Sam Taylor

Most sales leaders focus on their top performers. But your best reps will crush quota whether you help them or not. Here's the uncomfortable truth about scaling revenue... Your top 10% will succeed despite you. They'll figure out how to sell your product and close deals even if you give them zero support, no collateral, and an undefined ICP. But you can't build a scalable revenue engine on top 10% talent alone. It's just math. Even with a rigorous interview process and strong recruiting brand, our 12-month retention rate at Levelset was around 55%. And that was GOOD. The key to scaling isn't finding more unicorns. It's raising the floor for everyone else. That means writing down exactly what success looks like. Not just hoping good people will "figure it out." I learned this the hard way. For the first 4 years (or so), we closed deals almost in spite of ourselves. No real sales playbook. No defined process. Just talented people working hard. When we finally documented our exact process - from first touch to close - our ramp time plummeted and consistency shot up. The uncomfortable truth? Most founders spend way more time recruiting than preparing to train and support their hires. Your playbook doesn't need to be fancy. Start with one document: "How to Run a Demo." Make it painfully detailed. Your top reps will hate it. Your new reps will love you for it.

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What are your thoughts on seeing their deals mapped out in a deal velocity scorecard? This is part of the performance dashboard we're building for MidFunnel. The idea is that sellers can see how their deals are faring. Managers can quickly get a pulse on deal progress. The velocity is calculated based on the responsiveness of communication. Next we're considering adding qualitative insights on prospect eagerness as well. #sales #sales-tech

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Do not read this post if your quota attainment per seller is >70%, Average Deal Sizes have grown >2x in the last year and if you don't need more Sales Pipeline. For those of you that do, I'm proud to announce a revolutionary way for your GTM teams to drive productivity with DatabookGPT. But, don't listen to me, listen to our customers: “As we pilot the new DatabookGPT, we find it’s driving down the creation of our initial account plans from seven weeks to seven minutes,” said Chris Smith, Chief Strategy Officer at Grant Thornton. “It's a game changer." "Every AE at Databricks lives by our value of 'customer obsessed.' Understanding the value the Data Intelligence Platform delivers for every customer is essential. DatabookGPT was built on Databricks and supports our sellers by giving them that account intelligence," said Ron Gabrisko, Chief Revenue Officer at Databricks. "Through our teams' use of Databook, we saw our average deal size increase by 54.8% in FY24", said Kirsty Mundy, WW Field Enablement Microsoft, Industry Solutions Delivery Learn more at www.databook.com. It's Generally Available now for companies looking to grow their deal sizes, shorten their sales cycles, and grow pipeline. #accountintelligence #enterprisesales #strategicrelationshipmanagement

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The way most SaaS companies structure sales leadership compensation creates inter-team competition in a *NEGATIVE WAY* that costs millions of $’s in revenue and 100’s of hours of headaches a year. Here’s why (and a simple change you can make to fix it): Typically sales managers are compensated on the performance of their direct reports. For example, if their 8 Account Executives crush their targets, the manager's compensation reflects this. This sounds reasonable, right? But what about the rest of the sellers? What about the other 25 Account Executives who need to succeed for your company to hit its growth goals? Sales Managers have different strengths and need to be incentivized to help the ENTIRE sales organization, not just THEIR team. That’s why every time I started a new sales leader role here’s what I did…. I switched the manager comp plan so 20% of their variable earnings were based on the total sales orgs performance, not just their direct reports. I often got pushback, but this simple change always led to stronger collaboration, teamwork, and unity. And helped us avoid account controversy, resentment and entitlement. Sales leaders aren't coin-operated, but they are human and humans respond to incentives. Make sure you're incentivizing the right behavior. And create one team.

