How My Entry Level Sales Job Helped Me Find A Huge Opportunity Years Later

My early struggles as a legal tech SDR forced me to identify first principles that eventually guided me to Ironclad

When I first joined Logikcull as an entry level sales rep in 2016, I had no idea what it would all lead to. I’d just left the practice of law for a small job at a small company, in an industry that was largely viewed by most lawyers as kind of a backwater. But the “smallness” of my role gave me the opportunity to develop some foundational insights about sales that guided me to an incredible opportunity years later.

Today I’ll share the story of how I developed those insights, and the role they played in helping me make the pivotal decision to leave sales for a community role at Ironclad.

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In late summer 2016, about a week before I started my sales job at Logikcull, I got a call from Connor,

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my future manager. “We’re super excited to have you join, but I wanted to share some news. Our VP of Sales just left the company.”

Author’s Note: If you want more context about how I landed that job, check out How I Found My First Legal Tech Job

I told Connor it was fine—I mean, what else could I say? But after we got off the phone I couldn’t stop thinking about it. Our VP of Sales just left the company. Should I be worried? I was new to the legal tech startup space and had no idea how things worked. Was it normal to change VPs of Sales often? Or did he know something that the rest of us didn’t?

I guess I’d be lying if I wasn’t a little concerned. A big reason why I took the Logikcull job over a much higher paying alternative, was so that I could learn. I knew Connor had no experience in the legal industry and just a few years of sales experience in the technology space. I was also aware that he got his job because of a personal relationship with that VP of Sales. In that situation, would I still be able to develop as a salesperson? Or was I completely screwed?

I guess I’d find out.

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Before moving on, I’d like to share some context about why I was so interested in sales in the first place. I mean, yes it was partly because I liked working with people and had a hunch I could be good at it. But a big part of it was because I thought it would be more of a meritocracy than working at a law firm. Because it’s gotta be pretty obvious if you’re good or not, right? Sales results are pretty binary. Either you made the sale or you didn’t.

That was important because I was terrible at corporate politics. I struggled at previous jobs working at larger orgs. It’s wasn’t enough to be smart and hard working. You also have to have the right mentors and sponsors, who will give you the best opportunities to do valuable work. That gets you the visibility you need to develop the reputation to move up.

Me, I just wanted to figure stuff out and do things. I really wasn’t interested in spending time in meetings impressing people who were often disconnected from reality. That was part of the thinking when I decided to take the startup sales route. I sensed that it might be chaotic and messy. Which was fine. As long as it insulated me from politics.

The fact that my manager got his job through a connection though, gave me pause. What if sales wasn’t a meritocracy? What if none of these people were good at their jobs and I just signed up for a low paying, highly political job where I’d end up learning absolutely nothing?

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My first assignment didn’t help assuage my concerns. “Here’s a list of 25 small law firms in San Francisco you should call,” said Connor. I did some quick research of the first few firms and immediately saw a problem. Logikcull provided e-discovery software, which would be used by litigators. The list of firms, however, included lots of different types of practices, like family law and immigration.

When I raised this problem to Connor, he dismissed my concerns. “They might not do litigation, but couldn’t this software be used to help with other types of documents?” It was a rhetorical question, and he was very busy, so I didn’t argue.

“Just call them,” he continued. “Besides, it’ll be good practice to get some reps in, so you can get used to cold calling.”

I tried hard to have a good attitude and really wanted to be a good soldier. So I decided to follow my marching orders. These prospects were just strangers right? It wouldn’t matter if they’d reject me. I could just move on to the next person. Which is exactly what ended up happening.

Every single person I spoke to rejected me.

Well, all except one. There was this associate from a small immigration firm. She wasn’t interested in buying though. She kept me on the line because she was curious about why I called her in the first place. “I don’t think it’s a good idea to call law firms like mine,” she said. “Would you like me to explain the difference between immigration law and litigation, and why we don’t need e-discovery?”

I really didn’t know what to say to that. Her response was devastating in its kindness. She wasn’t trying to be mean. She assumed I was too young and inexperienced to possibly know anything about e-discovery. I wondered what she might think if she knew she was talking to a lawyer with litigation experience at one of the world’s most prestigious law firms.

That call had a pretty big effect on me. It was humiliating. It dawned upon me that I needed to immediately stop following marching orders. Because she was right, it made absolute zero sense to call her. I wondered if our spray-and-pray sales plan was connected to not having a VP of Sales. We were missing a coherent strategy on how to approach sales, and the SDR’s day-to-day was being dictated by someone who knew nothing about the legal industry.

