🧥 Don't Kid Yourself
VC is just Sales in Disguise
Welcome to Startup ROI! I’m Kyle O'Brien, an early stage deep tech investor — alongside Rand Hindi — and community builder based in Paris, France. I write what I see. These days, it’s mostly explorations into various categories of interest including:
The Future of Computing
Blockchain Infrastructure (Privacy & Encryption)
Frontier Health
I enjoy taking complex topics and reducing them into accessible articles and top-notch memes. I also throw bangin’ dinner parties for cool people in tech and venture — sign up here and never miss a meal again.
A little over a decade ago, when I was coming out of college, the “high status” path was in banking or consulting. I don’t think this has changed much (although public perception likely has). Moving to San Francisco and joining (or founding) a tech company was entering the picture, albeit it was viewed as a much riskier proposition. I knew exactly zero peers, however, that strived to become a venture capitalist upon graduation.
Maybe I was hanging out with the wrong crowd, but my intuition tells me there’s a different answer. The internet likes to refer to those earlier days as venture capital’s “cottage industry era” — arguably a misnomer, but compared to the current moment, a fairly accurate depiction. At the time, there weren’t that many funds to choose from and the university pipeline — well established in other sectors — had not yet been formed. A myriad of factors have contributed to the tech boom and as a result, what is effectively a niche sub-category of private equity has become a desirable landing pad for recent graduates.
But like many entry level roles, the job can be less glamorous than it appears from the outside.
These days there are programs, boot camps and incubators to help aspiring graduates or startup operators looking to pivot to the world of venture investing. In my opinion, we’ve jumped the shark here: coding boot camps > founder boot camps > investing bootcamps. Like other roles, there are certainly some fundamentals that help you gain footing in venture capital: reading a term sheet, assessing valuations, running due diligence etc. But like many industries there are elements that invariably suck (grunt work) and some that are more mysterious and intangible (network, experience, intuition).
I’m here to tell you that despite some of the glitz, glamour and extravagant dinner events, VC is a sales motion at its core. Sales tends to have a negative connotation, especially when compared to the high status perception of venture capital. My objective today is two-fold:
Bring some humility to the role of VC: it really is a sales role wrapped in marketing disguised as a financial services business.
Mount a defense of sales roles in general: while it does contain drudgery and repetition, it can be highly strategic and rewarding. Get off your high horse!
I saw a tweet (that I can no longer find…) suggesting that young VCs get disillusioned by this fact (VC = Sales) after a short time and decide to quit altogether. I can relate because I was once disillusioned with the messy reality of a sales role early in my own career.
Death Birth of a Salesman
I started my career in Sales. This wasn’t by design. Upon leaving the comforting embrace of my tidy, Ivy League bubble, I was under the impression that I was destined for something *important* — a role that encompassed the wide-ranging knowledge endowed to me by my reputable liberal arts college. A title with the word Strategy sounded right. Perhaps a vaguely interdisciplinary role with a job description including words like transformation, innovation and cross-functional. What I lacked in practical, hands-on experience I most certainly made up for in deep critical thinking and transcendent communication skills. Or so I thought.
I joined Salesforce as a post-grad intern before the company had become a household name. I knew the company was well-respected and that upward mobility was all but assured, but Jr. Business Development Rep didn’t have the same caché as Goldman Sachs Analyst or McKinsey Associate — entry level roles that I was once told to aspire to. My first 3-6 months were what you’d expect from an internship: grunt work, some shadowing, a bit of office antics and networking up the ladder. I spent my fair share of time at the ping-pong table enlisting older “Account Executives” to impart whatever wisdom they had in their relatively short stints in corporate America.
When the allotted time as intern ran up, I was ushered into a conference room with my would-be managers from the entry level SDR team (Sales Development Rep) one rung above me. I assumed, perhaps naïvely, that this was a formality. An opportunity for them to welcome me to the SDR team and set expectations for my future role. The meeting started as expected: you’re bright, well-liked and appear to have an aptitude for the work, they said. But what came next was unexpected. Do you even actually want this job? I’d been steadily observing what the job was for the past six months and was foolishly frank in my response to the two men that essentially served as gatekeepers to my future employment. Not really, I said, with a pretentious smile meant to signal that they were supposed to be in on the joke.
This was when I realized that my charm only goes so far. Despite close interpersonal relationships with these managers, they had a business to run and metrics to attain. What looked to me like a call center for overly educated 20-somethings was really a training ground for tomorrow’s sharks operating at the upper echelons of enterprise software. My innocent, inexperienced mind had created a fantastical facsimile of what it meant to do work and add value. But I was about to discover the real thing.
Bad Reps = Bad Raps
Throughout history you’ll find examples of salesman and the associated negative traits.
The Snake Oil Salesman (Liar)
The Traveling Salesman (Cheater)
The Used Car Salesman (Sleaze-Bag)
The B2B SaaS Salesman (Douche Bag)
These stereotypes are culturally pervasive and undoubtedly have an impact on how we perceive the role itself. It wasn’t until I read the The Challenger Sale (it was floating around the office around this time) that I discovered there’s a bit more to it. Unsurprisingly, there are parallels in the world of VC.
