Kraig Ward

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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This year, I've spent 160 hours meeting with strategic account sellers. Here’s the #1 issue driving them crazy (and how to escape this hell): Being forced to sell by activity rather than strategy. I hear this story over and over again. Senior sellers at SaaS companies being pressured by their leaders to meet high outbound activity metrics each week. They're treated like glorified SDRs rather than Strategic AEs… But with $150K-$200K base salaries. Here's the problem: Surpassing $1.5M-5M+ ARR quotas will not happen by running call blitzes using senior reps. 7-figure transformation deals unfold by designing a high-quality executive buying experience for a smaller subset of accounts aligned to the AE's unique characteristics. So if you’re a strat account seller and find yourself in this sticky situation, here’s a playbook you can use to get out of it: STEP 1: Break down how you spent your time over the past 4 weeks The key is a deep understanding of revenue-generating activities (RGAs) vs non-RGAs. Remember: Research, prep, and follow-up are RGAs - not just the call or meeting. BTW, I like using Timeular for detailed time tracking. STEP 2: Draft up an internal business case Use this to present your case for replacing cold outreach time with more creative and impactful strategies, which will improve your performance and grow the business. STEP 3: Outline your strategy Structure your plan like this: ⇢ Title that includes your BLUF (Bottom Line Up Front) Example: “The path from $400K to $4M deals” ⇢ Headline Example: “I will replace 2 mandatory call blitzes per week with strategic account win design sessions. This deep work will result in elevating my executive status within my top 10 tier-one accounts.” ⇢ The Problem Statement Example: “For the past 4 weeks, 200 cold calls during the mandatory call blitz windows have produced 2 meetings (a 1% call-to-meeting ratio), resulting in a 50% attendance rate.” ⇢ Recommended Approach Example: “By allocating two 1-hour blocks for strategic account win designs instead of the cold call blocks, I will develop specific plans for my top 10 accounts using tools such as account maps, creative strategies such as crafting open letters, and arranging peer network exchanges which have been proven strategies from other 7-figure sellers within a strategic sales community I have invested in. I will still have time to meet the required 80 weekly outbound outreaches.” ⇢ Outline The KPIs You will want to drill down into the key levers that matter (show current vs target): - Win rate - Deal size - Deal cycle Remember to set a date for your targets. The beauty of this model is that it’s also a blueprint for selling more effectively with prospects. Going through this exercise proves to both you and your leaders you can be more strategic. Which, in case they forgot, was what you were hired for in the first place! 🐝

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Does your SaaS struggle to increase revenue & maintain high profit margins? 99% of the time it's a sales process problem. Here's how you can significantly increase revenue without spending more money. {thread} 1. Review Your Sales Process This is the most crucial part in getting new sales. It is the glue that keeps things together. Without a consistent & updated sales process your prospects will be mishandled, leads will be nurtured incorrectly, and your sales reps won't be able to close. Until it is in sync with everything (will have to be tested) it won't be doing its job and your company will fall apart. 2. Enhance The Funnels Your funnels are the most important part of your sales process. It is what your leads are seeing in real time before purchasing your product. It must be formatted in a way that the prospect can easily follow and sell themselves into. You must be creative, you must follow up, and you MUST have your ICP dialed in. Outbound & Inbound funnels both work; they just need to be very specific & creative to work at full effect. 3. Leverage What's Working Utilize the tools that are already working. You see that targeted LinkedIn ads work for your inbound funnel the best? Scale that up and forget about anything else until you hit a cap. You see your sales reps are crushing KPIs? Invest into a sales director and invest into more junior reps. You can easily 2x revenue by just doubling down on strengths. 4. Create Compelling Sales Assets Your pre call workflows define the close Your post call workflows create the relationship and CLV The assets you send to a prospect before the sales call are almost always the reason they buy from you vs a competitor. The assets you send to a client/prospect creates the start of a relationship that makes the person stay loyal for life. You can easily 2x closing rates and CLV by just having super personal, creative, and well put together assets. 5. Develop A Stronger Offer Sometimes, the key to increasing revenue lies in the offer itself. Developing unique value propositions and fine-tuning your pricing models can attract more customers instantly. Understanding your market needs, ICP, and your own services is what sets your offer in place. Your offer isn't your services, most get it confused. Are you ready to scale instantly without excessive marketing spend or exorbitant capital? Book a free 30 minute consultation to see if we're a good fit- https://lnkd.in/gnPXyD43