So yeah, I decided to start ignoring my marching orders. But then that left me in another predicament. Because if I don’t do what my manager says, what should I do instead? Who should I take direction from?

Maybe I should ask the Account Executives.

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It didn’t take long for me to realize that none of the AEs knew what they were talking about when it came to outbound sales. It wasn’t surprising, I guess. Account Executives are usually experienced sales reps who haven’t done cold calls in years. It was obvious once you asked them for advice. Because they’d repeat platitudes like “you gotta keep grinding” and “focus on calling the right people” without being able to articulate how exactly it could be applied to my situation.

I felt completely lost. With absolutely no help, I decided to do something I’d never done before.

I’d start from scratch.

Part of my decision came from the realization that no one in the company had any insightful advice for me. Even stories from the early employees weren’t really helpful, because they were so anecdotal. After speaking with dozens of colleagues, I boiled the problem down this: Everyone had formulas but no one had a framework for understanding sales.

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Instead they were all repeating truisms from an outdated playbook called “Predictable Revenue.”

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Years ago, Salesforce pioneered the “Predictable Revenue” model. Before Salesforce, the dominant form of sales was to make your sales reps responsible for “the full cycle” which meant they had to find their own leads and close them. Salesforce’s genius was splitting up those two core tasks—prospecting & closing—and creating separate teams to specialize in each one. They were able to dramatically increase sales productivity, which helped them become a massive publicly-traded success story.

In 2011, a former Salesforce director of sales named Aaron Ross published a book called Predictable Revenue: Turn Your Business Into a Sales Machine with the $100 Million Best Practices of Salesforce.com. The book described the entire playbook on how to specialize your sales team. It involved splitting your team into (A) young, inexperienced prospectors—SDRs; and (B) and experienced closers—Account Executives. Startup founders who read Ross’ book and followed that playbook seemed to all do well. So the book became a sensation in the tech startup community.

By 2016, everyone in the tech space was following that same exact playbook. I mean, why not? It worked. There was no need to innovate. Which oddly enough, made the playbook far less effective. New problems emerged. Because even though specializing your sales team enabled you to make a ton more calls, who exactly do you call? And how do you incentivize SDRs to target the right prospects vs. setting appointments with just anyone?

And more importantly, how do you think potential buyers will respond if they’ve been bombarded by a million calls from a million different SDRs?

By the time I started at Logikcull, these were the real problems in sales. But no one at the company had any answers. They all (rightfully) believed that the VP of Sales, whoever it was, was responsible for figuring that out. And in his absence, the job fell to Connor.

Connor was in a really tough spot. On top of his normal job of dealing with us SDRs—doing 1-1s, running meetings, funneling leads to the team—Connor was also responsible for demonstrating the SDR function’s value to the rest of the exec team. Having an outbound sales team gets expensive really fast, because it’s so headcount driven and results don’t appear for a long time. So you need to show momentum to earn more time to show results.

How do you show momentum? By producing activity numbers, like calls made and emails sent. The higher the activity, the better we all looked, which meant we could keep our jobs.

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That’s why all of our marching orders were disconnected with sales outcomes. It didn’t matter whether we were calling the right people. We just needed to make calls.

It wasn’t long before I realized that no one actually knew what the SDRs should be focused on.

That’s when I decided to figure it out myself.

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At Logikcull, I quickly realized that I was in a very unique position because of two strengths I brought to the table. First, I knew how to evaluate prospects qualitatively, because I was a former litigator who used e-discovery. Second, I was also comfortable with making cold calls. Which meant I was well positioned to leverage trial and error to figure out what SDRs should be working on.

To do that, I understood that I needed the conviction describe what we SHOULDN’T DO. What didn’t work. Charlie Munger once said, when you’re trying to figure out a thorny problem: Invert, always invert. Find out what doesn’t work because avoiding stupidity is easier than seeking brilliance. That meant I needed to make a ton of calls and find out firsthand what was failing.

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Which meant I needed a way to generate big lead lists so I had people to call. It was a super time consuming task. I needed to find a way to get access to pre-built lists. That’s where our Director of Marketing became super helpful. I learned that he wanted the SDRs call the leads his team was generating, but had to stay in his own departmental lane, because he wasn’t the sales manager. (Politics or standard operating procedure? I’ll let you decide.)

No matter. The Director of Marketing and I built up a strong working relationship (and became fast friends) and it wasn’t long before he started surreptitiously passing me leads that needed working.

