Procurement Contracts pt2: Smells Like Legal Spirit

Your Legal Team Isn’t the Problem. Your Process Is.

In a Jam Session special, legal experts Alissa Harvey Dawson (ex-HubSpot, Gusto) and Ana Erickson (ex-IBM, McKesson) join the hosts, Natasha and Conrad, to tackle the friction between Legal and Procurement. Their diagnosis? The delays aren’t about difficult lawyers—it’s about a broken partnership and a reluctance to embrace transformative technology

The discussion reveals a clear path to stop the bottlenecks and build a true strategic alliance:

• Embrace AI—or get left behind. AI offers exponential advantages in efficiency. The person who knows how to use it will take your job, not AI itself.
• Fix the partnership before the process. Without early alignment on business goals and risk tolerance, any new process or technology is doomed to create friction.
• Move from reactive to predictive. Use AI and data to anticipate disruptions and prepare for them, rather than just responding after they occur.
• Trust, but verify the technology. AI is a powerful starting point, but human intervention is non-negotiable to check for bias, errors, and hallucinations.

If there’s one message from this episode, it’s this: technology is not a magic wand for a dysfunctional relationship.

By first repairing the partnership between Legal and Procurement and then strategically embracing AI, you can eliminate the friction and elevate both functions into invaluable strategic partners.

Watch now or read the transcript below.

Transcript: Proc-N-Roll | Procurement Contracts pt2: Smells Like Legal Spirit

Conrad: Welcome to Proc and Roll. Today, Natasha has invited two very special guests, Alyssa and Anna, who are legal pros. All of us in procurement know that legal and procurement work hand-in-hand, so we’re excited for this conversation.

Natasha: We’re honored to have Alyssa Harvey, former Chief Legal Officer at Gusto and HubSpot , and Anna Erickson, a former procurement professional from IBM and McKesson who is now a lawyer and founder of Erickson Law Group. Today we’ll discuss three themes: tech and AI in legal and procurement, building the relationship between these two functions, and risk management from a supplier resiliency perspective. Alyssa, let’s start with your perspective on technology in legal.

Alyssa: AI has completely accelerated the entire equation. It’s a foundational technology that is going to disrupt everything, and it is going to change the way we work. If you aren’t on board with that, you’re way far behind because you’re missing out on the advantages of efficiency and proficiency. People are concerned about the risk, but you have to work through that. Knowing there’s a concern and letting that stop you is a mistake when there’s something so obviously better for productivity.

Ana: I think legal is often the slowest to adopt technology. There’s a resistance, especially from older-school lawyers who are used to doing things their way. One of the biggest barriers is adoption, so you have to bring people along and educate them on why it makes their work better, cheaper, and faster.

Natasha: Anna, can you share some practical examples of using AI responsibly?

Ana: We always hear the buzzwords responsible AI, hallucination, and bias. There is a responsibility for us to fact-check and validate the output from any AI tool we’re using. AI can only take you so far; there’s a human intervention element that you cannot skip. The other aspect is data privacy; you must be careful not to put sensitive or personal information into a public AI instance. My practical advice is to use AI as a jumping-off point for summarizing contracts, comparing clauses, or drafting initial outlines, but always gut-check the output.

Conrad: I agree. I recently uploaded a partner agreement to an AI tool and asked it to identify risks. 30 seconds later, it had identified three or four real problematic areas in the agreement. This is just the beginning of the speed and automation we can achieve.

Alyssa: Exactly. An AI tool can do what an entry-level attorney or contract manager would do, and you can get an answer in minutes instead of waiting five to seven business days. You can’t say that that’s not valuable.

Natasha: Let’s shift to the relationship. Anna, having been on both sides, what are the key components of a productive relationship between procurement and legal?

Ana: The biggest challenge is a lack of legal and business alignment. Oftentimes, the CPO and the General Counsel are not aligned on the company’s strategy or risk tolerance. This leads to the perception that legal is the bottleneck when they’ve had a contract for weeks. You have to establish clear rules of engagement on when to bring legal in and what information they need from you upfront.

Alyssa: Anna’s right—the key is early alignment. My best collaborations worked because we were aligned on the business goals from the beginning and marching in the same direction. Bringing in necessary parties late in the game literally only slows it down. And that alignment has to start at the top; there has to be a high-level principle from leadership that then flows down to the teams.

Natasha: Let’s bring it home with resiliency. When you think about supplier resilience, what are the key things to consider?

Ana: The first step is to identify your most critical suppliers—the ones whose services would absolutely cripple your operations if they were interrupted. For those suppliers, you need a resiliency review of your contracts, looking at the disaster recovery and force majeure language to understand what triggers an event. And you should be testing that plan with your suppliers during QBRs.

Alyssa: I love what Ana said because you’re moving from reactive to proactive. When you layer on AI, you can move to being predictive. You can use data and insights to anticipate and prepare for disruptions before they even happen, rather than just responding to them.

Conrad: This has been an awesome conversation. The key takeaways are that AI is coming, so be the manager of AI, not the one being replaced. Underneath the technology, the relationship really matters, so take responsibility for creating alignment. And finally, resilience must be proactive, not reactive.

This transcript has been edited for clarity while maintaining all substantive content