Developing a Sales Playbook

In 2 years, we cut Aligned’s sales cycle from 75 to 22 days, while moving up market and increasing ACV 44%. The key? Our team meets EVERY WEEK to optimize our sales playbook. Here’s our end-to-end workflow: 1. Playbooks get old within a few months—Build a regular update cadence How buyers evaluate you and make decisions constantly changes as your product, market, competitors, and economy change. Discussing these changes weekly forces us to adapt. We figure out if we need new enablement assets, training, or if our workflows need a refresh. 2. Most playbooks are “Set & Forget”—Build a system to monitor & analyze At Aligned, we use Deal Rooms to run our playbook. We analyze our best and worst-performing rooms weekly based on buyer engagement. This helps us understand what aspects of our process are effective and identify gaps. For example, an AE might create a new tab to run competitor comparisons or a business case framework that drives more exec engagement. 3. Most wait too long—Quickly turn gaps into sales or buyer enablement assets Most teams lack a routine to find OR fix gaps. Also, most teams put too much weight on sales enablement assets like scripts or training materials. Last week, Kevin "KD" Dorsey told me he sees deal rooms as an excuse for constantly creating buyer enablement assets like ROI calculators and guides. He said, “Investing in buyers must become a habit, or you’re not going to get far”. I couldn’t agree more. 4. Most skills stop at training—Embed every new skill into a dedicated template I’m a 4x sales leader. One thing I was NEVER able to do right is to get the team to consistently follow the playbook. At Aligned, we’ve tackled this by updating all customer-facing workflows in our deal room template (e.g. How we run MAPs, POCs, Business Cases...). We then use the internal-only view to templatize resources like discovery and demo frameworks. Centralizing it in one place makes it easier for the team to follow our processes. 5. Over-standardization is as bad as winging it—Encourage breaking your process A sales leader’s dream of having the ‘perfect’ process executed by their team can also be their worst nightmare. Yes, you want AEs to see what good looks like and follow what works. But do it too often, and you end up killing intuition and creativity. THE essence of what makes complex selling work is knowing how to dance. That's why our biggest updates to our template come from our team on the front line, not top-down. TAKEAWAY: There’s no quick fix for improving Deal Velocity metrics. Simply increasing price 15% won’t magically solve ACV. There are multiple potential root causes to identify. And multiple ways you can address them. But what you truly need… Is a structured way to enhance your process. Monitor, Analyze, Iterate, and Scale. That’s what has worked best for us. You have to be strategic about it. EDIT: People asked—Aligned is the Deal Room we use. It's 100% free to try https://lnkd.in/dwX_Zizk

I think we’re measuring the wrong stuff… and it’s quietly killing momentum. 2026 has to be the year we fix it. Impressions. Clicks. MQLs. “Engagement.” The real game is happening in DMs, Slack threads, forwarded newsletters, and meetings. Here are 6 metrics I’d focus on in 2026 GTM (and why they matter). 1) Conversations → conversions What it is: Of the conversations your content starts, how many turn into a real next step (intro, meeting, opp). Why it matters: Content doesn’t “generate leads.” It generates conversations. Pipeline comes from what you do next. How to track: Tag every inbound convo (DM/email/reply) and mark the outcome: no fit / nurture / meeting / opp. 2) REAL ICPs engaging with content What it is: Not “engagement.” Engagement from the right people (titles, seniority, company tier, intent). Why it matters: 1 CFO at a target account > 1,000 random likes. How to track: Maintain an ICP list (titles + account tiers) and measure: % of engagers who match ICP of target accounts engaged per week repeat ICP engagers (X touches in 30 days) 3) Brand mentions inside ICP-relevant conversations What it is: How often your brand comes up when your ICP is discussing the problem you solve (not when you post). Why it matters: This is the difference between “content that performs” and a brand that gets recommended. How to track: Collect signals: customer calls (“we heard about you from…”), community moderators, partner chatter, dark social screenshots, and sales intel. Even a simple monthly “mention log” works. 4) Conversation velocity What it is: The speed from publish → first qualified conversation, and from convo → meeting. Why it matters: Velocity is the earliest indicator your messaging is landing. If it’s slow, you’re not sharp enough yet. How to track: time-to-first-ICP-convo after a post/report time-to-meeting after first touch “conversation depth” score (comment → DM → problem share → meeting ask) 5) Brand + category position What it is: Are you being associated with a clear “lane” (category/point of view) or just “a vendor who posts”? Why it matters: In 2026, positioning is distribution. If people can’t summarize your POV in one sentence, you’re invisible. How to track: Quarterly “message recall” check: ask prospects/customers: “What do we do?” “What do we believe?” “What are we known for?” 6) Dark social + word-of-mouth What it is: The off-platform sharing that actually drives deals: forwards, screenshots, Slack drops, “my friend sent me this.” Why it matters: A huge percentage of B2B buying happens in private. If your GTM can’t see dark social, you’re flying blind. How to track: “How did you find us?” (mandatory field) inbound screenshots / Slack mentions private replies after posts If your 2026 GTM dashboard doesn’t include conversations, ICP quality, dark social, and category position, it’s going to keep optimizing for attention… while someone else captures intent.

