Billy Sheng

RevOps leads - is leadership tasking you with AE-sourced pipeline initiatives? As companies use this channel to close gaps in 2025 pipe coverage, many RevOps leads struggle to operationalize the goal. Why? Even with a fancy tech stack, prospecting gets deprioritized when AEs go deep on active deals, and without a structured process, the habit breaks entirely. The most effective RevOps teams tackle this head-on by embedding prospecting into the daily workflow. They make it simple, manageable, and aligned with their broader revenue strategy. Here are a few tactics helping RevOps teams drive AE-sourced pipeline: Manageable daily lists: Reps receive 2–5 high-priority accounts in their inbox each day, based on historical signal and ICP performance. Contextual alerts: Insights from enrichment and signal data surface clear reasons to engage, cutting down necessary research time. Streamlined sequences: Pre-built outreach tied to each account’s context minimizes research and effort. Streaks: Gamifying daily prospecting with streaks and leaderboards, while simple, goes a long way in maintaining the prospecting habit. Manager-level reporting: Clear metrics empower leaders to drive accountability and reward engagement with spiffs. In summary, RevOps should strive to eliminate all friction for AEs, create a daily prospecting habit, and maintain leadership focus on the initiative with data. Without this process and attention, AE-sourced pipeline initiatives usually fizzle out for most AEs. RevOps leaders, what’s working for you to ensure AEs hit their pipeline goal?

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Pipeline generation went down 47% in 2022 (see chart below). And 63% of companies have reported facing significant challenges with outbound in 2023. Yet, we're told there is this new magic wand, called AI, that will solve all our problems. My nuanced take (sorry, this post won't call "outbound dead" or "ai overrated") is: - Pipeline is hard to generate today *and* - AI can help, but it's not a silver bullet. One way I've been helping companies to use AI in their outbound is through creative, thoughtful "micro-campaigns" (read more here: https://lnkd.in/erSS5Kbm). Micro-campaigns are: - Small, highly-targeted lists of, say, 50-250 contacts. - These lists are generated using *very* specific filtering and/or signals (usually using AI/agents at least for certain parts). - Each list (aka "micro-campaign") is relevant this week, but won't be next month. On January 16th, I'll be hanging with the legend, Erol Toker to talk about micro-campaigns and "irresistible offers." Topics we're going to jam on: 1. Why Email Has Changed: Understand what happened last October and how to adapt. ​ 2. Crafting Irresistible Offers: Learn how to create compelling offers that target click rates and NOT JUST reply rates. ​ 3. Building Signal Stacks: Discover how to stack together your best signals to find the best time to outbound. ​ 4. Weekly Micro-Experiments: Learn how to build your team around a cadence of small, highly focused campaigns using proprietary signal stacks. We're going to brainstorm with audience members during the call. So, register and join us live for a chance to have us come up with an irresistible offer or micro-campaign for your company (Jan 16 at 9am PT): https://lnkd.in/gaRaAn2N

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"My bet is that the SDR will move away from a low skill, high input job and instead become more of an ops-focused builder and maintainer of a humming pipeline." In the last 12 months, I have seen a number of start-ups leveraging modern tools to automate their top of funnel efforts. Hat tip to Troy Doles at WarpStream in teaching me the new rules of the road 😎. I believe that Founders should drive this cultural change when setting the GTM foundation early on. https://lnkd.in/evCUmRgB

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TollBit just landed $24M in Series A funding, and this is the kind of deal that doesn’t just raise eyebrows—it rewrites the playbook. Lightspeed led the charge, but they weren’t rolling solo. Heavyweights like Section 32, Sunflower Capital, AIX Ventures, and more piled in to back this rocket ship. Massive congrats to Olivia Joslin and Toshit Panigrahi for pulling off what every AI startup dreams of: solving a huge problem and locking down the resources to scale it like nobody’s business. Now let’s talk impact. AI companies have been cruising through the internet, gobbling up content like a buffet, while publishers have been left holding the bill. TollBit is here to fix that. They’ve built a platform that tracks AI bot traffic, charges for every content use, and does it all automatically. For publishers, it’s not just a payday—it’s getting paid on time without the hassle of chasing down AI companies. And for AI businesses? They finally get a legitimate, scalable solution for content licensing—without stepping into legal quicksand. That’s a win-win. But that $24M isn’t just for show. It’s getting funneled straight into infrastructure. We’re talking faster payment protocols, even smoother integrations, and the muscle to handle the tidal wave of new publishers and AI companies jumping into the mix. And with Time Inc., Penske Media Corporation, and ADWEEK already signed up, this isn’t just a proof-of-concept. TollBit is the real deal, sitting at the intersection of AI innovation and media monetization. Olivia Joslin doesn’t mince words: “This market’s moving at light speed, and neither publishers nor AI companies can afford to be bogged down by manual deals. We’ve made it frictionless for both sides to come out on top.” Toshit Panigrahi sees the bigger picture: “What we’re building isn’t just a platform. We’re creating a future where publishers get paid for the content that powers AI, and AI companies keep innovating without stepping on any toes.” Here’s the real takeaway: TollBit just carved out their place as the go-to for AI content licensing. They’ve figured out how to make sure the creators behind the content get their fair share while helping AI companies keep the innovation engine running. This $24M Series A? It’s just the beginning. Everyone else in the space? Better start taking notes. #Content #Publishing #Publishers #ContentLicensing #Technology #Innovation #AI #MediaMonetization #Technology #Innovation #ContentPayment #AIInnovation