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28 CCOs and Post-Sales leaders have spoken 📢 What is the CURRENT STATE of Customer Success? -- Over the past 6 months, I asked 28 podcast guests this question. Nearly everyone had the same answer. What's the Current State of CS? ➡ "Unsettled" ➡ "Identity Crisis" ➡ "Transformation" ➡ "Really messed up" (but don't listen to me, hear for yourself directly from folks who feel this way... totally unprompted). -- Why is this function in SUCH a state of flux? ✳ The problem is not CS... it's a CEO / Board problem Very few Enterprise SaaS companies today actually have strong Product-Market Fit (PMF). There are tons of non "mission critical" products out there justifying themselves for a spot in the stack. For 70% of leaders I speak with, they say their CS teams are filling key product and value gaps that the company has not yet addressed. Just because you had PMF at $10M does NOT mean you will keep it at $20M, $200M or beyond. It's always changing and the only way to keep it is to listen to your customers selflessly. ✳ Without strong market fit, CS becomes focused on "Checklist Management" rather than Change Management Tasks, journeys, and "busywork" that comes out of a lot of CRMs and CSP workflows are designed to show CS activity is up... but it is not at all aligned to moving the needle for the Customer. In order to become "mission critical", post-sales MUST. DRIVE. ADOPTION. And that has very little to do with what your company thinks is important (sentiment, engagement, usage) and everything to do with what your customer feels is important (improving their workflows, achieving their business goals, hitting their leading indicators). ✳ CS efforts do not correlate to Revenue nearly as much as they need to CEOs, CFOs, and Boards look at two metrics: how much $$$ did you bring in, and how much $$$ do I need to pay you? If the first is less than second, you are literally a cost center (not just perceived as one). CEOs, CFOs, and Boards are expecting the payback period of investing in CS to be one-year. If teams are expecting CS activity to generate revenue WITHOUT a Customer Value Framework proven to increase adoption... teams will end up spinning cycles and burning cash (and unfortunately RIFs are not far behind) -- So... what does the FUTURE of CS and Post-Sales look like? (teaser: video coming out in 2 weeks) This is really a question that CEOs, CFOs, and Boards will have to answer. They have to see demonstrated quantifiable value coming out of post-sales to continue investing in the function. To position CS and Post-Sales in the best possible light, we have to reimagine our function through the lens of our Customer. It's less about how we define Customer Success. We need to ask: How does our Customer define Success? What is your take? #FutureCustomerValue #CustomerValue #CRO #CCO

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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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At DataBased, we see this all the time—a startup with $5M in annual revenue and a growing 12-person sales team hits a wall. Deals are stalling, reps are disengaged, and growth has plateaued. The company realizes it needs a sales leader to scale effectively. - The Wrong Hire The company brings on a seasoned VP of Sales with enterprise experience, offering a $400K package. Six months in, the VP hasn’t delivered. He’s focused on high-level strategy, disconnected from the day-to-day, and struggles to adapt to the fast-moving, hands-on needs of a smaller team. Morale dips, reps leave, and the leadership team realizes the wrong choice was made. - Reevaluating the Approach When DataBased steps in, we help the company rethink its approach. Instead of hiring a VP of Sales, we recommend bringing on a Director of Sales—someone with experience in startups, skilled at leading small teams and driving results in the ~$5K–$75K deal range. With a sub-$300K package combining salary and equity, this new hire aligns with the company’s stage and goals. -The Results The Director quickly makes an impact—streamlining onboarding, coaching reps directly, and improving deal execution. Within a year, the team grows, revenue increases, and turnover drops significantly. By hiring for fit, not flash, the company sets itself up for sustainable growth. - Takeaway At DataBased, we’ve learned that for small teams, a skilled Director or Manager often outperforms a high-profile VP. The key is aligning leadership with the team’s size, deal complexity, and growth stage. When you hire right, the results speak for themselves. If any of this strikes a nerve, contact DataBased Recruiting, https://lnkd.in/gywN7DVF we love helping companies get out of these kinds of jams by finding them amazing people.

