Why You Want to be the *Second* 1st PM

Wait, what??? What is a “second” first?

If you’ve been a first product manager (PM) at a company before you know what this means. For the rest, let’s take a look.

What is a first PM?

The first product manager (PM) is exactly what it sounds like: it’s the first product manager hired at a company.

Typically, that means you’re taking over for one of the founders who is now too busy to handle the responsibilities.

In other cases, the company has not really had anyone serve as product manager, and finally hits a point where they recognize the team needs stronger product direction and focus than a variety of people can figure out ad hoc.

In both cases, that usually happens somewhere between employee #8 and 20. So the team is small enough to be nimble, but big enough to make some serious progress.

So what’s a *second* first PM?

Joining a company as first PM is a big risk. The company usually has some traction but not a lot. They’ve likely raised some money (or have substantial revenue), but not tens of millions in the bank.

However, that’s not the greatest risk.

The greatest risk is that the founders that hired you don’t know what they really need.

Unfortunately, the first first PM often ends up being a sacrificial lamb so that the company can figure out what they really need in product leadership.

Today, we take a look at why it happens, and what product people considering being a first PM should think about before taking such a role.

 

The Unique Challenges of the 1st PM

The first PM is a special job. You’re coming in to bring order to chaos, and disciplined habits to a company with some (or a lot of) traction.

With that comes a lot of challenges starting on Day 1:

1) Metrics: You may or may not have *any* metrics, which makes decision making looking back hard. If there are some analytics implemented, you’ll likely be the first person to seriously look at them regularly and use them to make product decisions.

2) Resources: The team may or may not be fully staffed. Chances are you’ll be working with a mix of junior hustlers who were early and are “figuring it out as they go” and the first executives brought in to bring order and scale. In particular, you may not have a full time designer to work with.

3) Process: Unfortunately, what worked in the “Figure it out” mode of early days, doesn’t work so well with a dozen engineers and a growing roadmap. You have to work hard to get buy in so that a little process can help everyone’s work go more smoothly. Sometimes, founders can be the most resistant to this.

4) Founder Passion: Giving up their baby to let you run product can be really hard. A founder’s vision & gut for what is “right” has gotten them incredibly far, and now you need to work with them to chart the right course forward. There’s a fine line between executing their vision, and being stuck forced to build things they want that you know aren’t the most important thing.

5) Founder experience: If they’ve never worked with a PM before, they may not know what that really means. Given how vague product responsibilities and outputs often are, it’s not uncommon to hear “I like how this project/new feature is going, but I have no idea how you’re contributing to that.” 

Now, these challenges make the job uniquely difficult, but also can generally can be overcome as long as you don’t face too many of the above issues together.

Unfortunately, it’s their combination with the 2 biggest factors below that leads to a first PM’s departure, and a second 1st PM being hired.

 

Why the *first* 1st PM often ultimately fails

Most 1st PMs are experienced product leaders. Whether they’ve been a product manager for years, or started their own companies, they’re generally very T-shaped employees that know how to deal with a variety of challenges.

Despite this, being the first 1st PM still does not work out in a lot of cases. I’ve seen this firsthand and commiserated with fellow PMs who have been through it.

So what are they unable to overcome? Why do they ultimately fail?

1) The founders don’t know what they really want and need

The earlier a startup is, the more haphazard the hiring process is. At 10-20 employees, they often don’t have a recruiter (or often any HR) on staff, so they’re making it up as go as they hire people. This means many hires are directly from their network or referrals from there, without a lot of vetting.

With all the problems that have built up leading them to realize it’s finally time to hire a product manager, they start asking around for product people they know.

Eventually, someone gets introduced to them that understands this early stage startup world. In the interview they’ll be able to point out some obvious problems the product or product team has with plausible solutions.

This makes the founder think, “Yes. I need this person to solve these problems!”

Unfortunately, when they hire this person, they later realize that while those problems did need fixed, they weren’t *the most important thing* they needed in a PM.

