Michael Olson

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.

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".

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.

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.

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 shared a similar response to a separate question, but positioning is such a nebulous and somewhat vaguely understood topic by product marketers and product managers, that I'd love to help. Here are the 5 main inputs I think about when defining positioning: * Market Category – the space in your customer's mind where your company and/or product fits. This is the frame of reference for your buyers. * Target Audience – your ideal customer profile + the buyer personas and user personas who are a good fit. * Competitive Alternatives – how your target audience would try to solve this problem if you didn't exist, and why they'd fall short. * Value Proposition – the main problem you solve for your customers, and the key benefit you provide. * Differentiation – how you’re unique or comparatively better than alternatives. April Dunford is probably the most authoritative positioning expert and I'd encourage reading her book Obviously Awesome or checking out her blog. She has a positioning matrix template which contains some similar elements as what you see above. One hot take I'd also offer up. You likely are familiar with the positioning statement template Geoffrey Moore pioneered, which goes like this: For < target customer> who <describe the need>, <our product> is a <category> that <key benefit>. Unlike <alternatives>, <our offering> <differentiation>. I love Geoffrey Moore's works and Crossing the Chasm may be the best business book ever written. But I'd steer you away from this positioning statement template. I've created many positioning statements in my career using this format, only to never look at them again. April Dunford has written about why the positioning statement lacks durability, and I've come around to this point of view after too many false starts creating positioning statement shelfware myself. I'd boil it down to this – positioning is an incredibly strategic and consequential subject. I'd argue it's the most important thing to nail outside of having a good product. Trying to shoehorn positioning into an oversimplified 2-sentence Mad Libs is a surefire way to cut corners and reduce clarity. The whole point of positioning is to create clarity around why you exist, the category in which you play, and your differentiated value. So don't shortchange it with a reductive template.

Other than building a good product that solves real problems for customers, positioning is probably the most important thing to get right, because it's so strategic and foundational to how you go to market. At its core, positioning is an internal construct. It’s what you tell yourself internally to align on your strategy, the perceptions you want to create, your differentiated role in the market, and your relevance to your customers. I think about 5 main inputs when shaping positioning: * Market Category – the space in my customer's mind where our company and/or product fits. This is the frame of reference for our buyers. * Target Audience – our ideal customer profile + the buyer and user personas who are a good fit. BTW, I think of ICPs and personas as different but related things. ICPs are an output of market segmentation and reflect the characteristics of companies and/or teams that make a good fit for your products. Personas are the actual people in those companies/teams who buy and use them. * Competitive Alternatives – how our target audience would try to solve this problem if we didn't exist, and why they'd fall short (de-positioning the status quo is so important). * Value Proposition – the main problem we solve for your customers, and the key benefit we provide. * Differentiation – how we're unique or comparatively better than alternatives. While not critical, I also find that it can be useful to document the market perceptions of my company that we want to create, shift or reinforce. I like to describe this in a set of From > To statements. This is particularly useful if you are expanding into an adjacent market via acquisition or new product development, or as you're repositioning your company to respond to changing market dynamics.

Short answer: a lot. And unless you are either 1) truly bringing new-to-the-world products to market or 2) already the clear, undisputed market leader in an established category, it's essential to pick your head up and pay attention to how competitors message themselves. Putting yourself in the shoes of your buyer, a lot of B2B vendor messaging tends to sound the same. Too many value propositions are watered down to the point of becoming too generic ("grow revenue", "reduce costs", "minimize risk") or so vague as to lose credibility, curiosity and persuasion. The result is that buyers tune out, are unable to differentiate your product from competitive offerings, and resort to making purchase decisions based on things like primacy bias or price alone. If you're marketing a premium product or are a challenger in your category, that's not a recipe for success. My team takes great care to ensure that our strategic narrative and the messaging we're activating in market sounds different from how competitors talk. Some examples of where to put this to practice: * Framing the customer problem in a different way. This may entail identifying a fundamentally different customer problem than what your competitors target. Or employing challenger sale techniques to reframe the problem in the minds of your buyer and show how there's actually this other thing you may not have thought of which is fundamentally the real issue, and you've been focused on symptoms vs. root causes. That reframe, if done well, can be a powerful way to stand out from the crowd, earn credibility, and get customers to buy in to your vision. * Spending time de-positioning the status quo and establishing why traditional approaches to solving the problem (i.e. incumbent or competitive products) fall short. I've spent a lot of my career marketing challenger products in new, emerging or existing categories, where it's really important to unsettle buyers and make them realize that there's a better way. * Describing the promised land or desired outcome differently. Typically, what I've found works here is to avoid being too reductive in how you describe desired outcomes. Unless I'm building messaging for the c-suite, I like to create messaging that comes in at a lower altitude, zeroing in on a more specific, tangible value proposition in support of higher-level outcomes like "growing your business", "improving digital customer experiences", "cutting costs", "stopping breaches", "resolving incidents faster", etc. As an example working at an observability company, we talk (publicly, I might add) about "taking the toil and guesswork" out of troubleshooting and "spending less time in war rooms" as a more specific, visceral way of saying "reduce mean time to resolution" (the latter of which is something EVERY vendor building software for IT Operations or Engineering buyers talks about). * Ensuring that our competitive positioning or answer to "why us?" is defensible, with product evidence and customer proof to back it up. The rule of 3 is a powerful thing. I often find it works best to have one main unique selling proposition which is the single big, grand reason why a customer should choose you over the competition. Then we back that up with 3 outcome-oriented differentiation statements which show how we pay that off. For each of those differentiation statements, it's useful to include punchy messaging on key product capabilities that are unique or comparatively better than competition at achieving the outcome, as well as relevant and specific customer stories. Remember that the best product doesn't always win on its own and become category queen/king. Clear positioning and compelling, credible messaging can make up ground and help you compete.

Great question. I'd encourage you to think about pricing and packaging as powerful tools for competitive differentiation. In any economy, selling on value is a winning strategy. But in this economy, the B2B buying criteria pendulum has swung, from top-line growth as the #1 priority now to bottom-line operating efficiency. Companies that are exploring packaging (including bundling strategies) as a way to remove friction from the buying process and deliver more value without a commensurate increase in their customer's TCO are thinking about it the right way. When I've been responsible for product packaging, my goal is to make it frictionless for customers to expand use cases and adopt new capabilities. Expansion leads to more value, and value leads to more stickiness. Onto pricing, Southwest, Spirit Airlines and JetBlue have historically differentiated based on value, undercutting competitors on price while packaging "features" accordingly to align to buyer needs. They carved out share targeting the segment of consumers who care less about premium upgrades, checking a bag, in-flight meals or fancy snacks. I will say though, I flew Southwest on a business trip last week and the pretzels were amazing. :-) But it can go the other way, too. Sometimes pricing can be used as a lever to reinforce perception as a premium brand. Häagen-Dazs is objectively more expensive than almost any other nationally-distributed ice cream brand in the U.S. But its target customers are willing to pay that markup based on a perception of quality, and Häagen-Dazs has leaned in to that by positioning itself as a super premium ice cream brand. One of the many ways AWS differentiated from VMware in its early days was based on its billing model, offering an innovative "pay-as-you-go" consumption model that felt like a breath of fresh air in an era when recurring subscription models were eating the lunch of perpetual licenses.