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Larger-Ticket Founder-Led Sales: Deliberately Capping Out! Founders leading their sales motion for whatever reason (fine-tuning product and channel strategy, or, pivoting their company out of necessity), will find that their conversions to first-meetings are incredibly high compared to your standard SDR. E.g. Outreach to 100 relevant individuals could yield 20-30% (or more) conversions to first meetings. After outreach to 200, assuming their value proposition makes sense and is high enough of a strategic priority, founders will find that they can't feasibly move and manage all the promising deals going to procurement. This can happen as quickly as a month! At this stage, they will have earned the right to tackle the next problem which is scaling their efforts while sustaining them: - Moving the deals to a close. - Identifying which deals to prioritize. - Continued sourcing and top-of-funnel generation. - Systematizing the playbook as it matures. At this stage, it helps to have some sales operational support (or from a key hire like a CoS or Biz Ops) to help them: - Scale their continued outreach. E.g. Sourcing and customizing some thoughtful customized messaging for outreach. - Project manage deals. E.g. prepare presentations, organize materials for different procurement processes, managing expectations and deadlines. sales hire (or a hire like a CoS or Biz Ops) to help scale outreach and sourcing. This is a positive problem to have as long as you and the team can document and transfer context and process to those helping you: - Template messaging - Template workflows - A clear understanding of stakeholders, what matters to them, and why. #founderledsales #startups

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Lately I’ve talked to several RevOps leaders about their trickiest data gaps. This isn’t about rep outreach. This is about understanding a market to determine TAM, ICP, segmentation and territory design—big strategic choices that massively influence next year’s financial plan. And there are SO MANY gaps. The gaps aren’t simple. The basics like phone numbers and simple firmographics are covered. It’s really about where data bleeds into information. Here are some types of gaps I’m seeing: * Industry-specific technographics. I’ve been talking with a customer in healthcare. Healthcare tech stacks are complex and fragmented. There are specialized data providers but they’re struggling to keep up. * Domain-specific taxonomies. One customer targets professional services providers for SMBs. Understanding the types of backoffice services those companies offer and which they prioritize is just as important as company size. There’s no good source for data like this and any scraped data needs to be heavily processed to fit into a meaningful taxonomy. * “Hard” firmographics. One customer recently did a market-sizing exercise that relied on the physical locations of each prospect. Another customer needs to understand the total number of front-line employees. Some providers claim to have this data, but it’s spotty at best. I think of these as “hard” firmographics. The hard numbers do exist, but they’re very hard to source. * “Soft” firmographics. I talked with a company in the food service space. The concept of a “well-established” restaurant is important to them. Another customer cares a lot about finding companies with “road warrior” employees. These criteria are tricky to precisely define but, much like the famous supreme court ruling on obscenity, you usually know it when you see it. * Classifications. This really isn’t about data, more like synthesis. Most companies need to put prospects into buckets—anything from use cases to personas to a set of defined market segments. Having to rely on reps to do this assessment means we can’t use these classifications to make strategic resource allocations. So we’re back in planning season. Yet again trying to compile data points from bulk enrichment providers, combine that with spotty data captured by reps, sprinkle in some self-reported customer data from apps and lead forms and then somehow—somehow—turn this shaky foundation into the hard commitment of a financial plan. It’s a difficult, high-risk job and RevOps is usually at the very center. I know because I’ve been there. I wish I could end with pithy advice about how to fill these kinds of gaps, but I’m afraid it’s not that easy. I’d love to hear from anyone that’s got a complicated strategic data gap. We might be able to help. But if nothing else, I’d love to talk shop, share what I’ve seen and learn how you’re tackling the problem.