Instead, these founders slowly discover that the skills of the PM they hired don’t align as well as they hoped:

  • Market: Are they well-suited for the nature of your market? Do they relate well to your target customer?
  • Stage: Are they comfortable with where your business is in finding product/market fit? Pre-P/M fit requires a level of experimentation and exploration some PMs can be very uncomfortable with, and is very different work than post P/M fit.
  • Non-Technical: Is it a very technical product? Then your UX issues may seem glaring now, but won’t matter when you’re trying to make core feature innovations quickly.
  • Too-Technical: Is technology not the most important differentiator in your market? Then, a technical PM may relate well to a technical founder, but not bring the customer empathy or design skills that are more important in your market.
  • Rapport: The PM and the founder they report to have to build a very close relationship. If they think too differently, or clash in personality, it won’t work.
  • Culture: How the company operates often follows the habits of the founders. If they’re disorganized it can be very hard for a process-driven PM to bring in process and get buy in from colleagues if the founder isn’t supportive of those changes.

Hiring a first PM is like the story of Goldilocks; you have to try a few to find the one that’s “just right.”

Unfortunately, first PMs often end up being like Goldilock’s first bowl of porridge; not quite right.

Given product management comes in many different flavors, it’s easy for founders to choose the wrong one for any of the above reasons, or similar ones.

Note: this post does a great job of grouping and explaining different types of PMs.

2) The company isn’t fully established

The other side of the coin is that this is still an early stage company. Even if at the time you hired them, the PM is the exact right fit technically, market-wise, and culturally, it still may not work.

Why? Because if your company makes a major change, so does the PM you need:

  • B2B vs. B2C: If you take the leap from consumer to being a B2B product, there’s a good chance that your first PM won’t be the right fit on the other side.
  • Moving Up or Down Market: Someone great at building for the enterprise with many stakeholders and permissions leveling may not be good at building for SMBs who are used to free trials, and a self-serve approach.
  • Solution format: If you were a consulting and services heavy business it’s great if they’re from that world as well, right until you want to build a product that stands on its own without any of that.
  • Industry passion: Just because the PM was excited by your original mission and industry does not mean they’ll still be in love with your business if you suddenly have a whole new customer base to work with that’s very different.

On top of all this, as other roles are hired, what the PM needs to do could change, too. For example, if you hire an amazing designer who loves usability research, then a PM strong in that is less important than another unfilled gap.

One person’s trash is another person’s treasure.

Due to all these factors we’ve explored, the first PM ends up being a very expensive learning experience for both the PM and the company.

The company learns all the things they really need in a PM, and the things they really don’t. They can now confidently write a much more specific job description, and will be more precise in how they source, filter, and evaluate candidates.

Meanwhile, the first PM is likely feeling pretty burned out and frustrated. They fought many unwinnable battles, and in the end saw that they were never in a position to succeed. They may have even raised concerns during the interview about issues that ended up being foreshadowing of exactly what would go wrong.

This first PM has a short, challenging stint at a company on their resume, and leaves either saying “What if?” or “Glad I’m outta there.”

The second first PM then reaps all the benefits.

The glory of being the *second* 1st PM

Being the second 1st PM has all the benefits of being the first PM, but few of the drawbacks.

There are many reasons it’s fun and tempting to be that first PM:

  1. Prestige: It’s really cool to be the first product person in the door. You call many of the shots, you get to bring in process *your way*, and put your stamp on a product with some momentum.
  2. Equity: A good first PM can get a sizeable stock grant (0.2 – 1%) depending on pedigree and need, so the upside can be high.
  3. Challenge: If you like rolling up your sleeves and making something from (almost) nothing, this is an amazing role, with other awesome, hungry, hard working people to go with it.
  4. Growth: If the company succeeds and grows (which you play a key role in), you get to build a product organization, growing into a management track.

And unlike the *first* 1st PM, you are being hired with a much clearer picture of what they need; they’ll have learned from their mistakes the first time around.

This is why being the second 1st PM is one of the rare times it’s *not* a red flag that you’re applying for a role that is being back-filled.

In fact, it’s better than hearing it’s a brand new role, because you get some extra things that were created thanks to the efforts of the now departed first first PM:

  • Buy in: After what the other PM started, there is more support by the whole team and especially founders to make changes. They likely hired you specifically for skills and changes they now know they need.
  • Momentum: Chances are the first PM laid a foundation that gives the second 1st PM things to work with; they’ll have some analytics tracking set up, some semblance of project management, etc so you have the basic tools you need to do your job from Day 1.
  • Potential: The company is now a bit further along, a bit more traction, a few more key hires. So while you get the title, equity, responsibility, and opportunity, there’s a bit more certainty in the business so you can be confident in the opportunity.

