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I step into scaling fintech and software revenue organizations when forecast discipline…
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Articles by Joshua
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Cannabis Retail Payments outlook in 2021
Cannabis Retail Payments outlook in 2021
While it feels as if legalization of cannabis is in full swing, this is just the beginning. Cannabis will be a 30…
11 Comments -
Building world class partner programs that drive long term revenue success
Building world class partner programs that drive long term revenue success
How I architected Flowhub’s partner engine and drove 25% of pipeline through ecosystem leverage. In early 2018, Flowhub…
5 Comments -
Formulating an A.I. strategy
Formulating an A.I. strategy
Evaluating artificial intelligence in the enterprise can seem like a daunting task. The Kylie.
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Executive Guide to A.I.
Executive Guide to A.I.
Several recent studies and surveys’ across several sources have shown that implementing an artificial intelligence…
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Poor leads, or Poor Sales Professional?
Poor leads, or Poor Sales Professional?
I love the 1992 film, Glengarry Glen Ross (One of my all time favorite sales movies). In my opinion, the best part of…
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When or when not to Scale?
When or when not to Scale?
So you’ve built some early sales traction and you as a founder(s) have sold your product gaining early success (1m<)…
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Build better teams in 5 steps
Build better teams in 5 steps
The only true way to move mountains for your business is by leveraging the collective brainpower (and, sometimes…
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3 Things to Remember When Building Your Workplace Wellness Culture
3 Things to Remember When Building Your Workplace Wellness Culture
So there is the average Corporate Wellness program, and then there is Google’s. Remember when corporate wellness meant…
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4 Low-Cost ways to reward your employees
4 Low-Cost ways to reward your employees
Myth: making your employees feel like rockstars at their jobs must be elaborate and cost a lot of money. Truth:…
4 Comments -
Hire the "Unicorn" candidate
Hire the "Unicorn" candidate
You know who they are, the go-getter, the one that people in an organization turn to for tough answers, they stay late…
9 Comments
Activity
11K followers
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Joshua Adragna posted thisThe real signal is not that people want your playbook... It’s that they want the output without formally valuing the operator who created it. That is where directors, new VPs, and revenue leaders need to be careful. Because a real playbook is not a template. It is context, timing, judgment, repetition, adoption, pressure, and trust. You can hand someone the document. But without the operator who built it, most teams just end up with a prettier Google Doc.
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Joshua Adragna posted thisThere’s a weird signal that shows up when your revenue system is actually working. People stop asking normal questions. They start trying to get the intel & playbook. -Not the philosophy. -Not the high-level recap. -The actual system. After one acquisition, I had people from the acquiring company poking around. -How did you train the team? -How did reps adopt the motion? -How did you keep deals moving? -How did you get everyone saying the same thing? On the surface, it sounded collaborative. But I knew what it was. They wanted the thing. And that’s a lesson a lot of operators learn too late. If your work is valuable enough for people to quietly extract, it is valuable enough to be owned, protected, and compensated. A real high performing playbook is not a Google Doc. It is years of reps, deals, failures, pattern recognition, pressure, and judgment compressed into a system other people can actually run. And the funny part is, giving it away usually does not work anyway. A playbook without the operator who built it is just a document. The value is not only in the steps. It is in knowing when to press, when to pull back, where the deal is lying, which rep needs confidence, who's distorting the story, and which signal actually matters -- That part does not copy and paste.
