How to create repeatable sales for your legal startup

And why you shouldn't blame all of your problems on lazy sales reps

Alex Su

Jul 18, 2023

One of my goals with this newsletter is to document everything I’ve learned about sales and marketing from my experience with legal tech startups. Today I’ll be writing about repeatable sales, and will be sharing an overview of a few thoughts I have about how to scale revenue.

This article is meant for founders & CEOs who are struggling to grow revenue for their legal startups. My goal is to help you diagnose your existing challenges, and provide a framework for creating a repeatable sales process.

Part 1: Why are my sales reps so lazy?

When you’re struggling to grow revenue, you might think it’s because your sales reps are lazy. Maybe it’s because they aren’t calling, emailing, or doing other activities to generate revenue. Truth is, it’s not (just) laziness—it’s that they’re often skeptical about your ideas. This is especially true when you’re selling to the legal vertical, and you (or your executives) don’t have substantial experience in this market.

Experienced sales reps generally have a strong understanding of how buyers actually buy. It’s hard to motivate them to engage in activities like cold calls or emails if they don’t think it works. Sales rep compensation plans are heavily dependent on performance, so the reps are dismissive of any tasks that don’t provide a proven path to commissions. If the reps don’t like your idea, they will ignore you, or even worse, fabricate data and feed your managers the narrative that traditional sales tactics “just don’t work on lawyers.”
Don’t expect your relationship sellers to engage in outbound. If you have sellers who rely heavily on their network or domain expertise to pitch buyers, it’s likely that they’ll never enjoy cold calling and emailing—even if you can prove that it does work. Relationship sellers are used to spending their time generating referrals and reaching out to warm contacts, and are likely a self selected group that prefers that approach to sales. If you’ve hired former partners from law firms to sell your product/service, you know exactly what I’m talking about.
Most sales managers won’t know how to solve your problems. The challenge with many gray haired managers & executives from other industries is that they don’t know how to diagnose the root cause(s) of your sales challenges. Especially if they’ve never worked at an unproven startup with zero brand, and have no experience in your niche legal market. So what ends up happening? These managers blame other factors (e.g. lazy sales reps, bad marketing, etc.) and launch internal training programs that have minimal impact. This all gets very expensive, very quickly.
You may be blaming sales for a marketing problem. Usually early stage companies hire sales teams before marketing teams. It’s easier to justify the financial investment, especially if you can attribute revenue directly to the sales hire. The problem is, reps are only involved in the laters stages of the buying process. They’re not suited to generate “top of funnel” activity. Sales reps are like spears—useful for hunting, but not particularly helpful if you’re trying to “catch” fish. (Spoiler alert: You need nets, not spears.) No matter how many cold emails and calls your reps make, they will never do it as well as marketers.

Part 2: Are you hunting or fishing?

Your sales process must be aligned with how buyers buy. For example, if you’re in a niche where lawyers use a particular product/service once in a blue moon—cold outbound probably won’t work. It’s likely they’ll keep throwing “bad timing” objections to your sales reps. You could have the perfect rep do everything perfectly and still end up with zero revenue. In these situations you need to focus your resources on marketing, not sales.

Is the buyer’s need on-going or one-off? Answering this question is key to understanding what approach you need to take. It also requires a nuanced understanding of your offering and legal niche. For example, if you’re selling e-discovery services—is that on-going or one-off? Well, if your product is used for early case assessment by in house teams, it’s probably on-going. On the other hand, if you’re a services vendor that helps with massive document intensive cases, it’s more one off. In tech, many execs come from vendors that sell to large organizations with on-going IT needs (e.g. recurring revenue SaaS) so their sales-driven tactics won’t work in the “one-off” world.
If you’re “hunting” you should rely primarily on your sales team. If the buyer’s needs are on-going (like in most enterprise software) then you’ll likely avoid “bad timing” objections. Complex buying processes are also well suited to having a sales rep lead the charge. In these situations, assuming that you have decent sales playbooks—you’re likely to see positive results from sales-led outbound efforts.
If you’re “fishing” you should rely primarily on marketing. This is especially true if your buyer is only in the market for a “one off” purchase, but when they are, they act quickly and engage in large dollar value transactions. In these situations, use marketing, because that will help you avoid wasting resources on pitching to this audience before they’re ready to buy. Use “nets,” like marketing content & e-mail nurture cadences. Social media can be unusually effective here as well. Once the buyer’s ready, they’ll be aware of your offering and reach out to you directly. It all leads to fast sales cycles and minimal sales rep time/energy.
Map out your buyer’s journey. You need to have an understanding of how buyers engage with vendors for your offering. How do they learn about what’s out there? Do buyers congregate at certain times and places, like specific conferences or trade organizations? At what point do they start evaluating options, and lining up budget to buy? This exercise is super important and honestly doesn’t take much time or energy to develop. But it’s critical to understanding the initial point of contact with a potential buyer.

Part 3: Turn the non-repeatable into something repeatable

In the early days of a company, all sales are non-repeatable. Maybe early deals were depended on the founder/CEO’s network. Or maybe the sale happened after a series of weird events that you can’t seem to replicate. Back then none of this mattered—all you needed to do was generate sales to get revenue through the door. Now that you’re focused on operationalizing your company, you need to make things repeatable. To do that, you must rely on anecdotes to develop hunches, then aggressively experiment & iterate.

