AMA: Splunk Sr. Director, Product Marketing - Observability, Michael Olson on Sales Enablement

I think this is a symptom of bad persona guidance more than anything else. I have seen a lot of persona guides created by marketing teams that get too cute – with whimsical fake names, esoteric archetypes, information that isn't actionable for sellers (like how prospects feel and how they want to be engaged with), and guidance that's too high level (for example, stating goals like "they want to grow their business" or "they want to save money" are not at the right altitude to be useful for sales rep). Putting yourself in the shoes of a sales rep, you need to understand things like: 1. What are the characteristics of companies that determine good fit from bad fit, so I can spend my time working the right types of opportunities that are likeliest to convert? 2. What are my prospect's critical business priorities/initiatives? 3. How do I navigate their org chart and find the right person/people to engage? 4. What questions should I ask in a discovery conversation, and what should I listen for? 5. How do I uncover challenges and align those to the right solution (use cases, required capabilities)? When designing a persona guide, I like to include the following things: * Ideal customer profiles & qualification criteria to determine good fit / bad fit * Sample org chart * Key personas (real job roles; not fake names or random archetypes like "the bold risk-taker") * Sample job titles (this is essential to help your sellers prospect effectively on LinkedIn) * Their key responsibilities (what they do) * Their tech stack (what tools they use today to get their job done; mostly relevant for B2B) * What they care about (their goals) * Their challenges * An elevator pitch that gets their attention The most important thing you can do when building a persona guide is to validate it with real sales reps and sales engineers (SEs). Get feedback from a range of folks – early-career BDRs, long-tenured enterprise account execs, sales leaders, and SEs. This will ensure that the guidance you are creating is credible, useful, and meeting the needs of different constituents in your sales org. Another pro tip to help you create effective persona guides: go find actual job descriptions for the personas you're targeting via their careers page or LinkedIn. They are a gold mine of insight on a prospect's key business priorities/initiatives/projects, their tech stack, and the key responsibilities for the role – all written in the customer's words.

This answer might come across as tough love, but you need to establish credibility with sales teams and prove your value by demonstrating a deep understanding of 1) the market in which you play, 2) the ideal customer profiles and personas who care about your stuff, 3) their needs, and 4) the competitive landscape, and 5) your differentiation. If you can consistently show up in internal meetings, sales training sessions and sales kickoffs with a mastery of your market, your buyers and how your products fit, you will earn credibility and your sales teams will see you as a strategic partner vs. a tactical data sheet monkey. Too many PMMs focus on becoming an expert on their product – learning all of the speeds and feeds, geeking out on features. But from my experience, what separates good product marketers from great ones and commands greater credibility with sellers is becoming an expert on the market and your buyers. This allows you to put your product in context for your sales team, which in turn enables them to do the same in conversations with prospects. Next, I think it's important for PMMs to remember that part of why we exist is to serve the needs of our sales teams. Sales enablement is one of the key pillars of the job. Bi-directional feedback loops are critical, and your sales team needs to be able to share how your messaging is resonating, where they are running into friction in customer conversations or sales cycles, and what they need to move prospects through buying cycles efficiently. If you're not testing/validating messaging with sellers before you roll it out at scale or sharing drafts of sales playbooks and enablement content with sales folks for feedback, how can you be certain that what you're producing will hit the mark? I'll close here by saying that a good product marketer can be a sales team's secret weapon. At times, I've spent as much as 20% of my time as a PMM on the road actively participating in customer meetings, sales calls, and speaking at workshops and regional field events. Spending time in the field is also the best way to conduct primary research on the market, customer needs, and to test and validate messaging.

