Chris Waldron

I’ve spent the last few weeks interviewing Fractional CTOs (turnaround specialists, PE advisors, startup operators, enterprise vets). The surprise wasn’t what they know. It was what keeps costing them deals. Most Fractional CTOs aren’t competing on capability. They’re competing on clarity. In almost every conversation, the same friction showed up: 🔴 Pipeline is fragile (mostly referrals + “someone I worked with before”). 🔴 Deals stall when the CEO can’t see the cost of doing nothing. 🔴 The client says “we just need you to fix this one thing”… while the real risk is buried underneath (spend, vendors, security, delivery, scalability, onboarding, all of it). 🔴 And a scary number of businesses literally don’t know what software they’re running or what they’re spending. One CTO said it perfectly: “Sales, marketing, finance all have dashboards. Tech doesn’t. I would’ve loved to have had that.” So here’s the bet we’re making with StackUp: If a Fractional CTO can walk into week one and say: “Here’s what’s missing, here’s the financial impact, and here’s the priority order” …they control the conversation. Faster decisions. Less fee compression. More strategic work. Less firefighting. If you’re a Fractional CTO: what’s the hardest part of winning the work -getting the intro, or making the value obvious once you’re in the room? (And if you want to see the patterns we’re seeing across 50+ conversations, DM me.) #FractionalCTO #StackUp #CTO #TechnologyLeadership

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Ummm can we pleaseeeee stop calling transactional $$s ARR?! 😑 As someone who has operated in both worlds, they require completely different approaches to GTM 🔑 But it starts with being honest about what type of revenue it is 🤷🏽‍♀️ 1️⃣ Recurring rev is much harder to land but typically easier to expand. On the flip side, transactional revenue is easier to land (experimental budgets, multiple vendors winning $$s) but much harder to retain and showcase long term value ✔️ 2️⃣ Recurring revenue is much easier from a planning perspective. Setting quotas / quarterly planning with transactional revenue is a different type of hell 😅 3️⃣ A generalist GTM persona (full stack AEs that prospect, close, expand and renew) may work better in the transactional rev world given the risks of retention. Vs a specialized set up may be better in the annual recurring revenue model for efficiency 🙌 Ofcourse buyer persona, implementation ease and product complexity also play a role in each company’s unique set up. But let’s start with NOT calling GMV / transactional $$s as ARR 🙄 🎤 Thanks for coming to my TED talk #revenuerecognition #cro #revenue #startups #sales

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Two of my fav questions I like to ask ask founders of VC backed companies to determine values alignment? 1️⃣ What was the biggest commission check you signed last quarter? 2️⃣ How many reps got to 90% of quota? *What* and *how* they answer typically give me all the information I need around their understanding and respect for sales 🔑 Things I don’t want to hear: “well last quarter was unique in why not a big % of reps hit quota…” 👎 “we are spending too much on commissions and need to raise goals” 👎 “It’s odd that a rep that went to a state school will make more than a PHD data scientist from Stanford” 👎 Even if some of these may be valid things if they are the first and only things you share with me, I know we are not going to see the world through the same lens 🤷🏽‍♀️ Best b2b founders that manage ent sales teams celebrate big commissions and respect sales just as much as they do engineering 🔑 #founders #sales #cro #revenue #commissions #startup #technicalfounder

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Quick builder update from inside Jewgo. Right now, our focus is split across two tracks 1. Tightening the Jobs experience 2. Laying the foundation for the first version of Eateries On the Jobs side, every change we’re shipping is centered on one idea: make opportunities easier to find, easier to trust, and easier to measure. That means: • Cleaner posting • Automatic expiration • Clear visibility on traction (views, engagement) Not flashy features. Just the kind that quietly change behavior. On the Eateries side, we’re building the first live version with the same philosophy: No noise. No clutter. Just structure where chaos used to live. That’s the work right now.

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Executives won't open cold emails, but they will open a package. This is my best advice for breaking into Tier 1 accounts... When we were trying to break into big enterprise accounts at Levelset, there was one approach that consistently worked. We sent our top prospects a gift in the mail. Most teams never try this. They send another cold email, another LinkedIn message, or another voicemail. Then they sit around wondering why nothing converts. When you’re going after companies that can change your trajectory, you have to operate differently. Start with the person you are trying to connect with. Before you buy anything, spend time learning about the prospect. Look at what they post. Notice what they care about. Listen for the problems they’re trying to solve. You’d be surprised how often people leave clues out in the open. AI is really helpful at pulling this together for you. It's important to understand what would actually matter to them. Pick a gift that shows you pay attention. It takes more effort to pick something thoughtful than it does to spray a thousand people with the same sequence. But you’re not going after a thousand people. You’re going after the handful who can meaningfully move your business forward. It doesn’t need to be expensive. It needs to be personal. Somewhere in the $25–75 range is enough to show you cared without feeling transactional. Include a handwritten card. Keep it simple. Three or four sentences. Tell them why you chose the gift. Tell them what it made you think about in their business. Then make a clear, easy ask. When everything else in their stack is automated, a handwritten note stands out. Send it in a bubble mailer. Nothing fancy. USPS works fine. A bubble mailer gets opened. People are curious. Just make sure the address is right. We double checked every single one. Full up after it arrives. Don’t assume they saw it. Don’t assume they connected the dots. Send a short email. “Just shipped you something. Should arrive this week.” Then follow up again after it lands. The follow up is where the meetings get booked. Did this work? At Levelset, this was our most reliable way to break into large accounts. The response rates were dramatically higher than anything we did through email or phone alone. And it wasn’t because we were clever. It was because we were willing to put in more effort than everyone else. Most reps won’t spend thirty minutes researching a prospect or writing a card. That’s fine. The ones who do will win the meetings with the best prospects. The Reality This work doesn’t scale. It’s not supposed to. You don’t run this play for your entire TAM. You run it for the hundred companies that would meaningfully impact your business if you earned their trust. For those accounts, a thoughtful gift is a small investment compared to the upside. And if you’re willing to do the work, you’ll end up in conversations your competitors never even get close to.