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Joshua Adragna posted thisA lot of startup traction is not built to survive real diligence. It is built to survive the conversation. I’ve seen this a bunch. A company gets a little momentum and the packaging starts. Big logo slides, inflated pipeline, selective metrics, loose expansion story, and activity dressed up like inevitability. It sounds good in the room. But that is not the same as building a business serious investors, buyers, or operators trust. Lots of founders optimize for pitch optics when they should be optimizing for buyer confidence. These have never been the same thing. The companies that get exposed later usually are not the ones with no story. They are the ones with a polished story stacked on top of fragile commercial truth. And that gap is getting harder to hide. Compressed markets expose what was always there. Weak pipeline, soft retention, vague expansion logic, and momentum that depended more on narrative than operating truth. A lot of companies did not build for diligence. They built for the room. The irony is that markets like this create real opportunity for the teams willing to face what is true. To get honest, tighten the business, and bring in people who know how to operate under this kind of pressure. Some founding teams will do that and get stronger. Others will keep preserving the story a little too long, and that is where a lot of unnecessary value gets lost.
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Joshua Adragna posted thisMost early-stage founders do not have a sales problem. They have a commercial clarity problem they are trying to hire around. I've seen it happen over and over. They hire a VP Sales before the business is clear enough to scale. The market does not understand the product fast enough. The value prop keeps changing. Deals are driven by founder force, not repeatable motion. Pipeline is full of hope. The motion is not actually there yet. So the new hire walks into ambiguity, gets buried in noise, and 6 months later everyone calls it a talent miss. It usually wasn’t. A lot of early sales hires fail because they were hired to scale something that was not clear enough to scale. Hiring does not create clarity, but does expose whether you had it.
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Joshua Adragna posted thisCompressed markets changes what founders should actually work on. > brand. > noise. > inflated pipeline theater. If funding or acquisition is even on the table in the next 12-24 months, your job is to reduce buyer risk, now. -Clean the revenue story. -Get honest about churn. -Fix sales-to-CS handoff. -Cut founder-led selling. -Make pricing stick. -Build forecast discipline. Know exactly where margins break. The majority wait until the process starts, which is amateur hour -- by then the buyer smells stress. Investor(s) knows you’re scrambling. Stronger companies aren’t perfect but they’re prepared. Prepared gets paid. Unclear gets punished.
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Joshua Adragna posted thisPlenty of founders still think prepping for funding or acquisition means tightening the deck. Wrong. In this market nobody buys the deck first. They buy whether the biz holds up under real scrutiny. -Messy pipeline. -Founder-carried revenue. -Weak retention. -No clean reporting. -Pricing that doesn’t hold. -Forecasts built on hope. That’s where deals get discounted. Investors slow down. Acquirers walk. Story matters less now while proof matters more. The companies still winning aren’t the sexiest, they’re the cleanest. Optimizing for buyer confidence > optimizing for pitch optics.
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Joshua Adragna posted thisAI isn’t fixing bad go-to-market. But it is scaling it. If your pipeline is garbage, AI gives you more garbage faster. When your messaging is off, AI helps you spray it wider. If your funnel is broken, AI just fills it with noise. That’s why some teams are “seeing activity go up” and still missing numbers. AI didn’t fail... It just exposed that the system underneath it never worked. Good operators use AI to compress time. Everyone else uses it to hide problems a little longer.
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Joshua Adragna posted thisAI can write the dealership email. It usually can’t tell that the real move is pushing on a 2-year pattern of issues, prior service history, and possible warranty coverage. That’s the same problem in go-to-market. A lot of founders are using AI for revenue decisions without feeding it real operator context. So the answer comes back polished, fast, and incomplete. and this is the gap. Operator-led AI won’t just sound smart, it will know what actually matters.
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Joshua Adragna posted thisEarly in my career, I used to think friction meant I needed to communicate better. Later I realized the friction was structural. I’ve sat in rooms where: the board wanted 5x growth pipeline math supported maybe 3x, product gaps were obvious but everyone kept talking about energy And yes, energy matters. In venture-backed companies, momentum can help bridge a gap. But only if everyone is honest that a gap exists in the first place. When I’d say, “The inputs don’t support the target,” the room would go quiet. Not because it was wrong. Because it interrupted the story. Operators who’ve been through it know this dynamic. Narrative can buy time. It cannot replace math. At some point, you stop performing optimism and start defending reality.
