Todd Grierson

Executives won't open cold emails, but they will open a package. This is my best advice for breaking into Tier 1 accounts... When we were trying to break into big enterprise accounts at Levelset, there was one approach that consistently worked. We sent our top prospects a gift in the mail. Most teams never try this. They send another cold email, another LinkedIn message, or another voicemail. Then they sit around wondering why nothing converts. When you’re going after companies that can change your trajectory, you have to operate differently. Start with the person you are trying to connect with. Before you buy anything, spend time learning about the prospect. Look at what they post. Notice what they care about. Listen for the problems they’re trying to solve. You’d be surprised how often people leave clues out in the open. AI is really helpful at pulling this together for you. It's important to understand what would actually matter to them. Pick a gift that shows you pay attention. It takes more effort to pick something thoughtful than it does to spray a thousand people with the same sequence. But you’re not going after a thousand people. You’re going after the handful who can meaningfully move your business forward. It doesn’t need to be expensive. It needs to be personal. Somewhere in the $25–75 range is enough to show you cared without feeling transactional. Include a handwritten card. Keep it simple. Three or four sentences. Tell them why you chose the gift. Tell them what it made you think about in their business. Then make a clear, easy ask. When everything else in their stack is automated, a handwritten note stands out. Send it in a bubble mailer. Nothing fancy. USPS works fine. A bubble mailer gets opened. People are curious. Just make sure the address is right. We double checked every single one. Full up after it arrives. Don’t assume they saw it. Don’t assume they connected the dots. Send a short email. “Just shipped you something. Should arrive this week.” Then follow up again after it lands. The follow up is where the meetings get booked. Did this work? At Levelset, this was our most reliable way to break into large accounts. The response rates were dramatically higher than anything we did through email or phone alone. And it wasn’t because we were clever. It was because we were willing to put in more effort than everyone else. Most reps won’t spend thirty minutes researching a prospect or writing a card. That’s fine. The ones who do will win the meetings with the best prospects. The Reality This work doesn’t scale. It’s not supposed to. You don’t run this play for your entire TAM. You run it for the hundred companies that would meaningfully impact your business if you earned their trust. For those accounts, a thoughtful gift is a small investment compared to the upside. And if you’re willing to do the work, you’ll end up in conversations your competitors never even get close to.

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Your outbound isn’t broken. It’s just under-instrumented. Most teams are flying blind on what’s actually happening in the funnel. Is it the list? The offer? The channel? The pitch? Nobody knows. They just throw more reps at it. Outbound should be treated like a GTM lab. Every week: new audiences, new campaigns, new copy, new call angles. Each test with a clear hypothesis and a tracked outcome. That’s how we helped a seed-stage PLG client 4x their cold email conversion in 30 days. Reached the same persona, but split-tested two wildly different pain narratives. One flopped. One landed 9 meetings in a week. Same list. Same ICP. Just better thinking upstream. Most outbound teams don’t need more volume. They need better experiments.

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61% of B2B buyers say they trust blogs more than sales reps. That means your blog is your new SDR. Except it doesn’t ask for salary hikes. But here’s the problem: Most blogs write like they’re applying for a government job Safe. Predictable. Emotionless. The SaaS blog that converts looks like this: → Starts with a real problem → Gives a real name to the villain → Uses data without drowning people → Makes the solution feel doable → Doesn’t hide the CTA like a guilty secret Your blog shouldn’t just educate. It should recruit. What else would you add to the list?

