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

Most sellers focus on top-of-funnel signals. But there is serious power in also using signals that surface after the demo – when buyers go quiet or deals stall. I was chatting with my friend Saad Khan at Aligned this week, and he broke down how they use Digital Sales Rooms (DSRs) to track buying signals deeper in the funnel. Most people use DSRs as a content dumping ground. But here’s how to actually turn it into a bottom-of-funnel signal engine: 1. Map the real buying committee Every org is different. Use your DSR to track who’s engaging – not just your known champion. → Cross-check with your account map → Talk with your champion about these new players → Tailor content for the real decision-makers 2. Use engagement (or silence) as a signal No activity = no deal. If your room’s been dead for 2 weeks, that’s a sign. Time to re-engage, reposition, or de-prioritize. 3. Stack signals from other sources Combine DSR data with: → Former users re-engaging → Trial activations → Job listings tied to your initiative → Competitor activity Example: The procurement team is deep in your DSR looking at competitive content while your competitor’s AE is liking their exec’s posts. That’s not random. That's a signal. The best sellers today don’t just read signals in isolation. They connect the dots.

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.

Every sales training company preaches the same tired playbook. After training 10,000+ reps, here's what they're getting dead wrong: #1 "Just implement our methodology and watch magic happen" Bull. I watched a PE backed company burn $300K on methodology training. Six months later? Their win rate was 8%. EIGHT PERCENT. You don't have a methodology problem. You have a systems problem disguised as a people problem. #2 "More role plays equals better performance" Stop making your reps practice fake scenarios. I've seen teams do 100 hours of role plays and still freeze on real calls. You know what works? Recording actual calls and dissecting what went wrong. Then REAL playing the EXACT same situation that really happened. Real mistakes. Real learning. #3 "Every rep needs the same training" Your rep crushing 150% of quota doesn't need the same training as someone at 60%. But every vendor sells you one size fits all. That's like giving everyone the same prescription glasses and wondering why half the team still can't see. #4 "Focus on closing techniques" Wrong. 87% of deals die in discovery, not closing. But these companies spend 80% of training on "assumptive closes" and "urgency tactics." Your buyers aren't stupid. They can smell manipulation from the first email. #5 "Sales training fixes revenue problems" This one makes me angry. Your revenue isn't broken because reps don't know how to sell. It's broken because you have no visibility into why deals stall. No accountability structures. No management processes. No playbooks. We just helped a $35M company hit their number for the first time in two years. Zero hours of sales training. We fixed their systems instead. The truth? Most sales training is a $50,000 bandaid on a severed artery. Fix the foundation first. Skills come second. — Hey Sales Leaders! If you’re starting to agree with me, we should probably talk: https://lnkd.in/ghh8VCaf

The worst thing in sales isn’t losing a deal. It’s not knowing why your team lost it. Because if your sales team is celebrating closed deals without understanding the “why” or worse, losing deals and shrugging it off You’re not building a sales process, you’re building on luck. And luck doesn’t scale. Repeatable sales success comes from listening to the people who said no, really understanding buyer behavior, not guessing it. Sales leaders, your sales reps can’t sell effectively if they don’t know how buyers make decisions. This is where win-loss analysis becomes your secret weapon. You can’t build a repeatable sales motion without doing win-loss analysis. So ask yourself: → Are we collecting the voice of the customer consistently? → Do we analyze both wins and losses, or just move on? → Where does the sales funnel needs work and increase your win rate → Can we coach based on actual data, not just gut instinct? When you incorporate win-loss interviews and track behavioral patterns, your sales motion stops being reactive, and becomes repeatable. Here’s how I help leaders build sales processes that actually work: --> Start with win-loss interviews Have your reps talk to decision-makers on both won and lost deals. The goal isn’t to defend, it’s to understand. --> Run a most-mortem on every major deal Not just the losses. Reverse-engineer the wins too Because replicating success is just as important as learning from failure. The best sales playbooks are built from what’s already working. --> Document & share what works Turn buyer insights into frameworks your entire team can follow. Don’t hide it in a 1:1, scale it across the org. Because wins leave clues, and when you surface them, you create a playbook everyone can execute. Sales performance doesn’t improve because you push harder. It improves because you understand why things happen and make intentional changes based on that insight. These insights can improve your sales strategy, identify strengths and weaknesses, optimize your customer experience, and increase win rates.

