I've been the first internal legal hire 4 times now, and now that I'm paying attention to the job market again I'm seeing the same mistake over and over again in the postings. When a scaling tech company in a highly regulated space (FinTech, HealthTech, EdTech, GovTech) makes its first GC hire, the temptation is to find a deep specialist—the "Health Care Regulatory Expert" or the "FinTech Licensing Guru." This is often a mistake. Your first General Counsel (GC 1.0) is not just a subject matter expert; they are the foundational architect of your legal, compliance, and governance infrastructure. Here’s why the Generalist Operator is the superior choice for your first in-house legal leader: The Initial Workload is 80% Generalist: The first 12 months are dominated by corporate governance, commercial contracting (revamping sales agreements, vendor paper, creating templates), employment law, IP management, and building your data privacy framework (GDPR/CCPA readiness). A specialist usually relies on expensive outside counsel for all these foundational areas. The generalist handles it all in-house from day one, drastically cutting OCL spend. They are the Exit Architect: The GC's primary executive task is to ensure the company is "diligence-ready" for the next fundraise or exit (IPO/M&A). This requires a deep, broad understanding of corporate structure, cap table management, SOX readiness, and internal controls—all generalist functions that specialists rarely lead. Risk Calibration vs. Risk Avoidance: The specialist's instinct is often to enforce regulation rigidly, which can slow down product launches and limit business optionality. The experienced generalist, by contrast, is a business operator who understands how to calibrate risk, negotiate liability, and find a commercially viable path forward. They know the $100M risk versus the $100K risk. The Strategy: Hire a Generalist to build the full, scalable legal engine. Then, when the company hits the scale that justifies it, bring in the specialist as the second hire to run the deep regulatory compliance function. You need a builder first. #GeneralCounsel #LegalOps #StartupLaw #GeneralistGC
Very true! But I disagree with the part about cutting outside counsel spend, in my experience the arrival of in house legal can reduce outside counsel spend on some things, but inevitably leads to increased spend on other areas that hadn’t previously been on the radar.
I’ve been trying to figure out how the GC is supposed to do all this and negotiate all the agreements 😂 when I see this in the job description right after “strategic advisor to the leadership team,” it tells me they’re not ready for a GC
Foundational & Exit architect. Love this & completely agree!! As a fellow builder GC, the founders who get this concept are my favorite to work with. They understand while I have a higher risk tolerance and can be scrappy, when I push back it really matters because we’re building a foundation to scale on. There’s an art to giving an early stage company room to run but ground to grow on.
100% agree Tanya. I’ve been the first lawyer twice, now looking for my third adventure and have been getting a specific form of the specialist mindset from a few companies - “we’re looking for an enterprise SAAS GC for this role.” I’d love to know if anyone else has experienced this and if they got past it, how?
Tanya Avila Totally agree with this. When I joined as the first Head of Legal, the function was actually reporting into HR — which said a lot about how the role was viewed. The first task wasn’t drafting contracts or building policies; it was building awareness — helping leaders see what legal can enable, not just restrict. From there, it was about building the foundations: setting up governance, creating templates, managing risks practically, and yes, building a team that could scale with the business. Being GC 1.0 is equal parts educator, builder, and connector. You don’t inherit systems — you create them. You don’t join a function — you build its identity.
Hiring largely for subject matter expertise, for a GC, can end up being a expensive mistake for the organisation. Hiring a GC from another domain, another industry, with expertise in other/subject matters can add value to the strategy of the organisation. Gone other days when a GC only did reactive Legal work. We live in a time when a GC can be a part of the senior leadership team and contribute to business growth through proactive legal strategies.
Excellent summary and great advice for CEOs of early-mid stage businesses, which aligns with my 20+ years of experience in the field. I would add that the "you need a specialist" advice to the company is sometimes provided by outside counsel, and I've wondered whether it's out of self interest. Interestingly, the comments here seem to be exclusively by lawyers (this lawyer included). We need to spread this knowledge beyond legal circles. Let me think how I can help.
Of all the posts about "what to look for in hiring your first GC", this is the one to read. If I can add my 2 cents, which I understand you're saying too: Look for someone knows the levers in your business and industry and how to pull each of them, not just one of them.