I met a sales team that tracks 27 different metrics. But none of them matter. They measure: - Calls made - Emails sent - Meetings booked - Demos delivered - Talk-to-listen ratio - Response time - Pipeline coverage But they all miss the most important number: How often prospects share your content with others. This hit me yesterday. We analyzed our last 200 deals: Won deals: Champion shared content with 5+ stakeholders Lost deals: Champion shared with fewer than 2 people It wasn't about our: - Product demos - Discovery questions - Pricing strategy - Negotiation skills It was about whether our champion could effectively sell for us. Think about your current pipeline: Do you know how many people have seen your proposal? Do you know which slides your champion shared internally? Do you know who viewed your pricing? Most sales leaders have no idea. They're optimizing metrics that don't drive decisions. Look at your CRM right now. I bet it tracks: ✅ When YOU last emailed a prospect ❌ When THEY last shared your content ✅ How many calls YOU made ❌ How many stakeholders viewed your materials ✅ When YOU sent a proposal ❌ How much time they spent reviewing it We've built dashboards to measure everything except what actually matters. The real sales metric that predicts closed deals: Internal Sharing Velocity (ISV) How quickly and widely your champion distributes your content to other stakeholders. High ISV = Deals close Low ISV = Deals stall We completely rebuilt our sales process around this insight: - Redesigned all content to be shareable, not just readable - Created spaces where champions could easily distribute information - Built analytics to measure exactly who engaged with what - Trained reps to optimize for sharing, not for responses Result? Win rates up 35%. Sales cycles shortened by 42%. Forecasting accuracy improved by 60%. Stop obsessing over your activity metrics. Start measuring how effectively your champions sell for you. If your CRM can't tell you how often your content is shared internally, you're operating in the dark. And that's why your forecasts are always wrong. Your move.

Old vs New Account-Based Marketing (ABM). 1. 𝐆𝐎𝐀𝐋𝐒. Old ABM: We need more leads. New ABM: -Focusing on new logos with a high probability to buy -Expanding business with existing clients -Preventing churn of the key accounts 2. 𝐈𝐂𝐏. Old way: Broad firmographic + decision-makers. We sell to CFOs from the US-based helathcare organizations. New way: -More specific firmographics and technographics -Qualification criteria -Tier segmentation -Detailed Buying committee -Account enrichment (business insights, common connections, where account is in their journey) 3. 𝐋𝐈𝐒𝐓 𝐁𝐔𝐈𝐋𝐃𝐈𝐍𝐆. Old way: Sales wish lists + databases. New way: - Check 1st party intent and engagement data - Define accounts that fit ICP and demonstrate a high level of engagement or interest 4. 𝐏𝐄𝐑𝐒𝐎𝐍𝐀𝐋𝐈𝐙𝐀𝐓𝐈𝐎𝐍. Old way: Vertical or job-role message distributed through programmatic, landing pages, and email outreach. New way: - In-depth account research - Content aligned with the buyer's journey and buying committee - Personalization based on in-depth account research 5. 𝐖𝐀𝐑𝐌 𝐔𝐏. Old way: Programmatic display ads + sales outbound cadence (that infamous 21-touch). New way: - Multithreaded engagement with the buying committee on social and communities - 1:few or 1:1 events - Content co-creation - Personalized content hubs 6. 𝐌𝐀𝐑𝐊𝐄𝐓𝐈𝐍𝐆 & 𝐒𝐀𝐋𝐄𝐒 𝐏𝐋𝐀𝐘𝐁𝐎𝐎𝐊𝐒 𝐀𝐍𝐃 𝐀𝐋𝐈𝐆𝐍𝐌𝐄𝐍𝐓. Old way: Lead handover from marketing to sales when an account clicks ads, downloads gated content, or sign ups to the event. New way: - Alignment on GTM elements: target segments, ICP, buyer journey, message, warm-up and activation - Joint playbooks that include interactions with the buying committee -Joint reports - Weekly ABM programs and pipeline review meetings 7. 𝐌𝐄𝐓𝐑𝐈𝐂𝐒. Old way: ABM success is measured by new leads only. New way: - Revenue that is generated from new logos, existing pipeline (accleration) and existing customers (expansion) - Sales pipeline velocity and revenue metrics: ACV, win rate, sales cycle length - Leading indicators for every program ---- ABM ≠ lead generation. Don't be fooled that you can buy an ABM platform, prospect thousands of accounts with programmatic ads and automated outbound cadence. ABM requires good GTM fundamentals and close collaboration between marketing and sales to: - Select accounts with a high probability to buy your product - Creating awareness and demand through manual engagement with the buying committee members and personalization - Thorough playbook planning and review It requires a lot of manual work. But this is the only way to generate enterprise, 6-7 figure deals. On 19th Oct I'm co-hosting a webinar with Leanne Chescoe from Demandbase to share practical examples of Sales and Marketing's Collaborative Journey to Revenue Acceleration. Save your spot here: https://lnkd.in/dYzjX2_w #abm #accountbasedmarketing