Good sales messaging + proper enablement is the solution to this problem. More often than not, when I've seen a lack of messaging consistency in my sales teams with every sales rep offroading and rolling their own, it's either because our messaging wasn't credible/didn't resonate, or we had an awareness/enablement gap. Here's what good messaging needs to do: * Be Relevant: is it germane to your target audience's day job and the things that keep them up at night? * Be Differentiated: does it sound different from how competitors talk, or does it look the same and make unsubstantiated first/only/best claims that make prospects skeptical? * Create Clarity: is it easy for your target audience to understand why they should care? * Drive Intent: is it compelling to prospects and does it make them actually want to buy and use your stuff? Here are some guiding principles I practice and coach my PMM teams on as it relates to creating messaging: TAKE AN OUTSIDE-IN APPROACH I’m a big believer that product marketers need to take an outside-in approach to developing messaging, not the other way around. That means leading with your customers’ problems, their needs, and using that as framing for how you describe the promised land and your solution. Prospects tune out when a vendor sales deck leads with the obligatory About Us autobiographical slide. Prospects care a lot less about your company vitals than they do about the problem they're facing and whether you have a vision for how to help them solve it. USE WORDS YOUR CUSTOMERS USE I have a zero jargon policy with my PMM teams when we create messaging, and our goal is to write it exactly like you'd say it out loud. In a conversation. With a customer. I call it conversational tone (I've heard it referred to as BBQ speak by others), and it's the best way to make your messaging sound like something a sales rep would actually be confident saying out loud in front of a customer. I'm also generally not a fan of initialisms, acronyms or jargon-ey terms that aren't broadly understood by "the uninitiated". You only get so many at-bats with coined terms before you confuse customers, so when in doubt, use conversational tone and default to approachable language that creates clarity for the masses. COME IN AT THE RIGHT ALTITUDE Your messaging needs to strike the balance between being technically credible for the prospects you are trying to reach, while simplified enough for those customers, your sales team, and your marketing team to "get it". Too many times, I see messaging get way too in the weeds on "the what" and "the how", with no synthesis on "the why" – specifically why customers should care and the value to them. Other times, sales messaging is too high-level and undifferentiated. In 2024, if you're a B2B company and the first slide of your sales deck still says "every company is a software company" or includes the word "digital transformation", you're doing it wrong and your messaging needs to be more precise. :-) BE CONCISE, BUT NOT AT THE EXPENSE OF CLARITY When your messaging framework becomes too minimalistic, or over-rotates toward short phrases that look like ad copy, the narrative gets lost and you increase the likelihood that sales and marketing folks are going to off-road when they start pitching to customers or creating downstream content. When done right, the content in a messaging framework gets copy/pasted liberally and becomes foundational for your sales messaging, your web copy, your thought leadership assets, and your press releases. Consistency is important. And a well-written messaging framework becomes a scale enabler for downstream content.

I'm a proponent of standardizing the core bill of materials PMM teams produce for sales enablement, both to keep your PMM team focused and avoid one-off requests, and to align with sales teams on what they need and what they can expect. Here are some of the foundational materials that I've found to be most essential at improving the sales team's confidence positioning and selling my products. Depending on what works best for the sales team, I either package all of these components into a cohesive sales playbook, or keep them as separate assets. * Market Primer: Summarizes 1) define the market in which we play, 2) the market context/dynamics that are impacting our buyers, 3) the market problems that keep our target audience up at night, 4) why traditional approaches to solving the those problems fall short, and 5) to summarize the competitive landscape. * Persona Guide: Guidance on ideal customer profiles (qualification criteria & characteristics of companies that make a good fit/bad fit), sample customer org charts + the key personas you target. The latter should include sample job titles, key responsibilities, their goals, key challenges, and their tech stack (useful for B2B tech companies). * Prospecting Email Templates & Call Scripts: I realize this is a tactical deliverable and in some companies your demand gen team may own this, but it's wayyyyy more efficient for someone in marketing to create good templates and scripts for your global sales team to use, vs. each sales rep needing to roll their own. * Discovery Guide: What to ask, listen for and say to qualify early-stage prospects in/out and help your sales reps confidently navigate discovery meetings. * First Call Deck (and gold-standard video recording): Used as a vehicle for discovery + to share your POV in under 10 minutes, answering questions like "Why Change?", "Why Our Company?", "Why Now?". * Exec Positioning Deck: A version of your POV/pitch geared toward an exec/c-level audience. * Cheat Sheets: These can take many different forms depending on your sales plays, but think of these as a high-level, 2-3 page summary of the main things a sales rep needs to be able to quickly reference to position your product, use cases, or differentiators. High skim-value is a key guiding principle here. * Competitive Battlecards: How competitors position themselves, their strengths & weaknesses, our differentiators, objection handling, trap-setting questions, and real-talk guidance on where to expect competitive friction (to help your sales team qualify out or steer away from points of weakness). * Demo Scripts (and gold-standard video recording): Scenario-based demos that show how your product solves customer problems and addresses use cases you've uncovered through discovery. * Economic Value Calculators: Interactive tools to measure and communicate the ROI of your product. * Sales Play Guidance: this can take multiple forms and fits best in a formal sales playbook, but I like to package up guidance on what to do at each step of the buyer's journey. For example, how to research your prospect's key business priorities, how to prospect into an account, what to propose as a next step from a successful discovery call, when to run a demo, how to pull together a proposal, pricing guidance, etc. Outside of sales tools, you may also want to look into sales enablement software platforms, which can provide an intranet portal to house all of your sales enablement content + make it easy for sales reps to find and use them. Most of these platforms also offer analytics and tracking on sales enablement asset usage, so you can see how the content PMMs create is used. I've used Showpad across two companies now, but there are several other software tools in this space. Highspot is another well-known vendor in this category.

