Rebekah Rombom

For the last decade, tech companies optimized for scale: repeatable hiring plans, functional specialization, predictable org charts. I think the next decade will be defined by something harder to achieve: leverage.  The defining trait of AI-first companies won’t necessarily be how much AI they deploy. It will be how willing they are to revisit long-held assumptions about what work exists, who should do it, and how organizations should be structured in the first place. Very excited to finally share the thought piece we at ICONIQ have been working on. Thank you to the many contributors Anu Bharadwaj Dennis Lyandres Diane K. Adams Kipp Bodnar Matt Eccleston Michael Curtis Michelle Morris Jesse Collins Patrick Forquer Rob Bernshteyn who shared their perspectives. This space is evolving faster than any single perspective can capture. If you’re experimenting with new workforce models, seeing something different in your organization, or simply disagree with parts of this thesis, I’d love to hear from you! https://lnkd.in/g66NxYVK

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One of the most common frustrations I hear from founders is: “Our headcount plan looked solid at the beginning of the year. Why are we still missing?” In most cases, the plan didn’t fail because of talent. It failed because it assumed ideal behavior. Approved headcount gets treated as productive capacity, but a start date doesn’t equal productivity. Between time-to-hire and ramp, it can take six to nine months before a role is truly operating at full impact. Additionally, if someone leaves, the financial model often captures the salary savings but not the vacancy gap, the hiring drag, or the reset in productivity. On paper, the org chart says, “fully staffed”. In reality, the team is still rebuilding. Headcount planning isn’t just about counting seats. It’s about having the correct job architecture to model how people actually behave. When you plan for the ideal state, you’re almost guaranteed to miss. When you plan for real behavior, your forecasts become far more durable. Join Karina Bensko, SPHR and I for The Scale Gap: A 3-Part Workshop Series on How Hiring, Headcount & Retention Impact Cash & Runway • Three live one hour workshops • Two 30-min 1:1 sessions • Workshop Toolkit (Calculators, Worksheets, and Models) Secure your spot: https://luma.com/nktfgt2i

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I spoke with Christien Louviere of BDE Capital about his journey from a $330mm exit to becoming an independent sponsor. Christien shared excellent insights for folks looking to partner with business owners, rather than buy sellers out completely. Below are a few of the topics we covered: - Why he moved from “zero-to-one” startups to a buy-then-build strategy - How Christien's background shaped a focus on growth vs. cost-cutting - Why 20–40% rolled equity is central to his deal structures—and how it builds trust with sellers - Using scenario analysis with AI tools to evaluate management teams and uncover hidden key-person risks - How to identify when a $3–5M EBITDA company truly has a middle management layer—or is still founder-reliant For anyone investing in or buying small businesses, Christien’s approach provides a fresh lens on growth, alignment, and deal structuring. 🎥 Watch the full interview here → https://lnkd.in/ekfkaiej 🎧 Listen on Spotify: https://lnkd.in/e86Agx6V

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💡Emerging GP Fundraising Insight #8: Rolling Closes Keep You Moving Small funds can't always afford to sit still until the target is hit. Rolling closes let you start deploying earlier, build a track record, and show momentum to prospective LPs. One GP told me that for Fund I ($5M target), he took capital as it came, signed, wired, and got to work. It wasn't perfect, but it kept the lights on and the deals moving. Sometimes the "sign and wire as it comes" approach is the only way to get moving. Takeaway: Momentum is a fundraising asset and rolling closes can help you keep it. Has anyone here used rolling closes as a strategic advantage?