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Your CRM thinks that deal is closing. Your buyer isn't even thinking about you. Monday morning pipeline review. Your rep says "500K deal, proposal stage, 80% probability." Three weeks later? Radio silence. Deal hasn't moved. Buyer isn't responding. Now you're scrambling to replace that revenue. I don’t know if you didn’t know but…  Your CRM stages measure what YOU'RE doing, not what the BUYER is thinking. That's exactly why your forecast accuracy is like flipping a coin. As a former #1 sales director who managed 110 reps, delivered $190 million annually in new business. I've seen this problem destroy quarterly forecasts, kill sales momentum, and get really good sales leaders completely fired. But I've also seen the fix. When organizations implement the ADVANCED method, their forecast accuracy jumps from 60% to 95% plus within the first quarter. ADVANCED tracks buyer progression, not seller activity: A - Acknowledged Problem (10%) Documented acknowledgment of a specific costly problem. "This security breach cost us $2 million and we need to prevent it." D - Documented Issue (15%) Written evidence. Email, internal memo, project brief. Something tangible that says this problem is real and needs solving. V - Validated by Team (25%) Multiple stakeholders agree this problem impacts executive-level metrics. Not one person complaining. A - Authorized by Executive (40%) An executive officially sponsors solving this problem. They've mandated their team to evaluate solutions. N - Narrowed to External (60%) They've decided they can't solve this internally. They're committed to buying from an external vendor. C - Chosen as Vendor (75%) You're the preferred vendor. They've stopped talking to competitors. The scope reflects all stakeholder input. E - Established Timeline (85%) Implementation timelines based on business outcomes. Not arbitrary dates. Timeline driven by business need, not sales pressure. D - Deal Terms Finalized (95%) Commercial terms agreed. Pricing approved. Contract in legal review. All decision makers confirmed. I was working with a $50 million e-health company. They had $30 million in pipeline in "proposal stage." When we applied ADVANCED? A very small percentage was actually at closing stage. Most hadn't gotten execs involved. Most didn't have multiple stakeholders. Most didn't have documented issues. They were sending proposals thinking deals would close. But they were creating false forecasts and fooling themselves. Your pipeline is either built on buyer reality or seller fantasy. There's no middle ground. — Sales Leaders, think you’re leaking revenue somewhere? You might want to check this out: https://lnkd.in/g8M-ah5s

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I've been working with a bunch of teams lately on the post-sale experience, and there's some patterns I keep seeing… The companies with the highest retention + expansion do a few things differently: 1. They bring CS into sales calls No “handoff”, the CS rep actually meets the customer during late demo/trial. Eliminates the awkward "tell me about your use case" conversation after signing. 2. They map out the entire user base We started asking "Who else will be using this?" and inviting those people to demos. Things go way smoother when users know what's coming, not just the person who signed. 3. They base expectations on past experience One team was saying “you can get set up in under 30 days” but it actually took 2-3 months for customers to see real outputs. When they switched to milestone-based rollout plans customers stopped feeling like they weren’t doing it right and were way happier. 4. They create mini-wins in the sales process Showing prospects their own data,, using their own process as the demo workflow, giving them something that already looks and feels like them. Putting the product in their hand gives way more confidence that it will work IRL (guided experience, not giving them a login). 5. They schedule everything upfront Send calendar invites for all your post-sales steps right when the contract is getting signed (don’t wait). Everyone knows exactly what happens next, no guessing or surprises. The teams doing this are closing deals faster because everyone feels more confident about what comes next. What's been working for you? ————————— 👋 Hi, I'm Monica. I help B2B SaaS founders grow revenue from $1-$10M ARR. If this is you, send me a DM. 

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Five metrics stress-tested in 15 minutes (Interactive version link in the comments). No detailed spreadsheets - Just six sliders and a conversation that actually mattered- walked into a Sales / AE capacity planning session last week with a react dashboard instead of the usual spreadsheet. Something shifted immediately... We were having a real conversation. The sliders made it visual - No ambiguity about what's driving what. Within 15 minutes we had stress-tested: Quota:OTE ratio vs. benchmark; Sales: Earnings ratio Does the commission rate still make sense? If attainment drops from 75% to 60%, how many more AEs do we actually need to hit the target and what does that do to our cost per dollar of new ARR? Can our AEs realistically close the number of deals needed in a year or are we kidding ourselves? What's the fully loaded comp expense look like at realistic attainment? The conversation stayed grounded because everyone could see the same math, in real time, with no one hiding behind a complex model. The simpler the tool, the harder the questions people ask. When you strip away the complexity, there's nowhere to hide behind "let me get back to you on that number." Next up - upstream/ connected metrics to turn this into a Sales + Marketing planner. Similar approach: Flexible assumptions, simple math to eventually model/ stress test unit economics Curious to hear how you are using AI tools to better partner with the business and drive clarity around these decisions. What's working for you?

