A new chapter

I'll explain why I took this new role and how it fits into my journey and the changes coming to the legal industry

Hello friends! I know it’s been some time since I last wrote in this newsletter and it’s because I got a new job! I’m now the Chief Revenue Officer at Latitude Legal, a company that provides high end contract attorneys to law firms and legal departments. I wanted to take some time today to share with you what exactly I’ll be doing, what’ll happen to my social media content, and why I think we’re well-positioned for the changes coming to the industry.

What exactly will you be doing?

The ultimate goal will be to guide Latitude to its next phase of growth.¹ The company has grown organically over a decade by leveraging experienced lawyers (ex Biglaw partners and senior in-house counsel) to serve clients looking for contract attorneys. It’s very different from most legal startups that bring on junior sales reps from outside of the industry.

As Latitude’s new CRO, my goal will be to lean on our competitive advantages, and help us take things to the next level by: (1) driving awareness of our offerings via my personal brand and social media audience; (2) supporting sales and marketing by sharing best practices from the legal tech startups I’ve worked with; and (3) help advise on operational initiates to help prepare the company to scale.

I’ll be bringing in everything I’ve learned over the past 8 years working at legal tech startups

Each of my jobs involved specific go-to-market roles at very different company stages and what I learned will help me achieve the 3 goals I shared above. For example:

• I joined Logikcull when it was a seed stage company, and worked my way up the sales org chart, from BDR, to AE, to sales manager. I ran a ton of experimental initiatives designed to drive upsells and revenue expansion.

• Understanding the full sales life cycle helped me build the sales machine from scratch at my next job, at Evisort, where I served briefly as its head of sales. Once it was up and running the company brought in an experienced CRO to turbocharge growth.

• In both of jobs, I learned how important having a large sales pipeline was to closing deals. That insight led me to drive pipeline via social media through my personal brand. E.g. LinkedIn, Twitter, IG, Tik Tok

• All that led me to my most recent job at Ironclad where I could laser-focus on driving social media impressions—because that would drive broad top-of-funnel awareness would feed into Ironclad’s established go-to-market machine.

In my new role at Latitude though, I’m no longer a specialist. As an executive my job is to think about the entire go-to-market machine. But I can’t immediately diagnose and try to “fix” things. My first few weeks have been humbling because I realized that despite my experience, I still have so much to learn. So I’ve shifted to leaning on the veterans of the team, to learn from them and understand why things are the way they are.

It’s all been fantastic though. The people are just as good as I thought, and everyone’s been gracious and kind. They’ve welcomed me with open arms. I’m eager to prove myself and have an impact quickly, so have to keep reminding myself that the best way to move fast is by slowing things down at first.

What about social media?

When I announced the job change on LinkedIn, one of the most common questions I received was “will you still keep making Tik Toks and memes?” I’ll say what I said there which is yes, of course! Creating engaging social media content has helped me get me to where I am today, and I haven’t forgotten. I just have to be mindful of how my content fits into the bigger picture. Which raises a point I’ve been thinking about over the past few years.

It’s easy to lose sight of what you’re doing when you start seeing success on social media. For me, it was always about driving business results. Somewhere along the way though I realized that I was no longer optimizing for impact. Instead I was optimizing for views and engagement. Which is important, don’t me wrong. But when you focus exclusively on views, it’s very easy to convince yourself that you’re having an impact when you’re not.

A couple of years ago I decided that I was no longer interested in growing my audience

There were two main reasons for that. First, I realized that it would take significantly more effort to grow to the “next level.” I was already kind of burned out and didn’t want to keep running on the content treadmill. Second, I realized that the most efficient way to grow was to put out polarizing content. At first I got away with some of it because I used humor. But over time I began to feel like I was turning into a caricature. And I didn’t like it.

At that moment I decided to shift my focus. I began to filter myself more and be more deliberate about what I posted. As a result my audience growth slowed. But that was ok, because I felt like I was deepening my connection with my core audience. Before long I started to receive economic opportunities I never did before. That confirmed my belief that social media was a means to an end, and not an end in itself.

That’s my long winded way of saying that I’d like to be more thoughtful about how to use social media. It’s an important channel for driving growth to Latitude and definitely an unfair advantage I have as an industry executive. Most CROs are great at managing people and leading organizations but have minimal connection to the industries they serve. I have a much weaker executive resume than them, but through social media, have a powerful connection to the community.

So yes, expect to continue to see social media content from me! But perhaps slightly different, or at a slower pace.

Why flex talent instead of tech/AI?

There are many reasons why but it boils down to this: It’s not clear to me who’s going to be the big winner in legal AI. However, it *is* clear to me that AI will have a dramatic impact on the future of legal work and how legal teams are structured. Especially amidst the changes taking place in the industry, where the balance of power in the value chain is shifting to clients.

Specifically we are seeing the following play out right now:

• Corporate in house teams are under pressure. With more work than ever, they are still unable to hire large numbers of full time legal staff because they have to jump through all types of hoops;

• As in-house teams start leveraging more technology and AI, they’ll find that they can do more work with fewer people, but it will be unclear what specific types of people will be most successful in this new environment;

• Established Biglaw will find that their rainmaking partners are underpriced, while juniors are overpriced. These firms will over time become more top-heavy but will find themselves understaffed when demand spikes;

• Biglaw as a whole will try to gain competitive advantages by creating proprietary AI. However, they will need associates to help train these models, but there’s a massive opportunity cost in shifting associates from client work (at, say $800/hr) to internal projects;

• Regional Biglaw / Midlaw / Smalls will experience growth as they win business from large corporate clients. But they will struggle to recruit talent to staff these new matters, because they cannot afford to pay Cravath scale salaries; and

• Biglaw will try to fend off these smaller firms by creating their own captive ALSPs with “staff attorneys” who can be billed at a lower price point. But the captives will struggle to find the talent because that’s not their core competency.

All of these challenges provide an opportunity for a company like Latitude. Flex talent, or high-end contract attorneys, can help solve a lot of the challenges firms and corporate legal are facing today, and the challenges they’ll face tomorrow.

This is probably the biggest untold story out in the industry. We know gen AI will have a big impact, and that shifting demand & optimizing for PPEP will lead to hiring frenzies and mass layoffs. This is all playing out in the backdrop of the rise of the independent lawyer, which is itself driven by changing generational attitudes and remote work.

I am excited to be working at the frontier of the legal industry, this time on the people side instead of the technology side. I will continue to share stories and observations in this newsletter, so hopefully you will all get to hear about the changes as they are taking place.

Thanks for reading and following along!

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1. You can read more about why they hired me in this article from Legal Dive titled Latitude Legal hires Alex Su to help fuel growth.