I'm curious about the experience of others, which group has been harder to work with––Product or Sales? And why and how y'all work through issues?

I’ve been in consumer businesses during my career as a Product Marketing so I can only speak to working with Product. I’ve had a lot of great experiences with Product partners.

First and foremost, when starting a new business relationship I find ways to add value before I start offering criticism. Figure out what the team needs that you can help with and start there for at least the first few weeks.

Next, make sure you’re picking your battles, and make sure your rationale for picking your battle(s) is anchored in some kind of insight (ie. this is the most important thing to our users and the research shows we’re not meeting expectations yet).

Lastly, best practice for influencing will require you to tailor your communication to your audience - figure out how your key product stakeholders make decisions and build your case to fit their style.

In short, neither. I wouldn't look at this as "harder to work with" as much as I'd suggest investigating how you set up your goals and expectations.

Both product and sales are invaluable partners. 

Both generate compelling user insights. Product happens to generally generate them earlier during the development cycles while sales (especially in B2B) can get them to you rapidly once a product is in market. That being said, one needs to be careful not to use insights from product or sales too much as a crutch since each team has it's own natural bias that could influence how they interpret your users and prospects reactions. Do your indepedent insights research as well as work with product and sales directly.

Both have their own timing & cycles to be mindful of. Sales is generally operating to hit monthly/quarterly/annual targets that have material impacts on their personal income. If your team isn't highly attuned to that or aligned to that financially it can make understanding where they're coming from very challenging. Similarly, product is typically working off of their own release cycles. It's pivotal to undersand their workflows to be able to time when and how to market new products you're bringing to market.

Both have a different degrees of agency. A passionate product and engineering team is deeply invested in what they've built - rightfully so. As such, they'll likely be very interested in how what they've built is positioned and sold, however, they don't control that. They are an influencer. Conversely, a passionate sales team positions how products are sold and wants new and enhanced products they can sell. But do not actually control what products are built. As a marketer, one needs to recognize this as well and create an environment where these natural tensions help bring the best ideas to the surface rather than create an 'us' v 'them' culture.

Long story longer, gone are the days of thinking that marketing was mostly about Sales/Marketing Alignment. Today's teams especially in Vertical SaaS need to be thinking about Marketing/Product Alignment just as much.

In most companies I've worked in, Product Marketing is often vastly outnumbered by Sales teams. The challenge is not usually in personalities or conflicting interests - but in sheer numbers. For me, managing PMM-Sales relationships comes down to understanding their goals (keeping large customers happy, hitting sales quotas, etc.), while also taking care not to become an unnecessary bottleneck for their work. 

In the past, I've used the following tactics to avoid/work through issues:

• Take time to walk Sales team members through the product strategy and marketing plan. Treat them as strategic partners, not just executional colleagues.
• Provide guidance to their sales strategy, and align on the right customers/prospects, so everyone's time and efforts are invested efficiently.
• Create sales enablement content that allows some flexibility - to a limit. Reduce back-and-forth discussion by empowering them to work within specific boundaries.
• If needed, introduce an exception process that has clear requirements around inputs requirements and expected lead times for your response.

In my experience, it depends more on the actual people you work with vs the function. I have had both incredible sales and product partners that understood the big picture, were always down to collaborative and problem solve together, and where we could openly talk about areas of disagreement. These folks came curious to learn other people’s perspectives and kept users' experience at the heart, making it easier to get alignment. I’ve also had experiences where that was not the case.

If you are experiencing friction, my advice would be to address it early and often. The more you can get everyone to assume good intent and work towards an improved operational model from the start, the better. This means that small issues don’t have the time to fester and bubble over, making the long-term relationship healthier and more stable.

I always say that Product and Sales should be the two best friends of Product Marketing! And I would say they both have their times when they are hard to work with or need more care. For both groups though, the most important thing is to listen and bring value. Come to them with ideas and ask for feedback early and often. Listen to their pains and challenges and come back to them with value add (assets, ideas, etc). With either group you want to help avoid or break down silos. Some tips for doing that are:

• Encourage collaboration and cross-team communication

• Use a buddy system

• Ask for feedback

• Hold post-mortems

Listening and learning from mistakes or looking for ways to improve are the key skills here for working with either group.