A Bootstrapped CEO’s Guide to Product Management

Kate Hopkins By: Kate Hopkins

Bootstrapped founders often build businesses to solve a pain point they’ve experienced themselves. But, as the company scales, it becomes necessary to add additional resources to understand and serve a broader set of target customers.  At Mainsail, we find that building a strong product management team can be hugely valuable for SaaS businesses as they grow.

Why invest in product management?

Product managers make scarce development resources go further. When you don’t have the bandwidth to build everything you’d like to, you need to prioritize. Product management’s job is prioritization.  Great product people make sure their companies spend the most time on the most valuable things by mapping out pockets of market opportunity, deeply understanding customer needs, and using time-efficient prototyping to test out ideas before committing to them.

Tactically, what should a product manager do?

Great product managers aren’t just project managers, they’re an invaluable link to the customer and the market. We believe success means doing the following four things well:

Market strategy – product should understand the market and competitive landscape to be aware of where there’s opportunity. On top of that, product should overlay who the target customer is (and equally important, which customers fall outside the area of focus).

Customer discovery – product should be in constant contact with customers, sometimes this means passively absorbing customer context by joining sales or customer success calls, and sometimes this means much more actively researching customer needs with planned interviews and prototype tests.

Product planning – prioritizing the roadmap is a key product responsibility. Especially when thinking a quarter or more into the future, product should be planning development thematically, identifying which customer types and needs will be prioritized (vs. spelling out which specific features will be built).

Product analytics – product usage data is critical for knowing whether development efforts are working, before lagging metrics like revenue manifest.  Product teams should track how customers are using the product to inform what should be prioritized.

How many product people do you need?

Product org rules of thumb:

1 PM for every ~3-7 engineers
1 UI/UX designer for every 1-2 product mangers
1 Director or VP of product once you reach 10-13 engineers

In companies with mature product organizations, we often see engineers divided into product teams, each responsible for one customer type or module of the product.  Each product team is made up of around 5 engineers, plus a product manager.  Sometimes product teams also have a dedicated UI/UX designer or scrum master, and sometimes those resources are shared between a couple of teams.

What should you look for when hiring a product manager?

When hiring for product, look for people with excellent ability to process and synthesize information from multiple sources.  Because the role is highly cross-functional and collaborative, product managers should also be strong communicators.  There’s no one perfect background for a product manager, but they shouldn’t be afraid of technical concepts and they should be interested in design thinking and coming up with new solutions.

Be careful with candidates who identify as project managers or business analysts (BAs).  Sometimes it’s just a matter of nomenclature, but sometimes those titles signal that the candidate has more experience with older software development processes.  Before SaaS business models were common, software was built in a much more rigidly sequential (waterfall) way, and a BA was responsible for gathering customer requirements, documenting them, and passing them to engineering.  Cloud software offers a huge advantage in allowing a company to iteratively improve its product, and modern product managers should engage in continuous loops of discovery and planning.

Don’t wait too long to invest in building out your product management team. We believe getting this right can be a major contributing factor to sustained growth, higher win/loss ratios, and happier customers.


Kate Hopkins
Kate is Vice President at Mainsail Partners, working with portfolio companies to accelerate growth. Her focus is in product and market strategy.
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