I’ve Got a Crazy Idea: How About We Focus on Next-Quarter’s Pipeline?
I’m frankly shocked by how many startups treat pipeline as a monolith. Sample CMO: “we’re in great shape because we have a total pipeline of $32M covering a forward-four-quarter (F4Q) sales target of $10M, so 3.2x coverage. Next slide, please.” Regardless of your view on the appropriate magic pipeline coverage number (e.g., 2x, 3x, 4x), […]
Pictures at an Oracle Exhibition: OpenWorld 2019
Oracle OpenWorld 2019 was a culmination of the earliest stages of a breathtaking transformation at Oracle and the beginning of a new phase in their growth and relationships with customers, prospects, other companies and the world at large. Is this a good thing?
What really is Product Marketing?
On the heels of this post about What Really is Go-To-Market?, I have had a ton of discussions about the constant tussle between product management and product marketing, especially at later stage growth businesses or divisional teams at large companies. Between Kahuna (startup) and at SuccessFactors/SAP as GM (ginormous largeco) I’ve seen this play out […]
What The Downturn Will Probably Look Like in SaaS
So, despite SaaS multiple and the public markets being at near record highs, we’ve seen things start to … wobble a bit overall in tech: The WeWork IPO simply failed, and the Peloton and Direct Smile IPOs were broken. No one really expected this. Having a high profile IPO like this fail is a bit […]
If Rebranding’s the Answer, What was the Question?
From time to time, every CMO faces a key question: to brand or not to rebrand? Often, it’s right after joining a company and you want to make a big splash. Sometimes, it’s after you’ve been with a company for a while and you and some told-timers are bored with the current branding and want […]
Things to Avoid in Selecting an Executive-Level Job at a Software Startup
This is a sister post to my recent one, Career Decisions: What to Look For in a Software Startup. That piece is all about what to look for when considering taking a job at a software startup. This piece is kind of the opposite: what to look out for when considering an executive job at a […]
Good CEO Habits: Proactively Update Your Board at the End of Every Quarter
I am surprised by how many startup CEOs leave the board hanging at the end of the quarter. As a CEO my rule of thumb was that if a board member ever asked me about the quarter then I’d failed in being sufficiently proactive in communications. In tight quarters I’d send a revised forecast about […]
Epictetus and APIs
First page of Discourses by Epictetus Don’t set your heart on so many things,” says Epictetus. Prioritize. Train your mind to ask: Do I need this thing? What will happen if I do not get it? What if it all happens all at once? I return often to this quote, to the point of boring […]
New ARR and CAC in Price-Ramped vs. Auto-Expanding Deals
In this post we’re going to look at the management accounting side of multi-year SaaS deals that grow in value over time. I’ve been asked about this a few times lately, less because people value my accounting knowledge [1] but rather because people are curious about the CAC impact of such deals and how to […]
Avoiding the Ten-Year Stock Option Trap (and Other Stock-Option Considerations)
I’ve increasingly spoken to startup employees who find themselves in a difficult trap. Let’s demonstrate it via an example: Say you joined a startup in September 2009 as an early employee and immediately received a stock-option grant of 400,000 shares with a strike price of $0.10 when you joined. The company, while having experienced some […]
