Ben Wessner

💡 The average B2B SaaS company loses $2.5M annually due to operational inefficiencies. But here's the kicker - this number gets exponentially worse as you scale past $20M ARR. The math is simple but brutal: • Delayed time-to-value • Inconsistent delivery quality • Missed expansion opportunities Each of these compounds over time, creating a massive drag on growth. For companies in the $20-100M ARR range, poor operational alignment can mean $50M+ in lost enterprise value. The good news? This is fixable. Companies that implement a standardized value delivery framework see 40% higher net revenue retention. Share this post if you're ready to stop leaving money on the table.

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Right about now is when Finance goes looking for reporting to come up with FY25 goals so they tap their head of marketing and their head of sales....... Who then taps their operational teams (rev/sales/marketing ops)....... Who then scrambles to pull historical data off models that aren't right or aren't there.... Because their finance team has only approved budget for "revenue-generating activities or technology." So in return receives bad data for funnel metrics and pipeline (likely pulled by the different teams in a silo) to create goals that aren't realistic, unattainable, and wrong. Meanwhile, the GTM operating teams lost a week(s) of productivity and are again behind on their roadmap. Moral of the story:  Invest in the foundation and data for GTM operations and educate finance on why it is important (even to them!)

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If your team hasn't hit its number for the month, you have some work to do tomorrow. Here's how you close your revenue gap in the next 24 hours... Thousands of founders and sales leaders across the SaaS industry are working late this evening. Coming through pipeline, looking to make one final push tomorrow to get the team over the July revenue target. I've been in this situation countless times when I was CRO at Levelset. This is the step-by-step exercise I went through each month to figure out which deals could get us closer to the number: 1. Pull up your pipeline and look for deals with a close date set for this month. Start with those closest to closing. The latest stage in your sales process. 2. Review each opp in the stage and check for a clear next step. This should be a calendar invite on the sales rep's calendar and on the customer's calendar. The next step could be a closing call, or it could just be a call to continue the evaluation. 3. Confirm that you have a champion on the deal. You should be able to see the email correspondence in your CRM. Review the emails with the champion to see if they are working closely with the salesperson to get the deal done. If it looks like there hasn't been a bunch of calls and emails over the last few business days, the deal is unlikely to close. 4. Check to see if there's a closing plan. This should be in the email correspondence with the champion. Look to see if a closing timeline has been communicated with the customer. 5. Make sure there is a compelling event. Usually this is a discount or some other economic incentive tied to a closing date. ______ Once you have reviewed the pipeline, you should have a handful of deals that look like they have a good chance to close tomorrow. Send an exec overlay email for each opportunity. This should come from the VP, CRO, or CEO to the champion and the economic buyer. Copy the salesperson that owns the opportunity: [champion name], [economic buyer name] - I know you have been working with [AE name] on evaluating [your company] as a solution for [prospect company name]. You are in great hands with [AE name] - we are excited to partner with you and your team. As you approach a final decision to move forward with [your company], I want to make sure you have the full support of our organization to make the right decision for your business. I assure you that we are 100% dedicated to this partnership for the long haul and are excited to work with you all. Let me know if there is anything I can help with. With your success in mind, [signature] ____ This sends a signal to the champion and economic buyer that your company is invested in the partnership. I've gotten a 50% response rate on this email. Once you have sent the exec overlay to the late stage deals that are in good shape, it's time to go through the rest of the pipeline. Find ways to deliver new business for your team. Get granular and insert yourself in the sales motion.

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I think the most interesting data companies are super niche verticals. Go deep vertically before you go horizontal. Something random like- Rubber pricing and demand. Insights on the automotive industry have always been in high demand. Deep insights into the storage facility space. A market that has publicly traded companies or a futures contract is where I see the biggest upside. What are some of your favorite companies with deep sector or industry specific datasets. I think J.D. Power is interesting. Aggregate Intelligence, Inc. is another one with a bunch of super specific industry datasets.

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Salesloft is in the business of helping companies create durable revenue growth, which inevitably means helping companies scale. Far and away the most common misstep I see leaders make in the scale phase is a failure to scale process and planning alongside headcount and revenue projections. It’s an absolutely critical step for business longevity. Smaller companies have the benefit of agility, but as businesses grow, it becomes increasingly difficult to make adjustments on the fly. It’s like steering a big ship – it just turns slowly. Adjusting to this new timeline can be difficult, especially for companies that have scaled quickly and within a different market dynamic than what we face today. They need to take a page from the book of their publicly owned peers and set goals for 6 or more quarters out, then work backwards to identify what needs to happen today. Every choice you make must be framed around the question, “Is this the most important body of work for our customer base, our ability to scale, and our ability to differentiate and win?” This also extends to software investments and digital transformation planning. Companies that intend to scale need to evaluate the platforms they’re considering through the lens of 2-5 years. That means making sure the option you choose not only solves the problem you face right now but can grow and adapt as your business evolves. Platform investments need to drive speed of execution, mitigate risk, and provide innovation that increases the return on investment in the future years. If you don’t trust your vendor to outpace your growth with their own innovations – or help you anticipate the challenges that will come with growth and prepare for the methodical turn toward them – then it’s not the right choice. Keep that in mind as you optimize your growth and investment strategy. #salestech #revtech #B2Btech #revenueorchestration

