Ryan Fleisch

Ryan FleischShare

Head of Product Marketing, Real-Time CDP & Audience Manager, Adobe
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Ryan Fleisch
Ryan Fleisch
Head of Product Marketing, Real-Time CDP & Audience Manager, AdobeJune 23

This somewhat depends on the resources your company has on each of those teams. If you have a full sales ops team then partner with them to understand win/loss and pipeline health. What you’re looking for is how much you’re winning/losing, why you’re winning/losing, who you’re winning/losing against, and what the forward-looking pipeline looks like considering all of those factors. If you don’t have a sales ops team, then you need to take some of this on yourself. I don’t believe a PMM team can be effective unless they have this foundation of data-backed insights. If doing these activities is a major strain on your PMM resources, then try to get some software to help automate these activities in the short-term. Longer-term, partner with sales to build a business case around why your company needs more sales ops people (or additional PMM headcount focused on this area).

Ryan Fleisch
Ryan Fleisch
Head of Product Marketing, Real-Time CDP & Audience Manager, AdobeJune 23

Great question – let’s tackle it from two angles: the strategic approach and then the content within it.


1) Strategic Approach: For this side of the equation, let’s all pretend we are the sellers for a second, and that the actual account executives are our clients. If we want to “sell” them our enablement program, we need to approach it the same way as they would approach any successful sales cycle: understand the buyer’s motivations and goals, uncover what’s blocking them from achieving them, offer a solution, tie it to value, and then follow-up and measure the success. The problem I see with many sales enablement programs (and many sales cycles for that matter) is they skip right to “offer a solution” and rarely is it the right one. For a sales enablement to follow a proper process and result in a strategically valuable program, you need to start with understanding that salespeople have a constantly looming quota to hit and every minute they spend out of the field in training programs can feel like an unwanted distraction (unless you prove the value). Next, you need to understand what’s blocking them from hitting their targets. This piece requires internal conversations, sales ops, and comp intel. Frame your program against those challenges: “we know that last quarter X% of your deals were against Competitor A with only a Y% win rate. And looking ahead at this quarter, Z% of the pipeline is also against Competitor A. We want to help you win those deals more, and as such, we’ve developed a sales enablement program with insights, collateral, and talking points specifically targeted at Competitor A.” Now you’re speaking a sales language they understand. Next, track the success of this program and use those data points next time around. “The last sales enablement program we ran had an X% attendance rate. Of those X% that attended, they saw a Y% increase in their close rates.” Whatever your metrics are, make sure they come through in your next “pitch” because these are the “case studies” of the sales enablement session you’re selling. If you don’t have easy access to aggregate results, then do a one-off deal deconstruction with an AE on a win that was tied to your program. If you can follow this strategic approach by ensuring your sales enablement has a foundation of market analysis, comp intel, and sales ops data, you’ll find that salespeople will drop everything to come to your programs rather than feel like they’re a distraction.

2) The Content: Whatever sales approach your AEs/SCs use, learn it and master it. This is critical. You need to understand the way they frame their pitches/cycles if you want your enablement content to resonate and get used within it. Do they use ValueSelling? MEDDIC? Demo2Win? Whatever it is, master it. If you can build your enablement program around the framework they are already about, you’ve just up-leveled your program to strategic value in their eyes.

Ryan Fleisch
Ryan Fleisch
Head of Product Marketing, Real-Time CDP & Audience Manager, AdobeJune 23

I’m going to answer this question the same way I answered, “How do you measure ROI of sales enablement?” because ultimately success should be ROI in some form. Here’s my response again: 


Ultimately you want everything to tie back to revenue (usually in the form of new versus growth versus retention), but you can never fully hold PMM accountable for those top-line numbers since there are so many other forces at play. This is why you need a set of secondary metrics you can use to measure your efforts a little more directly. For starters, measure the attendance rate of your sales enablement sessions, measure the views/downloads of the content from it afterward, and run quick surveys to measure the effectiveness of the session (even a one-question 1-10 satisfaction survey will do). Next, look at the metrics that you have more (maybe not full) control over that should ladder up to revenue. Are win rates increasing against a certain competitor? Are there more in-quarter sales-stage progression of deals? I love this one because a deal may not close for a number of reasons out of your control, but if you can say “we moved X% more deals from discovery to solution validation” (or whatever your sales stages are), this is a powerful metric.

