Developing a Sales Playbook for Training

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

Sales teams often build from the top down. That’s why they break. I’ve spent decades studying what separates consistent performers from one-hit wonders. It comes down to this pyramid. Start at the foundation. Habits. Three clear priorities every morning. Follow up with purpose, not just to check in. Maintain clean systems. Build momentum through small daily wins. Consistent structure beats motivation every time. Next level up. Skills. Discovery that uncovers real impact. Objections handled early, not late. Negotiation anchored on outcomes. Demos that show value created, not features listed. The best sellers talk less, listen more, and guide with intent. Then comes Mindset. Treat rejection as feedback, not failure. Build confidence through preparation, not personality. Stay curious. Optimize for learning first, outcomes follow. Growth-oriented sellers outperform those chasing quick closes. Now you’re ready for Process. A predictable pipeline rhythm. Templates that move fast but personalize where it matters. Measure what converts. Forecast with evidence, not optimism. Disciplined process closes more deals than instinct alone. Finally, Edge. Build a reputation that precedes the meeting. Share wins and playbooks internally. Run experiments, not guesses. Coach others. Visibility and credibility create warmer referrals and more inbound.

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!

Founder-led sales is often the most misunderstood advice given to early-stage entrepreneurs. Too many founders think it means they need to be a charismatic 'closer' who can single-handedly land the first 20 customers. The true purpose isn't just to sell, it's to build a repeatable system, a playbook so effective that you can hand it off to your first sales hire and it just works. I often meet founders who are amazing salespeople, but their entire process lives in their head. In fact, I was one of these founders so I know from experience that it's 1) not a scalable solution 2) has key-person dependency. The founders I know who have nailed their sales process know they are not just selling a product, they're building a system that scales. Here’s some ideas on effectively building a sales playbook that I've observed over the last 10 years of investing into early stage startups: ✔️ Document Every Step As If for a New Hire. Seems obvious but create a living document that outlines your entire sales motion from the first email outreach template, to the questions you ask on a discovery call, to the way you handle common objections. Write it with the discipline of a training manual, because that's exactly what it will become for your future sales hires. ✔️ Record Your Calls to Create a "Greatest Hits" Library. Use a tool like Gong or Fathom to record your sales calls. This isn't just for your own self-improvement, it's to create a scalable training tool. A library of your best calls is an invaluable asset that teaches a new hire the nuance of how to talk about the product, navigate customer concerns, and articulate value. ✔️ Build a "Minimum Viable CRM." Even if it's just a simple Pipedrive/HubSpot/Airtable setup, start tracking your pipeline with rigor. Proving you have a disciplined process and understand your conversion metrics is just as important as proving you can close a deal. It shows investors (and the team) that you think like a system-builder, not just a solo operator. The goal of founder-led sales isn't to be the hero salesperson forever. The ultimate success of founder-led sales is when you've built a machine so effective, you can fire yourself from the job. Love to hear other ideas on building a sales playbook from founders who have experimented with this 🙌🏼

Every rep on your team can explain what your product does. Half can explain the benefits. Maybe three can explain why it matters to the person they're talking to right now. That's the problem. Almost nobody connects the dots to show buyers why any of this actually matters to their specific situation. Features: Our platform has advanced analytics.  Benefits: You can track performance metrics in real-time. So What: And...? Why does that matter to this particular buyer? Kimberly Pencille Collins from #samsales Consulting laid out a framework during a Sales Assembly course this week that forces you to answer six questions before you're allowed to send an email: Question 1: What challenge is this buyer facing? Not generic pain points. Specific, day-to-day frustrations for this persona in this role at this company size. Question 2: Why is it happening? This is where you prove you understand their landscape. Not just what's broken, but why it's broken. This is your insight moment. Question 3: What happens if they do nothing? Cost of inaction. Make the status quo intolerable. What do they lose by staying put? Question 4: What do you actually do? Not "we make your life better" - tangible, concrete, specific. Are you consultants? Tech? Services? Tell them. Question 5: How does this solve the problem? Connect what you do directly back to the challenge you laid out in question one. Question 6: So what does this mean for them? This is where most reps stop too early. You've explained the solution, now connect it to their actual life. "Your teams will be able to create a playbook of simple plays that keep the pipeline ticking while you nurture difficult buyers." That last sentence isn't a feature. It's not a benefit. It's RELIEF from a specific anxiety that VP of Sales has about pipeline coverage. The exercise creates longer emails initially. You can edit down later. But you HAVE to answer all six questions or you're just throwing features at people who aren't thinking about your solution right now. Kimberly's point: This is your mortar. The messaging you're fed from marketing is your bricks. This framework is how you bring it together and become a consultative seller instead of a walking product brochure. Try this on your next three cold emails. Answer all six questions. See what changes.

