Welcome to SaaS PM 101

Tips and Q&A about Product Management in B2B tech startups

This is a blog about doing product management in a small B2B SaaS startup.

Most PMs work at large companies. As a result, both supply and demand for SaaS PM-related content skews towards advice that may not work as well in smaller companies. It’s also easy to find “founder stories” about how they landed their first customers and achieved product/market fit. But there’s a dearth of info for PMs about how to navigate the time in between: the Series A-to-C period when a startup has 20-400 employees, $0.5M-$50M ARR, and 1-10 Product people.

But there’s a lot for PMs to do during that time! For example:

  • Crossing the chasm from early adopters to mainstream customers

  • Growing a single product into a portfolio of products for different segments

  • Improving prioritization and roadmapping, and building a “just right” process for both that enables predictability without slowing everyone down

  • Keeping the company in sync, despite massive headcount growth and brand-new teams like Customer Success, Support, and Finance coming on board

  • Fighting serious competition, often for the first time in the company’s history

  • Supporting the transition from “founder sales” to repeatable Sales & Marketing

  • Efficiently collaborating with many newly-hired engineers who won’t have the business context nor interpersonal history of the OG engineers

I’ve spent the last 10 years figuring out solutions to these “Series A-C” PM problems, and I’d like to share some practices that have worked well, as well as some fails.

Why Am I Writing?

“When you read, try to understand the writer’s goals. No one ‘just writes’.
Everyone has an angle.”

— my 10th grade English teacher

Here’s my angle: I’m starting to look for a new job leading the Product function for a “Series A-ish” B2B SaaS startup, either as the first Product hire or inheriting a team from a founder who’s been leading Product as a side gig. I’ve done exactly this before at Cantaloupe and loved it, and now I’d like to do it again!

But Head of Product is a scary hire for a small company, because most startup founders and early employees have never worked with a PM who’s good at “SmallCo” product management. There’s a few reasons for this:

  • Many founders and early employees started their careers in big companies, so they’ve only seen BigCo PMs in action.

  • PMs don’t exist in university CS programs.

  • Some startup denizens have only worked at tiny companies (<10 employees), which usually don’t have nor need full-time PMs.

  • Many PMs are not very good, perhaps for the same reasons that product management tends to vary a lot between companies.

As a result, many startup founders and employees have a fuzzy idea of what what successful SmallCo product management looks like. This blog is an attempt to clear up this fuzziness with examples, tips, and tricks from my and others’ experience of doing Product in small B2B companies.

In addition to de-risking the Head of Product hire (which might be me!), writing a blog is a good forcing function to clarify my own thinking about PM.

I’m also hoping to get feedback from other PMs and PM-curious folks, and to learn from readers’ experience while you’re learning from mine. So I’ll leave comments open for further discussion. Just stay polite, OK?

BTW, I’ve been answering PM questions for many years over at Quora. I’ll use some of my answers from there to jumpstart this blog. Later posts will be new, though.

About me

I’ve been doing Product for a while. Here’s some details:

  • VP Product @ Cantaloupe Systems, the largest SaaS provider for the vending industry. I led PM from from $2M->$16M ARR, and from a single early-adopter product to a portfolio of products for mainstream customers. After a $85M, 4x-to-investors acquisition in 2017, I led PM for the acquirer (recently renamed Cantaloupe, Inc.) for a year before leaving to work on my own startup ideas and side projects which I may discuss in later posts. (Spoiler: COVID killed my startup!)

  • Senior PM @ Splunk. I was PM #4 and was responsible for Splunkbase (Splunk’s app marketplace) and product-to-web integration in general. I also led the cross-functional team that built Splunk's Application Management solution V1.0, which focused on analytics, operational reporting, and troubleshooting for Java Application Servers.

  • Principal PM @ Microsoft (MSDN & TechNet) - I was PM of msdn.com and technet.com, which at the time were the Web's largest community sites for developers and IT-Pros. I was responsible for terabyte-scale analytics, integrating MSDN with Visual Studio, and trying to fix navigation and site search across millions of pages.

  • Group PM @ Microsoft (Server Management Products) - I co-founded the team that built Microsoft's first Application Management product, leading a team that grew to 20 PMs responsible for Microsoft's server-operations-management products including Operations Manager (now called SCOM).

  • Various Developer Roles. Before moving to PM, I worked as a software developer at various startups during high school, college, and for a few years after. Here’s some highlights:

    • I was employee #7 at Stockpoint, a financial information startup. I led the web development team, managed site operations, and scaled out Stockpoint's SaaS offering.

    • A part-time college job turned into me being employee #3 at the company that became ask.com.