First, I’d go for a SaaS expert over a domain/target market expert in just about any senior hire — VP Product, VP Sales, VP Marketing.

The general reason is this: we overvalue domain expertise. Everyone else in the company already understands the market. The new guys should have plenty of wingmen until she or he picks that part up. If I’d looked for great e-signature experts in ’06 and ’07, we’d have gone bankrupt before I’d found any. Didn’t much matter.

The reason I strongly recommend SaaS experience (from a successful but probably not BigCo experience) is the sheer volume of features and workflows and customer demands over B2C or freemium products, and other domains. Folks outside of SaaS and enterprise can struggle to manage dozens of enterprise-grade integrations (with deep workflow integrations in each), juggle 1000s of customer-centric feature requests, and balance that all out with the Future Vision …

As much as we’d all like to believe it’s enough to Just Build A Great Product, in SaaS, that’s necessary — but not sufficient.

Second, I’m skeptical most product folks from B2C, from Gaming, from low-end freemium can make the jump to more enterprise-y SaaS B2B. It’s too many endless, somewhat boring, new features, new functions, new enhancements, new use cases, new corner cases you need to provide for. E.g., Salesforce is just very, very different from Gmail.

I wish they could make the jump, the B2C folks, because they make prettier, easier-to-use products.  But they just fizzle out when it comes to managing the endless myriad of workflows in more complex and more enterprise B2B software.

SaaS apps get endlessly complex under the hood over time, as features compound upon features — even if the best ones maintain a very elegant, easy-to-get going user interface.

Third, whatever you do, don’t hire someone too junior as your first VP / Head of Product.  You have to hire someone that has truly put features into production.  Junior product managers usually haven’t.  They don’t know how to do it, and don’t command the respect of the dev team because of it.  Hire someone that has ideally managed a project or two themselves into production.  And push and make sure they have,  Not just a small part of large project.  Which is often all you learn at Big Tech Cos and even at Bigger, Later Stage Startups.

So many founders will tell you the same story.  They hired their first product leader from a Top Late Stage Startup or Top Public SaaS company, and they just sort of sat by themselves all day writing specs.  That engineering mostly ignored. And without really talking to any customers.

And as a bonus, it really helps if your VP of Product has managed at least a very small dev team themselves, at least once in their career.  At least an outsourced team, or something, at a minimum.  First, this almost assures they’ve truly put products into product, per the prior point.  Second, it means they’re likely senior enough to do the role.  And third, it dramatically increases the odds your engineering team will respect them.  Many engineering teams just plain don’t respect product managers and leaders that don’t have an engineering background or at least something close to it.

(product image from here)

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