When you're not in the board room, you're always wondering, "What's going on in there?". I have now worked with seven companies where I'd regularly present to a board, a mixture of PE and VC-led, and it's almost always centered around a few key topics. If you're meeting your numbers: - what's your future forecast  - how are you going to continue to grow - how will you grow faster and more efficient  - update on money in the bank and spend If you're not meeting your numbers (along with the things I mentioned above): - what is your plan to turn things around and meet your numbers (this includes new logo, back-to-base sales, and churn reduction) - what resources can they offer to help - do you have the right players in the right seat This is an oversimplification because many nuances are at play, but this is generally it. While board meetings can be stressful, almost every board I've worked with wants to be helpful. Of course, their interest is, first and foremost, that the business is healthy and growing, so there's always that undertone, but overall, they want to help. After all, they are guardians of the investments they make on behalf of others and have to report back on their performance. Think of them like they are CSMs for their investors (the folks that give them money). They need to get a great return on the investment they made on their behalf.

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This is why you don't get demos or meetings. What early-stage companies can do about messaging: Message-to-Market-Fit. MMF is the relationship between 1) the words in your value prop and 2) how RELATABLE those words are to your market. It's similar to Product-Market-Fit. 1️⃣ PMF is about solving for customer retention. 2️⃣ MMF is having customers stick around to hear everything you have to say. Imagine your acquisition funnel as an upside-down pyramid. What you do exactly in your funnel is irrelevant, to some degree. As long as that funnel is a nicely sloped pyramid. ❌ When your MMF is poor, your pyramid looks jagged. • Fewer people stick around to hear your full message, how it works, and why it's better. • Your value proposition doesn't resonate. It's not relatable. • They drop off more frequently as you share more messaging with them. • Before they get to the core of your offering, you already missed out on potential leads, demos, and meetings. • You are safe to ignore. ✅ A healthy MMF creates a smooth, nicely sloped pyramid. • More people are interested in what you have to say next. • Your message is clear and relatable. • They see themselves in your words, feel understood, and want to click to learn more. • Your funnel is fuller at each subsequent stage. • This leads to better conversion rates and ultimately more customers. The best driver of healthy MMF is, in a strange way, the things that are hardest to keep up with. - Customer interviews - Engaging and listening on social media - Attending niche events - Building relationships with influencers - In-person visits - Customer advisory boards Doing these things might take time and effort, but they can make your message fit your market better.

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Wake up. Try. Fail (probably). Do it again. Just make sure you’re learning along the way and enjoying the journey. Then one day... maybe just maybe… you’ll have built something big. Matthew Volm, CEO of RevOps Co-op has built the premier RevOps community (13k+ strong!). His modest answer & clear-eyed takes are worth a listen (will be posting more in the coming weeks). Matthew’s Playbook for Revenue OKRs is now available in Daydream and available to you when you connect your CRM. It will help keep your GTM teams aligned with each other, focused on company-level goals, and learning quickly. 👇 Check out the link in the comments. 👇

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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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🛠️ In early-stage SaaS, it's common for teams to wear multiple hats, especially in the cost of goods sold (COGS) area. Let's address Tech Support and Customer Success in COGS. We know CS is a hotly debated topic. COGS or OpEx? 📓Key Concepts to Learn💡 1. Tech Support 🛠️:   - Tech support handles inbound requests from customers.    - This could be questions about using your application and/or bug reports.    - If the tech support team can't resolve a bug issue, they escalate it to the development team. 2. Customer Success 🤝:   - Customer success focuses on product adoption and guiding the customer journey.   - Unlike tech support, they don't handle "how-to" questions or bug fixes.    - The main goal (lots of different definitions here) of customer success is ensuring customers successfully use and adopt the product. They don’t sell (to be in COGS), but they do find leads and pass them to Sales. 3. Onboarding / Services 🚀:   Services involve customer onboarding. This could include training and the set-up and configuration of your product for your customer.   - In early-stage SaaS companies, the onboarding function is sometimes handled by tech support or customer success if you don't have a formal PS org yet. - Eventually, you create a Professional Services org that handles the onboarding and training of your customers. 4. Cost of Goods Sold (COGS) vs. Operating Expenses (Opex) 💰:   - COGS includes expenses directly related to revenue delivery.   - OpEx includes R&D, sales and marketing, and G&A.    - It's crucial for SaaS companies to accurately categorize expenses as COGS or OpEx to calculate gross profit correctly. 5. Specialization of Roles 🧑‍💼:   - As a SaaS company grows, roles within the organization become more specialized and refined.    - In the early stages, employees may wear multiple hats and span multiple departments. Don't over allocate!   - Over time, assigning headcount to specific departments becomes easier. 6. Revenue Stream Margins 💸:   - As the company matures, it becomes important to calculate margins by revenue stream. 📉   - A well-defined COGS area and correctly coded expenses are essential to calculate revenue stream margins accurately. 📝 #SaaS