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Most founders are terrible at investing in their teams. They'll spend $50k on ads. Six figures on new hires. But won't invest in training, coaching, or upskilling the team they already have. We brought Joe Stolte onto an all-hands Q&A where he shared advice, frameworks on delegation, systems thinking, and high-performance habits. Watching our team lean in, ask sharp questions, and immediately start thinking about how to apply the lessons- that's when it clicked for me again: When you invest in your people's growth: - Their skills expand and output 2x's. - They stay longer because they feel valued. - Impact compounds as your best people build momentum together. Monty Ngan and I are obsessed with empowering our team because your company's ceiling isn't what you can build alone. It's what your people are empowered to build with you. The best investment you can make is in the team you already have. #startups #entrepreneurship #leanstartups #leadership #businessgrowth #recruiting

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AI doesn’t have to be complicated, but it does need to work for society’s most critical industries. From healthcare to defense, current solutions lack the deep knowledge to solve organizations’ highly complex use cases. Enter Trase, led by Grant Verstandig, Baskar Sridharan, and Joe Laws. Trase is combining industry-leading tech with deep domain expertise to deliver autonomous, end-to-end, turnkey agents designed to drive real ROI across highly regulated sectors, with compliance, trust, and security guiding their every move. Today, Trase launched out of stealth with $10.5 million in pre-seed funding from Red Cell Partners and VIPC | Virginia Innovation Partnership Corporation. Learn how we’re enabling last-mile AI adoption across various enterprises, starting with healthcare, energy, and national security: https://lnkd.in/egJYdNKz

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The fastest way to get ruled out of a PE role? ⤵️ Say AI doesn’t apply to you. (Shared by someone who’s built and scaled portfolio companies for two decades) In a Thrive Community session, Azra Kanji, Founder and Partner at Astira Capital Partners Capital with 25+ exits, shared how private equity leaders assess executive mindset before making a hire. She said: “The minute we hear an executive say AI won’t affect their business, we walk away.” Not because they expect you to build AI tools. But because that statement reveals a bigger issue: rigid thinking. Here’s how Azra and her team actually evaluate readiness when it comes to AI: ↳ They’re not looking for early adopters. They’re looking for practical thinkers ↳ Executives who understand AI as a lever for efficiency, automation, and decision-making ↳ Leaders who ask, “Where could tech give us leverage?” not “Do we need it?” And here’s what separates credible operators from risky ones: ✔ The credible leader says: “I may not be fluent in AI, but I’m exploring where it fits.” ✘ The risky leader says: “That doesn’t apply to our business.” Azra made it clear: Private equity isn’t hiring titles. They’re hiring mindsets. Your ability to adapt is part of your value proposition. If you’re preparing for a move into private equity, the question isn’t whether you use AI now. It’s whether you’re thinking like someone who can. Want more insights from leaders like Azra? Join the Thrive Leadership Community and learn how investors evaluate executive fit in today’s portfolio environment: 🔗 https://lnkd.in/ea7E9j53

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I’m thrilled to announce defy.vc’s investment in Birches Health as part of their $20M combined Seed and Series A funding round, alongside incredible partners like AlleyCorp, General Catalyst, Will Ventures, and others. As someone deeply passionate about backing companies that tackle important problems for our society, I couldn’t be more excited about what Birches is building—a national virtual clinic dedicated to treating gambling addiction and related behavioral disorders like gaming, sex, porn, and internet addictions. What excites me most is Birches’ innovative health assurance model: proactive, accessible, and affordable care that’s evidence-based and delivered right at home. With the explosion of legal sports betting—think nearly $1.5 billion wagered on this year’s Super Bowl alone—we’re staring down a looming public health emergency. Traditional options like hotlines or generic therapy fall short for this high-acuity issue, but Birches changes that by offering specialized therapy from trained clinicians, multimodal treatment, and peer support, all covered by major insurers like United Healthcare, Cigna, Aetna, and Blue Cross Blue Shield. It’s available in all 50 states, breaking down geographical and financial barriers that have left so many without help. The impact is already profound: 96% of patients report an improved quality of life, and 94% give Birches a 5/5 rating. By partnering with state governments, payors, and policymakers, Birches is pushing gambling addiction into the spotlight of behavioral health conversations, where it’s been neglected for too long—often leading to shame, worsened outcomes, and higher suicidality risks. This funding will supercharge their growth: expanding the provider network, boosting clinical excellence, scaling infrastructure, and deepening insurance and state partnerships to meet surging demand. Very excited to partner with Elliott Rapaport and the entire Birches team! See more about our POV in the blog post linked in the comments. #GamblingAddiction #BehavioralHealth #HealthTech #VentureCapital #Innovation

