PastSight

My whole life I’ve suffered from anxiety. My mind often goes to the worst case scenario. Here's a recent real-life example: Last week we lost a deal. I started to think, what if our solution isn’t good enough? What if we lose the next deal? What if we never win a deal again? I’d  have to shut down the company. I’d be humiliated. I’d a be a failure. I might have to go back and get a sales job. You see how it works? That how my brains functions like this can scares the sh*t out of me! I’m sure I’m not alone. Of course, I'm getting help. My therapist tells me that everyone has some level of anxiety, but what matters is what you DO about it. And she says I'm controlling it well because it's not limiting me from taking risks. To me, the image below says it all (👇) Anxiety and fear is OK as long as you don't let it consume you. My advice? Learn how to become aware of these feelings. Don't let them sneak up on you. Don't be surprised by them. Don’t try to fight them. Let them wash over you and then... Go pursue your dream anyway.

In 2023, I did over 1,000 win-loss interviews for 25 SaaS companies doing about $1.5B ARR in total. Here are the 5 biggest blindspots we uncovered for their sales and customer success teams: 1. Companies don’t know how their prospects or customers truly evaluate their solution. It’s almost never about results. It’s almost always something else. For example, you may be driving 10x ROI, but they viscerally hate their point of contact. 2. Customers know they are churning way, way earlier than when they tell the vendor. Over half the time it’s over 90 days from renewal. They’re not lying per se, but they hate confrontation and are terrified you’re going to provide shittier service. 3. You’d be surprised how often lost prospects simply don’t think they are the right ICP, even when they are. Big companies think you’re a vendor for small companies, small companies think you’re a vendor for big companies. We see this over and over again in the data. And it’s almost always a sales execution problem. 4. The way prospects describe a vendor’s solution is DRAMATICALLY different from the way the vendor wants it described. In short, they don’t know what the hell you do or what problems you solve. Or at least can’t articulate it to themselves. SOOO much time is spent on positioning and it’s just not landing. This is common across 95% of win-loss interviews. 5. Every executive thinks pricing and product is why they’re losing deals. Why? Because that’s what it says in their CRM. That’s what their salespeople are telling them. That’s what they hear in call recordings. This is WRONG. It’s what customers want to tell you in order to avoid confrontation, but once you dig in it’s almost always something else. Here’s the good news. And why I’m so optimistic about 2024. All 5 of these things are easily fixable. They are small tweaks. That won’t cost you million of $’s. That won’t take you a year of building product. That won’t mean having to replace your team. The solution is simple. Talk to your customers. And make the changes. P.S. If you want to inject the voice of the customer into your GTM strategy, DM me. Let’s chat.

While we won a lot of deals last year, we didn’t win them all. In fact, we lost 77 opportunities, which made up over $3.5M in pipeline. That’s why we’re doing PastSight's no bullsh*t win/loss analysis on PastSight. And I'm going to share the full results right here on LinkedIn: BACKGROUND At first, I thought it was too early to do win/loss analysis on ourselves. We're too small, I said. It doesn't work for Founder-Led Sales, I said. Our ICP is higher volume, 5 sales reps, 12 months of lost deals. But that was just a mindless objection, just like our current losses. Win/loss analysis works at any stage company. Why? Because you can ALWAYS learn more. And there is no better way than the voice of the customer. Here’s my *hypothesis* on why PastSight lost deals in 2023: 1. We didn’t educate the market on the importance of revenue-driven 3rd party win/loss analysis 2. We didn’t get to a big enough pain, priority or company initiative 3. We were too transactional in our selling approach and needed a more prescriptive process 4. We made it too difficult for companies to see the magic of the insights we provide 5. We didn’t overcome common objections (i.e. thinking they can do this in house when you can't) So that's why I "THINK" we lost... But after doing win/loss analysis for a over a year, I can tell you this: I'm probably wrong. The only person who really knows is the customer. That's why you need impartial win/loss analysis. Excited to share the results soon. Stay tuned!