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Enterprise SaaS deals aren't progressing, denying clients increased efficiencies and vendors the revenue needed for growth. When it comes to helping Account Executives prevent stalled deals, companies face a crucial decision: 1. Engage an Fractional Enterprise Deal Coach on a low monthly retainer - or - 2. Staff a centralized deal desk with full-time employees bearing significant salary, benefits, and tax implications. Here's why a Fractional Enterprise Deal Coach might be the more financially strategic choice: Fractional Enterprise Deal Coaching: 🚀 Expert deal coaches engage at the beginning of a sales cycle, coaching the rep on how to help their clients improve the business, having conversations that matter, using the language of the C-Suite. 🚀 Unlike traditional employee compensation, a Fractional Enterprise Deal Coach operates on a low monthly retainer, ensuring you pay for results rather than time. 🚀 Enterprise Deal Coaches bring a wealth of industry experience, expertise and insights with sales strategies customized to your specific challenges. This expertise is leveraged to maximize deal value and recurring revenue. 🚀 The impartial and focused approach of a Fractional deal coach enhances forecasting accuracy, enabling more predictable financial planning. 🚀 Additionally, the flexibility offered by a coaching engagement allows for adaptive strategies that evolve with market and business needs, unlike fixed employee roles. Centralized Deal Desk: 💵 ‘Deal Desks’, ‘War Rooms’, ‘Win Rooms’ and the like typically don’t get involved until a deal has stalled and then routinely ask the same questions the sales rep has asked vs helping the rep progress the deal. 💵 Operating a deal desk involves ongoing expenses related to salaries, benefits, and payroll taxes, which can accumulate significantly, especially as headcount grows to manage larger volumes and complexities. 💵 While offering centralized control and potentially improved process scalability for highly transactional, low-cost deals, the financial burden of recruiting, training, and retaining a dedicated deal desk team - even using the most advanced AI tools - can outweigh the operational benefits for some companies. Choosing between a Fractional Enterprise Deal Coach and a centralized deal desk hinges on understanding the long-term financial impacts versus the immediate needs of your business. A Fractional Enterprise Deal Coach offers a financially agile model focused on specific, monetized business outcomes—ensuring that spending directly correlates to results, not time.

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I've been mulling over the fascinating, intricate world of Semi-Trailer Asset Management of late. It’s not a topic that most people have on their radars, but for those in the transportation and logistics industry, it's a vital piece of the puzzle to streamline operations and elevate profitability. 🚚 Firstly, the semi-trailer is an asset - a valuable, substantial asset. It’s more than just a metal box on wheels; it's an integral instrument for businesses to transport goods across states, countries, and continents. ✏️ Secondly, every trailer tells a story - where it’s been, what it’s carried and when it’s due for maintenance. These details, when captured correctly, can provide a wealth of insight into the operational efficiency of your fleet. 🔎 But the big question is - how do you manage these assets effectively? The key lies in adopting a comprehensive, tech-enabled approach. The traditional pen-and-paper methods just don't cut it anymore. Today's technology offers unprecedented opportunities to transform the way we perceive and manage semi-trailer assets. • RFID and GPS technology can provide real-time location tracking. This leads to greater utilization of assets, fewer lost trailers, and improved customer service. • Predictive maintenance using AI and ML can evaluate patterns in data to anticipate when a trailer might need repairs, mitigating the risks of unexpected downtimes. • Integration of data analytics allows for an in-depth understanding of trailer utilization to streamline operations, identify bottlenecks and inefficiencies, and make more informed business decisions. What this all implies is the transition from managing trailers reactively to proactively – a shift that can significantly impact a business' bottom line. The future of Semi-Trailer Asset Management is exciting, and as we continue to embrace digital transformations, the sky is truly the limit. Let's continue these conversations, pushing boundaries, and leveraging technology to the fullest. Armed with the right tools and the passion to innovate, there's no cargo too heavy, no route too long and no challenge too big in the world of Semi-Trailer Asset Management 💪🚛. Let’s optimize those wheels on the road – intelligently, proactively, and efficiently. #semtrailer #assetmanagement #transportation #logistics #innovation #technology

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Want proof that multi-threading works? Here's our own data: We only win 4% of deals when there's one contact engaged. Scott Tower posted today about this https://lnkd.in/g2y-xjE4 This shows that buying is a team sport, and if there's only one person involved in a buying process it's likely going nowhere fast. One contact usually means they are on an information-gathering tour - typically a person with no decision-making authority - talking to vendors to collect pricing and present it to an executive team. This is the dumbest way to buy anything. People need to stop trying to avoid talking to sales reps. Great sales reps don't pressure prospects to buy products they don't need - they are there to help them buy and ensure their needs fit the solution. They can't do that if they aren't talking to the person with the pain and who has the authority to make the deal happen.

