James Winter

James WinterShare

VP of Marketing, Spekit
James Winter
James Winter
VP of Marketing, SpekitMarch 7

Some random thoughts in no particular order:

  •  The importance of prioritization and how to say no: you will be under constant barrage for requests from all angles: the ceo, sales, CMO etc... These requests will range from the silly to the idiotic and you will never be effective if you don't have the ability to figure out how to TACTFULLY push back on requests and make clear prioritizations
  • Spending more time with customers: However much time you're spending with customers, it's not enough. 
  • How to inspire: Often times in product marketing you will be the first and only person to realize some sort of important thing: this product is really not that exciting and we shouldn't spend a long time launching it, our positioning isn't really resonating with our customers etc... It's not enough to point these things out and be right, you have to be able to bring people along with you and get them as fired up as you are. 
  • Segmentation: Segmentation is hard, requires a lot of research and collaboration, and can be divisive to some people. It's also one of the most important things you can possibly do at the beginning of any role in product marketing. Learn how to meaningfully segment your customers and develop a framework that will align the company in how to talk to them, target them, and inspire action. 
  • Targeted positioning: I learned this one very early on as a devout student of Crossing the Chasm but it's still the thing that 9/10 startups struggle with the most. You are not everything to everyone, just because anyone can buy your product it doesn't mean they should all be treated equally. Take a stand. Create targeted messaging, don't let your fear of alienating a few people that will never buy your product dilute the impact to your best segment. 

James Winter
James Winter
VP of Marketing, SpekitFebruary 21

Talk to people! Talk to your customers. Do win/loss calls. Understand their pain points. Understand their eco-systems, how they acquire customers, what challenges their industry is facing. What keeps the executives up at night. 

If you don't have access to the people you need, find them on linkedin and bribe them with amazon gift cards. If you have the budget use something like Alphasights or GLG to get you on calls to talk to people that know the industry extremely well. Or, use something like Respondent.io to source them yourself. 

James Winter
James Winter
VP of Marketing, SpekitFebruary 12

I've used both Showpad and Docsend in the past. 

Showpad has some additional capabilities that Docsend doesn't have but Docsend could not be easier to get the sales team and SDR team to actually use.

I also put all of our gated content on Docsend which allowed me to sync visit times and view rates to Salesforce as activities e.g. John Smith and Acme Corp spent 3:51 reading Ebook X 

James Winter
James Winter
VP of Marketing, SpekitDecember 12

Adding on to all of the great advice above:

  • Build your network: meet as many marketing leaders as you can so that when they're ready to hire someone externally you are on their list. Also get to know some good recruiters. 
  • Be flexible and ready to leave your current company: your chances of being promoted at your current company are miniscule compared to the jobs available elsewhere 

If you wait to get promoted at your current role, you're limiting your chances immensely. The math is pretty simple: if you wait at your current role, they either need to be creating the role for the first time (unlikely) or someone needs to leave (also unlikely). When you stop limiting yourself to your current company the number of director level positions becomes MUCH higher. 

James Winter
James Winter
VP of Marketing, SpekitAugust 23

One thing I'd add that's very tactical to the great stuff that David has already laid out: Find your allies. 

Talk to everyone within the org that you can and assemble a shortlist of people who have good understandings of things like the customers, the tech etc...

Befriend a good sales rep, the best sales reps in complex sales cycles are often product marketers in disguise. If they've been there for a bit they have a ton of knowledge that has never ever been documented or made sense of and they can accelerate your understanding immensely. 

James Winter
James Winter
VP of Marketing, SpekitJune 28

Build out a matrix in a spreadsheet or PDF. In my company we've done that by having use cases as the rows and verticals as the columns. So if you're looking for a case study where the main use case was driving sales in the fashion space, you just go to the intersection of those two. 

I think you more or less are on the right track already. 

It's not super pretty but it gets the job done. Obviously we're still building this out and it'll never be fully complete. 


James Winter
James Winter
VP of Marketing, SpekitJanuary 17

Hopefully I don't make this answer overly complex. 

I think the more important question here is what are you actively working on? Because product marketing can cover such a wide variety of activities and tactics, we can't exactly tell you which metrics would be important. 

Greg Hollander and Derek Pando both had great insights to share when they spoke on a panel about the topic of prioritization in product marketing. The key takeaway there is to know what the greater organizational goals are, and align yourself where it makes the most sense for the impact you can have. 


Your company has great awareness and lots of leads, but isn't closing enough deals. In this case, there are lots of different factors that could be contributing to the funnel leak (people entering but falling out). As a product marketer it may fall to you to understand why this is happening and address the problem. 

For the sake of simplicity, let's say that you have great demo show rates but don't convert these into customers at the rate that you think you should be. Assuming that the prospect knows your pricing and terms ahead of time, this likely points to your demos being bad. Bad could mean a lot of things so it will require further analysis.

Are your sales people doing enough discovery? Are they talking about things that actually matter to the prospect or are they just reciting from a script?

In this fantasy scenario, with the information that you've been given, it's probably fair to assume that a good metric for you to track would be increase in conversion rate. 

James Winter
James Winter
VP of Marketing, SpekitJanuary 14

In my experience, it's rare that a single persona would be particularly valuable. For example, in my current role, there are at least 3-4 main personas who all have very different motivations, roles, etc... 

One of the most basic examples of why you'll probably need at least two personas, at least if you're selling a B2B product, is that it's very rare that you are every selling to just one person. In most B2B scenarios, there are at least two people involved in the purchasing decision process. As you go up market and begin selling to enterprise, this number can skyrocket to 7-8 people. 

For example with my product, there are almost always at least two people involved: the economic buyer, and the user. It's rare that someone purchases our product (annual contract, >$20k ACV) without the input of their boss. 

It's important for our sales reps and the rest of the organization to understand that even if there is only one point of contact at the company, that social media manager (our main persona) is often submitting everything to their boss for their review. 

As you go up-market, there is at least two steps to making the sale: 1) selling to your user, and 2) selling to the rest of the people they need to convince. 

James Winter
James Winter
VP of Marketing, SpekitNovember 30
James Winter
James Winter
VP of Marketing, SpekitOctober 27

More tactically, here's a sample template originally from Salesforce that I use for training sales on demos. 



Credentials & Highlights
VP of Marketing at Spekit
Product Marketing AMA Contributor
Lives In Denver, Colorado
Knows About Technical Product Marketing, Product Marketing Career Path, Sales Enablement, Messagi...more