Paul Keen’s Post

You don’t need more leads. You need fewer distractions. Welcome to Q1, where everyone’s chasing “pipeline growth.” More opportunities. More capabilities statements. More color team reviews. Spray and pray, but with compliance. But most small GovCon firms don’t have a pipeline problem. They have a focus problem. Here’s the thing: You don’t need 50 opportunities in your tracker. You need 5 you actually understand. The kind where:   ✅ You’ve talked to real humans.   ✅ You know who you’re going up against.   ✅ You’ve built messaging that’s sticky.   ✅ And you can do more than just check the compliance box. The more “open” your pipeline is, the more closed-off your strategy becomes. Because when everything feels possible, nothing feels urgent. The real flex? Walking away from 90% of what hits SAM because you’ve already built your position upstream.

💡 THE WIIFY 💡 What's in it for you? One of my favorite and most used acronyms over the last decade. In 2015, I was in a room with Jeff Lawson Lee Kirkpatrick Roy Ng and Patrick Malatack preparing for Twilio's IPO with a wonderful coach Jerry Weissman. We had worked a TON on our materials, but I remember Jerry asking at each slide - what do you want an investor to understand from this specific data or slide title? We realized a lot of our materials weren't telling the right story to investors. It's pretty easy to tell stories about things that are important to yourself. It's harder to think about what's relevant, unique and educational for the specific audience in mind 🤨. I talk to customers, employees and investors. Even within those categories, each type of person and each specific individual tends to care about something slightly different. > Some of my sales reps just want to know how changes impact their commissions. Others care most about how to navigate tough customer convos. > Managers often want to understand how they should explain things to their team, what it means for their ability to hire and retain their leads > My peers want to know how their specific functional area ties into what we're doing (or want to look around corners to see what problems I'm about to cause for them 😜) Bottom Line: Everyone wants to know how new information helps them win, personally and professionally. It always pays off to cut to the punch line and give folks the information they want. Plus, I think my colleagues would agree, it's REALLY fun to keep saying "WIIFY"

𝗧𝗼𝗼 𝗺𝗮𝗻𝘆 𝘀𝗮𝗹𝗲𝘀 𝗰𝗼𝗻𝘃𝗲𝗿𝘀𝗮𝘁𝗶𝗼𝗻𝘀 𝗻𝗲𝘃𝗲𝗿 𝗺𝗮𝗸𝗲 𝗶𝘁 𝗽𝗮𝘀𝘁 𝘁𝗵𝗲 𝘁𝗲𝗰𝗵. Last week, I saw what happens when they do. In two very different boardrooms, we watched the same shift unfold: We stopped talking about features. And started solving problems they couldn’t afford to get wrong. That’s when the energy in the room changed. That’s when the real decisions were made. The truth is: if you’re still leading with capability, you haven’t earned the right to talk about impact. The only way to get there is to start with their operational reality. ❌ Not “What can this software do?”  ✅ But “What’s the cost of doing nothing?” In enterprise sales, clarity isn’t optional—it’s your competitive edge. It cuts through internal blockers, misalignment, skepticism. And if you do it right? You don’t need 10 follow-ups or endless demos. You get the shortlist. You get the next steps. You earn the conversation that actually moves the deal. Because you're not selling tech. You're solving the right problem, at the right time, with the right people in the room. #ClarityOverComplexity #EnterpriseSales #IndustrialTransformation #CROPerspective #Akselos #BusinessOutcomes #B2BSales

Kaseya's new Chief Revenue Officer and Chief Technology Officer are set to drive the next phase of AI-led growth. Read more about their roles and impact in this CRN article. #Kaseya

I've done 9 tech stack audits in the last 3 weeks & here's what I can say to 90% of revenue leaders out there: I'm almost positive your "tech stack" is hurting you more than helping you. I'm talking to you Sales & RevOps Leaders. Here's what I'm seeing: - too many tools - duplicate tools - overpaying for seats - underused tools - old playbooks - outdated tools - low pipeline conversion rates from outbound channels I say 90%, though 100% of the 9 tech audits I've done are in this position. I just don't want to speak in absolutes. These conversations are a blast because as I walk through their tech stack, in real time I talk through changes I'd make, tools to explore, and where they may be falling short. You can see their ears perk up. They always interrupt to ask questions. They get off the call with a ton of value, for free. There's something to be said about providing tangible value immediately.