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I made a lot of calls during my first six months at Logikcull. Every week I’d be at the top of the call activity leaderboard, and routinely doubled the team’s average number of calls. Part of it was pure competitive nature, but part of it was also because I knew I needed to gather anecdotes about what worked and what didn’t.

I needed evidence.

It wasn’t easy. The actual cold calling and logging responses wasn’t the hard part. The psychological stuff was much harder. I don’t know how to fully articulate it, but I mean, it was mentally challenging to do my job. Like, my friends would ask me what I did at this cool new tech job I’d left the law for, and I’d have to explain that I was just making hundreds of cold calls every week.

“Your company is dumb,” they’d say. “Why don’t they have you doing more valuable work? You’re telling me the best way they know how to use a former federal clerk and ex-Sullivan & Cromwell lawyer who has such a valuable network—is to have him make cold calls??”

Part of me agreed. What the hell was I doing, anyway? Putting in so much work on the lowest value tasks in the entire company? I was one of the lowest paid employees at the company. Why shouldn’t I just clock in and clock out?

But at the same time, I was curious. I wanted to figure this out. Because at the end of the day, my job meant more to me than the money. I desperately needed a career win. Figuring out a thorny problem could be that win. I knew there was no way they’d promote me immediately, anyways. Which I guess I could complain and be bitter about. Alternatively, I could just get to work solving problems.

Which is what I decided to do.

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Over the next few months, I did some of the most rewarding work in my entire life. Because of my laser-like focus, I was able to hit my cold call activity quotas very early on in the day, every single day—almost always before lunch—and spend my afternoons trying to figure out what was happening and deriving first principles from all that activity.

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I learned a ton. And I started to develop a framework for understanding how to approach top-of-funnel sales. I mean, in retrospect, everything was kind of obvious. I gained no brilliant insights. But what I took away from that experience was conviction. After making thousands of cold calls to law firms and corporate legal departments myself, I felt confident about the patterns and principles I’d gleaned. Which was super helpful in understanding how I should prioritize my job duties.

Here are examples of some of the general principles I derived.

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1. Attention must be earned every step of the way. There’s no silver bullet. No magic sales pitch. Just a bunch of little ones. Like, the moment someone gets a cold call they are thinking of every possible way to push you off the phone. This is especially true of lawyers who have little time and are immediately skeptical of whatever you say. So everything you say in response has to earn you a little bit more time from the prospect. The goal should be to convince them to ask you to elaborate more, because that means you’ve successfully earned the right to a response. Too many ineffective salespeople try to dump a bunch of words on a prospect and hope that it’ll convince them.

2. Adapt your pitch to what your prospect wants. One of the biggest mistakes most people make when cold calling is that they focus on the pitch up front. They spend too much time saying what they want to say, not what the other person wants to hear. Maybe they lead off with the strengths of their offering. But that first call should never be about your pitch. It should be about learning what your prospect wants, and generating enough interest that they’ll be interested in more. Yet so much of sales training and coaching involves discussing how and what you should say.

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3. Once you figure things out, you can scale your sales—but only if you keep the persona the same. Every audience is different. If you take a successful pitch for, say engineers and try to use it on marketers, for example, you’ll find that it won’t resonate quite as much. And yet so many outbound sales teams use the same (or similar) value propositions across the board no matter who they’re talking to. Perhaps it’s because the company is trying to target new personas, in order to expand their market. Usually there’s not enough time to create an entirely sales/marketing approach. So it never works. And when it doesn’t, it’s blamed on inexperienced sales reps or lack of training.

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4. Even the most effective pitches have an extremely high failure rate. Just because you get rejected a lot doesn’t mean what you’re doing isn’t working.

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Instead, you’ve got to look at relative success rates. Maybe your pitch works 1.5% of the time vs. 1% for conventional pitches. That’s a HUGE difference! Much of sales is a game of inches. When you combine incrementally higher conversion rates at each micro-step of the sales process, you can see some pretty dramatic results on the back end.

5. A personal connection is incredibly powerful. One of the biggest challenges I faced was the no-show. The better I got at talking people into agreeing to an appointment, the more often they no-showed.

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It got to be a real problem, but I solved it kind of by accident. One day I started directly connecting with people on LinkedIn right after they agreed to an appointment. I found that doing just that (with no other conversations or follow ups) increased my appointment attendance rates. Significantly.

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None of these principles are ground-breaking or novel. Maybe you’ve heard of some of them before. The reason why I’ve highlighted them above though, is because of how powerful they are, and how they interact with one another. They override plenty of bad advice repeated by sales and marketing leaders. And they’ve helped me either support or avoid specific tactical sales decisions, even after I moved on from Logikcull.