This is a tough one, and it has been a journey to figure out how to measure the success of the sales enablement work PMMs do. In larger companies with a dedicated field enablement team, there's often better instrumentation and PMMs can partner with another team to activate enablement programs (like certification programs or sales enablement platform/portal implementations), whereas in a start-up, you're much likelier to be DIY'ing it. Here, I think it's critical to look at both leading and lagging indicators. If you only rely on lagging indicators like sales pipeline and revenue, it's a bit like looking at a star through a telescope: that thing you're seeing? It happened years ago. Leading indicators are less strategic and less tied to the success of your business, but they'll give you early detection and more real-time insight to course correct or shift strategy before you miss plan in a quarter. If your sales team isn't generating pipeline, that's going to show up as a bookings miss in a quarter or two or four. If your sales team isn't using your enablement assets or participating in training, that's going to show up as a pipeline gap in a quarter or two (or four). Here are the main metrics I care about: LEADING INDICATORS: * Sales enablement asset usage - I look at usage of core enablement assets like sales playbooks, pitch decks, demo scripts, economic value calculators, solution briefs, call scripts and email templates. If you're producing effective sales enablement content, your sales reps are going to want to use them because they know it will help them close more deals. There are sales enablement tools out there that can help you monitor content usage. I've used Showpad now across two companies, and Highspot and Outreach are a few others that come to mind. * Sales certification - While it doesn't correlate as closely to your top-line revenue, I've often partnered with sales enablement teams to ensure sales reps are certified on pitch decks and sales messaging, in addition to certifying sales engineers on demo scripts. If you've got your sales messaging right, it's going to influence purchase intent and help your sales reps close deals faster and more easily. * % of sales reps with active pipeline for my product - just as you don't want to be dependent on a few big whales in your deal pipeline, in a healthy B2B business, you don't want to be dependent on a small number of sales reps to hit your number. LAGGING INDICATORS: * Sales pipeline is more useful to me than counting MQLs (marketing-qualified leads), because it's a more reliable indicator of forecasted revenue. Another metric I look at is pipeline coverage ratio, which is a measure of your total pipeline divided by your bookings target. Most SaaS companies I've been at target 2.5X-3X pipe coverage. If you're operating in an emerging market or aren't a leader in your category, you'll likely need a higher pipe coverage ratio to hit your bookings target. If you're in an established category and/or a category leader, you may be able to get away with a lower ratio. * Bookings and/or Revenue are the ultimate success metric, and as a PMM, you should bird-dog this closely, tracking sales opportunities, asking how you can help, making yourself available to tag in and join sales calls and meetings with prospects to help your sales team close deals. Good PMMs are a sales team's secret weapon, and you should be getting tapped to join customer meetings and help your sales team get deals over the goal line. * Win rate is the percentage of opportunities that turn into closed won deals, or the dollar value percentage of sales pipeline that turns into bookings. It's one of the most reliable measures of sales efficiency: how effective is your sales team at winning new business vs. alternatives such as competitors or "do-nothing's".

