Umair Malik

Most sales hires follow the playbook. Jenni Cocoa Lee rewrote ours. In week two. This is what happens when you hire builders, not just sellers. It all started with a LinkedIn DM to Julia Lang, who passed Jenni along as a promising candidate. Genevieve Flynn took the call and came back raving. "Former Faire seller who is moving to NYC. Has helped start several businesses there. I think she could be the one we're looking for" Jenni's Final Interview: Clear demonstration of the pain point we are solving, but more importantly, how to show value to the customer & articulate it clearly. I vividly recall Jenni sharing how she likes providing her feedback on product and questioning things. Yep. That's exactly what I want to hear. She was the one. I told her we'd be preparing an offer before she left the room. When we find the right person, we move quickly. Offer accepted. Day -5: She showed up before showing up Jenni joined our team onsite before her official start date. While most people would be soaking up their last days off, she was asking questions that made us rethink key initiatives. This was the second time I knew we'd found something special. Week 1: Value over features Most new AEs spend their first week memorizing feature lists. Jenni? She went straight to understanding customer outcomes. "Features are what we built. Value is why they buy." She's already coaching our SDRs on this mindset shift. And our discovery calls are transforming because of it. Week 2: Product feedback that matters Here's what caught me off guard: Jenni's not just selling our product. She's making it better. Already flagged product improvements that would directly impact deal velocity. Proposed solutions, not just problems. Acting like an owner from day one. Here's the thing about hiring: Most companies hire salespeople who can hit quota. We hire people who can build the future. Jenni came from launching multiple businesses at Faire. She chose us over an AI startup after digging into our own AI roadmap and experiencing our culture. She saw what we're building. And decided to help us build it. What Jenni's teaching us: ✅ The best salespeople don't just close deals. They create believers. ✅ Process improvements compound. She's already optimizing our SDR-AE handoff. ✅ Dive into pain funneling to help remind brands of the true pain of losing customer data That's how you build a rocket ship. One exceptional person at a time. Welcome to the team, Jenni Cocoa Lee. Something tells me this is just the beginning. 💙 To every founder reading this: Stop hiring people who can just "do the job". Start hiring people who think like an owner. #hiring #sales #startuplife #teambuilding

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Most cold emails don’t fail because of bad deliverability. They fail because they are too easy to ignore. Here’s why your prospects aren’t responding: 1. Your email looks like a pitch • If your email sounds like every other sales email, it’s getting deleted. • “We help companies like yours increase revenue” = instantly ignored. 2. Your CTA asks for too much, too soon • “Let’s book a 30-minute call” is too high-friction. • The best CTAs are low-commitment questions that make it easy to reply. 3. Your email is too long • Decision-makers skim emails. • If your email is over 80 words, you’ve already lost them. Cold Email works when it’s timely, relevant, and effortless to reply to. Would you respond to your own email?

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Top 5% AE's understand that differentiation of how you sell is more important than what you sell. Every interaction is a micro demonstration of what a partnership with your company will be like, and feel like, for a customer. One helpful framing is Maslow's pyramid. Foundational 3rd- show up on time, prepared, with the right materials, do your homework, develop a point of view, sending an agenda before a meeting, and follow ups after.... Middle 3rd - Be consistent, protect the buyer from mistakes, transparency about pricing, risks, scope, reduce uncertainty for the buyer. Make them know that you're on it and on their team. Top 3rd - Arm your DMU with narratives, decks, and ROI to help them build their credibility, help them build an internal vision for future state, ensure everything is tied to outcomes (not your inflated ROI calculator - I am taking about real outcomes for them). Do this and you'll be differentiated by the change you helped drive, not what you sold. This is what enterprise selling is all about...