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Wondering how to merge PLG and SLG for maximum impact? Japna Sethi talks about how they made this work at companies like Dropbox, Productboard, and Calendly. She calls it "defining the API" between the two growth motions so the right PLG leads get passed on to your sales team and shares the details on the approaches at the companies she has worked. For the full episode: https://lnkd.in/d-2ZAvir

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Scaling an outbound team from 14 reps to 150 reps. My 12 lessons from Checkr's journey. Carrie Bosworth, SVP of Sales at Checkr, shared how they did it on the Science of Scaling podcast. Here are my 12 key takeaways from the episode: 1) Scaling with Inbound Leads Only • Rarely do companies hit massive revenue through inbound alone. • When Carrie joined Checkr, they were scaling fast but knew inbound would dry up. • They diversified by adding outbound selling to maintain growth. 2) Transition Challenges • Moving from inbound to outbound is hard. • Different profiles and skill sets are needed. • How you hire, create books, and approach the market changes. 3) Preparation Time • It took Checkr 6-9 months to get ready for outbound. 4) Executive Involvement • Executives should also engage in outbound. • Reps write notes for execs, who adjust them to sound authentic. • Execs don't run long sequences but help break into top accounts. 5) Deep Research for Enterprise AEs • AEs with public company accounts spend 2 months on research. • They buy the prospect's product, use the app, and create detailed reports. • This deep dive helps them secure meetings and close deals faster. 6) Inbound to Outbound Transition • Initial reps were order takers with no BDR experience. • Given a chance to switch, many opted out or moved to other teams. 7) Hiring and Expectations • AEs with outbound experience only. • Enterprise AEs need more experience. • BDRs require 1 year of previous BDR experience from top companies. • SDRs are often college athletes for their motivation and work ethic. 8) Territory Management • Started with 14 reps using Round Robin. • Grew to 150 reps with balanced territories based on company size and location. 9) ICP Definition • Focus on LTV, retention, and CAC. • Targeting accounts with high LTV and reasonable CAC. 10) Territory Alignment Post-Covid • Shifted focus from geography to best ICP. • Created extra territories to accommodate growth. 11) Outbound Playbook • Inbound is reactionary; outbound requires operational rigor. • Dedicated time for outbound activities is crucial. 12) Accountability Measures • Monthly scorecards with more weight on outbound activities. • Comp plans, daily dashboards, and pipeline meetings ensure focus. Outbound sales require strategy, preparation, and the right team. --- P.S. What's the biggest challenge when transitioning from inbound to outbound?

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Most CMOs secretly hate their boss (aka their CEO, aka people like me). Here’s why Marketing can’t do miracles when the product is bad . Yet CEOs think Marketing bringing new pipeline will magically erase all the product problems. No. News of a bad product travels fast, and it has to be fixed at the core CEOs understand well outbound, close rate and pretty much everything that the sales department does. But they have a lot less understanding when it comes to marketing. Why? Because marketing can be done in many ways And a lot of it can’t be tracked fully (yet) One has to understand deeply how a brand plays a role in outbound, overlapping channels to decrease sales cycle, mixed attribution, and so forth As a result, many think of marketing as the department that spends but has little ROI to show  Or the department that creates blog posts, pretty website pages, spends a fortune on the booths, or spends a fortune on swag A lot less understand how to create a brand. And to recognize brand talent in a marketer. And to truly let them shine. They want quick results. There’s nothing quick when it comes to brand work. It is always a long game, and few have the patience to see it play out They just expect that ad spend will just fix all the fundamentals that are missing In addition, few understand that culture and EX plays a big role in brand/marketing. Because the way your team shows up on calls/at events is a reflection of it. If your employees are unhappy, there’s no easy fix a marketer can deploy Marketing has to collaborate with many stakeholders. If the right culture is not cultivated and the right metrics to align the various teams it’s very hard to get everyone to collaborate. People fighting for metrics that make them look good is not fun  It gets exhausting to push everyone towards the same goal if you feel you’re at odds with one another All the marketers out there are tired of short tenures where they have short times to deploy quick fixes that won’t do miracles But there’s some hope: I see more and more founders understanding that this is a long-term game And those who hire genius marketers make it a lot further than those who don’t So maybe maybe the tides are turning slowly P.S. this photo is of Tim Davidson trying to convince me not to spend a fortune on a booth