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Top performing AEs achieve 4.8x FASTER DEAL VELOCITY. Imagine 1 report & 6 Qs accelerating your Q3/Q4 deals! Every quarter feels like a short quarter. Q3 and Q4 are no exception. Summer getaways, mid-term breaks & the holidays. → Good AE performance is exiting H1 on 40%. → Most AEs need to close 60% + to hit quota. → Speed is everything in Q3 and Q4. If you can add 4.8x deal velocity, then it gives you a great chance to exceed quota! How do top performing AEs achieve 4.8x deal velocity? They prospect the best-performing personas. Here is the rub... You need to check the data first hand. Check the CRM for closed deals. → Run a report for closed deals in H1. → Run a report for closed deals last FY. Get a decent sample size. It can be deals closed in your patch. Deals closed by your team or wider org. It can be deals closed in your vertical globally. Run a report that fits your situation. Then check the Top 5: Q1. Top 5 Largest Deals Q2. Top 5 Shortest Deal Cycles Q3. Most common Personas? (Champions, Economic Buyers) Then take it a step further. Q4. What were the exact pains? Q5. What were the exact use cases? Q6. What were the desired outcomes? tldr: to achieve 4.8x deal velocity... hat tip to Ebsta for the data. → Pipeline Generation: Use this to prospect the right persona so you can find deals with higher velocity. → Progress Pipeline Get all the top personas involved in your deals. Make a concerted effort to have more stakeholders engaged. p.s. If you’re an Account Executive looking to fill your pipeline and exceed quota in 90 days or less, I've space for 5 AEs in August. Send me a DM saying "90" to find out more. 🔥 🍾

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How we drove $2.5+ mil in pipe for a 50+ BDR org: Look at a list of key contacts who left their previous company Enrich in Clay with current company, company size Cross reference with Salesforce to see account owners, ROE Check previous, current accounts with Gong AMA to build out an account brief Push into Evabot AI for Sales Outbound 2.0 to build a 100% custom AI sequence BDRs execute Super admins start a new deal cycle $2.8 mil and counting in pipe generated (Granted... 1 mil came from Coca Cola... but if we helped start an opp at Coca Cola, I'll take it)

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Maintain a sufficient pipeline of 4 times your quota. Adequate pipeline helps to relieve the stress to perform on specific deals. Reduced stress allows you to approach sales as a competitive game and a fun challenge. Do not take success per deal personally. Treat each deal as a competitive contest you can walk away from proud of knowing you gave your best effort. Building relationships with your customers is the fun part of sales. Ask personal questions. Invest time to learn about your customers as humans. Personal relationships require empathy, time, and patience. Extra credit challenge: Getting a hug from your customer confirms you have a personal relationship. Credit to Drew Elam

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Salesforce revised its pipeline coverage ratio to 3x, shedding light on the math keeping execs up at night. How can 1 ratio blow up your entire GTM model? It's not rocket science. It's just math. Particularly, pipeline generation math. Salesforce went from 2x to 3x. You might be going from 3x to 4x, or even 4x to 5x. What does this mean? Assumptions about pipeline coverage are falling like dominos and leaving GTM orgs with a massive hole in their forecasts. When this happens, the math gets really bad, really fast. Picture this: you're a best in class GTM org like Salesforce and you've just updated your pipe coverage ratio from 2x to 3x. Needing 50% more pipeline is painful enough. But the punishment doesn't stop there. Pipeline generated by your sellers is also down. Buyers are reluctant to champion products, and budgets are tight. This leads to longer sales cycles, more discounting, and plummeting deal sizes. Across the board, reps are producing less pipeline. Ranges vary by category, but let's assume pipeline creation is down 25% for illustrative purposes. (We're going to keep the math simple, because specifics will vary by company). On a $100M new business goal, you'd previously need $200M in pipeline. At $1M in pipeline per AE, you could bring it in with a team of 200. Now you need $300M of pipeline to close that same $100M in revenue. AEs are creating $750k instead of $1M, so that same team of 200 is bringing in $150M in pipeline, only half what you need for the year. Draw out the math and you suddenly need 200 additional (fully ramped!) sellers to deliver the same $100M in revenue. That's DOUBLE the headcount. Your CEO and CFO's heads are spinning, because this wreaks absolute havoc on a company's operating model. But that's a post for another time. You can tweak the assumptions if you'd like, but it's terrifying any way you look at it. No amount of passion, skill, or dedication can overcome math. You can't escape math. The bad news? This doesn't seem to be going away any time soon. The good news? Recent advances in AI can change some of the assumptions around the people, process, and technology equation required to generate new pipeline. In the old world, the only answer would be to double headcount. In the new world, there are ways to drive enormous leverage into the equation. Scaling with people doesn't have to be the answer, you can scale people with AI like no time in history. Which means the cavalry could be on the way...

