As a Product Marketer, what typical tasks, projects, or commitments do you find the most challenging in your job? How have you excelled in those challenges/solved those problems?

There are two things I found challenging for the PMM role. 

1. Prioritize all the things we can work on and make sure we are having the biggest impact on the business. Our role at Square is very broad. At any time, we can be pulled in from working on the next 18-month product strategy together with the PM, to fix the pricing of the product, to develop a set of growth experiments, to put together sales collaterals. Our stakeholders (execs, PMs, channel marketing, sales) will have a ton of requests to us. If we don't prioritize, we can easily drown in all the tactical work. As a PMM, we need to have a really really good understanding of the value drivers of our business and work on initiatives that are going to move the needle. For example, in the first 6 months of a new SaaS product launch, my product team got really concerned about meeting subscriber and revenue goals and kept asking about increasing marketing budget. BUT, we had huge churn problem after the initial GA. So I stuck with "don't worry about $; let's close feature gaps and fix churn first". At any time, we need to have a good sense of what is the pecking order of metrics we need to move to grow the business (acquisition? paid conversion? churn? increase in ARPU?) and what are the underlying drivers to move these metrics (product features? pricing? messaging? dollars?) That is the North Star for me on a quarterly, monthly, weekly basis to decide what me and my team are going to work on. 
2. Inspire the creative team and make sure we develop kick-ass marketing communication. Whether we work with in-house creative or outside agency, at the end of the day, the creative is what gets in front of the end consumer/ customer. How do we evaluate creative? How do we ensure it's on strategy without being prescriptive to the creative team? A lot has been written by the general marketing community about good vs. bad clients but it is still an ongoing learning curve for me. In the PMM/ creative relationship, initially I was deferring more to the creative team since they've been here longer and arguably knows our business and customers better than I did. Overtime I've figured out that as a PMM, my job is to represent the customer and the business. My job is to help the creative team understand who are the customers of my product(s), and what benefits my product(s) bring to them. It is exactly the positioning and messaging piece that Marcus mentioned above. So I won't provide stupid feedback like whether the logo should be bigger or smaller, but I have every reason to comment on whether the creative delivers on the positioning and messaging I want for my product and why. Additionally, getting the creative team excited about your product! Help them understand the business opportunity. Bring the product to life during the creative briefing/ kickoff - product demos are always helpful in those situations! (BTW, if you cannot do a product demo as well as the PM, in my opinion you are not a good PMM). I'm learning but honestly think getting better at creative brief and feedback is something I need to continue working on.

Chiming in here 

1. Messaging and positioning - can be difficult, again its very industry and segment dependant as well as what type of product/technology. Being on enterprise infrastructure and software in my career, in the current scenario, where you have to influence and convince multiple "personas' who have a say on a big deal, will require some creative process. Breaking it down to personas, understanding their journey, priorities, and what values they would appreciate, how deep to go into the technology, what is competition saying etc. Getting alignment across the company, so you can make everyone learn to sing the same song, thats a tough one. If you have the right leader in place who enables you, then half your job is done. Once you have that nicely put together messaging brief , a 1-2 pager, then creative, content - everything becomes simple execution after that. 

2. Managing long term versus short term, how to keep everyone to think big, where we need to be next 12-18 months, and what needs to happen immediately on a weekly basis. Thats a fine art. I often use my engineering design background infact, to "marketing campaign design"....It helps me to break it down to smaller focused efforts. Just how my head works, others may have found solutions that work for them. 

I think it takes experience and a well developed muscle to be great at product positioning. Writing simple, easy to digest copy that communicates the value and function of a complex product is not easy. Take a look at most startups websites and you'll see what I mean. It's easy to fall back on jargon and buzz words and write something that doesn't help you standout. To me building great, simple to understand, and highly benefit oriented creative that makes your product unique is the challenge for most PMMs. I think really understanding your customer, space, and product is the best way to get good at positioning. To get great you need lots of practice and to constantly be trying new things, getting good critical feedback, and reading as much as you can about your space so you can tap into the right narratives.