It’s difficult to describe anomalies without insulting everyone. Many very fast growing software companies had just one very good salesperson until several million ARR, even tens of millions. So why do startups sub $1M ARR claw to hire tons of salespeople?
The founders of anomalies get sales, so they de-risk why the exceptional salesperson might leave, before they ever show up. Selling themselves allows them to hear what customers are saying and make changes to the product, leading to a product that sells and retains itself faster.
When that Zero to One salesperson shows up, there are examples of what has worked on top of an immediate admiration of the effort applied. They just have to apply tweaks and gasoline now. They don’t lose sleep about money, so they instead think of how much they could make.
The reason most founders scale sales sub $1M ARR is because they assume they are more intelligent then their salespeople, which becomes self-fulfilling. They end up managing many newbies too early, which isn’t good for their development, either. This distracts them from product.
The moral of the story is I believe in founder led sales until $1M ARR. Then one person from $1M ARR until whenever they make too much money, or you want to expand. Your destiny is yours then. The ideal floor for hiring younger folks is that expansion point.
If you are a young salesperson, it is unlikely you will work for an anomaly, and more critical to become one yourself. Anywhere that will hire you, past the point of one. After you put up numbers, you can use your W2 as a resume and have your choice of employer.
I have never understood the talk down to sales team angle. It is notorious in ad sales in NYC. The best of the best will naturally outflow to where they are valued and stimulated. You want to align with these future Oprahs and Benioffs.
The future Sarah Blakely’s don’t need software sales school, it may even piss them off. They are already crushing it wherever they are. Everyone follows their move. Hypothesis: non-tech sales anomalies will hemorrhage from sub-optimal environments.
“The first rule of any technology used in a business is that automation applied to an efficient operation will magnify the efficiency. The second is that automation applied to an inefficient operation will magnify the inefficiency.”
— Bill Gates
— Bill Gates
If you can’t get one salesperson to quota, don’t hire another one. Before that, figure out what a typical quota is and hit that quota before the first salesperson shows up. Every subsequent hire should accelerate the rate of returning money.
You want to move point to point. Time based decisions are stupid.
Software anomalies (lead rich) build acquisition into the product (like Hotmail), so when SDRs do show up, they spend more of their time on qualification than creating awareness. In the meantime, Sales Development should be more of a background process for that first closer.
Modern examples of built-in acquisition:
1. A branded survey says “Powered by Delighted” at the bottom.
2. Plaid’s Bank Auth
3. ShareFile’s Outlook Plug-In
A potential buyer sees it in action from a brand they trust. They then inquire preheated.
1. A branded survey says “Powered by Delighted” at the bottom.
2. Plaid’s Bank Auth
3. ShareFile’s Outlook Plug-In
A potential buyer sees it in action from a brand they trust. They then inquire preheated.
A good way to stand out in sales interviews (especially the meet the CEO part) is to highlight an idiosyncrasy of a product. I noticed you did X brilliantly. Deconstruct craftsmanship as a lead to avoid Googling what questions to ask. Think n minus what every sales bro will ask.
Hiring is a two way street. During my mock demo at Delighted, the CEO asked a question referencing a back-page tweet: “The savviest buyers always ask, what questions am I forgetting to ask?” That callback made me want to work there even more.
LiveRamp is an anomaly. It was acquired by a big 4 ad tech co then outpaced every other unit, until the child consumed the parent. The CEO asked a 25 yr old me if I could take a pill that made me smarter, or a pill that could reduce the amount of sleep, which one would I take?
A younger Aynul didn’t realize the correct answer was to take both. I assumed I was smart enough and felt short on sleep, so I went with a justification of the latter. I don’t doubt I could have sold the product, but that was the ideal question to filter for culture fit.
Everyone I interviewed with was ex-Ivy, and credentialed af. As a 2x state school dropout, I felt a chip on my shoulder. I don’t doubt I could have jived but in the flow, I didn’t feel like I fit the mold. My lack of degree came up, even though I had an insane record at Citrix.
I didn’t pass the top most, mutual exclusivity filter game. I felt this happen earlier and withdrew emotionally. I was barely there for the final chat with the sales leader, after the CEO. His tone exuded a “lost cause”. I don’t blame him, it was. My superpower is reading people.