Last quarter the VP of Sales at a $50M Series D Martech company hired PastSight to find out why they were losing 80% of their enterprise deals. They *thought* it was because the cost didn’t match the value and their team needed to do deeper ROI studies. What we discovered was far different: 👇 Customers simply didn’t think the value add was worth the switch. They liked the new solution better, but didn’t want to rock the boat. So the the company shifted their sales messaging to focus on how seamless switching is and provided a ton of customer testimonials around it. The results are early, but we're already seeing a 25% lift in prospects moving from Demo to Proposal. What's the point? Stop making assumptions on why you’re losing. Figure out the real reasons. #saas #voiceofcustomer #winloss

Emails like this are why founders get up in the morning. We're proud of the work we're doing with CHEQ the last 3 months. Thanks for being an amazing customer Marc Jacobs. We're just getting started!

In 2014, I got my first Head of Sales job and failed miserably. I only got the role because I was a great AE and interviewed well. This wasn't even an internal promotion, I went to a new company as a head of sales with no management experience. I was 10 years younger, arrogant and needed to be humbled. I thought because I was a top rep I thought I could do anything professionally. But... I didn’t know how to hire. I didn’t know how to create a process. I didn’t know how to build a sales team. I didn’t know how to do anything except sell. When I look back, it was the most painful part of my career. But I learned a shitload. And made some crazy strong connections. So while I might look at it as a failure because I missed my numbers, I wouldn’t trade the experience for anything. Failure is part of the process. Don't be afraid of it. Embrace it. #growth #mindset #careercoachingtips

If you’re an AE at Salesloft selling into an account that uses Outreach, and they decide to stay with Outreach, you did NOT lose the deal to Outreach. You lost the deal to the status quo. A fine distinction, but incredibly important. Too many companies OBSESS over competitors. Distracting them from truly understanding why they lost. More often than not, your competitors had nothing to do with it. You weren't missing product features or functionality even if the prospect told you that was the reason just to be nice and avoid conflict. When in fact, you simply just didn't create enough value for them to switch. Go back and figure out what the REAL objection is on why they didn’t make a change. And focus on that. Not your competitors. #competitiveintelligence #winloss #objectionhandling

Time savings is a bullshit ROI. If your business case is something like: "Buy my software because it saves you X hours per week" You’re not winning the deal. It just doesn’t resonate. Sell what they can accomplish using your solution. Or at least sell the opportunity cost. But stop with this time savings BS. Stop being shocked when saving someone 3 hours a week doesn't win the deal. Stop pretending you know how they justify the cost. Stop coming up with convoluted ROI calculators. Stop guessing at the value your customers see. Instead, do the smart, simple thing. Go ask them. So much effort is put into not talking to your customers. Just do it. #voiceofthecustomer #ROI #saas

Founders always think they’re good at sales. When really, they’re just the founder. As an operator, it would drive me crazy when founders would teach my team sales. As a lot stuff they said usually wasn't applicable. Take PastSight as an example: I’ve already closed 20 deals since starting the company. It’s not because of my special sales genius. People just like to work with founders. They like to hear their vision They want to understand why they started the company They feel more valued when the founder is talking to them AE's cant do that. So if you’re an AE getting crushed by the founder. If they’re telling you how easy it is to sell. If they're saying because things worked for them it should work for you. Just remember this post. Having been on both sides now, I can assure you: It’s always harder to close a deal as an AE than a founder. Don’t get discouraged. #foundersales #saas #sales

Every successful founder says there are certain “lucky” breaks they get along the way. My first one break was getting connected to Joey Dean, our research manager. He interviewed well, had a great experience and was clearly hungry and scrappy. But he’s exceeded even my highest of expectations. His willingness to go above and beyond, pride in his work, and attention to detail are all huge factors of PastSight’s early success. I couldn’t be more grateful. We're just getting started and I can't wait to see how much he grows as we grow. PS - you know you've made it when you have company t-shirts (which we FINALLY got)