peel ai (Techstars '24)

With great excitement, pride, and a few nerves… I'm excited to introduce peel to you! We built peel to transform how businesses and customers connect, engage, and learn. Simply put, we use AI to reduce cost, friction, and pressure of connecting with buyers. During my decade-long B2B sales career, I’ve seen a significant pullback in buyer engagement. As an SDR fresh out of college 10 years ago, I remember cold-calling CIOs. It wasn’t easy, but it worked and the economics made sense. Today, it's challenging to achieve even a 1% conversion rate from outbound efforts, driving CAC to unsustainable levels. It’s not just me. Over the past 12 months, we’ve spoken with over 250 revenue leaders, all of whom share concerns about their ability to connect, engage, educate, and influence purchasing decisions. Buyers are frustrated too. They feel overwhelmed by the sheer volume of our GTM efforts. And they’re disillusioned by the lack of value and true engagement that we, as vendors, provide during the buying process. It’s no wonder that it’s harder than ever to engage buyers. We all (buyers and vendors) deserve a better way to engage and learn on our own terms. That’s exactly what we’re building at peel - a new way to engage buyers that delivers real value to them (and to vendors). I’d love to show you how peel is already helping some incredible GTM teams engage buyers in a fresh, new way. Please let me know if you’re open to a quick feedback call! We also have a few more openings in our charter customer/design partner program. We make it really easy to spin up a pilot so you get immediate ROI and you get to shape our roadmap. By the way, I’m also excited to announce that we just completed our over-subscribed pre-seed round, have grown to 6 team members, and are participating in the fall class of Techstars!!! Not bad. You can learn more about peel on our new site (link in the comments).

Incentives aren’t about buying someone—they’re gestures, a reasonable exchange that shows thoughtfulness and makes the experience about someone else. After we wrapped up Techstars Mentor Madness, Kerty, Misti, and Carly sent a $25 gift card as a “damn that was intense, but worth it” kind of gesture. It was simple, but it hit home. I’d just lost a thermos I’d had forever, so I used it to buy a new one to bring my coffee into our new office. Now, every time I use it, I think back on the TechStars cohort with a smile. Small gestures can make a big impact.

Excited to back the incredible team at peel ai (revtech startup). I don't do a lot of early stage investing, but a few things got me over the finish line here. I looked at typical early stage investment criteria like: the founding team’s domain expertise (deep); TAM (large); early customer traction (yes), and so on. Lots of people do that. I’m really more interested in unconventional criteria. Things that other investors may not pay attention to. With Peel, I found some things I really liked: - The product is unique. In fact, when I tell people what Peel does, most people say, “Really? That works?” That’s a great sign and yes, it does work. - Peel has an opportunity to go-to-market via a channel that is not very well known/uncrowded. That is hard to find these days and they found it. - I really like startups where there are logical “intermediate” exits available. In other words, you don’t have to do a massive IPO to be successful. I think that’s good for founders and can be good for investors who aren’t getting tsunami’d by AUM. That’s the case here. - I like companies where I can add value on day one. Peel is in the revtech space, an area I know fairly well based on my experience at TOPO. - Trust is a big deal at an early stage startup that’s taking on its first investors. Basically the company doesn’t have a track record, but wants a bunch of money. You can’t get there as an investor unless you trust the team. The founding team has deep expertise, a strong work ethic, etc. But most importantly, I just trust them. Anyway, I’m into these unconventional investment criteria. It’s just a great way to avoid what has become a crowded investment space (early stage startups) and help founders who are building unique companies. Thanks Brannon Santos and Ben Henson - looking forward to working together! ?? ?? BTW, right now, Peel is focused on getting product feedback. If you’re open to helping us out with that, please let me know!

I’ve been an early stage founder/CEO for a little over a year now. One of the biggest things I’ve learned? There’s this crazy tension between two contradictory facts: It’s never been easier to start a company (cloud platforms, open source, shared GTM best practices, etc). It’s never been harder to get to an exit (1,200 unicorn software companies are "waiting" to IPO according to Battery Ventures). So how do you manage this semi-absurd contradiction as a founder? Well, you need a certain mindset which can best be described as a reality distortion field. But when it comes to actual management, I focus on two things to stay sane: First and most important, I spend a lot of time asking myself “Are we delivering sufficient value to our customers?” It’s the number one thing you can do on a daily basis to drive towards an exit. Without this, your odds of a successful exit are basically zero. So I spend lots of time on customer conversations and lots of time translating customer needs into actual product. Second, I’m trying to build a business where intermediate offramps (or exits) are available. The data shows that the odds of an IPO are extremely low. The data also shows that it takes 10+ years to get there. I don’t know about you, but that’s bad math. So I think about the type of business we’re building, how it should be valued, who the logical acquirers are, what their balance sheets look like… I don’t spend a ton of time on this, but it’s in the back of my mind. Of course, the other thing you can do is just put your head down and do the work. But that’s just a baseline requirement for any founder and not really worthy of a LinkedIn post.