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For example, I’ve come to realize that in the early days of a startup, you should never craft your pitch in a vacuum. Instead, you should come up with several different pitches and rapidly test them across multiple personas. See which ones get rejected. Which ones earn you an appointment. Try to understand why different personas resonate with the same pitch differently. It goes without saying, but do not, under any circumstances, rely on some pitch invented by a sales pro in a conference room on a whiteboard. It won’t work.

But the most important takeaway for me was that these principles could be applied beyond sales. My success on social media today is due in part to my application of this framework to a completely different context.

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I mention why I focused on LinkedIn in footnote 12, but one of my early key decisions was to stay focused on lawyers, instead of trying to expand my follower base as quickly as possible.

Author’s Note: If you want to learn more about how I developed the skills to be successful at social media, check out How My Failed Solo Practice Set Me Up For Success Years Later.

That would let me provide the same “value” proposition to my audience, which would snowball follower counts later down the road. For content, I designed my posts to “hook” users right at the outset, and avoided calls to action until the very end (or in the comments) because of the importance of earning the right to their attention every step of the way.

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However, the most surprising application of these principles wasn’t social media. It was something else entirely.

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About a year ago, I was approached by Ironclad’s CEO, Jason Boehmig, to help build up a new function called Community.

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The timing could not have been more perfect. I’d been thinking about how the pandemic created a unique opportunity for innovate the old methods of tech sales & marketing. Lockdowns and social distancing meant people had very few ways to connect with one another.

There was a void that needed to be filled.

That’s what I’d been doing since the beginning of the pandemic in March 2020. By then, I’d grown my LinkedIn audience to about 10,000 followers. When the lockdowns first came, I decided, on a whim, to host a regular Zoom meetup to discuss law and legal tech. I invited speakers from my LinkedIn community and created a space for people network and connect with one another.

There was some part of me I think, that was trying to solve for the challenges I faced in those early days of sales. To be clear, I enjoyed meeting & talking to people at the meetups generally. It wasn’t purely sales-driven. But at the same time, I invested a lot of time and energy into it because I saw the commercial application. It did wonders for my personal brand and led to inbound inquiries for sales—for me, and for other sales reps at my company.

By the end of 2020, I was extremely proud of the little community I had built, and began to wonder what could be possible if more resources were invested into it. So when I was approached to help build this new community function, it was very interesting, and very exciting to me. I decided to quit my sales job and join Ironclad as the Head of Community Development under the legendary Mary O’Carroll, their new Chief Community Officer.

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This part of my story is still playing out. I’m about nine months in, and there are lots of things that I either haven’t figured out, or can’t talk about. But what’s become abundantly clear to me is this. The old way of selling is never going to be as effective as it once was. The legal tech space has been flooded with money, and even relatively small startups are recruiting seasoned sales teams to go after the market. Predictable Revenue alone won’t get you to where you need to go.

When you look at community, it incorporates so many of the principles above. You earn attention each step of the way, because instead of immediately converting a prospect into a customer, you’re creating space to build trust in your corporate brand before any transaction takes place. By engaging in a broader conversation online, you’re learning what your market wants—without annoying them with calls and emails. And you can really scale your go-to-market efforts—not by paying for expensive headcount or ads—but by moderating peer-to-peer conversations.

Creating a community function isn’t something just any company can do though. You need to have trust among the broader community. You need goodwill. Which means if you’ve relied in the past on aggressive sales and over-promising customers on features that aren’t really there—you’re probably not going to be able to successfully stand up a community function. People will just join to talk shit about you.

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That’s why when I had the chance to join Ironclad’s community team, I jumped at the opportunity. My friends (who happened to be customers) raved about their product experience. The goodwill was there. And then I saw how community could be an incredibly powerful asset for Ironclad that would become even more valuable over time. By harnessing energy from their community members and customers to “sell” on their behalf, Ironclad could bypass so many of the problems created by the Predictable Revenue playbook.

I knew how valuable that was firsthand. If you can execute on Community successfully, it’s an incredible moat for the business.

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So when you bring my story all the way back to those first few weeks as a SDR—everything I did was valuable. The dots really did connect. The chaos and confusion of those early days, with me having no idea what I was doing at my job forced me to put matters into my own hands. And in doing so, made me develop a framework for sales and understand what the hell was going on. And years later, it let me quickly see when something magical was happening right before my eyes.

To be sure, it’s far from the end of the game. And we’ve still got a long way to go at Ironclad. But I’m thankful for those challenging early days and feel extremely privileged to be in the situation I’m in.

I’m very excited about the future.

