Finding a great job is really difficult in general.

But it’s particularly difficult in Product Management as the definitions and expectations for PMs of all seniority levels vary wildly from company to company. Even role to role.

I already wrote about the complexities of choosing between multiple jobs last year, but one thing was missing.

How do you actually get to a point where you have the luxury of choice?

Well, guess what? You’ve been rehearsing for this very process all your professional life as a PM! It’s time to figure out how to manage, market, and ultimately sell the product of YOU!

Product Management to the Rescue!

A healthy perspective into getting a job is that it’s just like a B2B go-to-market process.

Ultimately, what’s happening is a product (you) gets marketed (CV, cover letter, website, LinkedIn), and then brought to market in a sales-driven motion (interviews).

The key to getting really really good at getting a job is leveraging your core PM skills in market research, segmentation, funnel analysis, value prop definition, qual/quant research, and iterative product development.

To put it bluntly: you’re the product and you need to approach this process as sales.

Photo by Marc-Olivier Jodoin on Unsplash

The Product of You

The foundation of all business is the product itself. The thing that creates value.

What can it do? What has it done? Who is it for? What are the features? What are the problems it solves?

If you can’t answer those questions about yourself, how do you expect someone else to decipher that information of you?

Just like any great product, you need to be very self aware of your value propositions and target market. The wider the spectrum you’re broadcasting on, the less impactful your message will be. More targeting = more impact.

The earlier you are in your career, the harder this advice is to follow. You can’t really define your sweet spots until you’ve had the opportunity to try on a few hats.

It took me almost 20 years to realize that I specialize in product leadership in growth stage SaaS companies that are either platforms or marketplaces in media or content verticals. That restricts my target market dramatically, but companies that need that specialty will be interested in talking to me.

Just like as a consumer I’m immediately more drawn to products that target 40-50 year old formerly rebellious Nordic hipsters turned lame American suburban dads. They just speak to me somehow.

This is also a great opportunity to get real about the features of your product, ie. your skills and traits. Is there something you’re missing that you could improve upon here and now? Read a book, take a course etc.

View it as a sprint of product development. Invest in your product.

But remember, you need to research diligently what value props your market values. A little more on that later on.

Product Marketing Yourself

When you’ve got a great product, you need to do some product marketing to begin the product’s journey to market.

What that means is you need to articulate the value props in a way that resonates with the target demographic.

There are a few different tools that offer different levels of personalization and are good for different approaches here.


You’ve probably made sure to perfect your LinkedIn by now. Great. There are plenty of posts out there giving general guidance on making an appealing profile, so I’ll skip the generics.

LinkedIn is very important in getting your product out there but its downside is that it’s by nature very generic. It provides the least opportunity to target by potential customer. Your LinkedIn profile is the same for everyone.

That’s why your LinkedIn is where you’ll have to make the most painful decisions on branding yourself. This is you at your broadest.

Don’t let that deter you from specializing. Make your LinkedIn have a stance on who you are and what you do. Don’t just say “product management generalist” or something bland like that. Pick a lane.


A CV gives a little more leeway in getting specific as most companies make you upload a CV as a file. Guess what, that’s an opportunity to customize the CV to the company you’re applying for.

Remember, the more you think about the customer’s wants and needs, the more your profile will resonate. Don’t tell your whole life story. Make sure to cherrypick the relevant bits to the company, the job, and the hiring manager.

Remember again that you’re showcasing a product. The product’s features (what you can do) and it’s past performance (what you’ve done) are important as validation, but nowhere near as important as what it can achieve (the outcomes for the customer).

I generally see two boring types of CVs cross my desk: ones that just list past responsibilities (traditional CV) and ones that are outcomes-focused, but miss the point (list past outcomes without any real context or connection to the job I’m hiring for).

What you want to do is create a feeling for the hiring manager that this person knows my problems and will solve them. Just like a great product. Don’t be a Nokia ad (list of features), be an Apple ad (bold statement on why the product matters).

This all follows Simon Sinek’s “Start With Why” framework.

For bonus points, you can always supplement a CV with a personal website.

Cover Letter

Here is your opportunity to show some real PM chops.

Note: Unfortunately your mileage on investing in cover letters may vary. Not every company or hiring manager values them. All I can promise is that I really really do. The cover letter is always the first thing I check when screening for applications.

The cover letter is the single most important place for a PM candidate to show if they know how to market products. It’s a succinct opportunity to connect a product’s generic value props with a customer’s (hiring manager) needs. It’s the simplest possible Product Management 101 test.

Don’t regurgitate your life story. Don’t say “please see attached CV”. This is your chance to pitch. Use it.

Make it short, make it snappy and most of all make it personalized! This is the time to really make every word about what you can perceive the customer needs.