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Joshua Adragna liked thisJoshua Adragna liked thisAnother article I came across today which demands the attention of the developer community. 80% of code written by AI tools. Zero industry standard for proving it behaves correctly. A new report out this week puts a number on what engineering leaders already feel in their gut: AI coding tools are now generating the majority of code at accelerating teams. GitHub Copilot, Cursor, Windsurf, Claude Code - the velocity is real. The output is real. What's also real: QA was never built for this. Manual review was designed for humans writing code at human speed. When 80% of your output is AI-generated, the review layer doesn't scale, it collapses. One engineering leader described it plainly: "Even with all company personnel dedicated to QA, they could not keep pace." This is the verification gap. It's not a tooling gap. It's not a headcount gap. It's a structural gap between how fast AI generates code and how fast anyone can prove that code behaves correctly. The risk isn't hypothetical. Active AI-generated code is running in production today at companies that have never formally verified its behavioral correctness. Not tested. Not proven. Shipped. The question for every engineering leader reading this: what percentage of your AI-generated code has been mathematically proven to behave exactly as intended? If that number isn't 100%, you have exposure. The velocity is worth it. The blind spot isn't. #aicode #softwareengineering #codequality #aitools #githubcopilot
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Joshua Adragna liked thisJoshua Adragna liked thisWe are hosting a webinar + live demo of our platform on Wednesday, April 29th, at 1:00 PM ET with Jake Heller from the AI for CRE Collective on AI for asset management. Learn how data consolidation unlocks AI's potential for commercial real estate portfolio workflows and decision-making. Phil Peña from our US team will be doing a live demo of JLL Asset Beacon, including what's new with our AI features and how they're helping firms make faster, data-driven decisions. You really don't want to miss this :-) We'll also hear from one of our customers, who manages $10B in AUM, about their experience, and participants will have the opportunity to ask live questions. Register below: https://lnkd.in/eX2b-XNF
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Joshua Adragna reacted on thisJoshua Adragna reacted on thisWhen I first came into the NBA, I could not shoot. My rookie year, I shot 27% from three. Some fans called me "ason Kidd" because I had no jumper. I had a choice. I could stay the player I was, or do the work to become the player I knew I could be. I chose the work. Years of early mornings, late nights, reps nobody saw, coaches who would not let me quit. By the time I retired, I had hit 40% from three for my career. More than 1,988 made threes. Not the most talented shooter in the league, just a player who refused to stay where he started. Where you start does not have to be where you finish.
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Joshua Adragna reacted on thisJoshua Adragna reacted on thisWe’ve had standout quarters, but nothing compares to what just happened. 2x the prior record of new customers. 🚨 But that’s not really the entire story. In Q1, the team shipped the industry’s first MCP for data privacy and launched Vera, the agentic solution that’s redefining how privacy work gets done. At the same time, we renewed customers at a record rate. Deployed 20+ AI agents internally in just 90 days, pushed our partnership program into full stride, and built even more pipeline heading into Q2 than we entered Q1. That kind of progress doesn’t happen by accident. Company building is a long journey. But, this was a special quarter. I’m incredibly grateful for our team, the people doing the work every day to make it happen. For our customers and partners, who trust us with something so critical. And for our investors, who took a bet on us early and continue to stand alongside us. On to Q2. 💪
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Joshua Adragna liked thisJoshua Adragna liked thisWe're live on r/legaltech for a H2H AMA hosted by Melia Russell and Alex Denne. I'm going head to head against 3 of the best founders in Legal AI. Good luck out there! Scott Stevenson, CEO of Spellbook Min-Kyu Jung, CEO of Ivo Ross McNairn, CEO of Wordsmith AI https://lnkd.in/eZgAV98B
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Licenses & Certifications
Volunteer Experience
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Big Brother
Boys and Girls Clubs of America
- Present 13 years 7 months
Children
Publications
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SaaS sales playbook
a 70+ page playbook designed to capture all facets of sales in high growth software sales.