DO NOT hire a salesperson until you do this first: Write down exactly what you want them to do every day to generate enough revenue to hit their targets. If you don't understand how to close $50k+ per month, then your new salesperson isn't going to figure it out for you. I see founders make this mistake over and over again. Everyone wants predictable revenue growth. We read books like From Impossible to Inevitable or The Science of Scaling and rush back to our teams, ready to implement what we’ve learned. But most of the advice out there is noise if you don’t have this one thing: A documented sales process. If you want consistent and predictable sales performance, you need consistent and predictable action from your team. And that starts with being painfully clear about what your team should do and how to do it. Here’s the formula that helps explain the idea: [Consistent Effort] + [Consistent Enthusiasm] + [Consistent Messaging] + [Consistent Lead Quality] = Consistent Results When your inputs are variable, your outputs will be too. So what’s the fix? Write. It. Down. Put it on paper in black and white. Give it to your team. Make sure every rep knows the exact steps to succeed in their role. Most founders spend more time recruiting than onboarding. That’s the mistake. They chase the “right hire” instead of giving new hires the tools to succeed. I’ve made this mistake myself. At one point, I had tenured reps all running different versions of our sales demo: different decks, different intros, different next steps. That was my fault. So I sat down and started a doc: “How to Run a Demo” It covered everything: - How to set up Zoom - The structure of the call - Questions to ask - Objections and how to handle them - How to use the deck to steer the conversation - How to end the call and set clear next steps That five-page doc turned into an 80-page playbook we used to scale to $30M in ARR. Was it overkill for experienced reps? Probably. But it absolutely helped us onboard and ramp new reps faster. Because it gave them direction and confidence. It showed them how to be successful in their role. So do this before you make your first sales hire. Write down how to do the job well, give it to the salesperson, and hold them accountable to running the process that you have given them. If you want consistent outputs, you need consistent inputs. And to get consistent inputs, you have to show people what good looks like So write it down, starting today.

If you’re still using sequence-based outbound in 2025, you’re doing it wrong. Here's why 👇 You know the play: Day 1 – Email Day 3 – LinkedIn message Day 5 – Bump email Day 8 – “Just circling back…” It’s mechanical. Predictable. Easy to spot from a mile away. And buyers aren’t responding to it anymore, because it’s not about them. It’s about your calendar. The best outbound right now isn’t based on days. It’s based on signals. Signals that show someone is thinking about the problem you solve right now. Here’s what I mean: They viewed your profile They liked or commented on your post They followed you last week They just changed jobs Their company raised a funding round They engaged with a competitor’s content These are all signals. And if you’re not acting on them, someone else will. At Atticus, we’ve rebuilt the outbound engine around signals, not sequences. Here’s what that looks like in practice 👇 1. Scrape the signals We track profile views, post engagers, comment threads, company milestones, and more. We use tools like: Valley Clay Breakcold PhantomBuster And combine it all into a dynamic lead list. New signals get added daily. No static list-building. No manual scrape sessions. 2. Filter for ICP fit Not everyone who views your post is a lead. So, we layer in job title, company size, industry, and recent activity. Then score them against your ICP. You end up with a live lead list updated daily, based on actual buying signals. 3. Trigger the right touchpoint Based on the signal, we trigger a message on the right channel: → Viewed your profile? DM. → Engaged a post? Comment > then DM. → Job change? Email with reference to the new role. → Competitor follow? Positioning-focused message that reframes why you’re different. All written to feel like a real conversation, not a sales sequence. 4. Track what converts Every touchpoint gets logged. We track responses, meetings booked, and what signals led to the highest conversion rate. You start to see patterns: “Profile views after webinars respond at 23%.” “New followers with job changes → demo within 7 days.” That’s how you scale what works. Not a guess. Not spam. Just signal > response > call. The result for us? → 40–50 SQLs/month → 3–5x reply rate compared to sequence-based outreach → No SDRs needed It’s a full-funnel outbound system. And it’s built to start conversations, not burn your domain. Still running outbound from a 5-day drip campaign? It’s time to level up. Interested in having us build this for your business? DM me. And I’ll walk you through how we do it.