Ryan Fleisch
Ryan Fleisch
Head of Product Marketing, Real-Time CDP & Audience Manager, AdobeJune 23

First, divide your efforts into “sales plays” (or depending on your company’s terminology they might be “sales motions” or “use cases”). Sales plays should each have a revenue target attached to them, and collectively, the revenue across all your sales plays should total the entire new business revenue goal. Next, define your “bill of materials” (assets) for each sales play. For our business, we have a Conversation Starter (2-4pg PDF of key market problem and our solution), Discovery Questions/Answers, Customer Pitch Deck, Internal Enablement Deck, Competitive Positioning, and Customer Success Stories. These are the assets I would prioritize creating, but this can be a lot, so you should also prioritize against your sales plays in terms of respective revenue goals.

Ryan Fleisch
Ryan Fleisch
Head of Product Marketing, Real-Time CDP & Audience Manager, AdobeJune 23

Great Our enablement decks follow this outline: Learning Objectives, Executive Summary/”Sales Play Made Simple”, Business Issues & Value, Key Personas, Key Messaging and Product Capabilities, Competitive Overview, Deal Examples, Customer Success Stories, Crawl/Walk/Run Sales Strategy, and Additional Resources. 


To pick this apart, I would say the Executive Summary single slide roll-up is one of the most critical parts. You need someone that people can refer back to and reference easily, and often times a 30 slide deck, isn’t the best fit. The Key Personas is a critical piece as well so everyone is on the same page of who this messaging is for and when it will resonate. Blanketing a sales enablement approach across all potential client types/levels can be a recipe for disaster.

Ryan Fleisch
Ryan Fleisch
Head of Product Marketing, Real-Time CDP & Audience Manager, AdobeJune 23

This is a tricky one because ultimately you want everything to tie back to revenue (usually in the form of new versus growth versus retention), but you can never fully hold PMM accountable for those top-line numbers since there are so many other forces at play. This is why you need a set of secondary metrics you can use to measure your efforts a little more directly. For starters, measure the attendance rate of your sales enablement sessions, measure the views/downloads of the content from it afterward, and run quick surveys to measure the effectiveness of the session (even a one-question 1-10 satisfaction survey will do). Next, look at the metrics that you have more (maybe not full) control over that should ladder up to revenue. Are win rates increasing against a certain competitor? Are there more in-quarter sales-stage progression of deals? I love this one because a deal may not close for a number of reasons out of your control, but if you can say “we moved X% more deals from discovery to solution validation” (or whatever your sales stages are), this is a powerful metric to hang your hat on.

Ryan Fleisch
Ryan Fleisch
Head of Product Marketing, Real-Time CDP & Audience Manager, AdobeJune 23

Exciting! Build a three-prong strategy around how you’re going to directly promote it, how you’re going to get the industry to promote it, and how you’re going to get your client-facing teams to promote it.


1) Direct: showcase it our webpage and make it a gated asset so you can collect leads from it. We put our Forrester and Gartner reports front and center on our website with this approach. Send focused emails around the report, include it in newsletters, and put some paid advertising behind it. All of this should be pretty straight-forward, and I’m sure you’re already working on it.