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Honors & Awards
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Winning by design
Jacco Vanderkooj
Demonstrating the expertise to master a customer centric approach to sale and sales management. Disciplines include social selling, and online selling through the use of modern sales techniques, command of modern sales tools, generate customized sales content and perform online demonstrations. Leading, influencing millennial sales reps to their max potential.
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Spanish
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Organizations
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Boys and Girls clubs
Volunteer
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Refery
🔥 These are the hottest early-stage startups in #California that recently raised funding. And yes, they’re #hiring. If you’re looking to join breakout companies early, this list is for you. #startups 💰 MoneyHash Payment platform offering fintech services 💰$5.2M 🧬 Segmed, Inc. RWE governance & clinical data platform 💰$10.4M 🛍️ Alta AI-powered personal shopping & styling 💰$11M 🔋 UNIGRID Battery Sodium-ion batteries for energy storage & e-mobility 💰$2.9M ⚡ Fourier Modular automated hydrogen production systems 💰$18.6M 📊 Hightouch Data sync platform from warehouse to CRM & marketing tools 💰$10M 🧠 Subsense Inc. Non-surgical brain-computer interface technologies 💰$10M 🎮 Layer Generative AI for game asset creation 💰$6.5M 🛡️ Cogent Security AI taskforce for vulnerability management 💰$11M 🛒 PublicSquare Marketplace for value-aligned local & national businesses 💰$7.5M 🎥 Hedra AI-powered content creation platform 💰$1M 📑 Patlytics AI-driven patent intelligence solutions 💰$21.1M ☕ Reborn Coffee, Inc. Global lifestyle coffee brand 💰$6.5M 📂 TransCrypts SaaS consumer record management services 💰$15M 📊 Anomalo Continuous data inspection & validation platform 💰$10M 🩸 Melio Quick, comprehensive blood test for infections 💰$3.5M 🫁 LEADOPTIK Miniature imaging platform for early lung cancer diagnosis 💰$4.6M 🧬 Elysium Therapeutics, Inc. Healthtech & biotech focusing on fitness, medical & robotics 💰$7.5M 🚗 Stic Ad tech platform promoting brand stickers in cars 💰$10M 🔍 Voyage AI by MongoDB Embedding models & rerankers for search & RAG 💰$20M 💳 Flagright AI-native transaction monitoring & AML compliance 💰$4.3M 🛡️ Legion Intelligence Agentic AI orchestration platform for security & enterprise 💰$40M 🚀 Heliospace Systems engineering for space flight missions 💰$1.06M 🧪 858 Therapeutics Small molecule drugs for oncology & immunology 💰$50M 📊 Truewind AI-powered accounting & finance services 💰$13M 𝐖𝐚𝐧𝐭 𝐦𝐨𝐫𝐞 𝐨𝐟 𝐭𝐡𝐢𝐬? If you want to get top, 𝐑𝐄𝐀𝐋 jobs that are actually hiring from elite tech companies delivered to you, subscribe to the waitlist for our soon-to-launch newsletter: 👉 https://lnkd.in/eV-JMpw3 #hiringalert #jobalert #hiringnow #engineeringjob #softwaredeveloper #softwareengineer
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Amplify.LA
We’re excited to release our latest Seed Report for 1H 2025, a full overview of all publicly announced Seed funding across Southern California. In the first half of the year, LA founders raised $364M across 85 rounds. Hardware continued its strong momentum, while AI showed up everywhere: over 40% of all Seed deals referenced AI, and companies with meaningful AI differentiation raised 45% larger rounds on average. If you’re tracking early-stage activity in Southern California, we hope you find this helpful. 👇 Full report below https://lnkd.in/gX3UzdtG #SeedFunding #VentureCapital #LAtech #Startups #EarlyStage
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Patrick Henry
Some great thoughts from my friend Neal Bloom🎩 about the critical importance of Founders in the starting and building of companies, and a startup ecosystem in a community. Sometimes we lose sight of this important fact. Service providers, non-profits, Angel investor, and venture capitalists are here to service the startup companies, and they are anchored by founders. He references a great book written by Brad Feld, “Startup Communities”. For those that don’t know, Brad is an entrepreneur, author, blogger, and venture capitalist at Foundry Group in Boulder, Colorado, a firm he started with partners Seth Levine, Ryan McIntyre, and Jason Mendelson. #sandiego #startups #venturecapital
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ZoomInfo
The missing key to explosive growth: true leadership alignment. 🔑 On the GTM Made Simple Podcast with host Sangram Vajre, ZoomInfo founder and CEO Henry Schuck revealed why Go-to-Market excellence depends on a rock-solid leadership trifecta. Without tight alignment between the CPO, CRO, and CMO, product teams risk building what sales can’t sell — and marketing messages fall flat. 🔗 Link below for the full episode.