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When RevOps is really just SalesOps (And the CRO is really just the VP of Sales) 𝗦𝗔𝗟𝗘𝗦 𝗘𝗡𝗚𝗜𝗡𝗘 - Closing deals should work - Clear pipeline management process - Forecasting is as accurate as possible - But everything before & after is an issue 𝗠𝗔𝗥𝗞𝗘𝗧𝗜𝗡𝗚 - Has different goals - Maybe the target is MQLs - Has their definition of MQLs - And their definition of SALs, SQOs - Has systems with different metrics - Their reports don't match sales' reports - Leads routed from one system to the next - With lots of things falling through the cracks - Classic case of marketing/sales misalignment 𝗢𝗨𝗧𝗕𝗢𝗨𝗡𝗗 - Do SDRs report to marketing? - If so, we're misaligned there too - The goal may be meetings booked - So AEs have lots of leads and meetings - But maybe not the ones they really need - The ones that convert to pipeline/revenue - We have more misalignment & finger pointing - Do SDRs report to sales? - What content do they have? - What events and assets do they share? - What visibility do they have into engagement? - How does marketing align with their outreach? 𝗢𝗡𝗕𝗢𝗔𝗥𝗗𝗜𝗡𝗚 - Sales is paid to close deals - How do they hand off customers? - What is the onboarding process? - Who builds/maintains that process? - What is done if sales drops the ball? - What is done if sales overpromises? - How are incentives and comp aligned? 𝗥𝗘𝗧𝗘𝗡𝗧𝗜𝗢𝗡 & 𝗘𝗫𝗣𝗔𝗡𝗦𝗜𝗢𝗡 - Which customers are easiest to retain? - Which customers are most likely to churn? - Which customers are the easiest to expand? - How is this data used to improve sales targeting? - How do we maximize NRR if sales is in their own silo? For me RevOps drives value by getting into the weeds and finding ways to generate more revenue with the resources available. That includes SalesOps and optimizing the sales process to close more deals. However, if we stop there we end up with an expensive and inefficient revenue engine with high CAC, high Churn and low LTV. We end up with different departments chasing different goals in different systems with different reports and different definitions of success. What would you add to this? Anything I missed? ✌️

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As VP of Sales, I helped Syte go from $1M-10M ARR in 24 months. Here are the 5 changes we made to our enterprise sales playbook to 3x ACV to $150K: 1. Promoted a product strategy and pricing shift The same product cannot be priced 3x more to the same market, if not positioned and delivered differently. So my team and I ran experiments with positioning our multi-products as a suite with single pricing. I then partnered with Product to create a new pricing model and built a business case for this change. 2. Shifted mindset from 'Selling a product' to 'Selling a transformation' 'Selling a product' means AEs are focused on product-level pain (i.e. for Aligned; Not knowing who are the ‘hidden stakeholders’ involved in deals). 'Selling a transformation' means you're focused on your prospects' core priorities (i.e. for Aligned; Ensuring the sales team can effectively make the shift up-market by making complex deals easier to manage). Of course, both levels of value are important. The question is... Is your champion telling a 5, 6, or 7-fig ACV story? 3. Utilized our Head of Analytics in ROI/Cost of Inaction (COI) talks We were selling to eCommerce people, who are very numbers-focused. The challenge was that to get a 6 or 7-fig budget, we had to show there was a problem that was causing them to lose more. Many reps struggled with the spreadsheets and speaking the buyer’s financial language. So we looped our Head of Analytics (and SEs to learn this process) and created a framework for how to properly run COI/ROI conversations. The trust levels with our champion and their internal discussions changed completely. 4. Slowed down and tripled the steps of our POC process Seeing our tech in action was mind-blowing. We knew it was how we drove trust and set up competitors to fail. However, it was risky if not managed right. So we updated our POC process. We didn't start until a Mutual Action Plan was created in a call, which included the POC scope, timeframe, success criteria, resources needed on their end, and ideally an executive summary at the end. 5. Standardized the Challenger Sales as our go-to methodology We were selling an innovative new category product, in an outbound-led motion. This meant we had to sell against the status quo, educate about problems prospects weren't aware of, and tie them to strategic priorities. AEs who were only teaching about our product, couldn’t create a compelling case for a 6-fig funding. The Challenger Sales became our go-to approach for how we run intro calls, how we teach, reframe how prospects approach their problems, and how we guide the POC process. TAKEAWAY: Being a startup sales leader is hard. It sometimes feels impossible. But Increasing ACV can be a magic bullet. Don’t be afraid to take big bets. Don't be afraid to run experiments. Don’t be afraid to go beyond your areas of responsibility. This is where your next level of growth lies. Get comfortable, being uncomfortable.

