Aligning Outbound Sales with Value Proposition

One question turns failed PropTech pitches into closed deals. And most vendors never ask it. Here's the strategy alignment secret nobody's talking about. Last week, I watched another great product get rejected. Strong features. Clear value prop. But they pitched long-term efficiency to a merchant builder focused on exit value. Now they're wondering why the deal went nowhere. Here's how to align your pitch with their investment strategy: 1. Focus on strategy, not just asset type The secret isn't just knowing office from multifamily. It's understanding their investment timeline: Most vendors only see: • Office vs. retail • Multifamily vs. industrial • Class A vs. Class B Smart sellers also ask: • Hold period length • Exit strategy • Value creation timeline • Cash flow priorities Most fail because they stop at asset class. 2. Tailor your pitch to their timeline For long-term holders, focus on: • Operational efficiency • NOI improvement • Portfolio-wide impact • Solution stability • Compound ROI over time For short-term players, emphasize: • Repositioning acceleration • Lease-up support • Quick implementation • Flexible contract terms The timeline mismatch breaks more deals than price. 3. Ask the right questions first Start with: • "What's your typical hold period?" • "Are you looking to stabilize and hold or exit?" • "How do you handle property management?" • "What's your current solution stack?" Not: • "What types of properties do you own?" • "How many units do you have?" • "What systems are you using now?" • "When can we demo our product?" 4. Connect your value to their strategy Your pitch should show: • ROI within their ownership window • Value that matters to their strategy • Implementation that fits their timeline • Flexibility that matches their exit plans Never assume: • All owners want long-term savings • All GPs prioritize NOI • All buildings are forever holds • All operators think the same 5. Become a strategic partner Investment strategy changes everything: • It shapes their decision criteria • It determines their value metrics • It drives their timeline needs • It defines their success The difference between just another vendor and a strategic partner is understanding their investment strategy. Want to learn how the best PropTech companies align their pitches to investment strategies? Check out our free PropTech Pipeline Playbook email course in the comments.

Odds are, the enterprise CXO on the receiving end of your cold email gives 0.00 f*cks about your value prop. They don't care that you "help others streamline operations." They don't care that you "help others enhance efficiency." Why? Because every other seller is making the exact same claim. It's become white noise in the inbox. What DO they care about? Themselves. Not in a greedy way. But, in a "I don't want to be the reason our company fails to achieve our CEO's business objectives, because that puts me at risk of losing my job" kind of way. Instead of dropping generic value props, try researching your target account's CEO business objectives with a simple ChatGPT-o3 prompt: "Who is the CEO of ACCOUNT and what are their most recent interviews on the company's growth strategy?" It takes ~2 mins to get great intel about what your CXO might be focusing on. We use that to bring a much more specific problem POV to the outbound message. Here's an example of the difference in the output: "Hi Jen, hope your 2025 is going well so far! I came across your name and thought I'd reach out. We're working with other Supply Chain leaders like you to help them streamline operations and increase efficiency. Would you be open to a quick chat to learn more?" vs. "Saw the news re: ACME's 12 new stores opening this year in CA. Seems like this might be part of the new strategy Elizabeth spoke about at RetailCon (shifting to a premium lifestyle brand). Zeta made a similar move when they scaled from 5 Charleston shops to 23 stores in NYC, LA, and SF. Open to hear how they kept their 2-day shipping promise and avoided new store fulfillment issues during that growth? Either way, congrats on the expansion. Can't wait to visit the San Diego store in Nov." Will everyone love that email? No. Does it guarantee a reply? Also, no. That's not how Sales works. There is no magic formula. But - our outbound is a reflection of what a convo with us will sound like. Lazy outreach? Prospect assumes it'll be a thoughtless pitch. Thoughtful research? Much better odds that seller won't run them through a one-size-fits-all pitch. Prospecting isn't a "low value activity". It's the movie trailer to the Sales experience our buyers can expect from us.