Something cool I realized over the years: you should build process in your company EXACTLY like you build software as an engineer. If you're starting a company or team today and want to build great processes, do what software engineers do, just replace "software" with "process": 1. Start with no process. 2. Make small, frequent updates to your process. Updates should be small but complete. 3. Solve real problems with your updates. - Always start with the most important problems. - Solve bugs and improve quality. - Identify real problems by performing a root cause analysis on events that ACTUALLY happened and that you’re trying to avoid going forward. 4. Push those updates to the machine that executes them. When you make process changes that humans need to follow, always “push it to their 🧠” by notifying them of the process change. 5. Don’t just accumulate processes. Perform “garbage collection”: occasionally reexamine your process and delete what doesn’t serve us anymore. 6. Your process should have one entry point. Every software system has an entry point. Build a central playbook for your team and company and make it the entry point, to ensure that everyone within your team has an entry point into your full process, and doesn't have "blind spots". Going deeper: --- 1. ACTION QUALITY I think about all actions in all processes in 3 categories: 🟢 GUARANTEED: these are actions that are software-controlled, and don't require human discretion. They are executed on 💻 Example: starting 2022, every sandbox sign up at Unit sends a welcome email. 🟡 MOSTLY GUARANTEED: these are actions that happen because we expect people to follow a playbook. We give them feedback and help them develop habits to do it. They are executed on 🧠 Example: in 2021, we had a step within the sales playbook to send a welcome email for every sandbox sign up. 🔴 NOT GUARANTEED: these are actions that are not written in playbooks: implicit expectations, reminders in people’s heads or a message in Slack 2 years ago. They are executed on 🧠 Example: in 2020, I had a reminder in my head to send a welcome email for every sandbox sign up. --- 2. ROOT CAUSE ANALYSIS In the Israeli army, there is a saying that "all rules were written in blood". If you instill a culture of root cause analysis in your company, it will AUTOMATICALLY upgrade your process over time: - Upgrade 🔴 not written in a playbook into 🟡 written in a playbook. - Upgrade 🟡 written in a playbook into 🟢 fully automated. Below is how we like to do root cause analysis at Unit.

I audited a 250 rep sales team last month. Only 7% were following the sales process. And leadership had no clue. Here's what I discovered when I dug into their "successful" sales operation: The company spent $250K on Challenger training. Built beautiful playbooks. Had detailed process documentation in Salesforce. Everyone talked about their "world class sales process." But when I listened to actual call recordings and analyzed their CRM data... → 47% skipped discovery entirely and went straight to demo → 73% never asked about budget or timeline → 91% couldn't articulate clear next steps after calls → Only 7% actually followed the process they were trained on The reps weren't broken. The system was invisible. Leadership measured activity metrics (calls, meetings, emails) but never measured behavior (did they do discovery? did they create urgency? did they build business cases?). You can't improve what you don't measure. Most sales leaders track vanity metrics: Number of calls made. Number of emails sent. Number of meetings booked. Elite sales leaders track conversion behaviors: ✅Percentage of deals with completed discovery ✅Percentage of opportunities with quantified pain ✅Percentage of proposals with business cases attached When you measure the right behaviors, you get the right results. Your team isn't ignoring your process because they don't care. They're ignoring it because there's no accountability for following it. Start measuring what matters. — Activity isn’t the problem. Your reps are busy.  The question is … are they effective? https://lnkd.in/ghh8VCaf