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Is Salesforce losing its grip on sales enablement? Every day, more companies are shifting sales operations to tools like Apollo, Salesloft, and Outreach. But here’s the paradox: Salesforce is still the source of truth, where the top and bottom of the funnel align in one place for reporting and insights. Yet sales teams are adding more tools, creating a sprawling tech stack—and everyone loses with sprawl. Here’s why: 🚩 CFOs don’t want to pay for sprawl. More tools mean more costs, more integrations, and more data silos to manage. 🚩 CEOs don’t care what tools are involved; they want clear insights into what’s driving revenue and closing deals. 🚩 CMOs need visibility into the middle of the funnel to understand what’s working and what isn’t in real time. But with data scattered across multiple platforms, that visibility fades fast. The reality? There are no winners with sprawl. It creates disconnected data, bloats budgets, and makes alignment across teams harder. So why keep adding more tools? Keeping everything in a core CRM is simpler, cost-effective, and keeps your teams aligned around the metrics that matter. Curious—how is your organization handling this growing sprawl? Let’s discuss 👇

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SDRs, stop talking about what you sell on LinkedIn. Start talking about HOW you sell. That's how you build a brand.

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I agree with my Silicon Valley buddy, Nick Mehta, CEO of Gainsight on this. ⚙ Why? One of the things I always say is that, "It all starts with sales." 🤔 Without sales, there is no company. The better the sales org operates, the better the company will do. So why not optimize and unify the sales organization by having the CCO report to a CRO (rhetorically asked). 📈 It's a great way to ensure that customers are delighted post-sales and that they keep coming back. 🤝I've seen this configuration foster a cohesive strategy for maximizing customer satisfaction and revenue growth. This alignment ensures that customer-focused initiatives are deeply integrated into the organization's broader revenue strategy, enhancing the effectiveness of both functions. 🙌 It seems to promote a unified approach to identifying and capitalizing on customer insights, ensuring that customer needs are addressed proactively. This reporting structure also facilitates better communication and coordination, leading to more comprehensive customer engagement and streamlined decision-making processes. 💪 I believe this configuration strengthens the organization's ability to enhance customer experiences and drive sustainable revenue growth, contributing to long-term business success. #leadership #management #sales #innovation #venturecapital

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The #SAAS revolution of ever growth of sales & market cap is not working for most users The impact of unspent licenses and unused tools are becoming an eye sore The use it or lose it philosophy with users are being used for many IT tools by business focussed IT departments I see decommissioning of SAAS tools becoming a trend as many companies see taking out systems that are just protecting old ways of doing work a value driver Those providers that try to arm twist customers into staying may succeed in the very short term, but are well served to remember that SAAS was sold on " pay per drink", rip and replace and their ilk #Salesforce #Microsoft