Much like VC, Sales is a numbers game. You build pipeline, work your leads and at the end of the quarter try your best to convert and close as much business as possible. There isn’t a single method for doing this successfully, although some work better than others. Sales people are often attributed with characteristics like persistence, gregariousness or cunning. Counterintuitively, these don’t always get the best results — especially in today’s complex, high-tech world.
The authors of The Challenger Sale argue, in fact, that most of the traditional sales personas are not a good fit for modern day sales. The “hard worker” puts in the effort but is missing the creativity. Relationship builders make friends with customers but their success hinges on these connections, not on customer value. A lone wolf is a “hunter” that’s independent but lacks team-work and collaboration skills. Problem solvers go the extra mile to figure out a solution but often get bogged down in the details without securing deals. Today’s shark is a challenger — someone who holds a strong point of view, challenges customers on their approach and builds trust through transparency.
These are, of course caricatures — you can adopt aspects of several. In VC, I’ve identified analogs that fit fairly neatly within the framework:
The Hard Worker : Hustle Culture Guy — the rise & grind, hyper-productivity investor who preaches the virtues of hard work on his podcast.
The Lone Wolf : Solo GP — independent fund manager, usually with a specific area of focus that has built a following as a result of their work in the space.
The Relationship Builder : The Scout — These are the consummate networkers. This is the person who shows up at every VC happy hour and startup launch party whether they were invited or not. Some are good at maintaining connections and delivering valuable deal flow, others network for networking sake.
Problem Solver : Technical Investor — These are former developers, PhDs or technical leaders who want to try their hand at investing. Often they understand product but will perhaps have trouble forecasting product-market-fit.
So where does The Challenger fit into all this? My view is that it takes the best aspects of all the others but pairs it with high conviction and a unique perspective (often contrarian) that can serve as a sparring partner as well as an unconditional supporter of your startup. A Challenger VC is well-networked but not restricted to an echo chamber of yes men. They solve problems alongside founders, not on their behalf. They work hard to sell the vision to various stakeholders. And importantly, they’ve experienced life in the trenches as a founder or operator — a lone wolf at the early stages of starting a business.
A VC is always selling. Whether selling their value add to a startup founder, their “edge” to an LP, their contribution to a co-investor or their brand to the broader tech scene — it is the one consistent motion across the venture landscape. If you’re going to be in this industry, you’d better learn to like selling or get comfortable with its trappings.
Sales Resurrection
After the folly with my future managers, I spent my remaining weeks convincing them (and myself) that I really did want the job. Either they bought it or someone vouched for me because I secured the promotion. And along with it, a radically different work schedule. Alarm at 5:45AM, at my desk before 7AM, filtering through inbound leads and prioritizing my call schedule and follow-ups before 8AM and then it was off to the races. Smile and dial as they say.
Early mornings, monotonous sales pitches, constant rejection — is this really what the working world had to offer? I thought my education was priming me for intellectual stimulation and complex problem solving not brute force customer outreach… As it turns out, both are required. And it’s a good thing I was subject to the latter at an early stage in my career because it set the groundwork for just about everything else.
Most of what constitutes “work” isn’t the heady strategy or the back room meetings. While it’s generally viewed as high-status it probably makes for about 10% of the overall effort required to achieve the objective. Sales is a “get shit done” kind of role, in some cases, by any means necessary. Which is why it is simultaneously the most critical part of any business and the most resented/distrusted/ridiculed/stereotyped no matter what the industry. Believe it or not, most highly sought after roles are sales roles at their core.
At the time, I was disheartened by this reality. But in hindsight, sales fundamentals positioned me well for my work today. If early in your career some work feels “beneath you” — it probably is. But it’s a necessary step in the progression, regardless of where you end up. Not to mention, strategic sales roles can be fun, competitive and rewarding. So stick with it!
VCs Congratulating Themselves
I recently discovered a great Twitter account called @VCBrags where they basically trash self-aggrandizing investors in hilarious meme format. I love it because it provides a check on the unbridled optimism and self-congratulatory nature of investors in bull markets. Most VC tweets don’t age well given a long enough time horizon.
This behavior from more seasoned investors has trickled down into the emerging VC crowd. As a result, you’ll find outlandish content from 22-year olds who’ve never done a deal but want to espouse their borrowed beliefs on China’s real estate bubble or the virtues of lab grown meat. Social media serves to inflate these egos while simultaneously creating the perception of VC as a design thinking cult nestled in an ivory tower. I’ll try my hand at a meme to show you what I mean:
20-Something VCs Talking About their Job on Twitter:
20-Something VCs Actually Doing their Job:
I’m not here to talk shit about young VCs. Nor am I espousing the virtues of your average tech sales bro. I’m simply encouraging VCs to come back down to earth and to cut "sales roles” a little slack.
Not everything is as it appears. And whether you like it or not, VC is a Sales role.
I planned to expand more on my time in tech sales, but I figured I’d spare you the details. I did, however, find a funny and shockingly accurate, albeit satirical, video series on the world of SaaS Sales. I highly recommend for an informative laugh.