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A very helpful enablement tool that almost no one has? List of initiatives / tools / programs to steal budget from + WHY our solution is a better investment. In most orgs… There are 1000 one pagers about random features. Zero one pagers about initiatives that we could get $$$ from and how to position for it.

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AVERAGE TENURE OF SALES LEADERS There's nothing fundamentally wrong with 18-month stints for sales leaders. It's become a popular gripe that lacks awareness of how startups actually work. The startup journey, from seed to IPO, is piecewise linear, with step-function changes along the way. These inflection points necessitate sudden leadership transitions. The more successful a startup, the faster and more frequent these leadership handoffs occur. One of the real problems is mis-guided startups orchestrate these changes when they aren't actually growing that fast and are merely cosplaying as a hyper-growth startup. This is what a great board and search firm should help you figure out. However, if a leader accomplishes their mission in 18 months (roughly time between venture rounds), and hands off to someone more suited for the next chapter, that's a massive success for everyone. The machine worked exactly as designed. The sensationalism around 18 month tenures propagates unrealistic expectations. Founders should hire for 18-month scopes of work. If a leader does what they are supposed to do, they should be celebrated. It is extremely rare for a head of sales to grow into a CRO. And frankly, when it does happen, there's more exogenous factors at play than them being exceptional. Leadership candidates should signup with the mindset that a 18-month run is the benchmark. Complete the mission. In fact, they should help support their own handoffs and help evaluate their successors. If things went according to plan, they have job security because they hold institutional knowledge and can continue to grow and learn under the mentorship of the new leader. Investors should provide references for leaders who performed well, even in short stints. It makes a huge difference for people's careers. In fact, they should recycle them into other portfolio companies. Again, that's if the leader did what they were supposed to do. And finally, recruiters need to understand the context of short tenures and surface credible references and data points to present a more balanced view. Sure, it's a yellow flag worth digging into but they should educate founders to look beyond the surface. All of this assumes the leader did their job and founder/investor reciprocates thoughtfulness. But without addressing the root issue, we will continue to see people gripe about 18-month tenures when the duration itself is not the issue.

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we're making progress with a Slack app that automates driving more & better practice / outputs / behaviors with your AEs & other sellers… goal: make role-playing practice more manageable, realistic, & consistent while applying it to actual deals during prep ofc we're plugging into AI for some fun feedback loops too 😊 our next phase is seeing how more teams react to decide what to build for early customers. we can focus on anything you're looking to improve right now: outbounding, cold calling, disco, negotiation, storytelling, improv, forecasting, testing champs, etc... let me know if you want to test it out with your team, or it's easy to get started with the link below. thx!

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There's a major gap between activity metrics and outcome metrics Sales leaders only have access to data from two ends of the spectrum: Top of the Funnel (Activity metrics): calls, emails, meetings run, etc. Bottom of the Funnel (Outcome metrics): quota attainment, win rates, average sales cycle length, etc. But what about the middle of the funnel? 🤔 The critical missing pieces: • How are reps selling? • When are they executing key actions or behaviors in the sales process? • Why are deals won or lost—as a result of how reps are selling and when they are executing these actions? 🎯 Why This Matters: Activity metrics show effort, but they don’t explain effectiveness. Outcome metrics show results but not the process behind them. Understanding the middle of the funnel enables personalized coaching and scalable success, resulting in increased sales effectiveness. How do you measure the middle of your funnel? #ForRepsByReps #SalesMetrics #SalesLeadership #SalesSuccess

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I caught up with a few excellent startup operators (also great friends) who are looking for work. They encountered one common problem in their previous roles: founder fit. Great founders are: → Strategic but also into the details → Deeply rooted in customer experience → Intense and somewhat maniacal And they know how to lead. It’s hard to find a founder with all of these traits. To my network, if you’re looking for world-class leaders at scaling sales and customer success teams, let me know.