I hope you enjoyed reading this as much as I enjoyed writing it. Feel free to forward this article to anyone who might enjoy it! Comments and thoughts are welcome, as always. Thanks for reading!

1. Name has been changed to protect his identity. Connor is an earnest, hardworking guy who was in the wrong job at the wrong time. After leaving Logikcull, things really took off for him and today he has a very successful career. We still keep in touch.

2. In fairness to the company, they did try to bring in a more theoretical framework from a sales consultant. However, after reading the materials, I thought they were pretty worthless because it didn’t discuss principles—it focused on tactics, some of which would never work in the legal industry.

3. If you want to dive deeper as to why many sales teams tend to focus on activity metrics, it’s because it’s something you have a lot of control over. Sales managers can ask SDRs to make more calls. It’s much, much harder to focus on improving the quality of your appointments. Because that requires time/energy to pore over historic call data, to understand which types of appointments lead to sales, and adjust your strategy accordingly. You need a lot of runway which is a luxury many early stage startups can’t afford.

4. This was especially true because I couldn’t just say “hey we should stop making so many calls.” Lots of SDRs say this. Usually because they don’t like making cold calls. So I needed to put up volume to also show that I was capable of making a ton of calls. So I could have the credibility when I described what wasn’t working.

5. By the way—we are still friends and text each other from time to time. He’s now the VP of Marketing at Logikcull and is a subscriber to Off The Record. Hi Robbie!

6. My wife was working very early hours at the time, so I’d commute with her to the city at 5AM. I’d go to the gym, get some breakfast, and go into the office between 630AM-700AM and just crank out calls. By the time the other SDRs showed up, usually at 9AM, I’d already put in 30-40 calls and was more than halfway done with the day’s work.

7. Although I only describe the fundamental principles, there were also second-level conclusions I drew (that relied on those principles) that were incredibly important to my career development. I won’t get into them here but a few examples include: (1) It’s incredibly hard to sell to large law firms because of their decentralized nature; (2) If you want to sell subscriptions, target corporate legal vs. law firms; (3) Respect the customer journey; leads who download your whitepaper aren’t ready to buy. There’s a lot more but these are just a few.

8. For example, let’s say you’re trying to sell bottled water. Your prospect says they’re not thirsty but they’re going to the beach later. In that situation, you should not talk about how refreshing your water is, or how natural it is, etc. You should instead focus on how convenient and accessible bottled water is for later, in case they (or their friends) get thirsty at the beach. The conversation should focus on hot beaches, dehydration, and how hard it is to find bottled water when you’re out having fun.

9. “Lack of training” is often described as a problem for early stage startups. I’m pretty skeptical of this explanation generally. Because while it may be true some of the time, there’s a huge conflict of interest. A savvy sales leader will always use “lack of training” as an excuse because the solution will get them more resources. Like more managers under them, experienced lateral hires (who happen to be in their network), etc. Prospective VP of Sales will always tell founders that their sales reps lack training, because the solution is to hire them (of course) so they can uplevel the team.

10. Relatedly, I always find it funny when experienced sales reps try to coach SDRs on how to pitch on cold calls without realizing that 95%+ of the job involves coming up with lists and waiting for someone to pick up. Very, very little of the job involves actual pitching.

11. I have a theory on why this happens. You can convince people on a call, through sheer determination and charisma, to verbally agree to an appointment. But when they go back to their busy schedules, they realize they have no time so they just skip the meeting. Email follow ups and reminders don’t help because they only solve for “forgetting” and not the real problem.

12. This fifth principle is what led me to double down on posting LinkedIn content. I knew there was something happening on that platform, even if very few lawyers were posting content. I followed a hunch, which served as the foundation for my success there today.

13. I never ended up applying these principles at Logikcull because after six months of being a SDR, I was promoted to Account Executive. By then we’d also found a new VP of Sales, and a new Director of Sales Development. I turned my attention to solving other types of problems which, while related, are beyond the scope of this article. I might write about them someday.

14. By the end of 2021, I’d amassed 150k followers across LinkedIn, Tik Tok, Twitter, and Instagram, and generated 56 million views during the calendar year.

15. This has led to higher dwell times (helpful for LinkedIn) and higher video view completion time (helpful for Tik Tok).

16. Ironclad has been focused on community for many years, but didn’t create an entirely separate function for it until 2021.

17. There’s a nuance here I’m brushing over. You don’t want to have a community of people who trash your company. But any community will include people who complain. It’s just the nature of the beast. Complaints to help improve the product experience vs. complaints about the company overpromising features are very, very different.