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What do you think is the most valuable part of the sales process for companies doing at least $50m a year when buying software? It's GOTTA be the business case, right? The ROI story? Surely, it's the pitch about outcomes? WRONG. WRONG. WRONG. Wynter ran a study and talked to 300 c-level folks in companies doing at least fifty million a year to find what part of the sales process provided them the most value. Guess what they said? THE PRODUCT DEMO. YOU READ THAT RIGHT. "Nobody cares about cares about features." "Sell the sizzle, not the steak." "The product is irrelevant. The only thing that matters is the business outcomes." These "best practices" are just patently false. They are concepts borrowed from B2C (where nobody is confused what the product is) and mis-applied to B2B software (where NOBODY knows what the product is or does by default). You cannot talk about value without first crossing the "what is it" barrier. This is why the demo is important. It answers "what the hell is this thing" — and that level of understanding is a BASELINE REQUIREMENT to talking about business cases, ROI, outcomes, etc. If we don't even know WHAT the thing is, it doesn't matter what outcomes you promise. Here's a short clip of me talking about this with Leah Tharin on her badass awesome podcast.

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SWEAT THE SALES STUFF EPISODE 10 IS LIVE!! 🔥🔥 This one’s special. I trained with Max Bashlawi — former #1 Enterprise AE at Cockroach Labs and multiple President’s Club winner. Max is the first Account Executive we’ve had on the series… and he didn’t disappoint. We got into: - His non-traditional route into enterprise software sales - Going from a public company to being the first AE on the ground in EMEA at Cockroach Labs - The mindset that separates top performers - Why every rep needs a clear north star - Asking the tough questions in deal cycles - Managing seven-figure sales processes Max is one of the best AEs I’ve spoken to. His mindset, attention to detail, and attitude to sales are second to none. 💡 My biggest takeaway? Ask others to pick holes in your sales process. They’ll spot things you don’t, and that could be the difference between closing a deal or losing it. I can’t recommend this episode enough for Account Executives - whether you’re already in enterprise sales or working your way up to make that move. Link to the full episode is in the comments 👇 Sponsored by 6sense - - - 🎥 Sweat The Sales Stuff is the FIRST and ONLY video series where software sales leaders are interviewed in a fitness setting. 👍🏾 Please like, comment and subscribe.

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Cold calling isn't dead. This week, two advisors onboarded with FINNY and booked prospect meetings within 48 hours of starting. The magic formula seems to be (for these immediate successes):  Familiarity + Intent + Urgency. For familiarity, they used local zip codes in their search.  For intent, they searched for prospects who engaged with keywords related to their offerings. Then, once FINNY generated a list of leads with high F-score (high propensity to convert), they called & emailed that list & were able to book meetings nearly instantaneously. There's something about picking up the phone and dialing (or having an AI do it for you) that really just works.

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Collin Schull and the team at Building Products Inc. are saving their outside sales reps 10-15 minutes per stop. Here's how: BPI's reps speak their sales call notes directly into Pronto instead of typing them out. The AI assistant pulls the info—who they talked to, what was discussed—and drops it straight into their CRM. But here's what's exciting: they're not just using it for call notes. Check out what Collin shared with Distribution Strategy Group about how else his team is using Pronto: "The guys that have found out it can write your email for you, they're using it quite often. We're not having to think of the perfect way to write an email. It gives you a general idea of the language appropriate to send out to a customer." That's the shift we're seeing across distribution. Reps don't want to spend their time on admin work—they want to be selling. When you give them tools that handle the tedious stuff, they can focus on what actually drives revenue: building relationships and closing deals. We're just now scratching the surface of this. Our engineering team is cranking out even more features to help sales teams cut back on busy work. Here are a few examples that are new since last month's launch: → Pronto now reads responses out loud—perfect for outside reps driving between sites → Reps can have Pronto create tasks with notes, assign teammates, and set due dates → Reps can now use Pronto to quickly generate quotes Congrats to the Building Products Inc. team—love seeing how our customers are using Pronto to make their lives easier and show up better for their own customers.