When you're struggling with something (lost a deal, missed quota, got fired), you may feel SHAME. Shame is one of the most debilitating human emotions. It's a magnifying glass on all your flaws. It makes you feel like you're a real piece of crap. And it totally gets in the way of learning from our mistakes. Because shame makes us feel like we ARE bad, Not that we just made a mistake. Our inner monologue says: "What's the point in learning from this? I'm just a big old piece of crap anyway." ---- Want to know the biggest antidote to shame? EMPATHY. When someone else can understand how you're feeling, it zooms out the magnifying glass. We suddenly don't just see our flaws, we see the full picture. A mistake or a struggle becomes a learning opportunity. This is part of the magic of Pavilion. You meet people that are struggling with the same things you are. They understand you. They have been there before. They can provide ideas and perhaps most importantly empathy. That's been my experience since joining last December. I've been lucky enough to meet incredibly smart and thoughtful people like Brannon Santos. Brannon is an entrepreneur who began his journey around the same time as me starting Inspirewell. We connected at first on the topic of sales rep coaching but have become an ongoing source of support as we both try to build great businesses. I wouldn't have met Brannon without Pavilion. It would be worth the membership fee alone for that relationship. But here is the thing. I've met a dozen other people through Pavilion?that will be in my corner for life. Sales folks -- it's hard out there. Don't go at it alone.

The buying experience for B2B has changed. The simple proof is how quickly you can get an AE on the phone. In 2011 I was at Yesware and we were looking at HG Data. I was behind on a project and needed to make a decision and purchase within a week. I filled out a Demo Request form on the site. I was put in touch with an SDR who was able to meet 3 days later. That "meeting" was a 15 minute qualification call to see if I was ready to be passed to an AE. They then booked a meeting 7 days later. I remember this because it was so insane that it took them 10 days when I needed it to get done in 3 days. This was common for sales teams, but now the account qualification is so much better because of providers like 6sense and ZoomInfo, getting connected with an AE is better because of Chili Piper and HubSpot. The AE's come better prepared to calls because of Zoominfo. The amount of quality content about the product has improved so I can do more research before getting ready to talk to sales. Looking back over the last 15 years, the change has been huge. But it's still changing. The promise of ABM is finally coming to fruition. For a while the investment went to glorified display networks, but tools can manage bits of the SDR process to better qualify (shout out to Shawn Green who enlightened me about ChatGems). The context you can provide sales before a call with is amazing with AI. But here is what I keep thinking. The innovation would have happened quicker with more centralization of marketing infrastructure. At CGM, I can see trends emerge quicker than I could have when I was at Monster or LogMeIn because I'm looking at datapoints across all clients vs. just the dataset for the one company I was at. I think we'll see B2B outsource more, not less in the coming years because change seems to be speeding up.

The definition of "scaling" changed recently. Well, Founders made the change a while back and the rest of us are finally following suit. 2020 - Scaling = increasing the number of people you employ 2024 - Scaling = increasing the number of end users impacted Brannon Santos at ChatGems and Andrew Douglas at siento.io are great examples. Very different businesses, but both of them have core concepts of maximizing impact using technology instead of people. What's wild is this. I went back and looked at some pitch decks from back in 2017-2019 and the early stage folks were already thinking this way. Meanwhile, most sales and ops leaders were highlighting the volume of their direct reports as key resume points ("built team from 5-50 in 7 months"). Now, the new perspective is really becoming ubiquitous. Us folks in contact centers are talking about how to keep teams small and amplify their impact with better self-service, more efficient systems, and AI-enabled automation. Us sales leaders are going back to hiring full-cycle helpers & advisors thinking about how we can be more transparent with prospects instead of leveraging information arbitrage to maximize meeting volume. Dollars to donuts this isn't limited to contact centers and sales. Yet again, the constraints on the earliest stage startups mean there's so much to learn from them about efficiency.

"What", "Why", "How", and "Why" Again One of the most valuable frameworks I've learned for teaching and communication came from my days as a fly fishing guide in Northern California. Early on, I apprenticed under some of the best guides, and one of them, Dax, taught me to: 1. first explain "What" you're going to teach 2. then "Why" it's important 3. followed by "How" to use it 4. and wrap up with "Why" it's important again to make it stick. This approach has been incredibly effective throughout my career in tech, from product demos to sales enablement. It's a method I even use in my personal life, with my family. Give it a try: What, Why, How, and Why again. It works. ...I looked for my old guide service business card. Unable to find it, so here is a better pic of my wife fishing.

"My customer just won a customer from my product." Celebrating a win with my mom, in simple terms.

Directorial debut... I'm going to be trying my hand at creating short videos that demonstrate the use cases and outputs of ChatGems Would love your support and feedback!!!