A Letter to Startup CEOs about Your First Product Hire

Skills and results make you a leader. Titles should confirm leadership but they can never bestow it. - Mark Sanborn

this was originally an email – which inspired the tweet below. it was my feedback to the CEO of a venture-backed seed startup when they asked for my feedback on a product role with a VP-level title but a mid-level PM job description.

posting it here for posterity.

'Product' is the label we've given to the discipline of metabolizing ideas into enterprise value by shepherding the process by which a team's creative energy is packed and shipped as value-creating software.

consider the interplay between roadmap and org, deeply
generally speaking though - i usually encourage founders to think critically about their roadmap and what *really* needs to be done. specifically, working on the product vs working on the product org.

don't try to future-proof your first product hire
by that i mean what percentage of [redacted]'s product function - between now and Series A - should be focused on shipping product vs building a product team.  
common mistake i see is founders attempting to future-proof their first product hire.

be honest: hyper-growth isn't coming as fast you tell your VCs
they hire someone who is more senior than they need now because of a deeply held assumption that hyper-growth is rapidly coming and it's better to have someone who can scale with the company. this is a well-intentioned ideal that rarely plays out in the real world.

hire for the job you need done today, not next year
this is because people who are going to be great 2-3 stages from now, are going to be mediocre at the stage you're currently in - shipping and executing as an individual contributor. which ironically jeopardizes tomorrow's growth by hampering design & engineering's productivity today.

Seed: build the product.

Series A: build the team.

Series B: build the product org.

the ability ship product is not an indicator of leading direct reports
the mistake finds its root in conflating the skills required to ship product vs build and manage a product team or product org. these are two distinct, virtually non-overlapping skill sets that usually occur at totally different stages of a firm's lifecycle.

if unicorn PMs exist, they'd be insulted by your comp package
it is exceedingly rare to find someone with the operating range to do excellent individual contributor work like shipping product and the capacity to lead and guide others to ship product excellently.

PMs build product, directors build teams, VPs build orgs
in my experience - observing ~100 seed stage startups and helming ~20 seed stage (or equivalent) product efforts - is that the needs at seed stage skew overwhelmingly for getting product out the door and generating business results.

don't prematurely scale your product org
yes it's important to think ahead on team composition and org design - i am usually the most vocal person in any org about this -  but not at the expense of getting today's job done today. hiring for a VP-level person out of the gate is the org-design equivalent of premature technical scaling: well-intentioned but usually leads to hell.

scaling headcount slows productivity
specifically - your JD mentions building a large team within a year - this hints at level of aggression that i'd interrogate relative to your strategic objectives, product roadmap and engineering hiring plan to see if you really need more bodies or just better process and standards. blitzscaling headcount usually slows velocity and reduces relative productivity because getting new people up to speed is a knowledge transfer problem, not a talent quality one. most companies - especially early stage ones - don't give much thought to documenting processes and standards in a way that accelerates asynchronous knowledge transfer between experienced employees and fresh new ones. as such it usually takes 9 months for a new employee to know their way around to not be a drag on someone else.

so my recommendation is this:

1/ hire 2 really solid Sr. PMs - split the responsibilities between growth (new user experience) and core product (return user experience).

2/ your 3rd product hire should be a sr. director with the following aims in mind:

  • to be a layer between the CEO and the IC PMs
  • to be a coach and mentor to develop the leadership capabilities of the Sr. PMs
  • to recruit, hire, manage the product team
  • to work down and across to define and implement solid product process, standards, & rituals.
  • groom the early hires for the transition to *jr. management* by having them apprentice under their new boss who should be able to effectively develop their leadership capabilities.

you need to hire the right skills and experience for each stage. The first product hire is not the head of product. the first head of product is the CEO. the only caveat to the this is where the CEO is a strong sales/marketing type and the startup needs someone to fill the gap between sales/marketing and engineering. in that scenario, you are hiring someone who will need to be treated as a shadow founder and compensated as such because they will be creating way more relative value

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