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Think a $500k OTE is a bulletproof vest? It’s not. It’s a mirage. The biggest lie in enterprise sales is that money solves everything. You’re dangling a massive check to distract from a culture that’s a total dumpster fire. Top reps aren’t coin-operated robots. They have zero patience for "performative" leadership and red tape. You can’t pay someone enough to endure a boss who manages by spreadsheet while the strategy is a bucket of ice water to the face. I see it constantly: You hire a heavy hitter, hand them a gold-plated contract, then suffocate them with "alignment" calls and pointless QBRs. It’s like buying a Ferrari and forcing the driver to navigate a parking lot of speed bumps. Eventually, the mental tax exceeds the paycheck. They’ll take a "pay cut" just to work somewhere they’re actually empowered. Stop trying to polish the turd with bigger checks. Fix the environment. Respect the talent. Or watch your best people jump ship while the ink is still wet on the offer letter. Money buys attendance. Culture buys the win. https://lnkd.in/eHT5J8hV

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Most SDRs aren’t actually selling. They’re stuck at building lists, researching accounts, and switching between tools. That’s admin work, not revenue work. Hire a GTM engineer to handle qualification, scoring, signals, and CRM uploads. Now your reps start the day with ready-to-call leads. Less busy. More productive. Are your reps selling… or just staying busy?

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The best sales teams I've led had one thing in common. It wasn't the product. It wasn't the comp plan. It wasn't even the talent. It was culture. And not the ping pong table, free snacks kind of culture. I'm talking about something deeper. Something you can't fake. Here's what I've seen on every winning team I've been a part of: (you may want to bookmark this for later) The leader actually cares. Not performative caring. Real caring. About the people, their growth, their families, their goals. You know that old saying “nobody cares what you know until they know how much you care? “It's real. And your team can smell fake from a mile away. Trust runs deep. Not just between you and your directs. Between the team members themselves. No gossiping. No saying one thing and doing another. You do what you say you're going to do. Period. The team has each other's backs. This is where the magic happens. When your people trust each other *really trust each other*you get cross-team learning. You get people jumping in to help without being asked. You get a team that moves faster than the competition because they're not wasting energy on politics. This fulfills a core human need: connection. And connection drives performance. One thing that's worked for me: the Life Map exercise. 90 minutes on a virtual call. Everyone shares their story. It blows the doors open on trust and connection. Google it. Another thing: at end of quarter when everyone's grinding, my team leaders would host daily office hour calls. Open to any AE. Come with your deal questions, your pricing issues, your internal blockers. The team helped each other through the chaos. That's what creates unfair advantage. That's what creates complete domination when you're competing externally. You want to win? Build a culture where people actually give a damn about each other. What's one thing you've done to build real trust on your team? ----------------------------- want more real insights from 25 years in B2B tech sales leadership? give me a follow. if this is your year for making the next big leap in your career...DM me.

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I’ve worked with so many clients. But this one left a mark. They’re a tech startup led by a powerhouse C-suite… all of them came from major brands and decided to build something of their own in the SaaS space. And they’re doing it. We were deep in the process of helping them hire a senior leader. One of my candidates made it to the final round with their executive team. Everyone clicked. The conversation was strong. The warm and fuzzy feelings were in the air. But a week before the final interview, the candidate called me. She had just received an offer she couldn’t turn down. It was the right fit for her family, her future, and she decided to remove herself from the process. I passed the message to my client. And you know what their response was? You’re not ready for this… “Can you send me her number? I want to congratulate her myself.” That’s exactly what they did. Within 10 minutes, they called her and thanked her for her time. They also celebrated her for this awesome offer and wished her well. They didn’t do this because it benefited them in any way. They did this because it was the right thing to do. The candidate told me she’d never experienced anything like that in her entire career. And honestly? Same. When good people come together, they root for each other… Especially when the outcome isn’t in their favor. That’s the kind of leadership I choose to work with. After 11 years at one company, I left behind my book of business and started over. Started from scratch. And I’ve been building something new... with intention. My book of business now? It’s filled with kind, human-first leaders… JUST. LIKE. THIS. If that’s the kind of leader you are, and you’re hiring, call me, text me, or DM me. I’ve got the energy, the time, and the capacity to help you build something worth staying for. Let’s work together.  I.AM.READY. #leadershipdevelopment #consciousleadership #emotionalintelligence #hiringstrategy #techstartups