When I started coaching an SMB AE, he was a quota ghost—5 months straight, barely cracking 25% close rates. His company could have fired him. Instead they brought me in We tore into 1:1s, call replays, deal autopsies. By month 7, he was closing 60% of his demos and got promoted to Sr. AE. Here’s the 5-step gut-punch playbook we used to turn his sales around: 1/ Kill the Product Hype: He’d lead with ‘Let me give you a walkthrough of [product]’—and lose them in 5 minutes. We flipped it: ‘Out of [all the problems mentioned], whats #1 on your list to solve in next 90 days?’ Discovery became the star; the product waited its turn. 2/ Name the Bleed, Then Bandage It: He’d rattle off features like a spec sheet. I taught him how to alley-oop it to the feature. Example: "You said [PROBLEM] is killing you—here’s how we stop it." Pain-first hooks them; solutions seal it. 3/ Drop the Commission Chase: He’d oversell every deal, gunning for the fattest paycheck. We flipped it: "This solves your headache—nothing more, nothing less." Honesty built trust, and deals started closing faster. 4/ Cut to the Chase: His demos dragged with fluff—prospects checked out. We slashed the word salads, hit their pain point in 3 minutes: Example: "This is why you’re here; here’s the fix." Speed won them over. 5/ Sell the Win, Not the Widget: He’d geek out on feature details—felt like a CS onboarding call. We reframed it around solving the prospects problems in the shortest period of time. Example: "Here’s how this gets you [GOAL] faster." He stopped being a demo monkey. SMB reps have the chops—they just need the right lens.

I once lost a $340K deal because I didn't know what I didn't know. My VP sat in on the final presentation. Afterward, she pulled me aside and said: "You missed three opportunities to address their unspoken concerns about implementation risk." I had no idea what she was talking about. Turns out, she had a whole mental playbook for navigating those exact concerns. Specific phrases that work. Stories that land. But none of that was written down anywhere. And she'd never thought to share it with the team. She was busy and didn’t have the time to impart all of the knowledge living rent-free in her head. This is the part that kills me: Your sales leaders have playbooks in their heads that could 3x your team's performance. → They know which questions expose budget vs. priority issues → They've seen every objection pattern and know what actually works → They can read buying signals you didn't even know existed But the playbooks are invisible to the people who need them most. And if that knowledge stays locked in their heads (or only comes out during deal reviews when it's too late), reps are flying blind. Coaching isn’t just about feedback; it’s about transferring how great leaders think. Science backs this up: the most effective coaching activates the same decision-making patterns top performers use in real time. So what can you as a seller do about it? Make it stupidly easy for your VP to share their playbook. Try this: → "When I'm in negotiations, what are the 3-5 'give/gets' you've seen work best? I want to document this for the team." → "You've closed deals at the executive level. What evidence do they typically need to build the internal business case? I'd love to capture this." → "What are the top objection-handling ideas in your head that you wish every rep knew?" Ask these in a 1:1. Record the 15-min conversation. Socialize it with the team. Make the invisible visible. But here's the thing— Even when you do this, it's a 1-time fix. Next quarter, new reps start. The playbook stays tribal knowledge. I recently saw what Allego built to solve this exact problem.   It's not just another training platform. It turns that invisible playbook- all the coaching wisdom sitting in your VP's head - into something your whole team can access every day. The AI coaching literally embeds frameworks, objection responses, & buyer insights into reps' workflow. Human coaching is essential, but recent studies show that when those insights are reinforced by AI, sellers retain & apply them faster. So instead of learning the hard way (like my $340K loss), reps get real-time guidance from the playbooks that actually win deals. Your sales leaders' wisdom shouldn't be a secret. When it's scalable and accessible, everyone performs better. Curious how the brain responds to AI vs. human coaching? Check out the study behind this insight. (In comments - out of room!) What’s 1 piece of wisdom from your 1st sales leader that should've been in a “team playbook”?