Expanding into an adjacent market (whether via new product introduction, acquisition, or a GTM strategy change) is one of the most fun and challenging resume builders for a PMM. Like with an early-stage startup seeking to establish product-market fit, focus is so important. Don't try to boil the entire ocean all at once. You want to focus your positioning, your messaging, and your sales team's attention on a specific market problem that your new product solves really well, in addition to giving them a baseline understanding of this different persona (job responsibilities, goals, key challenges, tech stack / incumbent tools). Starting small now helps you build repeatability and momentum, so you can go big later on. I'm a big fan of The Challenger Sale and Insight Selling and both methodologies offer great guidance on how to craft sales messaging that works in this type of scenario. By framing the market context and customer problem differently from category incumbents and encouraging a new way of thinking (i.e. a reframe), you can carve out an early niche for your new product and also stand out from the crowd in the mind of the persona you're now targeting. Here's how I try to focus sales messaging for this type of scenario: * Name a big change in the world – This is the market context in which your customers live, and you want to establish credibility and demonstrate empathy by showing that you understand their world, the challenges they face, the goals they have, and that you can anticipate how this change may impact them in the future. * Identify the problem that change creates, the impact on that problem to this different persona, and the consequence of not solving it. Companies that frame the problem most persuasively are the ones that win. They’re the ones that get customers to buy into their vision for solving it. * De-position the status quo – Next, you want to show why traditional approaches won't cut it and why a better way is needed. This helps reinforce the need to explore new ideas and new ways of thinking, while de-positioning the old way and the companies you displace. Super important if you're trying to catch the attention of a new persona. * Describe the promised land – This is the ideal state or customer desired outcome your new product will help unlock. It's the overarching need created by the problem you identified. * Set the rules – lay out how the new persona you're targeting can get to the promised land. Specifically, your differentiated approach to solving the problem (i.e. what makes you different from incumbents). If you can apply this messaging construct to your pitch (i.e. first call deck) as well as your enablement materials and training, you'll start to level-up your sales team's understanding of the market in which this new product fits, the buyer, and how to confidently engage them. This will help break the cycle of sales reps defaulting to selling what they're most comfortable with (existing products).

Speaking as someone who has created a lot of bad sales playbooks that have collected dust during my career :-), this is a topic that I'm passionate about. Here are the main ingredients that I've found make for a sales playbook that will actually get used by sales teams. * Market Primer: Particularly for sales reps who are new to your company or space, I've found it useful to 1) define the market in which we play, 2) the market context/dynamics that are impacting our buyers, 3) the market problems that keep our target audience up at night, 4) why traditional approaches to solving the those problems fall short, and 5) to summarize the competitive landscape. I look to do this in 3 paragraphs or less. Keep it tight, but don't resort to pithy bullet points or the context will get lost. Successful knowledge transfer and taking what's in your head and inception'ing it in the minds of your sales team should be the goal. * Ideal Customer Profile: this is different from your buyer personas. Here, you're documenting the characteristics of companies that make a good fit for your products. * Target Audience: The teams and specific roles who buy and use your products. Here, I like to include guidance on example job titles (useful for prospecting), their key responsibilities, the main things that keep them up at night, their tech stack (relevant for B2B), and how our product helps them. I also like to include sample org charts in a persona guide to help sales teams conduct more effective prospecting. * Sales Process: Most sales playbooks are justifiably oriented around messaging. Messaging focuses on what to say, but a good sales playbook should also outline the sales process or buyer's journey, with guidance on what to do at each step. For example, how to research your prospect's key business priorities, how to prospect into an account, what to propose as a next step from a successful discovery call, when to run a demo, how to pull together a proposal, pricing guidance, etc. * Discovery Guidance: What questions to ask, what to listen for, and what to say in order to help your sellers confidently navigate conversations with early-stage prospects. Including guidance on what to listen for is crucial here to help sales teams learn how to pattern match responses to determine good fit/bad fit and also to design the right solution. Just providing a laundry list of discovery questions with no context on why a sales rep should ask them isn't all that useful. * Competitive Differentiation: What makes you unique and/or comparatively better than alternatives in your category? Differentiation is one of the hardest things for a product marketer to nail, but it's one of the most important since the most common question sellers field from prospects is "how are you different from competitor X?". * Use Cases: What are the scenarios or jobs-to-be-done in which a buyer would use your product? I take this a step further by aligning required capabilities (i.e. things your product does) to pay off each of these use cases. * Demo Script: What do you show during a meeting with a prospect to pay off your messaging and prove value / technically validate your product as the solution to the customer's problem? I like to structure demo scripts in two-column layouts, the left column documenting what to say (with clickpaths embedded in the talk track) and the right column showing a screenshot or animated gif of the main capability or workflow you're showing. Also, demo scripts should NOT be feature tours. The best demos tell a story by outlining a relatable scenario that's tailored to your prospect's problems and desired outcomes. * Customer Stories: What are your best customer examples that you want every sales rep to internalize and be able to share with prospects? * Resources: Lastly, it's helpful to curate a list of your most helpful sales tools (sales decks, cheat sheets, prospecting tools, economic value calculators, etc.) and customer-facing content (eBooks, white papers, solution briefs, analyst reports, blog posts, etc.) that reps can share with prospects.