Fact: Outbound sales is broken. Incentives and strategies are misaligned. Tools like Salesloft and Outreach didn’t cause it. They amplified it. Now marketing and sales need to work together to fix it. The real issue is that sales managers push SDRs to prioritize volume over quality, leading to generic outreach that no one wants to read. Fixing this starts with focus. Give SDRs a small set of accounts, 30 per quarter, and tier them into A, B, and C priorities (using tools like Clay, Tofu, Unify). This makes it clear who they’re targeting and allows them to spend their time understanding the industries, companies, and people they’re reaching out to. Instead of chasing volume, they can dive deep into the problems their prospects are trying to solve. With the right tools, resources and 𝘁𝗿𝗮𝗶𝗻𝗶𝗻𝗴, SDRs can educate themselves on the pain points, motivations, and challenges of their target audience. They can craft outreach that adds value and speaks directly to what matters most. Take me as an example. If you’re reaching out to someone like me at MoEngage, don’t send lazy, cookie-cutter emails like: “Does getting more pipeline keep you up at night” “Would you be interested in getting more qualified meetings” “Do you want customer lists of your competitors?” “Are you still interested?” “I haven’t heard back. I’ll assume this isn’t a priority.” These don’t work. They’re noise. If you want my attention, show me you’ve done your homework. Understand that I’m focused on growing in North America. Recognize the challenges of expanding into a crowded market. Tell me something valuable about how companies like mine are navigating those problems and how you can help. This approach may lead to fewer meetings overall, but the meetings you get will be better. SDRs and AEs will know their audience. They’ll understand the pain points. They’ll deliver messaging that lands because it’s relevant and thoughtful. And this isn’t just a sales problem. Marketing has to help. Marketing should train SDRs and AEs with insights about the market, the ICP, and the problems worth solving. Outbound sales works best when sales and marketing are aligned, working together to get the right message in front of the right people. Stop trying to get more meetings. Focus on getting better ones.

In February alone, we generated 180 leads for a B2B tech company. It came from building an engine where each part does a very specific job in the buying process. On the content side, we built a distributed executive presence across five accounts. Not generic thought leadership, but deliberate coverage of how the company shows up: product depth, market perspective, commercial thinking, and the underlying beliefs driving decisions. When someone lands on any of those profiles, they’re not trying to figure out “what does this company do?” or “are these people credible?” We take complex products and ideas and make them easy to understand in a way that helps buyers make decisions. The content becomes a structured narrative: how they think, what they’ve done, who they’ve done it for, and what they stand for. The second layer was outbound. Instead of broad ICP lists, we worked from signals: hiring, growth, role changes, timing triggers, and built outreach around that context. That means fewer messages, but significantly higher reply rates. And when that message lands, the natural behaviour is to see who it’s coming from. Prospects check the profile. They scan the content. They look for credibility, authority, and relevance to their situation. They’re effectively running their own due diligence in a few minutes. If that layer is strong, the conversation starts from a very different place. By the time they show up to a call, they already understand how you think, what you’ve done, and whether you’re relevant to them. Which means less time explaining, less skepticism to overcome, and faster movement through the sales cycle. Most teams treat content and outbound as separate functions. In reality, one reduces perceived risk, and the other captures intent at the right moment. When those two things are aligned, the pipeline becomes far more predictable.

Outbound is dead in cyber. Long live AE-owned prospecting. I will die on the hill of "outbound is dead". But it's been misunderstood when I've brought it up here. In cybersecurity, generic mass outreach is dying or it's a zombie waiting to be whacked. Targeted, value-driven prospecting led by Account Executives is thriving. SDR's have a hard time doing this not because they can't, but because the system is not setup for them to do it (i.e. comp plans, org structures, etc.) We know from research that personalized outreach based on deep account knowledge delivers 3x better engagement than templated SDR approaches. Yet we keep trying to build outbound motions with higher volume and worse conversion rates 🤮 Here's my framework for building a repeatable pipeline development program where AEs actually own the process: 👉 *The Value Hypothesis Approach* 1. Narrow the focus dramatically: Your target account list should be small enough that each account gets hours of dedicated research. 2. Make AEs accountable for contact mapping They need to identify key stakeholders and understand the organizational dynamics before any outreach begins. 3. Develop specific value hypotheses This is the game-changer. Each account gets 2 customized value proposition based on their specific situation. 4. Collaborate on hypothesis refinement The best teams involve SE/PreSales, Product Management, and Sales Leadership in critiquing and improving these hypotheses. 5. Execute with precision With this foundation, outreach becomes a targeted conversation rather than a generic pitch. 6. Close the feedback loop: Sales leaders need to document which value hypotheses resonated and which fell flat - this becomes your competitive advantage. The best-performing enterprise sales teams allocate at least 1/3 of AE time to this process. Yes, it's resource-intensive, but the results speak for themselves. 2 hours a day (minimum) every day, every AE, for 3 months. Then come back and tell me 'thank you' Unexpected benefit: When AEs spend 10+ hours weekly on strategic prospecting, your inbound and partner-led conversion rates automatically improve. Why? No AE will let warm leads slip after experiencing how much work cold prospecting takes. Pro-tip? Spend 'Training Thursdays' evaluating value hypothesis together. Double pro-tip, combine Value Hypotheiss with 'Show me You Know Me' on your messaging (follow Samantha McKenna - She crushes SMYKM content) Anyone here that calls value hypothesis something else? I used to call it my 'angle'. Need something more catchy and less scientific-sounding 😆