Working on the vendor side of tech, you speak to a lot of prospects who either: - Don’t really know what they’re looking for in a platform - Don’t have time to look while juggling their day-to-day job - Have a specific problem they need to fix, but get tunnel vision and miss the bigger picture After seeing it that often, you start to think that this is just “part of the process”. Prospects not doing enough research or needing more demos. But the truth is, it’s not their fault. Most people aren’t buying software every day. They don’t have the time or context to map out the whole ecosystem. They’re just trying to solve the pain that’s screaming loudest. With Hyphen Digital, we take the time businesses don’t have, bring the knowledge they can’t be expected to know, and help them see the bigger picture. Instead of chasing shiny features, we focus on fit. The right apps, in the right stack, working together. Because the best tech decisions don’t come from picking a tool in isolation. They come from understanding how your processes, people, and plans for growth all connect. #Xero #DigitalTransformation #SMEs #BusinessTechnology #AppAdvisory

You don’t need more leads. You need better signals. Here are 45+ of them (free). We used to send emails that looked like everyone else’s. Then we built a signal-led playbook. Now we reach out to companies when the context makes most sense and the correct time to maximize the possibility of closing the client. Example: Before: “Hey, saw you’re in SaaS. We help SaaS companies grow revenue.” → ignored. After: “Noticed you’re hiring 3 AEs. Need tools to ramp them faster?” → conversation. We put together 47 intent signals you can use for your own outreach, along with examples of how to apply each one. If you want it, comment “Intent” and I’ll DM you the doc.

TA in 2025: Teams are leaner, workloads are higher 😬 Mandate = More Efficiency! From "Recruiting Benchmarks & Email Outreach Strategies," Steve Bartel at #RecOpsCon

I just remembered a conversation with a VP of Product and he said something yesterday that made me physically uncomfortable: "Customer success is just product failure with a salary." Ouch. But here's why he had a point... “We'd just posted our third CS job opening this quarter” “Not because we're scaling - because our product still needs a 47-minute walkthrough before users can do anything meaningful.” That's not growth. That's life support. Look, here's the thing: Every dollar we spend explaining basic functionality is a dollar we didn't spend making it obvious. Slack didn't become Slack because they had amazing CS reps in 2013. They obsessed over making adoption feel like magic. You signed up, you got it, you invited your team. Linear does this brilliantly right now - 90 seconds from signup to your first issue created. No hand-holding required. So, what changed my mind? If 80% of your CS team's calendar is "how do I..." calls instead of "here's how to maximize..." conversations, you don't have a hiring problem. You've got a product problem wearing a customer success uniform. Don't get me wrong - CS is critical for expansion, enterprise deals, and feedback loops. But when it becomes your front-line defense against confused users? That's your product screaming for help. What's the tipping point for you? When does CS stop being strategic and start being a crutch?

When a deal breaks at midnight,  you’ve got two options: Go to bed. Or go to war. I had a 200K ARR deal ready to close. Contracts signed. Onboarding scheduled. Then came one last legal redline. A tiny sentence  that broke everything. We’d already said yes. But the change required editing a core template in our product. And the platform didn’t allow it. If the client noticed, the deal was dead. So I did what any obsessed AE would do: I went to war. All day: Slack with an EMEA Director engineer 9pm: Slack with an engineer in LATAM, new shift.  2am: another in the US. 4am: legal joins from the U.S. We manually rewrote the clause. Re-inserted it into the platform, without breaking it for others. Tested it. Fixed it again. By sunrise, it worked. The client onboarded that morning. 200K ARR closed. Here’s what I learned:  The biggest deals aren’t won by luck. They’re won by people who refuse to lose. Because great sellers don’t just close deals  they protect them. Ownership isn’t a buzzword. It’s the difference between “almost” and “closed won.” What’s the wildest thing you’ve done to save a deal? PS: I've added a few other valuable lessons from that night in the comments. Follow me for more sales stories from the trenches @Jonathan Molina.