Key traits of successful PropTech sales

I just discovered why 90% of proptech sales fail, and it has nothing to do with the product's features. It's because founders don't understand how real estate developers actually make money. Let me show you the secret math that drives every decision they make. I was catching up with a proptech founder last week. His client, a GP, passed on software that would cost him $500/month. "They said it's too expensive!" he told me, frustrated. Then I showed him the math through the GP's eyes: $500/month = $6k/year = $120k hit to exit value (at a 5% cap rate) With his 20% promote, that's $24k straight out of his pocket. But here's where it gets interesting: Most vendors think real estate is about NOI. It's not. It's about the waterfall. Here's how it actually works: First, debt gets paid. Then, LPs get their principal back + preferred return (usually 8%). Only THEN does the GP get their promote (typically 20% of remaining profits). I used to tell founders: "Pitch the NOI increase!" Now I say: "Show them how to get past their pref faster." Different message. 10x the conversion. The promote is everything. It's why a GP will obsess over a $500/month expense but drop $50k on a lobby upgrade without blinking. One adds to NOI (and helps hit the promote). The other is just a cost. Want to sell into real estate? Stop thinking like a SaaS founder. Start thinking like a GP chasing a promote. Here's the framework I teach: • Calculate the NOI impact • Multiply by the exit cap rate • Show how it affects the promote • Watch them lean forward in their chair Example: "Your current vacancies cost you $10k/month in lost NOI. At a 5% cap, that's $2.4M in lost exit value. With your 20% promote, you're leaving $480k on the table." Now you're speaking their language. Most proptech founders think their enemy is the status quo. Wrong. Your enemy is the 8% pref. Every dollar matters. Every timeline matters. Every basis point matters. Because missing that promote doesn't just hurt the deal. It hurts the GP personally. I spent years watching smart operators pass on great solutions. Turns out they weren't cheap. They were doing math that the vendors didn't understand. Now I teach founders to lead with the waterfall. Sales cycles cut in half. The best prospects? Opportunistic developers 2 years from exit. The worst? Core owners collecting management fees. Different math. Different motivations. Different pitch. Stop selling software. Start selling promotes. P.S. If you want to master this (plus 50+ other frameworks for selling into real estate), we cover all of it in our course on 19th May. Join us- link in the comments. But honestly? This waterfall trick alone will transform your sales. Try it tomorrow. Thank me later.

