of #workgoals? Photo by Drew Coffman on Unsplash

And if they’re good at feigning talent and motivation, but when hired, they hide behind non-ambitious targets and the promise of a calm work environment?

Just ponder this question for a second:

Do you want to attract talent that expressly shies away from a challenging environment?

Wait, I thought this was supposed to be about Product Management?

Yes, just one sec.

Why does this look like stock imagery to start a watch dropshipping business? Photo by Collin Hardyon Unsplash

How can Freelance Product Managers solve this?

Circling back to the initial scenario — your business, revenue and staff being stable for the most part: just because you’re not in a highly transformative space or a complex organization, that doesn’t mean you’re safe from being disrupted. You aren’t.

Others are coming for your business. Maybe even startups that are faster than you, or enterprises that have more brand trust and infrastructure.

Don’t take it from me — according to the World Bank, although SMEs create more new jobs than large firms, they also suffer the majority of job destruction/contraction.

So you need to keep your staff on top of things. But what if some of your people don’t want to partake in that? 

SMEs are “We’ve always done it that way”-Land

As soon as you hear that phrase a lot (“We’ve always done it that way”), you know you’ve got a problem. This reactive attitude might very well endanger your company’s future.

Don’t enter! Photo by Edwin Hooper on Unsplash

Especially product managers get comfortable with this: after an initial phase of “figuring out the process”, they’ll establish one that just works, and get rewarded by management for continually successfully executing on that tried-and-tested workflow. 

When there’s no imminent external pressure to further improve and develop this process, they’re less incentivized to go out of their way to try something new — and even if they do, other team members might stifle that endeavor.

“If it ain’t broke, don’t fix it!” Photo by Headway on Unsplash

With a lack (or an absence) of drive to innovate in the team, plus a rather strong social bond (why put your popularity among peers on the line for a mid-to long-term business goal?!), it can be super helpful to bring in an external party — such as a freelance product manager — to navigate this journey.

The SME Product Workshop

To drive meaningful change in SME product orgs, 2 things are key:

  • Impulse: Presenting and evangelizing ideas on how & what to improve.
  • Follow-Through: Actually doing the nice stuff that was decided on in the aforementioned.

A common format is a one- to few-day workshop in which a product consultant will:

  • gather information about the current product process — who sets what goals when, what influences product strategy, how does delivery happen, who’s involved etc.
  • zoom in on what’s lacking, and why (this usually lays bare interpersonal issues and has the most potential for conflict among staff members) — are individuals forgetting to follow an agreed-upon system (or actively deciding against doing so)? Are individuals prioritizing their own goals and interests over the company’s for management clout? etc.
  • establish the progress you’ll want to have made up to a given point in the future — i.e. what can be rectified in a week’s/month’s/quarter’s time?
  • define actionable steps to reach them — as well as responsibility and ownership for these steps — it’s best to transfer ownershop to staff members, but consultants can also keep track of certain progress items in some situations.
Sticky notes aren’t mandatory, but highly encouraged. Photo by Leon on Unsplash

Can’t I just do this on my own?

Technically, yeah — but lemme guess:

  • You don’t have the time to do that yourself. (upper management)
  • You don’t feel like it’s part of your job. (associate-level PM)
  • You definitely don’t feel like it’s part of your job. (developer)
  • You’d be able to do that with the developers, but are lacking the Product sensitivity necessary to properly guide & enrich the session. (scrum master/agile coach)

Flexible Project-based Support

Quick jump back: your organization is mostly stable. This also makes SMEs less reactive to change; consider these scenarios:

  • One of your PMs goes on parental leave and/or sabbatical.
  • You just won a big client, and need to assemble a task force to build features in support of agreed-upon SLAs.
  • You’re partnering up with a complementary business (e.g. you’re a small bank, and partnering digital accounting provider) and need that done quickly on a project basis.

You get the jist…

If you have a shortlist of trusted freelancers you can call to help you out when these things happen — imagine your level of gladness!

😌 Photo by Etty Fidele on Unsplash

Sounds expensive. Us SMEs don’t swim in money.

Maybe — but wouldn’t it be more expensive to lose business & opportunities, be late to market or have burned-out staff quit on you?

Can’t I just hire a working student?

Nope — that’s the opposite of what you want to do in this situation. Working students need attention and training, and shouldn’t be entrusted with significant responsibility. 

So, this won’t unburden your staff — adversely, it’ll create an. additional burden! Now you’ve lost money and created a new problem!

But working students aren’t all bad?

Of course not. But hiring them serves a rather specific purpose and strategy — which is a topic in itself that I won’t explore further. (Maybe someone will feel compelled to open up a blog called productmanagementworkingstudent.com or so…)

My List of Exemplary SMEs

As promised, here’s a collection of SMEs that (in my opinion) are doing a stellar job of being — and staying —on top of their game:

The Remote Hipsters: BufferDoistZapier and more

They went remote before it was cool — and used that not only as an advantage to attract top talent globally, but have shaped remote & distributed company culture and are now so far ahead of the curve that their staff is not just among best-in-class, but also fiercely loyal. That’s what happens when you unwaveringly execute on your vision of a new org age — pay attention, “We’ve always done it that way”-ers!

Firm On DEI: WherebyCalendlyPendo and more

For these players, diversity, equity and inclusion are more than lofty marketing speak — aside from offering flexible work, they’re drawing in exceptional diverse talent by following through on those core values, and retaining them by letting them thrive. Whereby holds a special place in my heart as their product team has obviously focused on exactly the right additions, and have added awesome functionality to guarantee the success they’re thankfully having right now!

Ethical & Sustainable Business: TomorrowAspirationYook and more

As someone with a soft spot for the world not bursting into flames in 10 years, I was one of the first to sign up for Hamburg-based Tomorrow’s sustainable banking account (I still have the old card!), and I’m super excited to see them hit all kinds of targets lately, especially closing a 3 million EUR crowdinvesting round within 5 hours. Another one to watch is Yook, on a mission to make online shopping climate-friendly.

Holacracy — and Beyond: Voys, MYCS, Me & Company GmbH and more

I know, Holacracy is a bit of a hot topic — but I respect SMEs that ventured into adopting it (and also tweaking/abandoning it) for the disruptive stance and innovation potential. It shows their dedication to constantly improving their own organization, which most probably does wonders for hiring & retaining people!

The “Best Boss in America”: Dan Price & Gravity Payments

I’m sure you’ve heard this story — in 2015, Dan Price made headlines around the world when he announced to the entire Gravity team that he planned to raise the minimum wage for everyone to $70,000. He called the move a “moral imperative” to do the best you can for those you’re leading.

The Gravity of 70k min · Gravity Payments
How a Million-Dollar Pay Cut and a $70,000 Minimum Wage Revealed a Better Way of Doing Business by Dan Price – CEO of…gravitypayments.com

Obviously, they’re now the most well-known medium-sized credit card processor in the world — and I’m sure they have no problem finding highly talented and disruptive people that want to join their team.

So, how about it?

As freelancers, do you have SMEs in your client list? Do you prefer working with SMEs? If you work for an SME, 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 9 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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