Conor's Startup Sales and Marketing Playbook™ I’ve been asked what our early playbook was and I thought it would be helpful to share. **When we were acquired for $70M, we had ~ $10M in ARR growing ~60% with 86% gross retention, 116% net retention, really good sales and marketing efficiency, and had done so with very limited investment ($4M). We are now north of $50M in ARR.** ----- STEP 1 - GET PEOPLE TO COME TO YOU 1️⃣ We turned our data into research that people subscribed to. Customers that come to you have more trust. This leads to higher retention, better profitability, and greater likelihood of signing up. 2️⃣ Be the first plumber to respond. ~70% of customers choose the first vendor that responds to them. Be first. Anybody who downloaded our research was sent directly to my inbox. I tried to email them within 5 minutes with a personalized message. 3️⃣ Get on the plane. I was on a plane constantly and filled my calendar as much as possible while on the road - 5-10 meetings a day. Nothing replaces face time. Getting on the plane also creates a sense of urgency for meeting while you are in town. 4️⃣ Meet with everyone. Helping someone that can’t help you creates a deep meaningful connection and creates a powerful reputation for you in the market. It's also just a nice thing to do. I would meet with students, teachers, consultants between jobs, influencer marketing enthusiasts. If you subscribed to our newsletter, I tried to be helpful. They told their friends, etc. STEP 2 - DON’T SELL. DELIVER VALUE. 5️⃣ Extreme preparation. Even if I was meeting for coffee, I would come into the conversation having researched the person, their brand, and their competitors. I would even print and bind the research. This made a very strong impression particularly when they didn't expect to receive the research. 6️⃣ Value first. I would never talk about what we do unless asked. I would center all of my attention on delivering value in the conversation. Helping people learn and get better. Inevitably they will ask, “How does this work? What are the next steps?”. This is much much better. STEP 3 - LONG TERM VIEW 7️⃣ 95% of customers aren’t buying today. Don't force a sales conversation. Let them come to you when it is the right time, but stay top of mind with regular touch points. Deliver value in every interaction (here is some new research, we’re holding a really cool event, etc.) 8️⃣ Focus. Sign up the right customers for the things you are best at. 70% of our new customers are either a referral or a user that brought us with them to a new company. Ensure that everyone you bring in is very likely to have a good experience. This compounds over time and creates trust. I turned a customer down for not being an ideal fit and they invited me on their board. I hope that was helpful! I'm happy to help anyone that is early in building their company. Just shoot me a message or comment. Onwards and upwards 🚀

I was ready to quit.  My startup was flatlining.  Sales were a rollercoaster—one month we were celebrating, the next we were scrambling to make payroll.  Then, everything changed.  We discovered a systematic sales approach that transformed our struggling venture into a thriving powerhouse.  𝗛𝗲𝗿𝗲’𝘀 𝘁𝗵𝗲 𝘁𝗵𝗶𝗻𝗴:   ↳ It wasn’t flashy.   ↳ It wasn’t revolutionary.   ↳ It was just consistent, measurable, and repeatable.  𝗛𝗲𝗿𝗲’𝘀 𝗵𝗼𝘄 𝘄𝗲 𝗱𝗶𝗱 𝗶𝘁:  1️⃣ 𝗟𝗲𝗮𝗱 𝗚𝗲𝗻𝗲𝗿𝗮𝘁𝗶𝗼𝗻 We defined our ideal customer profile and launched targeted campaigns.  2️⃣ 𝗤𝘂𝗮𝗹𝗶𝗳𝗶𝗰𝗮𝘁𝗶𝗼𝗻 We built a scoring system to prioritize high-value leads.  3️⃣ 𝗢𝘂𝘁𝗿𝗲𝗮𝗰𝗵 We created templates for every touchpoint—cold emails, follow-ups, you name it.  4️⃣ 𝗗𝗶𝘀𝗰𝗼𝘃𝗲𝗿𝘆 We developed a framework to uncover customer pain points.  5️⃣ 𝗣𝗿𝗲𝘀𝗲𝗻𝘁𝗮𝘁𝗶𝗼𝗻 We standardized our pitch decks and demo scripts.  6️⃣ 𝗡𝗲𝗴𝗼𝘁𝗶𝗮𝘁𝗶𝗼𝗻 We set clear guidelines for discounts and terms.  7️⃣ 𝗖𝗹𝗼𝘀𝗶𝗻𝗴 We implemented a smooth handoff process to customer success.  𝗧𝗵𝗲 𝗿𝗲𝘀𝘂𝗹𝘁𝘀? ↳ 37% shorter sales cycles   ↳ 52% higher conversion rates   ↳ 215% revenue growth YoY   ↳ 28% lower customer acquisition costs But the real win?  Predictability.  We could forecast with accuracy, scale efficiently, and sleep at night knowing we had a repeatable path to success.  𝗛𝗲𝗿𝗲’𝘀 𝘄𝗵𝗮𝘁 𝗜 𝗹𝗲𝗮𝗿𝗻𝗲𝗱: Consistency > Charisma   Data > Gut Feelings   Process > Luck This systematic approach didn’t just save our startup—it became our competitive advantage.  👉 Want to transform your sales?  Stay tuned for the launch of “The B2B Sales Playbook”—a step-by-step guide to building a scalable, predictable revenue engine.  P.S. What’s your biggest sales challenge? Drop it in the comments, and let’s brainstorm how a systematic approach could help.  #SalesTransformation #StartupGrowth #B2BSales

