Ian Siegel

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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CEOs want AI for everything. CHROs know it's more complicated than that. ...was one of the themes at Hone's executive dinner in Phoenix last night. AI can provide meaningful gains. For example, a recruiting team able to maintain throughput with half the headcount. However, when it comes to processes where humanity is an essential part of the equation, like scaling customer or franchisee relationships or effective employee development, there was reluctance to go all-in on AI. People leaders are right to take a sober look at AI's true capabilities in the here and now, and be wary of throwing the baby out with the bathwater when it comes to human connection. By all means scale, amplify, automate, and enhance with AI, but when empathy, nuance, accountability, and shared experience are key, find ways to retain the human dimension in your workflows. Or you'll be correcting your over-correction later. If others have grappled with this let us know! Thanks Kristen Bracamonte Switzer, CPTM, Sandra Lamartine, Heather Brazik Smith, Lauren Patel, Jill Patterson, Cindy Jones, Cammy Wood, Will Briggs, Cameron Warner, Stacie Bartow and Steak 44 for a fantastic night 🎉 🌵 💡

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The Headline family is experiencing incredible momentum, and today our portfolio company DeepIP is announcing a $25M Series B, bringing total funding to $40M.  This is the kind of company that doesn’t just add AI to a workflow, but it sets the standard for an entire category. The momentum speaks for itself: 1️⃣ 10x ARR growth in < 18 months 2️⃣ Trusted by 400+ law firms and leading corporate IP teams globally 3️⃣ 2M+ chats on the DeepIP platform We’ve had the chance to back FX (Francois-Xavier) L. and Edouard D., leading their Seed round with Headline. Watching them take on a problem as complex and high-stakes as patent work has been genuinely impressive. And working with them has been an absolute pleasure: these 2 are coupling very high ambition and humility. Tech built in Europe, but opening the US office very early and FX starting a life in NYC with his family with 0 hesitation in order to build a global category leader in the IP industry. What convinced me early is still what stands out today: patent teams don’t need another standalone AI tool. They need something that fits the way the work actually happens: documents, long-running matters, multiple stakeholders, and zero room for sloppy context handoffs. Big congrats to the whole DeepIP team + Korelya Capital, Balderton & Serena Proud that we’re doubling down at Headline and continuing the support for what’s next!

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Lessons from the Pitch: Standing Out in a Sea of Startups In San Francisco, every day brings another pitch event, mixer, or founder gathering. The competition is fierce, but the learning is exponential. The best founders aren’t just pitching—they’re storytelling, connecting, and adapting in real time. My advice: Focus on clarity, authenticity, and the unique value you bring. Investors see thousands of decks; make yours unforgettable. #Pitching #StartupAdvice #Founders #SFStartups

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Owning your narrative is leadership. Last week in San Francisco, we gathered with AAF SF Bay Area to talk about positioning in competitive markets. Three themes emerged: Be memorable. Be clear. Be consistent. The market doesn’t reward talent. It rewards clarity. Grateful to everyone who showed up thoughtfully. #personalbrand #careergrowth #leadership

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