The cover letter is an opportunity to flex your customer research muscle. If you’re having trouble coming up with a connection between your offering and what the company needs, you might have to dig deeper—or acknowledge that you’re not the right person for the job.

Advanced Media

If you really want to go above & beyond, you can always use platforms like Loom, Unbounce etc. to create personalized landing pages or videos for a specific company. They are usually cheesy as heck, but executed well can really make the difference in a sea of undifferentiated CVs.

The hard part is getting them in front of the right person’s eyes. This is where taking some calculated risks with cold emailing might really come in handy.

Just be careful about coming across as overly eager.

The Sales Pipeline

All that product development and value prop definition goes nowhere without a great sales process.

I’m talking about actually getting out there, pounding the pavement, and ultimately closing the deal.

The only difference is that contrary to a normal sales pipe, you only have to close one deal. But getting multiple customers ready to sign puts you in that wonderful position of power where you actually get to choose who you’re going with.

NOTE: Make sure you read up on sales ops. Not only will it help you understand the concepts in this section, but it’ll make you a 10x better PM if you ever venture into the B2B world.

1. Don’t Go For Your Dream Gig First

I had to learn this the hard way: you will suck at interviewing at first.

Early on in your process, your ability to narrate your product pitch and be really confident in what you’re selling is at the lowest possible point.

I’m sure you’ve scoped out the perfect role in the perfect company right out the gate, but I can guarantee you if you go at it with all guns blazing, you’ll probably do much worse than you thought.

Let yourself get comfortable with selling your product. Every interview is an opportunity to learn about what resonates and what doesn’t, so don’t go high stakes when your current understanding of your value props is at its lowest.

2. Be Open-Minded With Your Top of Funnel

The very top of your sales funnel is everything between sending resumes through job sites to personal intros. Anything that gets your hat in the ring.

While you should be diligent about not wasting anyone’s time on obvious bad matches, make sure to take some chances and be open minded.

Don’t assume too much about different ways of getting in the door. When I switched jobs last year I had every possible flavor of getting in: VC intros to the CEO, ex-colleague referrals, recruiter outbound, and good ol’ CV through the front door.

The truth is, once you’re in the pipeline it doesn’t matter that much where you came in from. Sure, a VC-to-CEO intro might put a big asterisk on your name, but you still have to work your way through the process all the same. Sometimes it might even be a detriment as some companies view intros from VCs as power plays.

I ended up going with Teachable because there was a super strong mutual connection between what they were looking for and what I had to offer. The initial contact? I sent my resume through a job site. I had one sort of distant ex-colleague at the company, but no other connection to them.

Another thing about Teachable: I wasn’t that into them at first. To be honest, I almost didn’t send my CV in. It didn’t feel exactly like “my market”. Had I been too strict about my top of funnel, I would’ve missed out on what right now feels like one of my best professional choices to date.

3. Keep Your Pipeline Strong—At All Times

This is very very very important.

I used to play a lot of poker. A critical rule in bankroll management when you play it for real long term is “never play a game you can’t afford to lose”.

When you can’t afford to lose a game, you will not play at your smartest.

The same goes for interviewing. When you let yourself get into that “I have to get this job no matter what happens” mindset, one of two things will happen:

  1. You will suck at the interview because your confidence is rocked by the pressure.
  2. You will ignore glaring red flags the company might throw your way and end up joining something you should stay far away from.

Both lead to bad outcomes.

Even the neutral outcome of you just losing your mind waiting to hear back from a company with nothing else to work on is not great for your mental state.

I’ve made this mistake several times: I get far into the process with a company I feel good about and start ignoring feeding the top of the funnel. Then at the final stages panic starts creeping in and I blow it with the final interviews because I let the pressure of “all or nothing” get to me.

Don’t be like me. Feed the top of the funnel. Always have irons on the fire at every step of the process.

4. Understand User Profiles and Empathize to Their Needs

Especially if you’re going for leadership roles, you need to start understanding how to pitch your product to different roles within the company.

Much like you would sell a B2B product with a very different spin depending on whether you were addressing the user (the one actually interacting with the product), the customer (the one ultimately getting the value), or the buyer (the one making the $$$ decision).

In every Product Management or Leadership interview process, you’ll be talking to cross-functional collaborators (engineers, designers, and their managers), different business people, product peers—maybe even executives or board members.

There is ultimately very little overlap between what these people want to hear.

Make sure you understand how to tweak your pitch and narrative to that specific persona.

5. Analyze & Iterate

Every interview, every “customer touchpoint”, and every success or failure are data points to analyze. What can you learn about your product, the way you represent it, or the market’s needs based on this experience?