I’m grateful for the opp and I admire the CEO, I continue to follow his thoughts. I don’t doubt my friend at Liveramp (
) thought I was a fit, but what matters the most is what the person at the top thinks. My intrusion could have created conflict.

I felt this credential insecurity, hair raised on the back of my neck feeling again, years later, just after Qualtrics bought the startup where I ran sales, for a split sec. Every job there had a college degree requirement and the handful of us had to onboard as employees. lol.
I thought I was going to have a silly conversation with HR about how I couldn’t verify my degree. That was the extent of my fear. I had no doubt the founders would have defended me to the death for the work I spearheaded, but it never came up. It was just a HR hurdle, non-issue.
Liveramp wasn’t big but it wasn’t small. I’m one of those scary early, sub 10 employee crazies. Han Yolo. I don’t like adhering to rules. I like writing them. Some orgs will care about things others won’t. Since then the climate changed, Google dropped college reqs and more will.
I had no issue ever resonating in the C-suite. If you can play ball, you can play ball. You might just have to find your people. You will know this best by the way you feel in the interview flow and trial and error. I can help you find where you fit.
I should clarify the pill prompt was an interview brain teaser not an actual offer to take a pill. lol.
ZenProspect (now Apollo) is another SaaS anomaly. They hit $1M ARR in a few months, before that happened. There is a Product Hunt launch where the founders are nowhere to be found. How many flash in the pan SaaS products obsess over their upvotes, still? Attention doesn’t swipe.
Email is Product Hunt for Decision Makers. People with authority don’t go looking for JS injections. It’s a work distraction for users. It’s not for pro repeatable b2b lead generation. Why did this anomalous SaaS company drowning in revenue not give a shit about its PH launch?
No one good at b2b sales is posting regularly on LinkedIn for the same reason. I used it close to zero in my *entire* career, lol. It’s full of sales amateurs indirectly yelling at each other because they don’t know how to directly ask for what they want from people that buy.
LinkedIn is where you go *after* sales. Haha, we sold our company, link. Haha, we wired $20k together, let’s connect. Haha, Max Levchin shared a screenshot of our product, like. Unless you are Bill Gates’ SMM or one of those chain mail letters, you shouldn’t be screwing around.
Authoritative speech eviscerates matter of factly. Salespeople are extensions of the CEO’s voice. They can’t be cowards that coddle cultural norms. They say what no one is saying that needs to be said, then twist the knife. They are not terrified of metaphors or contact.
When I email CEOs to get them to hire candidates I endorse, they will look at my Twitter and LinkedIn before taking the meeting or referring me. They are looking for why I might have edgy insights about sales. They might even read this Tweet and think I’m meta and woke.
CEOs will say things like “Oh wow your network is already referring you employers and candidates are reaching out to you on their own? You haven’t even launched on Product Hunt! Must have been some career! Dang, could I know you?”
Lots of medium to large companies, like Citrix, have entry level sales development positions with training. The most ambitious reps will “graduate” and after a bit want to use their chops in a startup. I did. This also emphasizes my disdain for sales schools — better ones exist.
Why go to an entry level SDR school that charges you with an ISA? Why go to a new school at all, even if free? High signal *companies* are lined up to pay you to learn. The brightest bulbs of the most battle tested trainees will not seek badges. Very unappealing to a younger me.
In my SDR intern days at Citrix, I had to cold call 100 accountants per day, while watching closing tape at any chance I could get. We were on the phones within days. I didn’t read the book we were supposed to. I was expected to book 4 demos per day. You should get real ASAP.
I figured out that I could cold email early on and get like half of my demo count. Eventually, I got so good at email based sales development that I didn’t have to call. My manager would get mad. Oh well. I just kept escaping to a promotion.
“I can’t remember the exact messaging,” says the younger Rahal, “but my dad said something like ‘Peter, shut the fuck up and sell 1,000 bars first.’ These are the beginnings of a $600M RX bar acquisition by Kellogg. https://www.chicagomag.com/Chicago-Magazine/January-2018/RXBar/
I was just on the phone with my friend. She got distracted by reading my tweets. I’m competing against myself. I think I can scale Peter’s dad.
The people scooping the froth salivate at the legends of the beginnings. How did Uber start? Before the software? Even after? How did they break into new cities? Why do the early employees talk about the inevitable sophistication so much differently?