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Spoke with an Operating Partner recently about a brutal situation. They walked me through the numbers on a CRO hire that didn't work out. Total damage was likely well over $10M (cash comp, stalled pipeline, attrition of solid performers).. For a hire that lasted 14 months. I'm sharing it because this pattern is everywhere right now. Funds are under more pressure now. Higher expectations on portfolio performance and they are cranking the operational dials all the way up.. As they should be. And somewhere in that velocity, the rigor around executive hiring gets compressed. Understandably. It becomes a speed problem instead of an accuracy problem. Here's what I think is happening: Most funds have world-class frameworks for deal diligence..which is great. But when it comes to executive hiring in portfolio, the process is slow because it's treated like a portco problem, not a fund problem. Until it becomes a fund problem. This is likely due to a lack of operating resources spread across too many portco’s in many cases. Executive hiring needs the same rigor as deal diligence because the stakes are ONGOING. A bad exec hire metastasizes. It consumes your time. It affects other portfolio companies because now you're pulled into firefighting mode instead of value creation mode. What does rigor actually look like here? - time up front to pressure-test what the company actually needs.. The job description and the value creation plan should line up neatly end to end. - Alignment between the CEO, board, and whoever's going to work closest with this hire - Pattern-matching to operators who've solved THIS problem. The answer is usually to take a breath and scope properly with the VCP in mind. If a hire fails, control the blast radius.

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Sales gets all the playbooks. Recruiting gets vibes and hope. But the patterns are nearly identical. Pipeline health. Follow up speed. Objection handling. Nurture sequences. Same mechanics. Different targets. The companies already great at sales can level up recruiting fast, if they apply what they already know. Because hiring gets predictable when you treat it like a go to market motion, not a last-minute scramble. Recruiting is not a guessing game. It’s a pipeline game. It’s a systems game. And the playbook already exists. #HiringSystems #SalesAndRecruiting #ScaleSmarter #korerpo

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🚫 Stop Calling It "Cold Calling." Start Calling It Proactive Value Delivery. The old idea of the intrusive outbound call center is dead. In the modern, customer-first economy, outbound teams are not a drain on resources, they are Growth Catalysts. The shift is simple; Value over Volume. When executed strategically, outbound doesn't just "dial for $"—it builds loyalty, prevents churn, and unlocks new revenue streams that passive support can never reach. 3 Ways Modern Outbound Becomes a Revenue Engine: 1️⃣ Proactive CX as a Differentiator The Shift: Stop waiting for customers to complain. Use data to anticipate their needs, flag pain points, and delight them before they even consider churning. The Impact: A well-timed, empathetic call can turn an at-risk user into a loyal advocate, securing long-term Customer Lifetime Value (CLV). This is CX-driven retention. 2️⃣ Revenue Expansion Beyond Sales The Shift: Outbound is not just for New Business Acquisition. It's the most effective channel for complex upsells, cross-sells, renewals, and win-back campaigns. The Power: A retention-focused outbound team often generates more durable long-term revenue than a single upfront sale. In my experience, re-engineered customer journeys have yielded a 15% reactivation uplift from dormant segments. 3️⃣ Human Connection in a Digital World The Shift: Automation handles the transactional volume; Voice handles the Value. In a landscape saturated with bots, the human connection bridges empathy with expertise—solving the complex issues that truly solidify loyalty. The Result: Outbound transforms from a low-FCR complaint channel into a high-touch advisory service. If you are treating your outbound call center as a necessary evil, you are leaving substantial revenue on the table. It’s time to equip these teams to become the growth catalysts they are meant to be. 👉 Question: What is the single biggest operational barrier preventing your outbound team from leading with value instead of volume? #CXTransformation #RevenueGrowth #OutboundSales #CustomerExperience #CustomerSuccess #B2B

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Two renewals escalated last month. Different AMs, different objections. Both times I asked the same thing: "What's your proposal?" Not because I didn't have an answer. But I've learned that giving it upfront might solve the deal but builds dependency. They come back next quarter with the same question, because they never had to think it through. After pushing back, this is what happened: One of them laid out three options: postpone the start of the contract instead of agreeing to a refund, offer a consultancy session to improve results, or make the ROI case before touching price at all. All viable. Some better than what I'd have suggested. The other was stuck on a customer who'd gone cold. "What do you know about their usage right now?". Something concrete surfaced. We built the angle from there. My default set of questions before I give any input: 1. What do you know about the account: value delivered, usage trend, any red flags? 2. If we can't just say yes to what they're asking, what else can we offer that still shows we want to make it work? 3. And if they want something (monthly payments, lower price, shorter term), what can we ask for in return? Most of the times, the team already knows the answers. They just want permission to use them. And that's the job. Not having the answers ready, but creating the conditions where they find their own and trust them to act. PS: this is very close to my reaction when they ask me what to do.