Founder-Led Sales Bootcamp #10: Systemise Before You Scale You’ve sold the first few deals. You’ve iterated. You’ve survived rejection. Now you’re thinking… maybe it’s time to hire a salesperson? Not so fast. Most founders make their first sales hire too early, and without a clear process, that hire ends up guessing, wasting leads, or burning out. Founder-led sales isn’t just about proving you can sell. It’s about building something someone else can repeat. If you're still winging it every time, you're not ready to scale yet. System first, sales team second: 1️⃣Your ICP is crystal clear - Everyone knows who to go after and who to ignore. It’s written down, tested, and used daily. 2️⃣Messaging is mapped - Cold outreach templates, objection responses, discovery call structure, and a demo flow - all captured, tested, and editable. 3️⃣ A basic CRM is live and in use - You’re tracking stages, calls, close rates, and reasons for deals lost. This data will help your new rep ramp 10x faster. 4️⃣ You’ve sold at least 10–15 deals yourself - You’ve heard the objections. You’ve tweaked your pitch. You know the red flags. You’ve built scar tissue that will become their training guide. 5️⃣ You’ve documented the playbook - One doc with everything: ICP, email templates, call structure, follow-up cadence, pricing talk, MAP examples, key metrics. Action plan: 💡Open a doc today called “Sales Playbook V1.” Start brain-dumping what’s in your head. 💡Record two of your best calls. Discovery and demo. These become onboarding gold. 💡Write a 30-day onboarding plan: shadowing week, joint calls, solo calls with review. Keep selling. You don't stop being a founder salesperson for a long while yet!

Why are the smartest sales teams focusing LESS on their pitch? Ordinary sales teams are laser-focused on their pitch, their products, their quotas. But the key to winning more deals is to forget about yourself and deeply understand the forces shaping your customer’s world. This is where Porter’s Five Forces comes in. Originally designed to analyse industries, it’s also a game-changing framework for sales strategy. Here’s how it works when applied to your buyer’s reality: 1️⃣ Competitive Rivalry How fierce is your customer’s competition?  Are they battling for market share, undercut on price, or innovating to stay ahead? The more you know, the better you can position yourself as a strategic partner, not just a vendor. 2️⃣ Threat of New Entrants Is your customer worried about startups disrupting their space?  If so, how can your solution give them a head start or build a barrier against competitors? 3️⃣ Threat of Substitutes What’s pulling their customers away - alternative products, new trends, or cheaper options? Position your offering as their answer to this risk. 4️⃣ Bargaining Power of Suppliers Are your buyers under pressure from suppliers?  Offering solutions that improve efficiency, reduce costs, or mitigate risks makes your pitch irresistible. 5️⃣ Bargaining Power of Buyers If your customer is in a price-sensitive market, how can you help them stand out or offer more value to their end users?  Solutions that improve their value prop can tip the scales in your favour. Here’s an example.  Imagine working with a retail client whose margins are being squeezed by rising supplier costs (Force #4). Rather than pitching a generic solution, you show how your product can help them optimise inventory, streamline operations, and ultimately negotiate better supplier terms.  The value becomes clear: you’re solving their specific challenge, not just selling. 💡The main takeaway from this When you understand the external pressures shaping your customer’s business, you’re no longer a salesperson, you’re a strategist. Are you incorporating these “forces” into your sales playbook? Let’s discuss in the comments, I’d love to hear how you’re positioning yourself as the solution in your buyers world! #salesstrategy #portersfiveforces #salesinsights #customercentric #b2bsales #strategicselling #salesleadership #businessstrategy #salesgrowth