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How To SaaS
Royalty-based growth capital gives founders another option beyond venture capital, bootstrapping or friends and family rounds. This structure is designed for high-margin B2B SaaS businesses that want flexibility, predictable repayments and no loss of ownership or control. Vik Thapar of Cypress Growth Capital explains how this model works best for revenue-generating companies with early product-market fit and can often be far more affordable than traditional equity financing if the business continues to grow. 🎙️ Tune into the Private Equity Value Creation Podcast: https://lnkd.in/gxkEsH3Z 👇🏽 Find Us Here https://lnkd.in/gTdPMk8P #privateequity #privateequitypodcast #privateequityvaluecreation
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CommercialEVs.com
What is ISEF? The Innovative Small E-Fleet (ISEF) program from California Air Resources Board (CARB), administered by CALSTART, is designed specifically to help small fleets in California make the move to zero-emission vehicles. Unlike traditional voucher programs, ISEF offers flexible funding options like leasing, rentals, charging support, infrastructure planning, and more. Why it matters: ISEF recognizes that small fleets face unique challenges in electrification — from limited capital to uncertainty about operations. This program removes those barriers by giving small operators the flexibility they need to get started and grow with clean technology. Who qualifies? ✅ California-based fleets with 20 or fewer trucks or less than $15M in revenue ✅ Businesses with fewer than 500 employees ✅ Independent owner-operators ✅ Those looking for alternative ownership models (e.g., leases or rentals) If you're a small fleet operator looking for support beyond just a vehicle voucher, ISEF could be the key to making zero-emission work for you. To find out if you qualify or to learn more, reach out to our experts Ryan Pritchard, John Lanham, or Scott Phillippi, or email us at info@commercialevs.com.
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BoxPower
BoxPower is honored to join Aggie Square’s January MIX event in Sacramento and contribute to an excellent lineup of innovators who are reimagining how Northern California communities are powered and served. Fallon Vaughan, our Director of Business Development, will share how utility-grade microgrids can act as scalable resilience assets and the need to treat these systems as core, long-term infrastructure rather than niche backup solutions. Headquartered in Grass Valley, just up the road from Sacramento, BoxPower is a one-stop shop from energy audit through operation for utility-grade, standardized microgrids that help organizations and communities enhance resilience, reduce wildfire and outage risk, and deliver reliable and clean power anywhere. #GridResilience #Microgrids #DistributedEnergy #BatteryStorage
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Yajur Knowledge Solutions
How do you know which companies in your pipeline are truly ready for a deal? 🏁 The smartest dealmakers don’t chase every opportunity, they filter, qualify, and prioritize. It’s not just about revenue or margins. Ownership signals like founder intent, investor timelines, and leadership transition plans often reveal the deal’s real potential long before the numbers do. Using these signals effectively can shorten diligence, reduce wasted effort, and strengthen mandate quality. Which ones do you rely on most when sizing up a potential mandate? 🎯
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