Multifamily operators don’t buy promises — they buy proof. They’ve seen the perfectly scripted pitch deck. They’ve heard the big claims. And, they’ve lived through the aftermath when a “seamless integration” turns into months of frustration. So when another PropTech company comes along claiming to revolutionize operations, skepticism isn’t just expected, it’s earned. Here’s where things break down too often: 🔻 𝗧𝗵𝗲 𝗶𝗻𝘁𝗲𝗴𝗿𝗮𝘁𝗶𝗼𝗻 𝗶𝘀 𝗺𝗲𝘀𝘀𝘆. Instead of streamlining workflows, it adds complexity. 🔻 𝗢𝗻𝗯𝗼𝗮𝗿𝗱𝗶𝗻𝗴 𝗶𝘀 𝗿𝘂𝘀𝗵𝗲𝗱. Site teams are left undertrained and overwhelmed. 🔻 𝗧𝗵𝗲 𝗥𝗢𝗜 𝗶𝘀 𝘃𝗮𝗴𝘂𝗲. And when numbers finally come, they don’t match the pitch. The result? Operators hesitate. They delay. They default to what they know, even if it’s inefficient. The best PropTech companies understand this. They build great products, they build trust, and they de-risk adoption before the first demo. Here’s what turns hesitation into action: ➡️ 𝗜𝗻𝗱𝘂𝘀𝘁𝗿𝘆 𝗳𝗹𝘂𝗲𝗻𝗰𝘆. Solutions need to reflect a deep understanding of how multifamily operates. Without that, even the best tech won’t get past the first meeting. ➡️ 𝗧𝗶𝗴𝗵𝘁, 𝗿𝗲𝗹𝗶𝗮𝗯𝗹𝗲 𝗶𝗻𝘁𝗲𝗴𝗿𝗮𝘁𝗶𝗼𝗻𝘀. If a tool doesn’t sync cleanly with existing systems, it’s a nonstarter. Operators don’t have time for workarounds. ➡️ 𝗖𝗹𝗲𝗮𝗿, 𝘃𝗲𝗿𝗶𝗳𝗶𝗮𝗯𝗹𝗲 𝗥𝗢𝗜. Promises aren’t enough. If a solution can’t quantify cost savings, efficiency gains, or revenue impact, it won’t make it through budgeting. ➡️ 𝗔 𝗿𝗼𝗹𝗹𝗼𝘂𝘁 𝘁𝗵𝗮𝘁 𝘄𝗼𝗿𝗸𝘀 𝗶𝗻 𝘁𝗵𝗲 𝗿𝗲𝗮𝗹 𝘄𝗼𝗿𝗹𝗱. Even great tech will fail if adoption is painful. Training, support, and change management matter just as much as the platform itself. Multifamily isn’t resistant to innovation. It’s resistant to risk. The takeaway is simple. Make adoption seamless. Make the value undeniable. 𝗠𝗮𝗸𝗲 𝗶𝘁 𝘄𝗼𝗿𝘁𝗵 𝘁𝗵𝗲 𝗰𝗵𝗮𝗻𝗴𝗲.

The biggest indicator of future sales success? It might surprise you. The best trait of a salesperson is coachability. I didn’t really get this until I’d hired and coached a lot of people. Most think coachability means that they take feedback. But that’s the shallow version. The real thing shows up in small moments: 1. They update fast. You give them a new angle, and they immediately shift their answer. 2. They don’t hide behind old experience. Instead of “this is how I’ve always done it,” they say, “let me try this new thing”. They are always looking for ways to be better at sales. 3. They test things on the spot. In an interview, a role-play, wherever. Test, and iterate, constantly. 4. They care more about getting it right than being right. You can feel when ego leaves the room. 5. They show the change. You give feedback early, and you see the improvement later in the same conversation. A leader once gave me a chance when all I had was the ability to learn fast. It shaped how I hire today. If you want a strong sales team, hire the people who adjust quickly. Everything else you can build. What’s the best example of coachability you’ve seen in a candidate? - Like my content? Let's connect Follow Tim for more on B2B sales.

He closed a $650k deal. 🤯 One of the biggest I've ever seen in SMB. He’s a rockstar. And here's how he won it. Hint: It all came down to post demo effort. What he did post demo: 1. Recapped progress constantly He kept everyone aligned at every stage. Summarized what they cared about, how we solved it, and why we’re different. Especially when new stakeholders got involved. 2. Pulled in leadership early He didn’t wait for a late stage “exec introduction.” He added his manager to calls immediately, strategized pricing with her, and had her message their team. Which built a ton of trust and confidence. Especially since our competitors didn't do this. 3. Tailored everything to their business case He created custom resources based on their priorities. The decks weren’t generic. They were written in the customer’s language, mapped to their goals, their metrics, their outcomes. They felt heard. 4. Ruthlessly prioritized the account He treated this deal like his only deal. Moved meetings if needed. Took calls outside of standard hours. If the customer needed him at 7am or 8pm, he was there. 5. Lightning fast response times Emails didn’t sit. If something came in after hours, he responded quickly anyway. Labeled their emails so they surfaced to the top of his inbox. Nothing more important than responsiveness imo. 6. Organized everything in one shared space Any piece of content that will help the deal move forward (slides, timeline, differentiators, call recordings, etc) live in his Aligned room. He monitors where stakeholders are spending time and is proactive with his communications. Which leads to… 7. Created a shared Slack channel Connected their team with ours: onboarding, specialists, leadership. Between his digital sales room and slack channel he eliminated long email chains. No bottlenecks. Problems got solved fast. 👉 Get the template here: https://lnkd.in/gtdbaGAB 8. Stayed close during onboarding He didn’t “throw it over the fence.” Stayed involved so the customer never felt handed off. Buyers love when their AE sticks with them through go live. 9. Validated priorities constantly Instead of assuming anything, he kept checking in: “Is this still the most important thing?” “Did anything change internally?” No guessing. No surprises. 10. Used customer proof instead of feature pitching Short, relevant before/after stories about customers he personally helped. He built trust immediately with real world stories and references. Who says you can’t close massive deals in SMB? – Mike G