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we’re seeing an influx of Recruiting teams and agencies wanting to build their custom recruiting stack in-house. not because the existing commercial platforms are bad - modern recruiting platforms are genuinely incredible, 10x better than what existed a few years ago. But great recruiting teams are like great investors. They have a thesis, they believe they have an edge, and they want to exploit that edge. Out-of-the-box tools give you a lot, but also limited. examples: -Predefined filters -Fixed ranking logic -A fixed definition of what "seniority" or "best candidate" That works great until your team's definition of best doesn't match the platform's. So we're seeing in-house teams and agencies start to think about owning their own system rather than renting one. Every serious recruiting team starts wanting to: -"Weigh recency differently by role type" -"Build a custom likelihood-to-respond model" -“Resolve identity + dedupe reliably across email, GitHub, and multiple data sources” In a closed system, those become: "We'll add it to the roadmap." With the right infrastructure, those become: "Ship it this week." you can't build that if the brain is a black box. But with structured, API-first data, you define the intelligence. Your own scoring. Your own signals. Your own feedback loops from hires, replies, and pass reasons that compound over time. That's the shift in 2026. The teams pulling ahead aren't just using better tools, they're owning the intelligence layer. If you’re building in recruiting, we power recruiting tools with live updated people data and their company data via APIs.

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So you want to build pipeline and think SDR-ING is the way. You’re a CRO or CEO at a early stage (Seed or Series A) startup. Here are your options (ordered by cost): 1. Hire a high volume Clay and pray agency 2. Hire 22 year olds out of college. 3. Hire a multichannel agency 4. Hire 2nd job SDR + fractional leader 5. Hire seasoned SDRs w/ a manager Let me break down what happens in every scenario. 1. Clay agency: - works great for 2 months… maybe 5 months at most. The TAM has been blasted enough times now and results are down 90%. The $3-6K per month is producing little leads… and the early leads didn’t convert to revenue. Abandon. 2. Hire college grads - this worked in 2014 because those people didn’t have Instagram or WhatsApp growing up. They did not grow up with smart phones in high school, so they actually picked up the phone to call their friends. In 2025? They don’t want to make calls (or receive them). They end up learning Clay and doing what the agency was doing. Works for a bit, not for long. $8K/mo in salary + benefits 3. Agency for $7-14K - there’s a range. But they’ll bring some framework to some hungry SDRs who make minimum wage and are trying to desperately get a better job. Half fail (in which case you fail) and half succeed (in which case they get promoted or hired away, and you get a new guy… who fails 50% of the time). Results are bumpy and it never delivers. 4. In house SDRs + fractional leader. - you hire 2 SDRs with 8-18 months of experience. They’re excited about your company. They come to try replicate the playbook they ran at Oracle… except you have no name. Either the VP of Sales, CMO or external consultant manages the team. They’re ok, but far from what your CFO projected. They get 2-3 meetings per month each, not 15. For 2 SDRs and fractional leadership you’re spending $30K per month for 5 meetings. Your top guy insists he’s ready for an AE role. You just decide to turn things off. 5. Hire 4 seasoned SDRs with a manager. - you decide to go all in. $60K per month in salaries, benefits, tools, etc. team starts strong but then wants more. You cycle through a parallel dialer, Hot Leads, AI personalization and intent data. Manager is doing their best. 1 rep is awesome, 2 are ok, 1 isn’t good. They’re averaging 18 meetings per month. Top rep gets promoted, results down to 10 meetings fir $60K… the engine isn’t worth it. You shut it down. Every time you shut it down, 3-6 months later the AEs are begging for pipeline. The board is begging for more AEs and Marketing says that pipe gen will take time. Way too familiar. There’s a 6th option. It’s in my DMs. It has zero availability before July 15th. Stop spinning your wheels, come talk to us just to hear how we do it. Maybe you’ll hire us some day, maybe you’ll just copy what we are doing. Don’t take too long though because we might end up fully booked.

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Last week I spoke with a series A PropTech founder who said something that stuck with me: “I’ve spent more time fixing my pitch deck than talking to customers.” It’s a familiar story. Founders and GTM teams are stretched thin, raising funds, closing pilots, managing teams yet still need to build beautiful decks for investors, clients, and internal updates. So I pulled together a quick resource to save you some time ⏱️ 10 AI tools that help you build clean, story-driven presentations in minutes: Gamma | Dectopus AI | SlidesAI | Powtoon | Storydoc | Prezi | Pitch | DeckRobot | PitchGrade | Storylane Each one turns text or chat input into professional slides ready for investors or customers. Small tip: try one of these next time you’re refining your GTM or fundraising deck. Spend less time formatting, more time telling the story of how you’re changing the built world. #PropTech #Startups #GTM #AI #Innovation

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