How do you get insight into the current state of prospect/sales interactions?

This is a passion area for me! I work to carve out time for learning and exposure. It's always tough when you have pressing timelines for deliverables, but that work will be far more efficient and strategic when you invest in time for the fundamentals. Here are a few things I invest in doing:

Know the team. Be of value to them. 

• Go where your sales team is, be a fly on the wall in the places they discuss their goals and strategies (live or async). Have Gong? Download the app. It's a treasure trove.
• Build off of your familiarity from these team settings to reach out to a diverse sampling of your Sales teammates. Ask them for 30 minutes 1:1 to talk through a deal they're working, and brainstorm how you can help support them. Listen for where they've discovered great strategies and where they're strugling. 

Know the customer. Be present with them.

• Create channels for yourself and your team to get regular insight to your prospects and customers. The more direct, the better.
• Set up a win-loss program (start by doing a call or two informally!) to get feedback from prospects about their path to purchase, goals, etc while it's fress. Capture this information, make it visible internally, and take action. You have 2 periphery jobs here: 1) build a relationship with the champions among new customers to plant customer story seeds and 2) be a markedly positive "last touch" among lost deals to keep doors open for the future.
• Identify and lurk among the forums, medium digests, etc. where your audience lives. Steep yourself in what they're soaking up. Get inspired. 

Listen to calls. There’s no other way thats really effective. We live in the world of Gong/Chorus - where we have unprecedented insight into prospect conversations. There is no excuse to not take advantage of this ability. You can set playlists based on topics, segments, keywords, competitive positioning - or any way your tool lets you slice the data.

I would put up filters for the topics and keywords that reflect what you need your sales team to deliver consistently at scale to drive your ideal brand and product positioning.

There are multiple ways to get insights into your selling motion:

1/ Listen to sales calls - that's an obvious one but you can get pretty systematic with it, create a regular cadence for reviewing calls by certain tags and keywords

2/ Join sales calls - highly recommended for PMMs to attend calls, present on these calls and get a first hands experience of what it's like to be on the front lines, how prospects are resonating with the message, where they get stuck, where reps are struggling, etc. 

3/ Build dashboards in Salesforce to track deals by product /pricing bundle/ICP segment /geo etc. so you can track performance and identify bottlenecks in stage progression 

4/ Talk to your sales team regularly, attend their team calls and QBRs, and have 1:1s with top-performing and bottom-performing reps and SEs so you can learn from them what's working and what's not working 

5/ Run win/loss analysis programs and interview prospects to understand what they liked about the selling motion and where there's room for improvement 

We have done a variety of things over time which I'll list out here:

1- Leveraged tools like Gong to get reporting on critical topics, key ways of selling, and also understand gaps in messaging

2- Align a GTM PMM team whose role is to stay connected to your field team. They are expected to have contacts in every sales role & region who can act as stakeholders when we have key questions or want to get a pulse on the business.

3- Leverage underway programs that are happening like Deal Reviews led by sales management to support sales strategy or Leadership Forums that Customer Success uses to bring customers together. Don't reinvent the wheel but be an active supporting participant in these programs.

Ask questions, offer help, and yes, also learn!

The simplest and fastest way is to talk directly with your reps! Not sales managers but the reps that are actually having the daily conversations - ask them (this is from the lens of B2B/enterprise SaaS sales) -

1. what deck do you use for first calls? Second calls? (ask them to send it to you - is there messaging in that deck that didn't come directly from PMM but is still working? Or is there messaging in that deck that doesn't align with the company's strategy)

other than that - 

2. check your conversion numbers for first call to second call, second to third call, and later. If first to second call numbers are solid, your initial pitch is probably fine. But if you're having trouble closing deals once they get into later stages, you may need to look at things like use case messaging - do you have content that really showcases your key use cases? Do you have strong competitive content?

3. invest in tools like Gong that allow you to listen to calls directly - you probably won't have time to join every customer call, but listening to calls will help you understand whether or not your messaging aligns with the words of the customer.