🧗🏻 Andrew Mahr’s Post

Weigh in here... Enterprise prospecting used to be all about network access. Has that changed?

The Enterprise buyers you’re cold calling are a lot better informed on tech than you realize. Which makes cold calls/emailsDMs about your Better Technology not just boring, but mildly insulting. Case in point - the US nuclear missile system relied on 8” floppy disks until 4.5 years ago. Do you think the DoD didn’t realize there was better tech? Of course they did. They lived with the problem everyday. But they also understood what a massive and risky headache it was to swap in something more modern and capable. Your prospects are no different. They know there’s better tech out there. No duh. But they also feel that swapping tech isn’t worth the personal political capital, expense, integration pain, re-writing internal training materials, project management, months of extra meetings, and more. Cold outbound to executives does 1 thing — start a conversation that maybe the trade-offs are worth it after all. And you lose that conversation immediately if your prospect can tell you don’t deeply respect that those tradeoffs exist for them. #enterprise

A huge waste of effort for many sales reps is trying to figure out “How should I position [uncomfortable topic] with this prospect?” Here’s the thing… Of the few things entirely in your control, few matter more for your success than whether or not your prospect trusts you. And every time you spend effort trying to spin or hide or minimize something inconvenient, several things are happening: 🔻 You’re creating an opportunity for your prospect to lose trust, where none existed before 🔻 You’re NOT spending effort on how to thoughtfully address or resolve the real issue is (the one you’re trying to minimize) 🔻 You’re missing out on an opportunity to build trust by demonstrating that you’ll err on the side of transparency and candor This is all self-defeating. Totally understandable given how humans are wired and what fear does to our brains. But also still totally self-defeating. Next time you find yourself wondering or asking your manager some version of “How should I spin…”, “How should I position…”, etc, here’s a thought exercise: 💡 What would happen if you started the conversation being transparent? 🤝 How might you turn that into a conversation that builds trust and confidence instead of causing the issue you’re afraid of? Transparency and trust work.

What’s the best indicator that a top performing sales rep will also excel as a manager? What I’ve observed may seem counterintuitive: 🟢 If the rep initially struggled (even almost failed) and had to slowly re-engineer their habits, processes, and strategies to succeed — they have a pretty good shot in first-line management. 🚩 But if a rep basically succeeded from the get go — sales came naturally to them because of their gifts/strengths — management may be a real struggle. This has nothing to do with grit or perseverance, though that doesn't hurt. The issue is that first-line sales management is largely about understanding what’s causing underperformance for an individual and designing a system for that individual's success. And that’s pretty challenging to do for others if you’ve never had to do it for yourself.

VC buzz is that AI will replace SDRs in the next 2-3 years. But that can't possibly mean what it sounds like when you read the fine print: 👮♀ First, the phone. This is a Regulatory issue with far broader scope than b2b sales calls. The FCC made it clear in February that AI-generated phone calls are considered robocalls and thus illegal under TCPA. "Wait, that doesn't apply to B2B." True, but again read the fine print: TCPA does cover ALL cell phones. Without a major change in climate in DC, AI SDRs aren't calling. 🛑 How about social? LinkedIn would be an amazing place for AI SDRs to operate of course. Buuuuut it's owned by Microsoft, who in case you hadn't heard is sort of invested in owning AI use cases, and isn't in a million years letting AI SDRs mine its data or operate independently on the platform. I know companies that have lost their Sales Nav licenses because their sales team was using basic LinkedIn automation tools. AI will scale video creation and that will make LinkedIn a very different place than it's traditionally been, but you're still going to need humans building the human connections. In my opinion offshore profile management options like what Jamie Shanks is building will be the affordable scale-up route in the near term. 📩 OK, so can AI SDRs own the email channel? I'll start with the easy party — yes, they'll handle your inbound email replies and meeting setting. That turkey's cooked. Outbound though? I just can't believe the hype here. I have managed and seen peripherally A LOT of "personalization at scale" email campaigns: use signals + write persona-based signal responses + automate contact workflows, etc. Did it the hard way before Clay hit the scene. And yes when done well, the numbers can work IF you are targeting SMB or some other very large market. But if you're selling to MM/ENT, the only way email prospecting works is by getting much higher open+reply rates than what the signal+persona route delivers, which means you need to deeply research people.... largely on social.... and write truly, amazingly personalized messages. See above on access to social data ⬆ 👬 Is the traditional SDR role safe then? No. Because there is a very compelling case for having it split into channel specialist variations. First, people have different strengths -- it never really made sense to have people who are great on the phone also doing a bunch of email steps, and vice versa. As folks like 💛 Shawn Sease - The Professor of Prospecting have demonstrated, phone is a completely different discipline than social. Second, channels are ultimately different lists -- there are people who answer phones and people who don't. People who get on social, and people who don't. And then the email crowd remains. Data will get better on this and you'll have different roles targeting different lists on different channels. At least, that's my forecast! I'd love to learn from others perspectives here. What am I missing?

