Jordan Stephanou

My biggest takeaways from @jjen_abel on the enterprise sales process: 1. Most people think enterprise sales is a five-step process. It’s actually around 15 steps. The classic CRM stages of a sales process (intro, demo, proposal, contracting, close) are a revenue forecasting tool, not how you successfully move a buyer through a decision and close a deal. 2. The “pincer” move for landing the first meeting: Target the executive or the n-1, and no one else. When prospecting into an enterprise account, there are only two valid entry points: the ultimate decision-maker (often the exec in charge of a department or business unit) and the person one step below. The pincer move runs both tracks at once: your company’s founder reaches out to the top, the AE targets the N-minus-one, and you work toward them from both ends. 3. Pitch the alpha, not the problem. Executives receive hundreds of cold messages; the oes that cuts through speaks directly to an unfair advantage they can get access to through your product. “We can save time on document review” won’t get execs very excited. “I can guarantee you a three-day timing edge on regulatory information your competitors will get later” does. 4. A healthy enterprise win rate is 25% to 35% of qualified opportunities, and higher means your price is too low. This number surprises founders who expect to close half of what they qualify. But enterprise buyers need time, organizational maturity, and internal alignment that sellers can’t always control. A significant portion of the market simply isn’t ready yet. Jen notes that roughly 25% of “lost” deals boomerang back within a year, so a no today is rarely a permanent no. Pushing price down to win more deals undermines the market: executives talk, and inconsistent pricing across logos destroys credibility faster than losing a deal does. 5. The intro call is the most valuable intelligence-gathering session in the entire sales cycle. Prospects open up on call one in ways they never will again, because it doesn’t yet feel like a sales process. Jen keeps it explicitly informal (“I don’t even know if we need a full 30 minutes”), lets the prospect go first, and uses open questions about organizational change (“What needs to be different in 2027?”) to surface priorities before ever mentioning her product. Do not record the call, do not show slides, do not demo anything. The more they talk, the more you can frame your eventual pitch around exactly what they told you they need. 6. Treat the demo as a carrot you withhold until you have co-authored it with your internal champion. Most sellers race from intro to demo in one jump. Jen always does a 15-minute “pre-demo prep” call with the champion to co-build the agenda: which features to show, which questions people will ask, and which attendees to include. By the time the group demo runs, the people in the room feel like the product was built specifically for them. 7. Demo 20% of the product—the 20% you know they care about. Showing the full product in a demo is one of the most common ways deals unravel. The moment stakeholders see features irrelevant to their team, they start calculating what they’re paying for that they won’t use, and the tight narrative you’ve spent weeks building collapses. Let the champion guide what to show beforehand, let curious prospects in the room pull you into additional features themselves (“Can it also do this?”), and keep the frame tight. 8. Text your champion for a raw debrief within five minutes of the demo ending. Before the room solidifies a polite consensus, get the unfiltered read: where you lost someone, where you landed, who needs another 15 or 20 minutes. There is always someone in the org who can kill the deal; your job is to find them early and protect alignment. 9. Time-box pilots to two or three days with three or four hand-picked users. Give a small group of power users (not the C-suite executive, who won’t be the daily user anyway) a specific set of tasks, a shared definition of what success looks like, and a 48-to-72-hour window to use your product. Any longer and you’ve added two weeks to your sales cycle with little additional signal. If the product requires deep integration before it can show value, charge for the longer pilot (typically one to two months) and credit the fee back against the contract if they proceed. 10. Your champion going quiet is a signal your deal is falling apart. The champion’s job is to help you navigate the people who might kill the deal, alert you to internal dynamics you can’t see, and keep the process moving when it stalls. If the champion goes quiet, something has shifted inside the organization. An enterprise deal is set up for maximum friction (deal-killers, procurement, legal, sponsor); the person on the inside is the key. 11. Sales is project management. After a strong pilot, email your champion a forwardable package—agreed timeline, price predicated on a signature date, and a kicker if they hit it—so they can loop procurement. 12. The expansion conversation starts the moment you sign. The close is five minutes of celebration and then back to pipeline. The real prize in enterprise is year-two expansion: moving from $100K to $350K, from a single team to multiple business units.

As AI makes it trivial to build and launch products, the biggest challenge for product teams is quickly becoming distribution: getting people to pay attention to your product in the increasing cacophony of launches. One of the most powerful tools to cut through that noise is positioning. Strong, specific positioning grabs people’s attention and helps them instantly understand why your product is for them. April Dunford (@aprildunford) is the world’s leading expert on positioning, and today's in-depth guest post, she offers a guide to advanced B2B positioning—four lessons for getting past the trickiest and most common roadblocks that teams run into: 1. Disagreement about what to position against 2. Product pessimism blinds the team to product strengths 3. The differentiated value is poorly defined 4. The company doesn’t know what they are positioning As April shares, “a single shift in positioning can mean the difference between a product that flops and one that breaks through.” Don't miss this one: lennysnewsletter.com/p/a-gui…