We didn’t know them. They didn’t know us. Four messages later, they were a client. Two months later, they were one of our biggest advocates. Here’s what worked: 🔹 Message 1: Lead with insight, not a pitch We started with a real observation about their onboarding. Something specific enough to matter. Not a copy-paste opener. That’s what earned the first reply. 🔹 Message 2: Share proof that matters Next, we sent a short case study from a company like theirs. No product talk. Just outcomes. That built credibility without forcing it. 🔹 Message 3: Ask a sharp question Instead of chasing a call, we asked a direct question tied to a pain point they were likely feeling. That’s what shifted the conversation from selling to problem-solving. 🔹 Message 4: Give value with zero pressure We shared a quick teardown of one of their workflows and suggested changes they could use straight away. No ask. Just value. Their response? “Let’s talk.” This didn’t happen by luck. It happened because every message was relevant, useful, and focused on them, not us. Outbound works when you stop trying to push and start trying to help. Curious to hear: What’s the single move in your cold outreach that almost always gets a reply?

Most people think outbound is a volume game. But sending 10,000 emails with the wrong message just gets you bad data faster. Here’s what we started doing instead using Instantly.ai 👇 Every new project begins with message testing, not “campaign launch.” We build 5–10 micro-variations of the same core offer -> different angles, tones, and pain points. Then we send each version to 100–200 prospects. Not to sell (I mean - we'll take what we can get..). To learn. Patterns always show up: - One angle gets curiosity, another gets ignored. - Some audiences hate the “ROI” talk but love a specific workflow fix. - Sometimes the best-performing line has nothing to do with your product, it’s the problem framing. "If you can frame the problem better than your customer, you'll sell". Your favorite "GTM influencer" calls this finding message–market fit. Once we know what lands, then we scale it with automation, sequencing, and volume. Not before. If you want to do this in Instantly.. Run a Copilot prompt like: “Write 5 different cold email angles for [your offer]. Focus on 5 different pain points and value props.” Then A/Z test them in small batches. It’ll tell you which version gets the best reply rate before you spend real money scaling. Outbound is still the best R&D lab your business will ever have. You just have to use it that way.

Outbound works. Just not the way you’re doing it. Tell me if this sounds familiar. Your team of 10 reps get... • 100 emails/day each → 5,000 a week • 2% reply rate → 100 replies • 20% booked → 20 meetings • 50% qualified → 10 demos That’s 500 emails for ONE qualified demo. 4,900 ignored emails carrying your logo, your name, your brand. That’s not pipeline. It’s death by a thousand cold emails. We hear it from sales leaders every day. Pipeline generation is down despite unchanged activity levels. So what actually moves the needle? Provide disproportionate value. When you add account-specific value, replies shift from silence to “tell me more.” It’s not easy. But it is effective. Run these 7 value-first outbound plays (12–18% reply rates): 1. Nail the list. Best-fit accounts only (firmo + techno + trigger). Start with your current customers. Who stuck around, who closed fastest, who’s paying the most? 2. Find the wedge. Identify one real problem you know they have (not a generic pain). 3. Do the homework Create a 5–10 min research brief for every account. More data is better (recent moves, stack, hiring, KPIs). 4. Solve a piece. Earn attention. Ship a teardown, ROI slide, or 45-sec Loom showing a problem you can solve in their world. 5. Keep it simple. Their attention is limited. One problem. One proof. One next step. No pitch decks. 6. Go multi-channel. Be everywhere. Email + LinkedIn + call + voicemail + a handwritten note if you have to (remember those?). 7. Follow up with value. Don’t “bump this back up.” Watch signals (opens, time on asset, site return) and follow up with something new. What changes when you do this? • Fewer sends. • Higher-intent conversations. • Real pipeline that doesn’t embarrass the brand. That’s why we're building an outbound teammate for every quota-carrying rep. With your input and approval, it builds a targeted list → creates research briefs → writes individualized sequences. Without turning your reps into full-time researchers. Want to see it in action? Comment “PIPELINE” and I’ll send you a sample value-first campaign for 100 of your target accounts.

