Probook

I wasted 9 months building a startup in college before I realized it was dead on arrival. The painful lesson: asking your friends if your idea is cool doesn't count as market validation.   The idea was called Slipstr.   Customers hate paper receipts. They're wasteful, dirty, they disintegrate in your pocket. And digital receipts aren't much better. No one wants to give out their contact info and get bombarded with marketing emails. So I came up with another solution: the Apple Pay of receipts. Using NFC, you could tap your phone at checkout and get one instantly.   I shopped the idea around to my classmates at Penn. Everyone in my entrepreneurship program said it was cool. I took that as my signal to start building.   I was 8 months in when one of my profs gave a piece of advice that I wish I had on day one: "Validate the market before you build."   I thought, better late than never. I went out and walked the streets of South Philly, pitching to restaurants, coffee shops, merchants - anyone who would listen. The most encouraging response I got was from a candlemaker who didn't immediately tell me to leave.   I quickly realized the market had every reason to actively work against me.   A digital receipt gives customers a clear path to a return. That's a liability. And merchants want your email address - it's how they remarket to you. Handing customers a convenient, frictionless receipt means giving up their data strategy with nothing in return.   The idea wasn't bad. But the people I was actually selling to were never going to validate it. If I could go back, I would have hit the streets and spoken to merchants on day one.

Until December, our 'sales team' was just me. I took pride in being the single point of contact. But not hiring a CRO sooner was actually my biggest mistake as a founder.   I never thought I'd hand over the GTM motion. I've personally met pretty much every Probook customer, run every demo, and traveled across the US to visit almost every shop. Some of our customers feel like family to me.   But in Q4 of 2025, I realized that being the only salesperson created a massive bottleneck.   When conference season hit in September and October, we booked 100s of meetings. I was on Zoom from 8am to 8pm, spending just as many hours on prep and follow-up. We were getting so much inbound that my CTO, Lewis Z., had to start running demos. These were revenue opportunities we couldn't pass up.   But the rest of the business halted.   So when we went to hire, we didn't start with a Head of. We went straight to the CRO level—someone who could build the whole function (not just hire a few people and manage a pipeline).   That's Mark Hoffman, who joined us last month. He's already hopping on calls, digging into our pipeline, and building out the team. That gives me time to do what I should have been doing for the past 6 months— company building.   I'm still going to be in sales. But I've started being honest with myself about where I'm actually high-leverage and automating myself out of everything else.   If I have a long-standing relationship with a prospective partner, I'm high-leverage. If I met them once at a tradeshow and it went nowhere, my team is going to do a better job than me, and that's how it should be.   Being stuck in founder-led sales isn't a flex. I wish I realized that sooner.  

After 19 months of running literally every demo myself, I couldn't be more excited to welcome Mark Hoffman as Probook's CRO. Mark is an absolute killer. He spent 8 years at VTS— a commercial real estate SaaS platform, working his way from Director of Sales to SVP. And before joining us, he was Chief Sales Officer at Tennr. He's exceptional at building teams from the ground up and driving outcomes. With how fast we've been scaling, it's the exact experience we need. I want to be involved in our sales process forever, but only in places where I'm truly high-leverage. Now I have someone who can give our team what I couldn't—real leadership, real development, and a real process. Welcome, Mark. We're stoked to have you.

Every engineer who's been through our on-site at Probook - regardless of whether they joined - has said it's the best on-site they've ever had.   That's not the pitch I usually lead with. But it's consistently what people walk away saying.   Most engineers assume our pitch is about growth metrics and investors. We have both. But that's not what makes this the right place to build.   The way I think about it is Probook runs on relationships. We show up to every customer in person. We're there when things go wrong. That's not a superficial strategy, it's just how we operate. And it didn't make sense to recruit any differently.   So instead of a transactional interview loop, our on-site is a 2-day mutual experience.   Candidates spend time with the entire team and get to know the people they'd actually be building with every day. That gives them the opportunity to figure out whether we want to work together.   That's the question we actually care about. Not just do we want to hire you, but do you want to be here?   The engineers who've come through get it immediately. The ones who choose not to join still leave saying it was unlike anything they'd experienced.   If you're a senior engineer thinking about your next move, come see it for yourself! DM me.

Over the last couple of weeks I’ve been able to sit it on two pre-implementation meetings with Probook for a mutual client shared with Powerhouse Consulting Group. I’ve been quite impressed with the care, guidance, and clear roadmap for the client. I love learning from our partners and taking bits into my personal knowledge base. George Eliadis, things have come so far since Zachary Dearing introduced us and you let me see an early version of the platform. Very excited for this shared client. Thanks Mia Parker for the tag team on this! 💪

Another week, another Probook is hiring post. We're continuing to scale fast and building out the team across the board: → Founding Technical Recruiter → Founding AE → Founding Marketing Director → Founding People Operations Associate → Deployment Strategist If you want ownership, speed, and the chance to build something from scratch, you'll love it here. Links in comments.

Probook 10x'd headcount in 2025. We’re 30 people, growing fast, and need help building processes to scale with us. If you want to work directly with me (the founder) at a hypergrowth startup and build things that will see a LOT of use - let's talk. We are 100% in-office, in NYC. Early-stage experience or ex-founder is strongly preferred. Email vincent@probook.ai or DM me here. JD in comments.