𝐍𝐨 𝐬𝐜𝐚𝐥𝐢𝐧𝐠 𝐰𝐢𝐭𝐡𝐨𝐮𝐭 𝐚 𝐒𝐚𝐥𝐞𝐬 𝐏𝐥𝐚𝐲𝐛𝐨𝐨𝐤! Last week, we had the pleasure of hosting Yann Aubry and Vasco Alexandre at Serena for a Sales Squad dinner focused on one of the most critical assets for any scaling B2B SaaS company: the Sales Playbook. 🎯 Yann shared insights from his impressive experience at MongoDB, Cloudera and Forter — with hard-earned lessons from scaling SaaS GTM engines. 🔥 Vasco, fresh off Dotfile’s Series A, brought a sharp perspective on how to build a playbook during the transition from Founder-led sales to a full commercial team. I was joined by a stellar group of sales leaders from our portfolio: Louise Bayssat (Lifen), Nicolas Furlani (Joy ), Renaud Enjalbert (Klarys), Thibaut Doubet (Formality), Ugo Basciano (Evaneos), Vincent Le Gallic (Cometh), Flavien Guillocheau (PandaScore), Maxime D. (Descartes Underwriting) and Yann Leger (Koyeb) — thank you all for the rich conversation! Here are some of my key takeaways: 💡 When to build your Playbook? Once you feel you’ve reached PMF, have some deal repeatability, and want to build a true sales machine. 💡 Why it matters? To attract top talent (especially those used to structured orgs), accelerate onboarding & ramp-up, create consistency across geos, and align internal language & expectations. 💡 What should it include? Both artifacts and processes: Artifacts: ICP, Buyer Personas, Product Capabilities, Differentiators, Battlecards, Proof Points, Value Assessment, Mutual Plan… Processes: Weekly Rhythm, Pipeline Gen, Forecasting Guidelines, Sales Stages, Negotiation Playbook… ✅ Do’s & Don’ts: 🎯 Focus your ICP on where you already have PMF. Less is more. 💡 Founders should handle non-ICP prospects (=bus dev) to keep the core sales team focused. 🔗 Link Feature → Use Case → Customer Value Drivers 👤 For each Buyer Persona, clearly define their expected benefits. 🧠 Build a strong discovery guide to help AEs ask the right questions and reveal the problem (you’re best at solving). 📩 Anchor each sales stage with clear, objective outputs — not gut feeling. (e.g. A "champion" replies in writing to your Champion Letter.) 📊 In forecasting, track not just overall coverage, but coverage of qualified, visible opportunities. 📅 Make reps accountable: ask them to commit weekly on their forecast. 📞 Even with a BDR+AE setup, AEs should still generate part of their own pipeline — never lose touch with prospecting. ❌ Avoid a 250-page document. Use a concise guide with Notion links to detailed resources. 🎓Sales Enablement : Regular training with recordings of the best demos. Practical exercices : Simulations, roleplays, objection handling. 👀 Curious to hear from you: Have you built a Sales Playbook? What worked? What didn’t? Any best practices (or pitfalls) to share?

