Welcome to this edition of The Wise Founder.

A newsletter for thoughtful technologists.

The mythical first PM - how to find, hire and set them up for success

A first product hire is a mythical creature. Legend has it they possess rare magical powers - a mystic quality, able to strategically see into the future; a gravitational forcefield to pull in engineers, designers and stakeholders for the ride; and a regenerative source of energy enabling them to forego rest.

Few have ever seen one in the wild. Most wouldn’t even know where to look.

But I’ve been one.

So I’m here to demystify their ways and to help you capture one in the wild.

My career has had two distinct chapters - chapter 2 (the current one) involves coaching founders and leadership teams and being a Partner at Evolution. Chapter 1 though, was in product, firstly as a PM in companies like ebay and GoCardless; and then joining a very early stage startup, Pelago Health (or Quit Genius as it was called then) as that mythical first product hire - initially very hands-on in building the product, and then building the team and the processes and becoming an Exec as we raised $150m in vc funding and went through the rapid growth journey that comes with that kind of money.

I share this as a way of saying that I’ve been on both sides of this topic. I’ve been the first product hire whose done the growth journey, and in recent times I’ve supported a number of founder clients in making that first hire. What follows is my synthesis of those learnings.

Do we even need product managers anymore?

This seems to be a question that’s got a lot of airtime of late. As far as I can tell that’s mostly because Brian Chesky went off the deep end, AI improved, and loads of companies do product badly.

My short answer is ‘yes’ - we do still need product people. I personally don’t care what their title is - they might be a designer, an engineer, a founder, or just a plain old product manager - no matter the title, it’s someone’s job to do the hard work of figuring out what to build that users/customers want enough to actually pay for. That person is a product person.

As for the AI part of the debate; I wrote recently about the prospect of the first single-person, billion-dollar company, so there’s no doubt in my mind that AI will enable organisations to deliver bigger impact with smaller teams; but, the skill in figuring out what to build becomes more rather than less important ****in the age of AI.

Not to mention that most companies are not tiny teams building from scratch - they’re big organisations faced with the challenge of reverse-engineering themselves into an AI-native one. Product people will be a critical part of that journey.

What skills do you have in the founding team?

There are really three categories I see here. Each with a slightly different path forward:

1. The experienced product founder - some founding teams include an experienced product person. They have the necessary skills for early stage product work but are also the obvious contender to lead the product function long-term.

2. The make-do product founder - the ‘make-do’ product founder likely has enough product experience, or at least enough adjacent experience, to do the early product work on the road to product-market fit. Some will grow into a long-term product leader whilst others will step back at the earliest opportunity.

3. The non-existent product founder - there is a total absence of any product skills in the founding team.

All of what follows will have some dependency on which of these categories you fall in.

When to make the first hire?

In lots of ways it’s highly nuanced and complex and in others it’s dead simple - if figuring out what to build and the questions that sit beneath that (Who for? In what order? Etc.) is critical at this moment, then you need a product person. If you don’t have a product person i.e. a founder, engineer, designer or whoever else, with the requisite skills AND bandwidth, then you need to hire one.

And the point about bandwidth is an important one. You might expect that teams with an experienced product founder would be the latest to make a product hire; but what’s interesting in the chart below, is that’s often not the case. In fact the two company’s that made the earliest product hires on this list - Coda and Snyk - both have product founders. It seems that some product founders know the importance of doing the product job well, and acknowledge that they don’t have the bandwidth.

By contrast, my old company GoCardless was already 100 or so people and around series B when the first official product person was hired. Prior to that the company prided itself on an extremely product-minded engineering culture - something that definitely served it well over time. But the company seemed to stall and lack direction for some time, which created the impetus to build a great product team. Now I won’t claim that the product team are entirely responsible, but the company did go on to create a bolder and clearer strategic direction and go from a lowly-valued startup to a payments multi-unicorn in the process.