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The top leaders are able to answer the most critical business question: Are you going to meet, beat, or miss on revenue? Spoiler alert: The answer lies in your revenue cadence. It’s the operating system for your org that helps you run revenue like a process every day, every week, and every month of the quarter. When done right, you can create, convert, and close revenue repeatedly and predictably. But if there’s even a slight leak, you’re leaving millions on the table. To help you protect your revenue, we’re hosting Charge: The Revenue Summit virtually on May 8th. You’ll hear from impressive RevOps leaders like Scott Peyser (SVP, RevOps, Clari) and Jaclyn Spillane (Director, Innovation PMO, Genesys) on how to design and run efficient revenue cadences to help you capture more revenue. RSVP here: https://lnkd.in/gFW5nxX7

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Customer Success isn’t just about keeping clients happy, it’s a boardroom-level conversation that investors will scrutinize. ⬇️ At #SaaStr2024, Nick Mehta from Gainsight broke down 10 critical questions that every founder and customer success leader should be ready to answer when engaging with investors. #CustomerSuccess #SaaS #TreeAndLeafPartners #NickMehta #Investor #Leaders #SaaStr2024

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Plenty of GTM math is getting more and more complicated, but one metric has always served me well by keeping it dead simple. Shoot for 3X pipeline coverage, 4X if you want to err on the conservative side. That's it. Anything under that means you're likely leaving too much good pipeline on the shelf. Anything over that implies either a qualification problem or a conversion problem. And that is NOT a sales problem, because you all own that together as part of a unified go-to-market team. The problem(s) could be any of a number of things - lead quality, imprecise buying journey mapping, sales process management, buying committee multi-threading, etc. I imagine even this simple math will stir up some debate for you internally. Better to have that conversation now in pre-fiscal year planning than mid-year when it's harder to course-correct.

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🎯 23% more expansion opportunities are closed by companies with documented value maps. Yet most account teams wing it when it comes to proving ROI. A value map isn't complicated, but it must be specific: • Measurable outcomes by segment • Clear success milestones • Quantifiable benefits • Timeline to realization This becomes your blueprint for: 1. Implementation planning 2. Success metrics 3. Expansion triggers 4. Executive reviews The best part? It takes just 2 hours to create your first one.

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In 2024 sales leaders are being asked to hit bigger targets with tighter budgets. On a macro level this can feel daunting, but if you boil it down team by team, rep by rep– the answer clearly sits in the efficiency and productivity of your rep’s day. And in order to drive that daily efficiency and productivity, you need to deeply understand the foundational systems + processes that actually allow your team to spend the bulk of their day talking to customers and prospects. If I’m a frontline manager or Dir of sales right now, I am revisiting this checklist quarterly to drive that efficiency and productivity within my teams: 1.) Revisit your deal cycle workflows and ensure your reps understand the ins and outs of the tooling and sales process. ↳They need to know how to navigate the sales methodology you use ↳They need a deep understanding of your CRM and entry and exit criteria for deal stages ↳They need to have clarity around forecasting expectations and how to keep their pipeline clean ^ All the logistics of getting the job done. 2.) Skills assessment/reinforcement and training around how to make sales conversations meaningful. ↳Revisit messaging and positioning ↳Regular objection handling practice ↳Understanding each persona, their problems and buyer signals that indicate it’s time to reach out to that specific prospect ↳Value, benefits, ROI, differentiation matters Fewer tools means less complexity. See where you can cut standalone tools and consolidate to more comprehensive and all-in-one tools (like Apollo) to give your reps a more centralized operating system and reduce the time spent navigating their tech stack. Simplicity will help your reps win. 💪🏼 The market and selling environment is changing rapidly. Your teams are growing and shifting constantly. These things should be top of mind and regularly revisited at the team and rep level to ensure they are as equipped and empowered to do what they do best (sell!) at all times. How often are you running enablement sessions with your team? Do you focus on process or skills more? #salesexcellence

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So your company has decided to add a partnerships department (*sigh*) ✅ Hires one partner person ✅ Shares data to get partner overlaps ✅ Assigns partner person a quarterly revenue number ❌ Does not create cross functional partnership strategy ❌ Does not assign partner focused KPIs to the sales org ❌ Does not engage in a partner enablement strategy 🤯 Cannot understand how partner referrals aren’t just rolling in the door. Partnerships is a strategy, not a department. Having a solid partnership strategy that envelops the entire GTM process is the quickest way to partnership success. And it’s still a long game. Best be getting started.