Just like in real go-to-market processes, you might not always get tangible feedback on what went wrong so you need to get really good at reading between the lines.

Pay close attention to which stage you usually drop off at. What’s the ratio of CVs sent to screening calls? Screening calls to first interview? Do you breeze past meeting with other PMs but consistently get scrapped after talking to executives? Analyze the funnel.

This is almost never a linear progression as every company has their own pipeline and process. That means you’ll have to improvise a bit on how you derive those insights.

But hard as it may be, this is where some of the most important work happens. If you’re getting consistently rejected, there’s something wrong with your value props—and chances are its with a very specific persona.

Example: I used to fall on my face with executives and engineers. For the former, I came in hot and heavy with “product speak”. Execs don’t give two damns about your scrums and your multivariates. They want to know how you make their business hum.

With engineers, I leaned in too heavy on my technical past and probably came across as a PM that wouldn’t respect my lane. I’ve written way more about this in Pros and Cons of Moving to Product from Engineering.

Photo by Greg Rosenke on Unsplash

Troubleshooting Rejection

If you’re getting rejection after rejection, make sure you’re being honest with yourself and constantly seeking out new information on your personal product-market fit.

Here are some potential questions to ask.

Does Your Product Have Flaws?

Is your product as good as you think it is? Do you actually have all the necessary skills and traits for the jobs you’re pitching yourself for?

Invest in yourself. Read books, attend a class, listen to podcasts, go to meetups.

This is the hardest one as it takes a long time to build a truly appealing product. I’ve been building my personal product for well over 2 decades and I feel like the more I learn the more I find out there’s still left to learn.

Especially since most of the things worth learning are always in the “unknown” sector of your Johari Window. Force yourself to consider the things you didn’t think you need to know.

Luckily this process is great for self-reflection and seeking out what skills or traits you didn’t even know existed.

Are You Marketing Your Product Poorly?

If you’ve got the skills to pay the bills, but nobody cares, you need to hone your messaging.

Have someone read through your LinkedIn and CV. Ask them for feedback beyond “is this good?” or “do you like it?”

Ask them for takeaways. Ask them what perception they have of the person. Ask them to skim and tell you what they remember.

Put time into cover letters. Especially work on brevity. Give yourself a strict word limit for cover letters and practice telling your story in an impactful way that always starts from the customer.

Are You Selling Well Enough?

I’ll admit, this one is the toughest for most people, myself very much included.

You can be the perfect product, have an awesome polished CV, but fall flat on your face in an interview setting.

I’m not even going to go into how many ways our standard hiring practices are broken and incapable of assessing anything beyond thinking quick on your feet. That’s a whole separate blog post.

But in the current environment, you need to find a way that’s natural to you to sell your product.

What I’ve found work for me is having a good selection of well rehearsed anecdotes from my career that I can narrate so well, I’m able to improvise on them just enough to match them to the question and combine them to offer a full breadth of representation for my skills.

A lot of selling your skills is in good storytelling. Even if your career has been a bit drab, you need to find a memorable angle to how you talk about it.

Obviously, never lie. You’ll get caught. And you’ll suck as a human being.

Practice storytelling with friends. Think about the details. Add details where it aligns with the narrative. Remove information when it detracts from it.

The more repetition you get, the more natural your stories start feeling and the more fluent it will be for you to connect them together. (Hence the recommendation to not go for your dream job first)

Most importantly, always edit the narrative to the person sitting across the table. For execs, build on the numbers. For cross-functional partners, show your empathy for the challenges of their crafts. Always remember the customer. Don’t talk about yourself. Talk about your skills in relation to their needs.

Are You Selling to the Right Market?

Get honest, are you targeting the right industry, the right business model, the right companies, and the right roles?

This is why job hunting is such a great period of self-reflection. It forces you to really figure out what your skills are and who will find value in them.

Test the waters outside of your comfort zone. Your product market fit might actually not be where you think it is. Let yourself be surprised.

Do You Know Enough About Your Market?

Knowledge is power. Have you done your homework? You can find a treasure chest of information on companies and hiring managers even by doing some passive scouring of the internet. LinkedIn, Glassdoor, Crunchbase, Medium and many other sites offer up tons of insight into how companies think, what might be ailing them, and what they are looking for.

Make sure to read the job description a few times over for clues.

If you’re connected to current or ex employees, now’s the time to put that social capital to use.

Research their industry and competition. Learn about their customers.

Make no mistake: This is a lot of work.


I’m not going to lie—job hunting is pretty shitty. Even in our privileged tech circles where demand dramatically outpaces supply.

This approach made it dramatically easier for me to make a bad experience into a palatable one. It helped me reach a very good outcome that I’m couldn’t be happier with.

Remember: you only need one conversion!

Happy hunting!