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Last week our GTM team flew to Scottsdale for a three-day offsite. We went in with one big question: What does our go-to-market motion actually look like in an agent-first world? Here’s what kept coming up. The issue isn’t that reps need more tools. It’s that most of their day still isn’t spent selling. They’re: – Manually researching accounts – Jumping between 5+ platforms to piece together context – Stitching together call prep from fragmented info – Logging and updating CRM after every interaction That’s not leverage. That’s busy work. Adding another tool doesn’t fix it. It just adds another tab. What we’re really talking about is removing the manual layer altogether — building systems of agents (and sub-agents) that handle research, personalization, and sequencing on their own. If that works, a few things change: – Capacity isn’t tied to headcount in the same way – Reps spend their time in conversations, not admin – Pipeline gets better because every touchpoint actually has context We spent three days pressure-testing this from every angle. Next week, we’ll share what we’ve been building at Warmly,. I genuinely think this is the biggest shift in sales since remote selling became the norm.

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Fractional GTM work forces one thing: ruthless focus. When you’re not in-house full time, you don’t have the luxury of chasing every opportunity. You have to zone in on the levers that drive growth fast. Recently, I worked with a company that struggled with bloated priorities: too many ICPs, unclear messaging, and scattered execution. By narrowing the ICP and refining their positioning, we turned “everyone is our customer” into a laser-focused strategy. Revenue followed. Here’s why focus matters: 1️⃣ Broad strategies dilute results. Narrow strategies amplify them. 2️⃣ The clearest ICP and messaging win every time. 3️⃣ Saying “no” to the wrong things opens the door to the right ones. Fractional work thrives on impact, not busywork. What’s one area where you’ve doubled down recently? 💬 DM me if you're interested in learning more about how fractional services can help drive your startup’s success! #GTM #GrowthStrategy #ScalingSmart #RevenueGrowth #StartupLeadership

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How does your team handle discounts? Not to call anyone out... but I see this all. the. time. 👇 Discounts getting thrown around randomly, reactively, and with no rhyme or reason. - One rep gives 20% off for annual billing. - Another offers 15% for hitting a volume tier. - Someone else throws out 25% just to close what they perceive to be a ‘big logo.’ All of this is costing you way more than the discount itself. Because when every rep guesses differently, you're not just losing margin. 👉 You're training customers to always ask for more. 👉 You're creating internal confusion. 👉 You're making every deal feel negotiable. Clarity starts from the top. So, if leadership can't answer ‘when do we discount and by how much?’ your team will always make it up as they go. Swipe across for the 7 most common SaaS discount strategies, and when’s best to use them. 👉

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Thanks, Matt Green, I love the insight here. Add lack of marketing support to the mix and it paints a picture where failure to hit targets is most often an organizational leadership problem and far less often a sales talent problem.

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In 2015, a rep on my team, Rachel, was trying to crack into Morningstar. I checked LinkedIn Sales Nav, "I know someone who knows our key buyer, XYZ, have you reached out to them?" "Yes. For 2.5 years. No luck." Text the pal that knows XYZ, "Hey! Do you happen to know this person well enough to make an intro for our team?" "I'm standing in his cousin's kitchen, how can I help?" 😳 Upon my pal reaching out, XYZ responded, "Yes, I know they want to meet. I have no intention of changing platforms, but as a favor to you, and if it makes them go away, I'll take the call." "Yesyesyesyesyes, we'll go away, just give us 30 minutes!", was what we were thinking, but we just politely and graciously accepted. *********************************************************** Rachel went on to break a company record when she closed that deal, a deal that just needed one different connection point to get started. Ten years later, the Executive Power Hour is still one of my favorite plays, and you can systemize it with the quick framework below. Prospecting doesn't have to be hard, you just need to look in the places that are potentially a little less obvious, something I've broken down across nearly 45 pages in our Prospecting Playbook, a masterclass not only in prospecting, but how to use Sales Navigator to actually sell. If you want to grab a copy, it's available for purchase - https://lnkd.in/e_i-Bb2B #samsales #linkedintips

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