The other part of the ‘when’ debate is whether to hire proactively or reactively. This is one topic where geography has a significant role to play given the different notice periods you can expect in the US vs. Europe for example. When hiring my Product team at Pelago, I was hiring PMs in both the US and UK. In the US I could hire someone who already had a job and have them start 2-3 weeks later. In the UK by contrast, most PMs (at least those at a senior level) would have a 3 month notice period. Add to that any time off they might want to take off to refresh in between, and the ramp up period once in seat, and we’re talking 6 months before they were meaningfully productive. That requires more forward planning.

Great first PMs in any location are hard to find though, so I would err on the side of kicking off too early rather than too late!

What to look for?

Dimensions to define

These are things that you as the hiring manager need to think about before kicking off the process:

• Level of seniority - this will usually be a function of a) make up of the founding team (the lower the product expertise on the founding team, the more senior you might hire); and b) what growth you’re expecting in the team (the more you’re expecting the product team to grow rapidly, the greater the flexibility you might have on current level of seniority). Hire too senior and you may end up with someone who wants to be too hands off - delegating and building a team rather than doing the early graft; too junior and you might see the opposite - they quickly get overwhelmed by the micro-tasks and don’t operate in a sufficiently big picture, strategic way.

• Technical knowledge - mostly this depends on the level of technical complexity of the product and who the target customer/user is. The more technical the product and the customer, the more technical you might index. Generally I’m of the view that there is a minimum bar of technical understanding for all product roles, but it’s not that high - just enough to ask questions of engineering.

• Domain knowledge - do you need an ‘insider’ aka someone who understands all of the detail of the specific domain already; or an ‘outsider’ who might bring fresh perspectives? The dream hire is both but that can be hard to find. As a rule of thumb, the more heavily regulated and complex an industry is, the more beneficial I’ve found domain knowledge to be, provided that someone doesn’t become such an insider that they’re no longer willing to disrupt.

The non-negotiables

The dimensions above will look different for everyone, but there are some attributes I’ve come to see as universally non-negotiable for a first product hire:

• Curiosity - all the best product folk I know are deeply curious. They like to learn, ask questions, tinker; and they do so with the low ego required to change your mind in the face of compelling evidence.

• Thriving in uncertainty - being the first PM is HARD. Everything’s uncertain all of the time. In order to stay sane you need someone who has a particular relationship with uncertainty.

• Values - firstly, no assholes. That applies for all hires but a first PM has a large influence so important to index heavily here. Secondly, you ideally want a missionary not a mercenary - someone who connects deeply with what it is you’re trying to do in a way that will energise them, even in the tough times.

• Problem solving horsepower - there’s really no substitute for this.

How to assess?

It starts with a good job spec

Here’s an example that I worked on with my client, Minimum, an environmental data startup. It was described by a couple of the applicants in the process as the best job spec they’d ever read. But I won’t pat myself on the back too much - most job specs are awful and all this one does is lay out the story clearly.

HELPFUL TIP - one thing I’ve started doing recently (since the example linked above was created) is using ChatGPT to help check for gender or other bias. Just copy and paste the job description into ChatGPT, explain that you want to attract a diverse range of applicants and ask for suggestions on better use of language.

Finding great candidates

Sadly there’s no one big party where all the great people are hanging out together. Here are a few tactics I’ve found helpful:

• Network - nothing new to say here. Good people know good people.

• Recruiters - I’ll admit that I used to tar all ‘recruiters’ with the same brush - some sort of annoying middle-person who feels like they’re getting in the way. But once I met genuinely great recruiters who knew their stuff, my perspective changed drastically. In the UK, I’ve had great experiences working with Nick and his team at Few & Far; and Tom Knights and his team at Scene.

• Targeting strong product companies - it’s always hard to determine from the outside which companies do product well. Partly it’s judged on the end product e.g. you always knew Monzo were doing something right based on the experience you had as a customer; and often it’s quite vibe-based, with places building up a reputation based on their public presence - speakers at conferences, articles online, number of alumni who go on to do impressive stuff etc. Having a hit list of target companies whose product people you reach out to can be fruitful but keep in mind the need to hire someone whose a good fit for the stage (see common pitfalls below)

What should the interview process look like?