I’ve been CEO of 4 different VC-backed startups, with valuations ranging from $0 to $150M+. Here are the 3 biggest sales mistakes I see at every company (no matter the size or stage): 1. Confusing “best” and “average” Signing a $300k deal with Coca-Cola was a game-changer. They got huge value, and were willing to tell people about it. So we told ourselves, “We just need to find more Coca-colas." Fat chance. This way is thinking is natural for us salespeople. You signed a $300k deal – the next one should be $350k! It’s tempting to think your your best deal is now your new standard. But it doesn't work that way. Don’t create a plan where suddenly every deal is supposed to be $300k. You’ll strike out and burn a ton of time and talent trying. 2. Premature scaling The math seems to make sense: Number of reps x Quota = Target. Hire the reps, make sure rep hits quota, and you’re golden. The problem is: it rarely works that way. New reps struggle to get up to speed. Response rates are lower → less pipeline Conversion rates are lower → fewer deals closed Average selling price is lower → quotas are missed Your reps doing 140% of plan can’t make up for 5 at 30%. It’s past time to throw out that old math. You can’t add reps to hit an aspirational goal. This market demands you match reps to actual demand. You don’t hire when your plan says you need more production. You hire when you have more in-ICP meetings than you can handle. But how do we hit the number we promised we’d hit??? Bad news – you aren’t going to hit it anyway. Signing up for a crazy goal on bad math just puts your head on the chopping block. Instead, reset expectations. Burn less, longer, to build demand. Grow when demand requires it. 3. Insufficient focus on after-the-sale In the olden days, you could sign $1M deals. Customers knew they couldn’t get value until they fully deployed your solution. Not anymore. SaaS has made trial simple. Time to value is faster. Deals start smaller. It’s easier to sell in. But it’s also easier to churn out. Churn is up in this market. Customers are looking to cut costs. Worse, they're looking to simplify tech stacks and cut vendors. Gone are the days when you can sell a deal and run away. But too many still do exactly that. It’s human nature. After all, Comp Plans get a lot less exciting after Closed-Won! The best sales leaders know that next year’s plan relies on keeping and growing this year’s customers. They deploy their time and people accordingly. TAKEAWAY: Each of these mistakes starts with natural thinking. But it doesn’t work. Hard markets demand focus and discipline. Focus your ICP. Celebrate your big wins, but don’t expect to repeat them every time. Don’t grow faster than actual, real, in-ICP demand. Stay connected to customers throughout the year. Renewal matters. Optimism is great. But hopeful planning is a business (and career) killer. Get it right and you can still win in this market.

Want to drive more expansion? Here's the playbook I learned at Salesforce - Find gaps with customers - Create offers to address gaps - Market this to your expansion list - Introduce offer in sales and CS mtgs - Lay the groundwork and spark interest - Start sales conversations with stakeholders - Close Expansion Opportunities and grow Accts! Whitespace is a key way to find those gaps. 𝗣𝗥𝗢𝗗𝗨𝗖𝗧 𝗪𝗛𝗜𝗧𝗘𝗦𝗣𝗔𝗖𝗘 - What products does each customer have? - What products does each customer NOT have? - Which products have you yet to present to them? *This is pretty basic but so often not executed well! 𝗦𝗧𝗔𝗞𝗘𝗛𝗢𝗟𝗗𝗘𝗥 𝗪𝗛𝗜𝗧𝗘𝗦𝗣𝗔𝗖𝗘 - Which key stakeholders do you know? - Which key stakeholders do you NOT know? - Where can you open up new key relationships? OVERLAP - Where do these overlap? - You can sell a new product to an old contact - You can sell more current product to a new contact - But man is it easier to sell new products to new contacts Let me share some examples from my days at Salesforce: - VPs of Sales bought Salesforce (Sales Cloud) - VPs of Service/COOs bought Service Cloud - CMOs bought Pardot or Marketing Cloud - CFOs bought more licenses at discounts We had a different play for each product and each stakeholder. It wasn't this cut and dry though. Sometimes VPs of Sales bought Service Cloud or Marketing Cloud. CFOs often wanted the best contract terms and were my bread and butter for expansion, but it wasn't always them driving this. Most often, though, our relationship started with the VP of Sales who bought Sales Cloud and didn't really care about anything else we had to sell. This playbook is how Salesforce "landed and expanded" accounts and doubled spend for the average customer within 12 months of the initial purchase when I was there. More details in yesterday's 📰 𝗥𝗲𝘃𝗢𝗽𝘀 𝗪𝗲𝗲𝗸𝗹𝘆 📰 https://lnkd.in/ezX9iMjr ✌️