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Summary of conversations at conferences about AI in commercial functions: Person a: what are you using AI for in your business? Person b: 🤷‍♂️ we tried to make a super cool predictive model but our data was too dirty. Also our revops team was understaffed. I did ask ChatGPT4 to make me a list of restaurants to visit at this conference. Person c: that’s weird, I asked it to make me a picture this morning Person a: 🙋‍♂️ still wondering….what are you using it for in your business again? I believe that AI will ultimately be really helpful to many different business functions. We’re in the very early innings, though.

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Did someone say FREE REVOPS?! I’m finally doing this… I'm looking for 3-5 tech startups doing something great for their space to benefit from some pro-bono RevOps advisory work - yup - free! You can expect 4x sessions with me and your GTM leaders/founders focusing on a core topic each session - see it as an intro to RevOps for your org - not a replacement to fractional work. Complete the Typeform if: - You're a manager or founder at a B2B tech company that doesn't have a dedicated RevOps function - You're under £ 10M ARR (£5m and under would be even better!) - You are using HubSpot but not sure if you're getting the most out of it OR don't have a CRM (yet) - You might be VC-backed - You're doing something great in your space *Bonus points if you're a B-Corp* https://lnkd.in/eCQBnu9T So… why am I doing this? I love working with tech clients, but not every company can pay the going rate, and not all of you realise you need support - so I want to give back to the community and open up ideas for you all. If you don't qualify but know someone who might - share this post to help others see it 🙏 In a couple weeks, I'll reach out to those I've selected and tell why - if you aren't selected I'll still have something for you 👀 Thank you - and let's keep the Startup Pulse beating strong.

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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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As a founder, hiring your first sales rep is a pivotal moment. It's the bridge between your initial traction and scalable growth. But it's also fraught with risk. Here's how to nail this critical hire: 1. Look for a builder, not just a closer Your first sales rep needs to be comfortable with ambiguity. They're not just selling - they're building your sales process from the ground up. 2. Prioritize industry knowledge At this stage, deep understanding of your market is more valuable than a rolodex of contacts. They need to speak your customers' language fluently. 3. Assess their ability to wear multiple hats Can they handle everything from prospecting to closing to customer success? In the early days, your sales rep might be your entire go-to-market team. 4. Test their resilience Early-stage sales are tough. Rejection is constant. Look for someone who can stay motivated without a big team around them. 5. Align on metrics Be crystal clear on what success looks like. Is it revenue? New logos? Close rate? Make sure you're on the same page from day one. Remember: This hire can make or break your growth trajectory. Take your time, run a rigorous process, and don't settle. What other traits do you think are crucial for an early sales hire?

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One of the biggest pieces of GTM that people just totally miss is meeting your prospects where they are. This is the biggest time waste I see people do. They do social prospecting on LinkedIn to all their prospects. Look at their posts and when you see they do the following: Only like career updates from internal employees Repost case studies Once a month or less. Don't waste your time. This is not the channel for them. Mark it as such in your CRM and remove any LI steps from the cadence for that prospect. You'll claw back at least 4 hours a week for dials. Happy prospecting 🤘

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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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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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