I’ve written a lot about the huge organizational and technical gulf between services companies and product companies. (See this and this and this and this.) …

Lately, I’ve been writing a lot about entirely predictable goal misalignments between the maker side (product, engineering, design) and the go-to-market side (sales, marketing, customer success) of tech firms, especially at B2B/enterprise software companies. That includes short-versus-long-term tradeoffs and single-account versus cumulative impact focus. …

Many of my discussions with product leaders (CPOs, VPs and others who manage teams of product folks) are about the substance of product management: portfolios, competing stakeholders, pricing & packaging, tarot cards as a revenue forecasting model. Last week, though, in my product leadership workshop, we had an extended discussion…

I’ve had a lot of discussion over the last few months with product leaders looking for their next opportunity. Some of this is normal exec-level churn (the half-life of a CPO role is about 20 months) and some from the recent wave of tech layoffs. …

In my experience, there’s usually a fundamental misalignment between two broad groups at software companies — especially B2B/enterprise companies — that I’ve been thinking/writing for a while. One group (sales, implementation/customer success, professional services, account-based marketing) is trained and paid and rewarded to focus on one customer at a time…

I’ve sat through planning for scores of major B2B migrations, and implemented a half-dozen of my own. Usually the discussion is highly technical: APIs, data transformation, feature ladders. But most of the migration failures I see are driven by organizations’ unwillingness or inability to stick with the very hard choices…

Building on a post from last July about Incompatible Worldviews… Almost every Go-to-Market-side enterprise stakeholder I interview tells me that their product team is unresponsive: that folks rarely get anything back after submitting an (urgent, strategic, well-considered) ticket through the company’s agreed-upon enhancement request process. …

Stepping out of leadership challenges for a moment, here’s a practical topic that some product managers struggle with: is the next thing we’re working on a feature or a whole product? IMO, there aren’t any universal/magical answers, but assorted hints and indicators. BTW for this post: a is something that…

Almost every week, I have a conversation with executives at B2B software companies who don’t see a bright-line distinction between software license revenue and customization/implementation revenue. Or why this distinction is essential to their investors. But when I do product due diligence for SaaS-focused PE/VC firms, it’s the very first…