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Taft Love 🛫 one thing I've seen that throws the decision off for a lot of companies is a misleading high average sale number. For example, when 95% of a company's deals are $10-25K and there's a handful of deals at $100K+ that drags up the ACV, leading to people thinking "Ok, most of our deals are now $50K+" when discussing things at the executive or board level. This is why calculating the mean / most frequently occurring value (vs. the average) is critical. If the vast majority of deals are X size from X segment, you need to be real about that vs. lying to yourself about how often you close deals that are above that magic threshold.

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CEO = BDR. The "Founder & CEO" title at an early stage company means you carry many disparate responsibilities. But I think the most prescient is "BDR" / all things outbound. I was Vidyard's first BDR and once a little bit of inbound started, it's first SDR. I would spend 6-10 hours / day on outreach while we were at Y Combinator. We had no brand, no content and no interest. The only path to revenue was to figure out who might have a problem we could solve and to try and connect with them. We built an on premise web-crawler (eventually named Nostradamus) that looked for corporate websites with videos embedded on the homepage. We then cross-referenced that against LinkedIn and Crunchbase data to rank a contact's "willingness to buy". Nostradamus provided me with ~80,000 accounts. I attempted to reach out to 100 contacts / day, manually finding contact data. This was both hard and fun. I learned to not take rejection personally, I learned that humans are wonderfully creative people. I met many friends through this process. Here's what I learned (and what I often tell first time Founder CEOs): 1. Embrace Multiple Roles and embrace the learning opportunity: As a "Founder & CEO" in an early-stage company, you must wear many hats, including outbound sales. It's unlikely you've done this before, but the learning process is powerful. 2. Persistent and targeted Outreach: Spending significant time on outreach (6+ hours/day) is crucial, especially when there’s no brand recognition, content, or initial interest. Identify potential customers by figuring out who might have a problem your solution can solve and actively try to connect with them. These conversations will help you iterate towards Product Market Fit. If you hear enough of the same feedback, build towards it. 3. Innovate Develop tools and try systems that identify and rank potential leads. We did this with Nostradamus, but products exist that do this today. Test and invest then aim for high outreach volumes (~100 contacts / day). Use data to prioritize efforts (ie. better response rates from certain roles / industries) 4. Handling Rejection: Learn to not take rejection personally, this is part of the process. Every "No" is a learning opportunity. This isn't as true for 'no response'. 5. Creativity = Relationships: Recognize that humans are creative and resourceful, which can lead to valuable connections and insights. This is your super-power in the era of AI. Through the process of outreach, you can form meaningful relationships, including personal connections. Curiosity is reflected. 6. Balance of Fun and Hard Work: Find enjoyment in the process. Celebrate the wins, learn from everything else. To this day, one of the biggest highlights of my week are talking to prospects / bringing one our amazing AEs into an opportunity that I've helped generate. In other words, I'm still doing outbound 😃 & I love it.

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I’ve seen CROs take two completely different approaches to generate recurring revenue: 1. Push the sales team to land bigger packages upfront, securing a higher initial contract value that will presumably grow over time. 2. Focus the team on selling smaller packages or individualized products to introduce customers to your catalog, gain their allegiance, and expand the deal later. The first method seems logical - and it can work - but approach #2 is a safer bet in the market we’re facing right now. Why? There’s a lot at stake when a client signs a substantial contract. They expect the ROI to merit the budget, and if all doesn’t go as planned, they’re not going to be satisfied. Every minor issue becomes a bigger thing because the product was so expensive, and if you don’t get the adoption rate you’re looking for or the results you intended, they’re not likely to renew. You’re better off starting small, at least when people are acting conservatively with their budgets. Numero 2 optimizes the conversion path by making it less intimidating for new customers to get a taste of your brand. Offering smaller packages initially can also help reduce friction in the early stages of the funnel. Your top priority should be to ensure everyone’s getting value from your product from the start.

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Most sales leaders don't understand that sales ramp time is crucial for accurate forecasting. It measures how long new sales reps take to reach full productivity. Accurate data helps align hiring with revenue goals. Integrating CRM and HR data provides better insights. Avoid using only quota attainment to gauge ramp rate. Tailor ramp assumptions to your business for precision. Automating these calculations can save time and improve accuracy. Optimized sales ramp tracking can significantly impact planning.

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Who's your favorite CMO / VP Marketing in Austin? We (the Exit Five team) are traveling to Austin in November for a team offsite, and we're going to host a meetup (happy hour, networking, etc.) I'd love to do a fireside chat with a B2B CMO for this event, but I'm not plugged in down in Texas. So: who's your favorite CMO in Austin? Who should be on my list to reach out to interview for a live podcast / Q&A with 100 B2B marketers in November?

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