For my sales colleagues out there trying to balance work pressures with raising a young family, here's something pretty quirky that worked great for us: No surprise -- my kids loved our time away from tech, being outdoors Maybe a surprise -- they also REALLY loved breakfast pipeline reviews Our system was dry-erase magnets on the fridge representing deals: ◻ each magnet = deal name + point value (1 point = $1000) ➡ magnets moved left-to-right to mimic deal stages 🎯 quota, QTD progress, and deadline also shown 🥞 most days at breakfast, I'd share news and they'd update magnets I started the whole thing because I noticed they like being invited into all my hobbies, so why not the thing I did 50 hours a week? How it played out: 🎢 For better and worse, we lived the drama of the quarter out together. Wins, losses, pushes. Sports were seasonal but quota was forever. I honestly didn't feel work-life tension that much because they weren't compartmentalized in the first place. 👏 Whenever I had to take a sales call at an inconvenient time (inevitable even while I tried to minimize it), the mood was never "Work's more important than family". It was always a deal they knew about, and the convo was usually, "Oh it's Intel? Dad go talk to them, we need that one!" 💯 Also, a few of them got crazy good at doing math in their heads to run what-if scenarios figuring out our best path to quota. I'd come home from work to find one of them studying the fridge, then saying, "You know Dad, if we can just get X in, all we'd need is A and B..." Let me know if you've done something similar, or if you give it a shot!

Believe it or not, booking first meetings is not the problem that enterprise sales leaders list most frequently as the bottleneck in their pipeline. It's failure to get above the power line. They describe this problem using a variety of colorful metaphors that sales leaders are known for coining (e.g. "we're stuck with the gnomes in the basement") but it's all that same issue. When I dig in, it's amazing how frequently this boils down to ambiguity on item: the seller says they have a champion, but doesn't know two laws of Enterprise Sales physics: 1. You don't have a "Champion" unless you have someone who has DEMONSTRATED that they (a) have a personal stake in you winning, (b) give you access to power, and (c) sell for you when you're not in the room 2. If you don't have a Champion, you don't have a deal When you're stuck below power, that is THE issue. You have a friend, sure. But you need to keep searching for a Champion. #enterprise

Prompt engineering can make your next sales meeting with an exec stakeholder 10x better. Here’s the process: 1️⃣ Draft an outline of your sales agenda as you normally would. Spend like 5 minutes on this. 2️⃣ Now here’s the prompt, and (surprise) the interface is your brain not an AI: “Re-write this agenda but pretend the prospect is paying me $1000/hour for my advice on this topic, and it’s crucial I earn it.” 3️⃣ Now do the rewrite, whatever it takes Here’s why this works: 🪄 It breaks the spell you’re under that makes you try to win by selling. It’s not just sales mumbo jumbo — execs really do want trusted advisors. The trick is to prioritize being one over selling. 💡It aligns your actions with reality. Time isn’t free. If an exec joins another 1-2 people to hear you pitch, guess what — their company is paying $1000/hr or more for that to happen. Show up and deserve the investment. 🏋️ It will make you sweat the details, over prepare, leave nothing to chance, and recruit help from your peers or bosses if you need it. $1000/hr is good money and it would be professionally embarrassing to show up, take the money, and give no value in return. What prompts do you use to trick your brain into doing better work?

2 things your enterprise sales reps should document, but most don’t, in their Q3 account plan refresh: 1️⃣ What is the functional deadline to be included in the next cycle of non-discretionary budget? 📆 If you’re past it, the amount you can realistically close this year is determined by… 2️⃣ What discretionary funds are available to DMs at different seniority levels? Every org (and dept) will have different 💸 rules: Sr Directors can spend $25k… VPs, $50k… SVPs, $100k It’s simple to talk about going “above/below the line”, but reality is there are many lines. Which one do you target given the above factors? Is a normal contract viable or do you need to aim for a limited POC to get your foot in the door? 🚨 missing those details? 🚨 Emissary.io isn’t 😉

Solid analogy I once heard for Enterprise sales: It’s like having teenage sons. Good luck forcing a convo on your timeline. But be consistently… present, helpful, proactive… And they’ll let you know when they’re ready to talk. Also, buy food. So much food.