There are different schools of thought on process from the highly structured to the more casual. Chances are that when you’re hiring a first PM the company will still be quite small/early, so some highly corporate feeling process just won’t feel right for either party, but at the same time some structure is essential to make sure you assess what matters, mitigate some biases, and ultimately make a better decision.

Principles

• Mix of modalities - you want to get as wide a view as possible of how they think, respond to different situations etc.

• Mix of people - you need the team to be bought into whoever you’re bringing in and you need them to be bought into the team they’re going to work with. Plus more perspectives will likely drive a better decision.

• Clarity in what you’re assessing for - it’s easy for a first PM hire to end up being very vibe-based. Good vibes are important. But more important is being really clear on what you’re assessing in the process. This helps remove bias, keeps the process focused on what’s important, and ultimately leads to better outcomes. I’ve tended to use a variant of the A method. I wouldn’t follow it to the letter for a first PM but I do thinking having a clear scorecard upfront is beneficial.

• No excuses for sloppy communication - unfortunately I just know so many people, particularly in recent times, who’ve had terrible experiences - chaotic communication, being ghosted after investing time in extensive interview tasks etc. The tech world is much smaller than you think and whether or not you believe someone is the right candidate, how you treat them in the process is important.

• Make space to get to know one another - a first PM hire is a big commitment for both sides. It’s a bit like dating so alongside the more structured process, make time to get to know one another in other settings too.

• It’s your job to sell them on you and the company - interviews are a two way street and if you find someone great then chances are they have options on the table. Keep in mind that throughout the process you need to be selling them on you as Founder(s) and the prospects of the company. FUN FACT - I actually pulled myself out of the interviewing process on two separate occasions with Pelago Health, due to external factors, and both times Sarim (one of the Founders) basically wouldn’t take no for an answer and convinced me to come back. Eventually I took his persistence as a good sign.

Process

• Experience interviews - interviews that delve into the specifics of what they’ve done in the past. I like using the example of the most complex product problem they’ve ever worked on as it roots the conversation in something interesting and immediately gives a gauge of what problems they’ve worked on in their career (sidebar - there are a lot of product people who’ve spent their career optimising button colours or redesigning ecommerce checkouts - these are not the people you need for this job). I’ll spend an hour with them to run through it end-to-end, starting with the origin story - why this thing? Why then? - right the way through to some sort of conclusion - what impact did it have? What happened next? Why?

• Product thinking tasks - it’s a topic of hot debate whether or not a task should be ‘take home’ i.e. prepped beforehand or in-the-moment i.e. minimal prep; and whether it should be based on the specific domain/product or something different. Having experimented over the years, I think there’s a happy middle ground - something that requires hours rather than days of prep upfront (that can’t be easily done by AI), and that allows plenty of space to see how they think on their feet too. As for the domain - the argument against it being based on your company or domain is that some candidates feel they’re effectively doing your work for free. I sympathise with this viewpoint but when it comes to a first PM hire, I do think the pros of something grounded in the relevant industry outweigh the cons. So here’s my suggestion - pull together some relevant data and insights, pose a question that’s real e.g. ‘we’re thinking about expanding the product to go after this new customer type - should we?’, set clear expectations on the prep you’re after (I might ask for max two pages of pre-written thoughts - no presentations or time wasted on the aesthetics), have a list of questions and potential scenarios ready for the conversation.

• Cross-functional interview - mostly I find this to be a good hygiene factor in the process to ensure they play nicely with others. At the very least I’d include someone from Engineering and Design in this step. Use the scorecard to set clear expectations for the interviewers on what you’re asking them to assess for. Depending on how experience they are you may need to do some interview coaching to guide them on what sorts of questions to ask.

• Bar-raiser - this is typically done at the end of the process. By this point you know this person is good else they wouldn’t have got this far, but it’s worth revisiting the question of ‘are they going to be great for us?’ late in the process. It can often be helpful to bring someone senior in whose not yet been deeply involved in the process at this point e.g. another founder.