Everything starts with non-repeatable sales. In the early days all sales are non-repeatable. Maybe a key customer found you randomly, or maybe the early sales were done through a unique / chance relationship you had with a buyer. The good news is, you probably have a bunch of one off anecdotes about where sales came from. Collect these stories and try to identify patterns. Don’t worry about sample size—just try to think through what might have happened, and how it might have worked.
Use anecdotes to develop hunches. Let’s say your earliest, biggest customer found you after hearing you on a well known legal tech podcast. This actually happened at one of my old startups, by the way. This might support a hypothesis that doing guest appearances on popular third party podcasts can lead to inbound sales. So moving forward you should try to get in front of many similar podcasts. Don’t worry about tracking or attributing. Very often the most promising channels are hard to track. Just focus on trying to get a second “win” so you can validate your hypothesis and start identifying patterns.
Once you notice a pattern, double down on it. Once you get a few “wins” you’ve successfully identified a pattern. Find ways to start investing resources & delegating some of this work. For example, if the pattern you identified is that key early adopter buyers find vendors at a specific conference, you should 100% attend that conference the next time. You can also start sending your execs to attend all similar conferences. Try to get more wins—not necessarily closed deals, but signs that you’re getting into the right conversations.
Iterate fast. I’m a fan of running multiple experiments at once. Most of your hunches won’t lead to much. But some will. Certain experiments will immediately lead to a feeling of being “pulled” by the market. For me, that was LinkedIn. A few of my posts in 2017 led to inbound leads from law firm lawyers, so I started to focus more on that, as opposed to my other less productive experiments. Iterating fast (doubling down on winners and discarding losers) helps you avoid banging your head on a brick wall and wasting precious resources on an approach that doesn’t work.

Part 4: Begin operationalizing your process

Once you’ve done some iterating you’re going to have a feel for what metrics or KPIs are leading indicators of success. One common one I’ve seen over the years is having a “first conversation” with a potential buyer. Incentivize your team to max out these “experimental KPIs,” and observe what happens downstream. Once you have a solid grasp of what works, try to turn everything into a formula—a playbook you can train a lower cost resources to replicate the same success.

Come up with leading indicators and turn them into experimental KPIs. If you’ve already mapped out the buyer’s journey, you have a sense of what type of activities lead to revenue down the road. For example, maybe the buyer’s first conversation with someone at your organization is the first step in the journey. Use “first convo” as an experimental KPI and try to measure it for your sales reps and marketing campaigns. You might find interesting patterns you didn’t expect.
Start with KPIs within your team’s control, and observe early results. A sales rep can engage in activities on their own accord (cold outreach, networking, etc.) to maximize KPIs. They can’t blame “lack of need” among buyers. It’s usually pretty motivating, especially if you incentivize them to optimize for these KPIs (more on that in the next section). You should also observe early results to see if they are leading to more promising sales conversations downstream.
Reward your people generously for hitting your new experimental KPIs. Since there are so many unknowns, you want to create certainty for your reps—ie. financial incentives—to get them to hit these numbers. A small cash bonus can be very effective. For example, a $50 payment for each “first convo” completed can help you get the data you need quickly and inexpensively. You might not be able to offer this incentive forever without negatively impacting your acquisitions costs. But for the time being, it’s exactly what you need.
Once you’ve determined that your experimental KPIs are actually strong leading indicators of revenue, try to reduce costs. Once you’ve figured a few things out, try to replicate these KPIs with lower cost resources or more junior people. Remove those small bonus incentives, and make hitting the KPI part of the job. For example, when I built out a cold calling operation targeting corporate legal departments, I figured out that 100 cold calls to in-house lawyers would inevitably lead to 1 scheduled meeting. I then created playbooks and hired junior sales reps in an attempt to replicate my success.

Part 5: Own your distribution

Your biggest go to market asset is a database of contacts. This is why customer relationship management (CRM) software, like Salesforce, has grown so much over the years. Keeping track of contact information (like email addresses and phone numbers), along with job title info, means that you can repeatably reach this audience forever. So you’ll want to create a “demand generation” program that adds more and more of these contacts to your CRM. Over time this will make everything more repeatable and operationalized.
Create gated marketing content to drive signups. Make sure the content is compelling to your target audience. The medium, e.g. webinar, e-book, whitepaper, etc. is less important than the substantive content. If it’s compelling, the buyers will show up. The goal shouldn’t be to attract buyers who are ready to buy necessarily—just get a large number of people who fit your ideal customer profile to give you their contact info. You can promote your content via social media, paid ads, cold emails, etc.
Make sure the content is irresistible. Most content is terrible and is designed to help companies generate revenue quickly. E.g. “Here’s a new buyer’s guide for software! Sign up for our ebook today.” Problem is, that type of content doesn’t get people excited or interested in consuming it. So no one signs up. But believe me—if your content is indeed compelling to your target audience, they will put in the legwork to promote it to their peers. This is why making irresistible content is so important. Advanced tip: You can make irresistible, un-gated content (like podcasts) and drive them to sign up for your gated content.
Use your contact list to create synergies between sales and marketing. You can have sales reps reach out to cold prospects by sharing content with them directly, which helps you build your contact database. Once that database grows, marketing can create webinar programs that repeatably deliver hundreds attendees—-which creates warm leads that sales reps can follow up with. If this works well and you have the resources, you can even run paid campaigns to promote your webinars, content, or just drive signups to your list.

Conclusion

Let me know (in the comments or replies) what you think about this article! I’m also working on a deep dive on how to create “irresistible marketing content” when you’re targeting lawyers. Exclusively for paid members of Off The Record—after all, I can’t give all of my secrets away for free. Subscribe/join to get the article in your inbox when it comes out.

My credentials: I’m a former lawyer who’s spent the past 7 years at three legal startups that all figured out scalable, repeatable sales processes. My ideas are also informed by my experience as an angel investor and advisor to companies that sell products and services to lawyers.