This playbook is the exact structure I rely on to keep my day disciplined, predictable, and outcome-driven I noticed one pattern across hundreds of reps: People don’t fail due to effort. They fail because their day has no order. They jump between tasks, chase notifications, and lose momentum without even realizing it. So I broke my workflow into 14 actions: 1. Start the day with “3-Lead Warm List” Pick 3 leads who showed: - job change - liked your post - visited your site or profile Message them first. Warm > cold. 2. Research each account for exactly 90 seconds Check only: funding hiring tool stack one friction point Stop after 90 seconds. Don't overthink. 3. Build a 12-contact sequence for every prospect Manual + email + LinkedIn + call. Same structure every time. This removes decision fatigue. 4. Send 2 custom Looms before 10 AM Each Loom: 20 seconds say their name show one problem That’s it. 5. Make 15 calls in the first hour No scripts. Use one question: “Want the short reason I reached out?” 6. Use the “3x3 opener” for every call 3 words → 3 seconds. “Caught you quick.” It lowers resistance instantly. 7. Use the “2-line LinkedIn first touch” Line 1: relevant event Line 2: question Example: “Saw you’re hiring 4 SDRs. Is lead volume keeping up?” 8. Block 25 minutes for pure calling (no CRM) Call 20–25 leads back-to-back. No admin. No notes. Notes later. 9. Send one “Insight DM” mid-day Simple pattern: “Most teams at your stage struggle with X. True or false?” This gets replies. 10. Run the “Reverse Follow-Up” Instead of “Any update?” say: “Pausing my follow-ups until you confirm priority.” This makes them reply. 11. Log notes within 60 seconds 3 bullets only: problem timeline next step Close the tab. 12. Send 5 “handover-ready” leads to AE daily Lead must meet: clear pain clear owner clear timeline Reps who pass clean leads get trust fast. 13. Revisit 3 “No replies” at 4 PM Use this line: “Found something better than my last message. Interested?” Gets instant opens. 14. End with “Tomorrow’s 5” Before logging out: Pick the top 5 accounts for tomorrow. Write their names only. This kills morning confusion. That's it!

During one of my mentoring sessions, someone asked, "How can I become a more successful sales leader?" Reflecting on my two decades of experience building businesses through consultative and relationship-based selling, it clicked that I had been following a consistent playbook. This playbook applies to B2B sales, such as opening and growing new accounts, and can be tweaked for B2C, like selling Tide Pods to billions of consumers. Here’s how it goes. Let’s say you are trying to sell business consulting services to senior leaders at a CPG company. 1. First, Sell Your Personal Brand Your personal branding gets you the first meeting. In sales, people buy from those they trust and respect. Position yourself as a knowledgeable and reliable expert in your field. 2. Engage on a Regular Basis, But Don’t Try to Sell Yet Find a way to engage with your prospect regularly. Spend time listening and learning about their world; don't try to sell yet. Share examples of what their peers are doing, preferably. Use these opportunities to subtly position your company brand in a way they hadn’t visualized before. 3. Sell the Problem Framework, Co-Expand the Framework To sell a solution, you need to sell the problem first. But before selling the problem, sell the problem framework that connects the solution to a bigger purpose, like SG&A reduction, revenue growth, or cleaner, brighter, and fresh-smelling clothes (Tide Pods). This is the most critical step. The framework needs to be logical and simple. Bonus points if the prospect co-develops the framework with you. Once they do, you occupy the space in their head on how they evaluate any solutions in the future, and your competitor won't even know that their proposals are being evaluated with the framework you defined. 4. Sell the Problem Once the prospect has the problem framework in their head, share what they are missing today within that framework that prevents them from achieving their bigger goals. That’s the part your company solves for, but you are not yet selling the solution until the prospect is in clear agreement on the problem. 5. Sell the Solution Once the problem is clearly defined and understood, present your solution as the ideal response. Your solution should address the problem directly and offer clear benefits in alignment with the bigger goals that can be evaluated using your framework. 6. Continue to Engage Until Sold, Continue to Engage, Period Just because you sold the solution doesn't mean the prospect will buy it immediately. They might think it over for days or weeks, consult peers, or evaluate your competitors. This is where you can offer references. If the prospect comes back with concerns or objections, don't panic—they are only trying to justify the purchase in their head. Help them with those points using data and proven facts. Eventually, they will come around and ask you for a formal proposal. At this point, you have increased your probability of winning. Focus on closing.