2) Industry: Think about how you’re going to use this report from a PR perspective. Here’s where you might need to get a little creative. I don’t know the exact nature of your research, but if it feels too self-serving/salesy, a lot of publications won’t want to pick it up (unless it’s a paid placement). Instead, consider pulling one or two interesting findings out of our research, and anchoring a compelling story on it. Our team just recently released a new research report on COVID-19 that got a ton of industry coverage. But what’s interesting with the coverage, is that none of it focused on the entire report – that would seem too self-serving. Instead, it focused on specific findings that we fed the publications such as “Gen Z has been most negatively impacted by COVID-19 but yet they aren’t hesitating to buy luxury goods.” Or “customers are tired of the ‘we’re with you’ messaging in ads. I would encourage you to dig into your research, find a few compelling elements of it, and shop those around to get industry coverage.

3) Promotion/Enablement: Make it easy for your client-facing teams to push this out. Draft emails they can send, arm them with talking points around it, and draft a few versions of social posts they can easily share. Creating a "how to use this report" guide is critical. It should outline with whom the report will resonate best, when to use it in a cycle, and how to effectively speak to the findings within it. 

Ryan Fleisch
Ryan Fleisch
Head of Product Marketing, Real-Time CDP & Audience Manager, AdobeJune 23

This is certainly a divisive topic. One school of thought is what I call “the Pepsi challenge” approach. That is, if you’re #2, you always mention #1, but if you’re #1, you never mention #2 (you don’t hear Coke bringing Pepsi into their ads, right?). While philosophically that might be the right approach, I believe the fact of the matter is you need to arm your GTM teams with targeted H2H approaches because that’s likely what the majority of their cycles entail. Do this with clearly defined internal versus external battlecards/material. The internal ones should not only tout your benefits over the competitors but also include the pitfalls to avoid. You’re never going to beat a competitor on every single dimension, so be honest with your teams on where they should lean in and where they should try to avoid. This will also act as a safety guard to prevent these battlecards from being shared externally. Now for your external material, I personally think it’s fine to create targeted H2H collateral that calls out competitors and your points of differentiation. However, try to avoid really “measurable” elements like using Harvey balls to represent capabilities because these are always up for debate and can lead to inaccuracies. You’re safer to talk about themes, approaches, and drop in case studies/quotes regarding that competitor. Also, 3P research is your friend here. Take your opinion out of it by anchoring on Gartner Magic Quadrants, Forrester Waves, industry news, etc… Finally, you can also create versions of this collateral that might be more publicly hosted with an “us versus them” approach that doesn’t specifically name the competitor.

Ryan Fleisch
Ryan Fleisch
Head of Product Marketing, Real-Time CDP & Audience Manager, AdobeJune 23

It should be collaborative and I would somewhat divide and conquer by you setting up the enablement you know will be needed based on your PMM roadmap such as product launches and other new collateral (comp intel, pitch decks, research reports, etc…), and by sales leaders coming to the table with where they see their teams needing more help. Maybe it’s in deals around a certain use case, for a certain industry, or against a certain competitor. All this should be clear from the sales op data you have and allow you to build a program around it to support it.

Ryan Fleisch
Ryan Fleisch
Head of Product Marketing, Real-Time CDP & Audience Manager, AdobeJune 23

Your sales enablement roadmap should be one piece of your larger PMM roadmap. If you can flight out upcoming product launches, new research reports that will be launching, etc… then you can tie an enablement approach and cadence to each of these. Aside from new enablement, it’s good to monitor and notice when your sales teams might need re-enablement on existing sales plays or content. Often times if salespeople have been around for a while they might stick to their approach out of familiarity and comfort, but the market and competitors may have shifted. Recognize when sales teams are not making the most of every opportunity and run re-enablement sessions that make each person “stand and deliver” their pitch and earn “certification” from PMM, their sales leaders, and their peers.

Credentials & Highlights
Head of Product Marketing, Real-Time CDP & Audience Manager at Adobe
Top Product Marketing Mentor List
Product Marketing AMA Contributor
Lives In New York, NY
Knows About Growth Product Marketing, Enterprise Product Marketing, Product Marketing Interviews,...more