Will Houghteling

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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Talking to users and thoughtfully integrating their needs and wants was woven through everything we did at IDEO—threaded through every prototype and product decision. Reading my colleagues Joanne and Leo's latest work brought that to mind. They describe a future where research runs continuously, with AI agents recruiting participants and instantly surfacing insights. Synthetic personas, carefully trained on consumer signals, mirror human behavior closely enough to extend live studies and compress timelines from weeks to hours. Today user research mostly runs in fits and starts, prohibitively expensive and locked away in dedicated project cycles when it could be a constant companion, seamlessly integrated into the product development process. Joanne and Leo lay out the full vision here: https://lnkd.in/gEUBSG_J

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In our 4th annual People Survey, we dove into how AI is impacting productivity, hiring, team structure, and more. It's early days, but there is already a massive shift in how startups operate. Check out our discussion of the findings 👇

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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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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 loved reading Olivia O'Sullivan's takeaways from Allie Garfinkle 's Fortune article because the market shift in hiring is already in motion! Allie spoke to six founders and VC firm talent leaders to get a sense of the changing landscape in hiring and trends they are seeing. https://lnkd.in/eTPCdY_G Hiring like it’s 2021 (chasing headcount and throwing "warm bodies" in seats ) instead of being hyper-focused on building talent density, is an antiquated playbook that doesn’t work anymore. AI has changed the game, capital is tighter, and the “growth at all costs” era is dead. What matters now is lean, high-impact teams of exceptional people, which is what I call "the right DNA in the right roles at the right time." Here are the 5 biggest shifts I see (and agree with) from Allie's piece in Fortune’s on startup hiring: 1. Talent density > headcount. AI is automating junior work. You don’t need more bodies, you need operators who can think critically, adapt fast, and deliver outcomes. 2. Learning agility > pedigree. Four years at Meta doesn’t guarantee impact. Curiosity, judgment, and problem-solving speed are what scale with you. 3. Strike while it’s hot. When you meet someone exceptional, don’t wait. Move fast, build trust, and show them the real experience of working with you. 4. Play the long game. Think like sports scouts by tracking promising talent well before you need them. When the time comes, your call gets answered because you’ve already invested. 5. Talent Density is dependent upon quality of environment. Talent density happens when A-players have what they need to thrive: clear goals, intentional culture, disciplined leadership, fair performance measures, strong rewards, and real-time, actionable feedback. 6. Retention is on the founder. Hiring is just the start. Retention comes down to trust, autonomy, and culture, which starts at the top. That means it's a shared responsibility with the founder, not HR’s alone.

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This really resonates. When Samuel Giraldo Hoyos, Rodrigo Burgos and I launched Aloi, we weren’t tax ops insiders—and that was the point. Fresh eyes let us challenge the “this is just how it works” mindset: manual workflows, fragmented data, reactive compliance. We’re rebuilding tax ops with an AI-first approach so large enterprises can become exponentially better at compliance, control, and audit defensibility. Rene Arturo Díaz García Ian Yoav Escobar #TaxOps #EnterpriseAI #FinanceOps #Compliance #Automation

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A really interesting work by Grove Ventures and their Head of Human Capital Einat Drutin to help founders identify strengths and blind-spots that will help them match their potential Co-Founders Take this quiz to discover your strengths and blind spots as a startup founder, and what you should look for in your startup co-founder: https://lnkd.in/eC7tUSg8 When choosing a Co-Founder there are many visible gaps but there are more invisible gaps around values, vision, skills and even personal intrinsic motivation that you need to dig deep, very deep to find. Here are some of the questions Einat offers founders to explore: - Do we want to build the same kind of company? - How do you define “success”? - What have you done that shows you can build things from scratch? - Can you disagree and still maintain a strong working relationship? - What would make you walk away from this venture? #VentureCapital #Startups #Entrepreneurship #Founders

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