The best CROs and VPs of Sales all seem to have a similar playbook. At Sales Assembly, we talk to hundreds of revenue leaders - some just stepping into a new role, others fresh off a funding round, and a few preparing for major scale. The best ones? They stand out. Not because they’re louder on LinkedIn. Not because they’re flashy. But because they’ve built repeatable systems that work. Here are six common traits we consistently see among top-performing revenue leaders: 1. They bring a process - It doesn’t matter whether it’s MEDDPICC, Sandler, Challenger, BANT, or some other 2-10 letter acronym, what matters is consistency. A clear sales process creates structure, enables accountability, and makes it easier to diagnose performance issues. According to HBR, companies with a formal sales process see 18% more revenue growth than those without one. 2. They bring a bench - The best leaders don’t build in a vacuum. They’ve built trust over time and that shows up when former colleagues are willing to follow them to a new company. It speeds up hiring. It builds immediate cultural buy-in. And it’s a huge vote of confidence when A-players want to work with you again. 3. They pick winners - Great sales leadership is impossible without a solid product. Top CROs have strong product instincts and pattern recognition. They can tell if a company has real market potential or if it’s riding a temporary wave. Lack of product-market fit is the #1 reason startups fail (CB Insights), and great leaders know how to spot that risk early. 4. They know their sweet spot - Most top revenue leaders have a zone of genius—whether it’s $1–$10M scaling, $10–$50M growth, or leading through IPO. They’ve done that thing before, multiple times. And they don’t try to be everything to everyone. Instead, they double down on where they know they can win. I'm sure they have crossed a chasm before, but they know which tranche will give them the best opportunity to succeed. 5. They have a network - Need a killer AE? A trusted RevOps lead? A GTM advisor? They’ve got names in the Rolodex. Great leaders don’t build in isolation, they bring a community with them. That network accelerates hiring, supports GTM motion, and opens doors to funding, partnerships, and customers. 6. They are accountable - They set expectations. They follow through. And they treat people with respect. Top leaders aren’t afraid to have hard conversations. They build cultures where performance and personal growth coexist—and where the team knows: if we follow the plan, we win together.

Some traits of the best sellers I've seen over the past 25 years: 1. Default to action vs. contemplating action 2. Confirm calendar appointments before the call ends 3. Respond right away vs. doing it tomorrow or later today 4. Understand the mechanics of their compensation plans intricately 5. When offered meeting options from a prospect, take the first one 7. Easily have a conversation with prospects about their market, broadly 8. Have deeper technical domain knowledge than their peers (re: product) 9. VERY accurately communicate deal status up the chain of command 10. Clearly understand if their product has product-market fit, and won't stick around the organization if it doesn't If you don't do all these things, doesn't mean you can't be great too. It's just a little bit harder. And you can see that a number of them relate to 'urgency'. It's clear in everything they do that urgency is paramount for them. And regarding number 10, great sales people usually know they're great, and great sales people realize their worth and don't want to significantly limit themselves based on a poor fit product. Compare 13,000 sales orgs based on salaries, product market fit, sales culture, and % of team hitting quota: https://lnkd.in/eyJNnytx You actually may be great but just haven't seen the results yet. ✌️