What size company have you found product marketing to be the hardest at? Where has it been most satisfying?

Great question! I've been lucky to work at a wide range of companies and while each was satisfying and challenging in their own way, I've definitely figured out what works best for me.

For me, working for a big company brings resources and clear growth paths, and I’m grateful to have started my career there.

• The pros: At a big company, you know exactly where you fall in terms of job leveling, and what you need to take the next step up. Your work is clear and tied to a very specific line of business and you feel confident in the company’s success.
• The cons: For me, the thing that was challenging about working at a big company was how “figured out” things were. I found lots of processes and frameworks were already built at a big company and it was up to me to execute on a clear set of activities, which was great as I was starting to learn, but started to feel restrictive after a while. 
• How I felt as a PMM: As a product marketer, the relationship between product, product marketing, and partner teams was tightly scoped and while those swimlanes were helpful bumpers at first, they felt a little restrictive as my skills grew.

After that experience, I made a 180-degree shift and was the 52nd employee at a very small company.

• The pros: When a company is that small, every day is a test of how productive you can be, how many good decisions you can make, and how much hustle you’ve got, which gave me a lot of energy at that point in my career. It was great to be able to directly see the impact my work had on the business, and the entire company felt like one team working together, which was incredible.  
• The cons: Even with all the positives, I’d say this size was hardest for me. As a product marketer, I wasn’t spending much time doing the type of product marketing I loved, like getting to know customers, helping drive the roadmap, crafting messaging, or launching products. Because we were such a small team, I wore a lot of different marketing hats and was spending a lot of my time working on lead gen efforts for the sales team - which is definitely not my area of expertise. In this type of company, you’re asked to do whatever the business needs and you don’t always have guidance on how to do it well. 
• How I felt as a PMM: After that experience, I realized that even if I didn’t want a role that was too structured, I did need some structure to succeed. I also realized how important it was to have a close relationship with a manager who I could bounce ideas off of, turn to when I needed feedback or guidance, and who helped make sure I was learning and growing, not just spinning my wheels.

Since then, I’ve taken a bit of a Goldilocks approach to choosing companies - not too big, not too small, just right. I’ve found that a Series B company of about 100-200 employees fits my personality and work style best.

• The pros: There are plenty of things to build and decisions to be made, but the company has gotten validation in the product and financial backing that gives employees space to breathe and think long term. I love that I don’t have to go through too many “checkpoints” to get a project off the ground, send out a survey, or put together a plan. At the same time, I love that there is enough process that we’re able to make sure we’re making the right decisions and doing work that matters. 
• The cons: It's still a small, early-stage company, which means that there are areas of the business that aren’t figured out. Your career growth is not well defined because the company is continually changing, as is what’s being asked of you, and the company usually hasn’t solidified its levels, titles, or career growth guides so it can be hard to feel like you can really show the progress you’re making because it’s not a clearly defined path.
• How I feel as a PMM: I love the role product marketing gets to play when a company is this size. The product has momentum and there’s usually a team of PMs who have a strong point of view on what they need to do next, but there’s still plenty of room for a product marketer to come in and help influence the roadmap and try new things for launches. As a leader at Envoy, I still get to get my hands dirty here and there while also creating the structure and processes needed for the team to scale.

All size companies have their own set of challenges. From what I’ve heard from colleagues and friends, Series A companies may be more challenging for PMMs because of where they are in their product-market fit journey, how they regard Marketing/PMM, and what their urgent needs are. PMMs get quite unhappy when other teams throw stuff at them without involving them in the process. This happens a lot at any stage company, unfortunately.

This will vary highly depending on the person and org. In a large enterprise, your PMM job will be narrowly defined, both from a scope of responsibilities standpoint and in terms of the product you are marketing. In many respects, that makes it a much easier job than at a startup, where your buyers are uncertain, your role is nebulously defined and you're expected to do way more than just the boxes on the Pragmatic Marketing framework. 

That's really a factor or where you are in your career. I started my product marketing career at HP (back in the 1980s) and that was fantastic as they had processes in place and great employee education opportunities to help accelerate my knowledge and provide a framework for getting things done. Some of those fundamental aspects such as the product life cycle, product/project teams and management by objectives have driven my work habits and career. I have since worked at larger, more political companies and very small start-ups. I find it more enjoyable and challenging (there's a relationship) at start-ups as there is very little friction between having an idea and executing on that idea. The downside is less resources and less process to depend on for driving necessary communication or action. I have had success in both environments (large and small) and take pride in those accomplishments. I was able to participate in a global product launch via sattelite to our worldwide field when with HP which was an amazing experience. At start-ups I have been able to drive an entirely new pricing strategy and define and launch new products which has been very challenging and rewarding as well.