Setting things up for success

A good first PM isn’t going to need too much handholding but setting things up for success is critical nonetheless. Here are a few things I’ve seen work well:

• Co-create a 30:60:90 day plan (or whatever timeframes seem appropriate) - this is a great exercise as a forcing function for conversation. A first PM is going to be thrust into 100 things almost immediately but having some high level guidance around what you both see as being of greatest importance over which timeframe is a great start.

• Have early discussions about areas of responsibility - the truth in a small startup team is that everyone’s kind of responsible for everything. Nevertheless, are you as a founder expecting this person to ultimately take primary responsibility of the product strategy or will that rest with you? What about software delivery - if something seems to be going off the tracks are you turning towards the PM first or your Engineering leader? Let’s be explicitly clear - just because one person is responsible for something, it doesn’t mean that it’s nobody else’s problem - but in drawing clearer lines of responsibility, much less tends to fall through the cracks.

• Make sure the team are clear on what the PM is there to do - given the common confusion over what a PM actually does, it’s likely that some members of the engineering team for example, might have very different expectations of this first PM. Being transparent around what this first PM is there to do and importantly what they’re not is important, particularly for less experienced teams.

Common pitfalls

There are lots of ways in which things can go wrong for a first PM. So much so that Jason Evanish wrote this great article about the benefits of being a ‘second first PM’ i.e. the one who comes in after the first first PM has been ‘a sacrificial lamb so that the company can figure out what they really need in product leadership.’

Here are some of the most common pitfalls I’ve seen:

The false promise of ‘owning’ strategy

Strategy is a huge part of the Founder’s job. One of the cardinal sins I see in job ads for early product folk is ‘you will define and own product strategy…’ I always ask myself, ‘is that really true?’ In a way I’d question any founder whose so willing to hand over the reins of something so critically important. Will this person be heavily involved in strategy - absolutely. But ‘defining’ or ‘owning’ is mostly untrue yet it seems to be the thing that some founders think they need to write on a job ad. End result = frustration and confusion for all parties.

Not being able to get to the heart of performance

Unlike a salesperson for example, whose almost always judged by a single number (sales is brutal), the challenge of figuring out what a first PM is truly responsible for and whether or not they’re doing a good job is messier. Yes there are important metrics for the product and over time they should be moving in the right direction, but a first PMs job is rarely so clean cut as to be judged on that alone.

Part of the challenge is that first PMs are destined to upset some people. I don’t mean by being a jerk, but by diplomatically saying no to things that they don’t judge to be a priority. One of the hardest parts of product is that other parts of the business tend to depend on you in a way that you don’t really depend on them. So the Ops team are looking at you to build that new dashboard that solves all of their problems; and the Sales team want that new product they just promised to a customer built yesterday; and the Partnerships team want you to integrate with the 17 archaic APIs of some enterprise behemoth. And guess what - it’s not all going to happen. At least not when they want it to. So you try to let them down gently.

Mostly this can be managed but sometimes leaders in other parts of the business start to poison the well, pointing fingers at the product and engineering teams in a manner that can go beyond reasonable questioning and justified critique.

At this point founders need to have an ever stronger sense of how they’re judging performance. Is this something to be concerned about or just a normal level of discontent under the circumstances?

I’ve often seen inexperienced founders (in my view) overindex too much on ‘are stakeholders happy?’ and not enough on ‘is this person doing a good job?’

Too much of a product purist

I believe that first PMs need to be deeply pragmatic. They need to bring some rigour and discipline and great product thinking to the table, but without being a purist who gets too lost in the way things ‘should’ be done.

Purists are likely to frustrate founders - to go beyond healthy challenge into the territory of obstinance, and that is destined to fail.

Hiring the big company PM

As mentioned earlier, I’ve been the first PM but I’ve also been a big company PM at ebay. These roles called for different skills and attitudes and thankfully I had a step in between at GoCardless to bridge the gap.

It can be very tempting for a startup to go out and hire the person with the most big brands on their CV - I’ve had multiple founders tell me that their investors have pushed them in that direction because it looks good in the pitch deck for the next funding round - but first PMs who have exclusively big company experience rarely adapt well to the role of a first PM.

So there you have it. My take on finding, hiring and setting a first PM for success. If you have any followup questions then send them to me by responding to this email.