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We kicked around a frustrating paradox in a meeting at Companyon Ventures this week: there's a flood of entry-level talent out there, yet founders are still having trouble hiring. While new grads are getting sidelined by AI that now handles starter tasks, early-stage companies are desperate for battle-tested operators who can actually navigate the grind of scaling. The irony is that while the market is saturated with candidates, the builder profile feels rarer than ever. Experienced people are understandably hesitant to leave established roles, creating a massive gap that a pile of entry-level resumes (no matter how many) just can’t fill. The traditional application process is basically dead; at this point, your network and your output are the only things that actually signal value. Hiring and firing are just mechanical skills, but recruiting and motivating? That’s an art. We’re finding ourselves looking for qualities that you just can't find on paper. We’re hunting for that internal drive to show up when things get messy, regardless of what a professional background says. The real challenge isn't a lack of people; it’s a lack of the specific, unteachable grit it takes to build something from zero. So I'll ask my network - if you’re a founder, hiring manager, or recruiter, how are you actually screening for this kind of intangible grit right now?

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I’m thrilled to officially announce our $3M seed investment in Propel People, a company we built inside the 1848 Ventures studio to tackle one of the biggest challenges facing the #construction industry today: the skilled #labor shortage. For small and medium-sized contractors, hiring isn't just a challenge. It's the number one threat to their growth, profitability, and safety. With 94% of contractors struggling to find qualified workers, it’s clear that traditional hiring methods aren't built for the trades. That’s why we built Propel People. It’s a mobile-first, AI-powered hiring platform designed for how construction actually works: in the field. By leveraging smart candidate ranking, instant #SMS-based screening, and a fully #bilingual interface, Propel helps contractors build great crews faster and more efficiently. I’m also thrilled to formally announce that industry veteran Dexter Bachelder is at the helm as CEO. Having worked with Dexter and the team over the last few months, we've already seen the impact of his leadership. His 25 years of experience scaling construction tech companies will be instrumental as Propel People enters this initial stage of growth. This investment reinforces our core thesis at 1848 Ventures: building AI-native companies that solve fundamental pain points for the #SMBs that form the backbone of our economy. A huge congratulations to Dexter and the entire Propel People team on this milestone. We are incredibly proud to partner with you to support the people who build our world. Read the full announcement below. #constructiontech #venturecapital #seedfunding #ai #skilledtrades #smb

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🥾 #bootstrapping as a mindset should be ephemeral, one that requires a deliberate transition away from as a business enters sustained growth Appointing an established auditor is often regarded as a luxury and not part of bootstrapping Audits discipline a business - to be methodical, thorough and deliberate - traits that acquirers often seek in due diligence After all, "What gets inspected, gets respected," Anon We will share the traits of venture businesses sought and respected by MNC acquirers, join us if your business is out of the #bootstrapping mindset #fulfillingpotential #hepmil #oobmil

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🚀 This month at LvlUp Ventures we’re investing in 100+ companies. Not over the next year. Not “by Q4.” This month. Why? Because the next iconic companies aren’t waiting for perfect timing. They’re being built right now — in dorm rooms, tiny apartments, co-working spaces, late at night after full-time jobs. And capital shouldn’t be the bottleneck to ambition. Because momentum loves speed. Because the best founders aren’t waiting for perfect market conditions. Because early belief changes trajectories. So instead of sitting on the sidelines debating spreadsheets for weeks, we’re choosing momentum. 👇 Drop your one-liner in the comments and I’ll DM you. #Startups #VentureCapital #VC #AngelInvesting #Founders #Entrepreneurship #StartupFunding #Investing #Innovation #BuildInPublic #SeedStage #EarlyStage #TechStartups #Fundraising #LevelUp

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