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I have been asking some of the top leaders in the short-term vacation rental industry to reflect on their Top 10 Mistakes. Why? Because I feel this is really where you start to get some real learnings. Here’s Brandon Ezra with Stakeholders VR (and former Founder of Grand Welcome) Top 10 Mistakes.... 1️⃣ Under Capitalized - Not having enough capital caused a trickle down affect that I felt right until exiting my company. It dramatically affected the growth and potential of my business and ultimately my personal financial outcome. 2️⃣ Hire a Strong Executive Team - I didn’t hire a strong enough players quick enough to support the growth that I was bringing to my business. 3️⃣ Adequate Infrastructure - Prior to my explosive growth my infrastructure was not good enough. This caused problems in almost every department and eroded some of the value that I was creating. 4️⃣ Hiring Locally - Hiring locally dramatically diluted the quality of the staff I worked with. Covid made this quite evident. 5️⃣ Wrong Capital Partner - My capital partner did not have the constitution keep up with my growth and my business scale. It was a silent killer. 6️⃣ Ignored Established PMCs - Working with existing PMC’s would have added stability to my franchise sooner. 7️⃣ Held Key Team members Too Long - If someone is not working, cut them immediately. I didn’t do this quick enough and it caused a lot of damage. 8️⃣ Didn’t Step Aside as CEO Soon Enough - I specialize in fast growth, generally with new concepts and ideas. Once I realized my business was exiting its fast growth phase I should’ve stepped aside as CEO. Perhaps moved to an advisory role. 9️⃣ Not Embracing My Talent - Many people can run a steady business, as opposed to explosive and rapid growth. I am the later. Once I realize that my partner is stifling my business’s growth and there’s nothing I could do about it, I should’ve left immediately and gone to the next opportunity. 🔟 Wasted Time on the Undeserved - Don’t spend time with people that simply don’t deserve it. 📚Did you find these insights valuable? If you’d like to uncover even more lessons from the top leaders in the short-term vacation rental industry, I’ve written a book compiling mistakes from 52 of the most successful leaders. I’d love to send you a copy—for free, no strings attached. Simply visit our website (link in comments) and I’ll mail one right to you! I hope it’s helpful for you.

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Most sales leaders and founders never properly learn how to train their reps. These are the ten most important rules you have to consider when training your reps: 1/ You start with a theory session, then show how it is done and then have them put it into practice. (I learned that one in officer training in the Army). 2/ After you gave the feedback, ideally you have them put that into practice right away in front of you. Then, another feedback and repeat again. 3/ Whenever you give feedback on a call/ email/ process, ONLY say one or two things. Don’t overwhelm your reps with feedback. They won’t be able to put anything in to practice. 4/ The feedback the recording and role-play tools deliver after the calls is usually worthless. It is too overwhelming and often not specific enough. 5/ Do repeated training sessions. Have the reps repeat the learnings from last session before you start again. 6/ Show how things are done by recording your client calls and share them with the team (and store them in the playbook). 7/ Practical sessions (role-plays) > Theoretical sessions 8/ Do training sessions in a group and have your reps give feedback first. Helping others become better is the best way to become better. 9/ Make training fun by using playful approaches like the cold call training I shared last week. 10/ Share your learnings on LinkedIn. This way, you force yourself putting it into practice even more so. Anything else you would consider? If you do not have time for effectively training your reps continuously, we have a solution for you. Check out the demo in the comments. 👇🏻

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Not everyone who’s great at selling is built for early-stage sales. Late-stage sales is about scale: repeatable motions, comp plans, playbooks, and process. Early-stage? It’s chaos. You’re figuring out what you’re selling, who it’s for, and why they should care. All while learning how to close. At Venn, we learned this the hard way. - The best early sales hires weren’t the most polished closers. - They were curious, scrappy, and eager to dive into every part of the sales cycle - They knew how to sit in the ambiguity and still move things forward. At a startup, there’s no playbook. You’re writing it while you sell. The goal isn’t to hire someone who’s just great at sales. It’s to find someone who’s comfortable being wrong, quick to adapt, and able to turn feedback into progress. Early-stage sales isn’t about repeating what works. It’s about discovering what works. What traits have you seen make someone thrive in zero-to-one sales?

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