what we changed to fix their outbound One thing I love about outbound is how quickly the truth shows itself. If the system is off, the results will drag. If the system is right, everything clicks.... even if nothing else changes. Last week we worked with a services company whose outbound “felt flat.” But once we dug in, the problem wasn’t just list or the copy …it was that their system was fighting against them. Here’s exactly what we changed: 1️⃣ We stopped selling the service at scale only a few people respond to They have 3 services. All great. But one is a terrible conversation starter. Cold prospects don’t wake up thinking: “Wow I really hope someone offers me a 40-page report today.” Their prospects literally respond ~2× better to the other 2 services, but outbound wasn’t aligned to that. So we repositioned around their two strongest conversation starters 2️⃣ We fixed the invisible killer → deliverability Their audience = mid-market + enterprise. Enterprise = Microsoft. Microsoft = “I will evaluate your entire family tree before letting your email through.” 😅 So yep… we’re have a different mix Google + Microsoft inboxes and all these inboxes are purchased to multiple resellers, so we can continously monitor which ones are performing the best and use the data from our inbox placement tests to make adjustments to keep hitting the inbox. 3️⃣ We replaced the “quick chat?” CTA with value Their CTA used to be a meeting request. (in a soft way which is GOOD). But (especially in the agency space), you’re likely selling something that is “easy” to execute, so the barrier to entry is low. So we introduced CTAs that give something instead of ask for something: - campaign ideas - roundtable theme maps - insight drops - quick audits Concrete example if you’re running an ad agency: → “I have analyzed your ads published in the last 90 days. Can I send over a quick audit to decrease the CPL?” → “Would you be open to exploring how we can help you decrease the CPL on your Meta ads?” GIVE → GIVE → GIVE → before you ASK. 4️⃣ We added intent + timing signals instead of guessing Before: outbound went out in usual prospecting campaigns Now: outreach triggers when something meaningful happens. Signals we added: → new senior hires → hiring for marketing roles → aggressive ad spends → thought leadership indicators → content activity 5️⃣ We refreshed the messaging (just enough) Not a rewrite — a refresh. We updated angles based on: the market’s current priorities 2026 plans current challenges in their space This avoids message fatigue The fun part? We didn’t change: ❌ the ICP ❌ the TAM ❌ the channel ❌ the core offer ❌ the send volume Takeaway: When outbound stops performing, people jump to copy first. But the real leverage is almost always in: → targeting → timing → positioning → offer → infrastructure Once the system is right, the copy suddenly becomes “amazing.” Even if it’s the same copy you thought was the problem. 😅

Always Be Closing. Coffee is for closers. IYKYK. But over 17 years in EdTech, my thinking evolved: ABC → ABS → ABSV Always Be Closing → Always Be Selling → Always Be Selling VALUE. FEATURE SELLING IS EVERYWHERE. If I had a dollar for every time I asked someone "What does your company do?" and they just read me a list of features... I'd have a room full of dollars. The problem? Most people start with the WHAT instead of the WHY. THE BEFORE & AFTER. Early days at FEV Tutor: "We provide live 1:1 online tutoring for Math and ELA, customized for your district." That's feature selling. If someone liked me, maybe we'd talk about a $10K pilot. Years later, same question: "FEV Tutor partners with K-12 districts to drive student outcomes AT SCALE — through integrated, data-driven High Impact Tutoring aligned to your critical outcome goals." Lead with WHY. Follow with WHAT. That shift? Top 50 districts. $300K-$700K pilots. Outcomes-based contracts. Same product. Different conversation. THE KEY: ALIGN TO BIG ROCK PRIORITIES. Value Selling only works when you connect to what actually moves the needle for the district, their strategic plan, their outcome goals, their Big Rocks. It doesn't have to be fancy or complex. Simple. Elegant. Powerful. A few slides or none at all. I believe in Deckless Selling. Like positionless basketball, but that's a topic for another day. VALUE SELLING ISN'T JUST FOR CLOSERS. It threads through everything: discovery, demos, negotiations, implementation, customer success, renewals. When you lead with outcomes aligned to Big Rock priorities... you become a thought partner. A strategist. Not a vendor selling shiny objects. Feature Selling: "Here's what it does." Value Selling: "Here's the outcome it drives --> aligned to your goals." I'll unpack Value vs. Feature Selling with more examples in future posts. For now: Always Be Selling Value.