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As I've gotten up to speed at Hatch, I've spent a lot of time talking to Chris Bache and Jason Dolan about our partners. Like many SaaS businesses, partners drives a substantial amount of revenue for Hatch. In particular, tech partnerships are really important to making Hatch a valuable product and experience for our customers. One of the most exciting partnerships is with ServiceTitan and I'm pumped that we're officially live in their marketplace today! Why is this partnership exciting? With Hatch AI we're enabling home services companies to engage with their customers autonomously over SMS and email. Whenever a customer comes inbound asking about a new HVAC system, a home remodel or whether windows will be a good fit, Hatch AI can ask qualifying questions, collect necessary information and even book an appointment directly on ServiceTitan. This is all without the intervention of person in a contact center. This is a big deal because contact centers are often overworked and CSRs and inside sales teams have too many customer conversations to deal with at any one time. Potential customers have to wait hours or even days for follow-up or to get questions answered. This can lead to serious revenue loss. Hatch AI, together with ServiceTitan, can help to solve these issues and drive substantial revenue. If you're a ServiceTitan customer, we're happy to share more about how Hatch and ServiceTitan can work together for you!

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🚀 Pitching RevOps to Your Boss: Unlocking Sustainable Growth 📈 Convincing your boss about the need for RevOps is like explaining why every high-performing athlete needs a dedicated coach. Here’s why having a fractional RevOps team can transform your business: 🔄 Streamlined Processes: Aligning marketing, sales, and customer success isn't just about removing bottlenecks—it's about creating a unified customer journey. At elefante RevOps, we adopt the Winning by Design approach, ensuring every interaction is optimized to deliver value and drive revenue. This means smoother handoffs, fewer missed opportunities, and a consistently excellent customer experience. 📊 Data-Driven Decisions: In today's competitive landscape, gut feelings aren't enough. Our fractional RevOps team leverages advanced analytics to turn data into actionable insights, similar to the models used by Winning by Design. This results in smarter, more strategic decisions that drive growth and improve ROI. 💡 Expert Insights: Bringing in a fractional RevOps team means accessing a deep well of industry knowledge and innovative strategies. Our experts, trained in the best practices outlined by Winning by Design, provide tailored solutions that address your unique challenges and opportunities. 💰 Cost-Effective: Building a full-time RevOps team can strain budgets, especially for growing businesses. A fractional team offers top-tier expertise and dedication without the overhead costs. This allows you to invest wisely and see a higher return on your RevOps investment. 🚀 Scalability: Your business needs evolve, and so should your operations. A fractional RevOps team provides the agility to scale processes efficiently, ensuring you’re always equipped to handle increased demand and growth opportunities. This dynamic approach ensures you can adapt quickly and stay ahead of the competition. At elefante RevOps, we harness the principles and methodologies of Winning by Design to help you align your revenue operations seamlessly. Our mission is to empower your team, enhance customer experiences, and drive sustainable growth. #RaaS #RevOps #FractionalRevOps #BusinessGrowth #DataDriven #WinningByDesign #elefanteRevOps

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A very thoughtful post from Nick Cromydas. Perhaps before tech and tech enabled companies can become broadly attractive to Tier 1 talent, there’s a process to complete that may take longer than 9-12 months. A process that includes founders and incumbent management teams… 1) being realistic about their TAM and stopping the overspend on sales/marketing (you might have a better, smaller company); 2) acknowledging a lack of product-market fit with scaling potential and mustering the courage and consensus (with investors, employees and customers) to execute the necessary pivot(s) in their offering; and predictably 3) making the organizational changes required that include reductions, upgrades and in some cases, wholesale functional changes in headcount. We’ve seen this process start in many companies; being self aware enough to execute quickly (to Nick’s point) is what will get companies closer to the “front of the line” for the Tier 1 talent that is most definitely in the market. But I do think the process will take longer than a year. Many tech and tech enabled firms are facing painful down rounds and in some cases will simply close their doors or be sold for valuations that completely flush the cap table. If previous cycles are any indication, this takes more time than is ever anticipated. And top talent, at all levels, takes more time to scrutinize the opportunities…

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Learn about driving value selling across the sales team

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Check out the latest GTM Secrets podcast by Identity Matrix with Saad Shaikh at CAST AI! He's a RevOps guru for both enterprise and mid-market orgs. Learn what he thinks we should be doing to accelerate the sales cycle, how to structure revops, and what it takes to rock in your gtm operations. Get the full episode on YouTube, Amazon, Apple, Spotify, and more! Link in the first comment. #gtm #revenueoperations #martech

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