How Freelancing Brought Me in Touch With My Inner Salesperson

Me whenever I see yet another “What a Product Manager does/should do/should not do”article on Medium. Photo by Christian Erfurt on Unsplash

As a Product Manager, a vital part of your skill set should be your ability to get in the ring with the Sales folk — Sales Managers, Account Managers, Client Solutions people. Don’t worry — this isn’t another one of these run-of-the-mill pieces around “What a Product Manager does/should do/should not do”, promise!

Ok, so what about Sales as a Product Manager?

Interfacing with Sales is likely to be the most overthematized and at the same time underpracticed aspect of Product Management — lots of talk & very little walk. Instead, a lot of PMs spend their time becoming user-centric with abandon — casually ignoring all the layers between them and the user. 

Another common misconception about a Product Manager’s interaction with Sales is it to be one-sided — i.e. the thought that salespeople are drones, merely good at talking a lot and wearing suits to impress other salespeople, and they need Product Managers to support them with their expert knowledge and technical aptitude. 

This might be partially accurate in terms of what Sales can learn from Product Management, but Product Management can also learn from Sales — the “art of persuasion”, consultative selling, active listening and many more conversational & interactional skills that can be immensely useful to Product Managers.

So spend more time with your Sales people & try to understand their process. And I mean — really do it; go hang out in their office, schedule meetings & jump on their meetings as an observer — you’ll be in for quite a ride!

Alright — and how does that tie into freelancing?

As a freelancer, you need to continually hone your sales skills. Yes, also because it improves your career trajectory, but most importantly because otherwise you might not be able to make rent.

Aren’t you being a bit dramatic?

Maybe, sure. But the reality is that you’ll always need to put on a good show to close a deal — if you’re seeking employment, you might only have to do it once to get the job, and then depending on your personal goals and how tough your organization’s work climate is, you’ll need to periodically get back to showbusiness for a bit.

If you’re a freelancer, not only will you need to sell yourself more frequently (as well as differently; for employment, you’re selling yourself as a team member, and for contracts, you’re selling yourself as an external expert resource), you’ll also need to be prepared to do it at any given time since you usually don’t have proper notice periods, and if your client cancels your contract, your source of work (and money) dries up from one day to another. And when that happens, it’s game time again — and the faster & better you can go out & sell yourself, the better the business you attract will be.

Disclaimer time: That said, building a buffer of at least 3–6 months of salary to carry you through all kinds of situations (such as COVID-19!) is to be considered imperative. This doesn’t defeat the argument at hand, but reduces the existential urgency. 

As an exercise about this, try to review the last 6–12 months and think of 3 key situations in which you believe that better negotiation on your part would’ve resulted in a better outcome. Also, try to assess why you think you fell shortfrom today’s point of view and how you can improve on this in the future — this gets really interesting if you do this as a small group with other Product Managers!

Cool, but how do I build on that?

Of course, this becomes most valuable if you track your performance over time:

• How many leads, prospects, customers did you generate? This could be measured in number of suitable ads you found, number of calls/responses you were able to initiate, client conversations you had, and then contracts you were able to close. Bear in mind that quantitative data is by no means representative of success here — you could close one phenomenal client for a long-running contract, and that could be far better than closing 4 short-term projects you didn’t really enjoy!
• What channels worked best for you? Another really important dimension in conjunction with the previous data — you’ll most probably find that personal proximity, correlates with success, or in other words, personal connections are best, platforms like Upwork are the worst. But also among those good connections, it’s valuable for you to know who you should contact first as soon as you’ll be available again.
• What’s the biggest surprise you found in that data, compared to an assumption you had beforehand? For me, it’s that a lot of “longtail” connections would most of the time not yield closing actual contracts, but that network effects compound over time, and I’ve actually had a good influx of interest not based on having worked directly previously.

And how should this translate back into my Product Management craft?

• You’ll understand your responsibility in selling your project. 
• You’re responsible for having your stakeholders buy into your product decisions, so do your best to make it happen. 
• Learn to speak their language — like you do with speaking developers’ language. 
• Sell to developers as well — usually, they prefer working on something with assigned meaning instead of “whatever’s in the backlog”.
• Remember that as a freelancer, your primary responsibility is meeting the buyer’s need. Again, this doesn’t mean doing whatever they say, sometimes actually the opposite of that — but you’re responsible for a) producing the best result you can, and b) having your buyer acknowledge that.

What if I was too lazy to read the whole thing?

Here are some TL;DR takeaways:

1. Spend more time with your Sales people & try to understand their process. And I mean — really do it; go hang out in their office, schedule meetings & jump on their meetings as an observer — you’ll be in for quite a ride!
2. Try to review the last 6–12 months and think of 3 key situations in which you believe that better negotiation on your part would’ve resulted in a better outcome. Try to assess why you think you fell short from today’s point of view and how you can improve on this in the future — this gets really interesting if you do this as a small group with other PMs!
3. Consider generating data about your ‘sales funnel’: how many leads, prospects, customers did you generate? What channels worked best for you? What’s the biggest surprise you found in that data, compared to an assumption you had beforehand?

So, how about it?

Do you also feel that Sales as a craft is underrated in Product Management? Have you tried any of the techniques we mentioned? Did you notice another advantage of keeping close to Sales in your own career? 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 6 minutes, you could’ve literally done anything else, and we’re very honored that you decided to dedicate them to our piece! ❤️