If your in-house legal team is still picking outside counsel based on legacy relationships, hunches, or internal reputation, you’re not alone. But you might also be holding back your company’s growth. In a recent episode of “Notes to My (Legal) Self,” I sat down with Otto Hanson, co-founder and CEO of TermScout and Screens, to talk about how contract review is evolving and how forward-looking legal teams can stop outsourcing by instinct and start scaling good judgment through strategy, data, and technology.
From Law Firm Burnout To Product-Minded Builder
Otto began his career in a familiar place, Biglaw. “I was a corporate attorney at Davis Graham and Stubbs, and I loved helping clients,” he said. “But so much of the work I did was tedious, menial, and didn’t justify the billable hour. It wasn’t a good use of my time or theirs.”
That realization planted the seed for TermScout, a platform focused on reviewing, benchmarking, and certifying contracts. But it didn’t stop there. With the rise of GPT-4 and generative AI, Otto and his team launched a second platform, Screens, which lets legal teams build and share AI-powered contract playbooks. “It’s about letting lawyers craft AI to think like them,” Otto explained. “The goal is to turn knowledge into scalable, defensible legal products.”
The Problem With Instinctual Outsourcing
One of the most dangerous defaults in legal departments is choosing vendors and reviewing contracts based on familiarity. “There’s this belief that big firms are always the safest choice,” Otto noted. “But that’s no longer true for low to medium-risk work. There are better, faster, more specialized options and most legal teams are leaving value on the table by not exploring them.”
Instinctual outsourcing leads to expensive inefficiencies, bloated deal cycles, and contracts that reflect legacy habits instead of business goals. Otto pointed out that many legal teams are told by their CROs or CEOs, “Legal, stop getting in the way of sales. Your job is to support the business.”
That wake-up call can be uncomfortable. But it’s also an invitation to lead.
Codify Your Judgment Before You Scale It
When legal leaders move from instinct to intention, everything shifts. Otto shared a simple yet transformative approach his team uses with clients: the risk-complexity matrix.
“We literally create a matrix: high, medium, low risk on one axis, and high, medium, low complexity on the other,” he explained. “Then we map all the projects from the past year and look at what was spent where. That becomes a blueprint for smarter allocation.”
This kind of thinking allows in-house teams to match the right task to the right provider, and to define why a given firm or solution is being used. That defensibility matters. Especially when legal is being asked to justify spend in language the CFO understands.
Certify Trust, Not Just Risk
Beyond better triage, Otto believes legal teams can go further by turning contracts into business assets. That’s where TermScout’s certification layer comes in.
“More and more companies are waking up and saying: we don’t need to win on every clause,” Otto said. “We need a contract that closes deals. Certification helps legal prove that the terms are fair, reasonable, and aligned with market expectations.”
The platform offers badges like Certified Balanced or Certified Customer-Favorable, backed by public benchmarks and transparent methodology. “It works,” Otto said. “It shortens deal cycles, builds trust, and signals professionalism. And it’s easy to implement.”
The AI Trust Gap And Why Playbooks Matter
Despite all the promise of AI, many lawyers remain cautious. Otto called it a “trust gap,” and he doesn’t expect it to close overnight.
“AI doesn’t have context,” he said. “It doesn’t understand the 20-year relationship with your customer. It doesn’t know what matters to your GC. That’s why coupling AI with human expertise is the way forward.”
Screens, his second product, lets lawyers build AI playbooks that reflect their firm’s judgment. These playbooks can be used internally, shared across teams, or even offered as products. “It’s not about replacing lawyers,” Otto emphasized. “It’s about letting lawyers scale themselves safely.”
What In-House Legal Should Do Next
If you’re in-house and want to move from reactive to strategic, Otto offered a clear starting point: “Just start playing. Take the free trial. Build one playbook. Certify one contract. You don’t have to overhaul everything. You just have to begin.”
Small steps matter. “The tools are changing,” Otto said. “And when the tools change, so should the business model.”
This shift from instinctual outsourcing to intentional decision-making isn’t theoretical. It’s the future of legal. And it’s one in which clarity, certification, and product thinking will separate the blockers from the business builders.
Olga V. Mack is the CEO of TermScout, an AI-powered contract certification platform that accelerates revenue and eliminates friction by certifying contracts as fair, balanced, and market-ready. A serial CEO and legal tech executive, she previously led a company through a successful acquisition by LexisNexis. Olga is also a Fellow at CodeX, The Stanford Center for Legal Informatics, and the Generative AI Editor at law.MIT. She is a visionary executive reshaping how we law—how legal systems are built, experienced, and trusted. Olga teaches at Berkeley Law, lectures widely, and advises companies of all sizes, as well as boards and institutions. An award-winning general counsel turned builder, she also leads early-stage ventures including Virtual Gabby (Better Parenting Plan), Product Law Hub, ESI Flow, and Notes to My (Legal) Self, each rethinking the practice and business of law through technology, data, and human-centered design. She has authored The Rise of Product Lawyers, Legal Operations in the Age of AI and Data, Blockchain Value, and Get on Board, with Visual IQ for Lawyers (ABA) forthcoming. Olga is a 6x TEDx speaker and has been recognized as a Silicon Valley Woman of Influence and an ABA Woman in Legal Tech. Her work reimagines people’s relationship with law—making it more accessible, inclusive, data-driven, and aligned with how the world actually works. She is also the host of the Notes to My (Legal) Self podcast (streaming on Spotify, Apple Podcasts, and YouTube), and her insights regularly appear in Forbes, Bloomberg Law, Newsweek, VentureBeat, ACC Docket, and Above the Law. She earned her B.A. and J.D. from UC Berkeley. Follow her on LinkedIn and X @olgavmack.
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