We just published our first issue of The Shortlist NY's bi-weekly newsletter, where we feature New York's top breakout founders who are actively hiring. Here's who's hiring this week: 1. Probook – AI-powered dispatching software for the $700B home services industry (plumbers, electricians, HVAC), backed by Tier 1 investors. Founded by Ben, Lewis & George. Hiring software engineers, founding account executive, chief of staff, strategy associate, marketing director, GM. -- 2. Basic Capital – reimagining retirement savings by providing $4 of financing for every dollar in 401(k) contributions, backed by Bill Ackman, Forerunner Capital, Henry Kravis, Lux Capital, BoxGroup Founded by Abdul Al-Asaad. Hiring full-stack software engineers, founding GTM associate, growth manager (IRL), and operations associates. -- 3. Lora – consumer AI software platform, sitting at the intersection of spirituality, self discovery, and astrology. Backed by AlleyCorp. Founded by the former Chief Product Officer of Hinge and ex Netflix, Spotify, Kayak product exec, Michelle Parsons. Hiring founding engineer, head of design, growth, product, and content roles. -- 4. Goodword – a smart networking copilot powered by AI and emotional intelligence. Backed by Futureback Ventures and Human Ventures ($4M seed). Founded by Caroline Dell (former Chief, Bain) and Chris Fischer (former Aaptiv, Shutterstock). Hiring full-stack engineer, AI engineer, frontend engineer, customer success associate, strategy & operations lead. -- 5. Carry – tax-optimized wealth platform for business owners, freelancers, and founders. Backed by Accomplice VC, Balaji Srinivasan, Sam Parr, Sophia Amoruso, and Codie Sanchez ($10M Series A). Founded by Ankur Nagpal 💰 (funder of Teachable; sold for $250M). Hiring software engineers, growth marketing manager, and content lead. -- 6. Heidi – AI-powered medical scribe that automates clinical documentation for healthcare providers, transcribing patient visits and generating notes, referrals, and follow-ups in 110+ languages. Backed by Point72 Private Investments, Blackbird, Headline, and Latitude, with a $65M Series B (valued at $465M). Founded by Dr. Thomas Kelly (former vascular surgeon) and Waleed Mussa (former Goldman Sachs). Hiring solutions engineer, designer, head of sales, partnerships manager, senior and junior customer success roles. -- 7. Upscale AI – platform that leverages AI to help brands tap into the power of streaming TV and video for performance marketing, so that they can generate, run, and optimize TV-quality video ads automatically. Backed by Microsoft’s Venture Fund and Eniac Ventures, with a $5.5M Seed. Founded by Mike Chang and Kevin Weatherman (industry execs from Google, Twitter, and Salesforce). Hiring: machine learning engineer, data scientist, software engineer, head of growth marketing, and account executive roles. -- See more: https://lnkd.in/eyHH7zp5

We just published our first issue of The Shortlist NY's bi-weekly newsletter, where we feature New York's top breakout founders who are actively hiring. Here's who's hiring this week: 1. Probook – AI-powered dispatching software for the $700B home services industry (plumbers, electricians, HVAC), backed by Tier 1 investors. Founded by Ben, Lewis & George. Hiring software engineers, founding account executive, chief of staff, strategy associate, marketing director, GM. -- 2. Basic Capital – reimagining retirement savings by providing $4 of financing for every dollar in 401(k) contributions, backed by Bill Ackman, Forerunner Capital, Henry Kravis, Lux Capital, BoxGroup Founded by Abdul Al-Asaad. Hiring full-stack software engineers, founding GTM associate, growth manager (IRL), and operations associates. -- 3. Lora – consumer AI software platform, sitting at the intersection of spirituality, self discovery, and astrology. Backed by AlleyCorp. Founded by the former Chief Product Officer of Hinge and ex Netflix, Spotify, Kayak product exec, Michelle Parsons. Hiring founding engineer, head of design, growth, product, and content roles. -- 4. Goodword – a smart networking copilot powered by AI and emotional intelligence. Backed by Futureback Ventures and Human Ventures ($4M seed). Founded by Caroline Dell (former Chief, Bain) and Chris Fischer (former Aaptiv, Shutterstock). Hiring full-stack engineer, AI engineer, frontend engineer, customer success associate, strategy & operations lead. -- 5. Carry – tax-optimized wealth platform for business owners, freelancers, and founders. Backed by Accomplice VC, Balaji Srinivasan, Sam Parr, Sophia Amoruso, and Codie Sanchez ($10M Series A). Founded by Ankur Nagpal 💰 (funder of Teachable; sold for $250M). Hiring software engineers, growth marketing manager, and content lead. -- 6. Heidi – AI-powered medical scribe that automates clinical documentation for healthcare providers, transcribing patient visits and generating notes, referrals, and follow-ups in 110+ languages. Backed by Point72 Private Investments, Blackbird, Headline, and Latitude, with a $65M Series B (valued at $465M). Founded by Dr. Thomas Kelly (former vascular surgeon) and Waleed Mussa (former Goldman Sachs). Hiring solutions engineer, designer, head of sales, partnerships manager, senior and junior customer success roles. -- 7. Upscale AI – platform that leverages AI to help brands tap into the power of streaming TV and video for performance marketing, so that they can generate, run, and optimize TV-quality video ads automatically. Backed by Microsoft’s Venture Fund and Eniac Ventures, with a $5.5M Seed. Founded by Mike Chang and Kevin Weatherman (industry execs from Google, Twitter, and Salesforce). Hiring: machine learning engineer, data scientist, software engineer, head of growth marketing, and account executive roles. -- See more: https://lnkd.in/eyHH7zp5