I was a second 1st PM.

I’ve had a few friends go through being the first 1st PM and run into the challenges outlined, and once I heard their stories, I realized how much I benefited in being the *second* 1st PM at KISSmetrics:

  • Foundation: The first 1st PM had gotten us started on a number of key things I could pick up with: processes, customer lists, habits, etc.
  • Buy in: The team was experiencing a bunch of challenges as the 1st PM had left a few months earlier. They knew exactly what they needed this time, and were supportive of what I wanted to do from Day 1.
  • Opportunity: An amazing VP Sales had just come on, the business had hundreds of paying customers, Series A was raised, and it was clear what they needed and that I could run with it. I couldn’t ask for more.

At the time, I didn’t appreciate the battles that had already been won, and the buy in that I inherited.  Now, I do.

To all the first 1st PMs, who often don’t vest any equity, and found a huge difference between promises during recruiting versus reality, we salute you. It’s not a job for the faint of heart, but there’s another PM who greatly benefited from your hard work.

What if I’m interviewing to be a first PM?

If you’re interviewing at a company that is hiring their first product manager, be sure to ask if they’ve already had a 1st PM before.

Their answer will be very revealing, and helps dictate what you do next…

If you’re the second 1st PM

Dig into what the founders learned from the first PM. Find out why they think the other PM didn’t work out.

Look for signs that what they need is what you can do, and that they’re accountable to their side of what went wrong (or you may be set up to fail, too). The more thoughtful and introspective they are, and the more what they describe are things that you’re great at, the better your chance of success.

You also likely would benefit from networking your way to that first 1st PM. They likely know the skeletons in the closet and can give you an alternate perspective on the company. Then, you can work to discern the truth that is somewhere between what they and the founders tell you.

Not all previous PMs will want to talk, so if they decline speaking with you, respect their privacy. Instead, look for other ways to learn about the company like Glassdoor, asking others you may know there, etc.

Meanwhile, if you’re the first 1st PM

Go in with eyes wide open. Proceed with caution!

Unfortunately, no matter your optimism, or pre-existing relationship, there is a high chance you won’t work out.  Make sure it’s the right time in your career for the risk, you’re confident in the founder you’ll report to, and you can work from day 1 to iterate to what they need.

Once you’re there (or if you’re already the first 1st PM) a few things that can help:

  • Understand why you’re there: One of the biggest challenges of the 1st PM is turning a vaguely defined role and need into a clear cut set of goals you can achieve. Spending time with the founders to clarify everything can help you start on the right foot.
    • How to do it: Take another look at the job description and what you learned while interviewing. Talk with the founders to confirm what they need most, then deliver on those things as best you can.
  • Over-communicate: Building trust and confidence with the founder you report to is essential. You need to calibrate with them so they understand what you do and why, while also understanding their vision and expectations.
    • How to do it: Use 1 on 1s, weekly emails, get their feedback pre-launch, and give them access to the tools you use so they can see what’s happening.
  • Create a clear plan: Make a 30-60-90 day plan of what you are going to do, why you chose those things, and mutually agreed upon success metrics. This helps them understand how you think, and make sure you’re heading in a direction they agree with.
    • How to do it: A Google doc with bullet points is often all you need, and allows them to comment and ask questions easily. Then keep updating and reviewing it as you pass those monthly milestones.

There are definitely times where the 1st PM has worked out the first time, so it is possible. However, whatever vetting you typically do for a role, triple it before taking such a role, or even consider consulting as a way to try before you buy if you’re unsure.

Is a 1st PM role right for you?

Being a first PM can be a great way to learn quickly, level up your career, and work with amazing people. It can also turn into a short stint on your resume, cause burnout, and create deep feelings of frustration over what could have been.

If you’re thinking about becoming a first PM, realize it’s very different than just about any other product role you can have. Take your time, talk to others who have been 1st PMs, and make sure it’s what you really want.

Have you been a first PM? Please share your story in the comments so others can learn from your experience.


>>> Are you passionate about building great products & live in New York City?

I just moved to NY and am looking to connect with other people that love building great products to share tactics, fresh ideas, and cool products.

Interested? Reach out on Twitter (I’m @Evanish) and let’s get coffee.

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