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Renewals are the lifeblood of every SaaS company. However, we don’t talk enough about what makes a great AM/CSM who handles renewals. Since there are so many lists on what makes a great AE, I thought I’d take a stab at what makes a great AM/CSM who handles renewals: 1/ They prioritize the renewals that move the needle Renewal rate comes down to simple math. What renewals are going to move the needle for them? Great AMs/CSMs spend their time where they’ll get the most bang for their buck. 2/ They prepare 6 months in advance Average AMs/CSMs prep 3 months in advance. Great ones plan 6 months in advance. This includes asking hard questions well ahead of time during a mid-year QBR, so they know where to spend their time. 3/ They can re-sell the product Stakeholders change. Priorities change. Competitors try to break in. Great AMs/CSMs can sell the product as well as their AEs and know how to position their value props and handle objections. 4/ They know how to negotiate I don’t know any procurement person in the post-ZIRP era who doesn’t try to negotiate their contracts. A great AM/CSM knows how to turn negotiations into win-wins. 5/ They know the difference between procurement and decision-makers Similar to point four, they know how to negotiate and with whom. Negotiating with procurement is much different than negotiating with a key stakeholder. Each party wants something different, and it’s important to recognize what that is. 6/ They know how to rope in their AEs or extended teams Just like the best AEs know how to “quarterback” deals, a great AM/CSM knows how to rally resources to help with renewals. AEs, Execs, SEs, and Professional Services can all be brought in to help show the customer extra love. 7/ They develop a renewal champion We always talk about champions in the presales process, but not enough about champions during renewals. A great AM/CSM knows how to develop champions to help push renewals through. An AM/CSM who knows how to do these things is worth their weight in gold. Keep them happy as long as you can!

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“Two-thirds of the money we’re spending right now in sales is not productive.” This is from Sam Jacobs, the CEO @ Pavilion. Good Sales Enablement can help solve this problem. Here are five things you can enable on *today* that can help solve this problem: 1/ How to expand deal sizes in your current funnel 2/ Deep dive on how to beat your #1 competitor 3/ Best practice sharing on successful outbound tactics between SDRs and AEs 4/ Enabling your CS team to find upsells and collaborate with AEs 5/ Better second-call execution (presenting solutions/demos) What else would you add to this list?

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SDRs can be taught to be AEs SDRs can be taught to be CSMs [shoutout to Eric Partaker for the post inspo] Also... SDRs can be taught to be Managers SDRs can be taught to be Marketeers SDRs can be taught to do almost any role Fact: It's better to hire someone who is 60% ready with the right behaviours. Than 100% ready with the wrong ones. SDRs deserve a chance. Do you agree? PS. Share ♻️ with others in your network. And follow Chris Ritson for more sales content like this.

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Outbound Sequences can do more harm than good for SDRs. (I think when used appropriately, they can be a massive help, but most teams use & abuse them -- completely missing the point of them & wonder why they can't land in the primary inbox & get no responses) I think the days of the traditional 27 day sequence are over. We need change. Most tasks get long overdue anyway and end up not being completed. Here's the issue with them: Often, SDRs are reactive to their sequences/cadences... When in reality, you should be pro-active. Let me explain: Imagine you send your first initial email and it gets opened 5+ times. Or you send a LI connect request and they accept it + look at your profile. Most SDRs will move onto their next task and ignore the intent signal. Instead, use prospect engagement as a way to be more pro-active. IE: do not wait 3 days from the day you sent your first email if there's a ton of engagement. Try calling them same day, bumping your email the next day and throwing a connect request on LI. You should try and switch your messaging up based on prospect engagement, too. IE: your cold call opener should be different for someone who has accepted your LI request + looked at your profile / opened your email a bunch vs someone who hasn't engaged at all. Be the quarterback of your sequences.. Don't let them control you! Second issue: most sequences end up piling up overdue tasks.. This is because sequences have way too many steps. If you liked this, I share 1 free outbound prospecting tip that 4200+ SDRs and AEs read every week. https://lnkd.in/e2cJkJqr

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