Most software founders, particularly in B2B, need to get radically better at sales. @Steli , who is the best person for explaining the scrappy stages in the beginning and then building out a team with scripts and processes, wrote a guide to:

For technical founders it is irrationally, obscenely hard to reverse years of programming (ba dum bum) that sales is a value-destroying activity. Sales is CLEARLY a value-creating activity, contingent on you have a value-creating product.
The world will not drop what they are doing to adopt your work. This is particularly true in B2B, where simply building a better mousetrap won't overcome the activation energy required to get people with additional non-mice problems to prioritize changing mousetraps today.
This is very non-obvious for founders because founders are not often people who *want* to be sold to. We often come from a background where trying out tools is a bit of a fun hobby. We like looking at all the options, making charts, and ripping out partially complete tests.
"This week I unsuccessfully trialed four software options for automating that thing that has been killing us. Our actual production process remains the same as last week. Don't worry; this was a great use of time." is not a thing you want to write in a progress report to manager.
The process of sales pushes the burden for understanding the market and distilling it from the customer to the sales person. That is a very valuable thing; it is why almost all businesses buy almost all of their big-ticket purchases (including e.g. employees) from sales.
(A candidate is absolutely doing a sales job when attempting to get hired by a company. This is one of the things that both sides of that market are frequently in denial about, but I digress.)
Simply getting oneself to be comfortable with sales (or at least present as being comfortable for a phone call or two) unlocks a crazy amount of success for founders, because founders have a few advantages over every other sales rep.
One is that they present as being almost irrationally obsessed with the market. Founders tend to live and breath the product for a few years, and it often shows, mostly in positive ways.

Unlike most sales reps, founders can credibly promise tight feedback loops for product.
Stealing a line from @asmartbear which has paid for at least a year or two of my kids' education:

"If you go with BigCo, you can call them at 3 AM. Someone will listen to you politely, explain they have no solution, and open a ticket. If you call at 3 PM, same answer."
"You can't get a useless answer from me at 3 AM in the morning. But when I'm up, your business *really is* important to me. I am the engineering team. I will push fixes so fast you will be amazed. I *will* get this right because it *actually matters* to my business that I do."
Founders have to sell.

Many, many technical founders of my acquaintance want to offload this to someone ASAP. I've never seen this work: you need to have a deep understanding of your market and customers to arm that first non-founder salesperson. It is gained by doing.
(And even if you don't do sales day-to-day anymore, you still have to sell candidates, investors, and partners on the desirability of using your company. Though most B2B SaaS CEOs that I know still very much have an account in their CRM and talk to "opportunities" frequently.)
The transition from founder-driven sales to founder-assisted sales generally starts with hiring a "maverick" sort of salesperson; someone who is comfortable extracting what you know about the market, iterating rapidly on scripts, and doing "things that don't scale" to win.
This may often be a necessary step, but it generally doesn't last for growing companies, partly because there is a crushing market undersupply of very effective mavericks.

These folks are capable of writing their own ticket and then, by construction, getting folks to buy it.
So eventually one tends to hire a VP of Sales who has done this before. They'll immediately start hiring reps under them, and start systematizing what you've learned about sales into scripts and playbooks.
You'll see this maturity model start to creep into all parts of the funnel, too, which will probably actually be written down for the first time somewhere around this stage.

Sophisticated, mature processes for marketing to pass leads over to sales for qualification.
Sophisticated, maturing processes for sales to actually physically close deals. ("What, you mean we don't just edit a few things in Word and then ask them to print, sign, scan, and send back?") Defined, scheduled startup calls, onboarding, and handover to AMs / CS aftewards.
(Sales, like many professions, benefits from specialization of labor. One that happens early is splitting the team into "account executives" (AEs) focused on getting new accounts and "account managers" (AMs), focused on keeping existing customers happy and expansion revenue.
(Some companies even split their AM teams into dedicated subteams for doing true expansion, for cross-selling products, for winning renewals, and for the generic "I want the direct contact information for someone at your company because our business must be important enough" job)
If you're at all interested in these topics, the people to read a heck out of are Steli and @jasonlk (who writes https://t.co/7FpEMvXdLZ ).

Steli is so effective at sales he has closed deals he wasn't even a party to. My favorite anecdote about this:
At a previous company I had invited myself out to lunch with a software CEO, with intent to get them to sign up, but was not really sure where we were at end of lunch.

"Hey apropos of nothing: do you know Steli?"
"Oh yeah he's great."
"He is. Steli wouldn't let me leave lunch...
... until you explicitly tell me you're going to use our product."
"He wouldn't, would he."
"He wouldn't."
"OK then; we will."
"Great! Email me and we'll figure out logistics."
That is called "asking for the sale" and, while that is a very unconventional way to ask for the sale, a *ridiculous* portion of all energy expended in the art of sales is to get conversations to the point where someone has to actually say yes or no.
Relatedly: in the highly likely event that you get an answer which is not a yes or no, effective salespeople follow up until the sun goes nova waiting for either a yes or no.

More from Patrick McKenzie

There are a *lot* of software shops in the world that would far rather have one more technical dependency than they'd like to pay for one of their 20 engineers to become the company's SPOF expert on the joys of e.g. HTTP file uploads, CSV parsing bugs, PDF generation, etc.


Every year at MicroConf I get surprised-not-surprised by the number of people I meet who are running "Does one thing reasonably well, ranks well for it, pulls down a full-time dev salary" out of a fun side project which obviates a frequent 1~5 engineer-day sprint horizontally.

"Who is the prototypical client here?"

A consulting shop delivering a $X00k engagement for an internal system, a SaaS company doing something custom for a large client or internally facing or deeply non-core to their business, etc.

(I feel like many of these businesses are good answers to the "how would you monetize OSS to make it sustainable?" fashion, since they often wrap a core OSS offering in the assorted infrastructure which makes it easily consumable.)

"But don't the customers get subscription fatigue?"

I think subscription fatigue is far more reported by people who are embarrassed to charge money for software than it is experienced by for-profit businesses, who don't seem to have gotten pay-biweekly-for-services fatigue.

More from Tech

Ok, I’ve told this story a few times, but maybe never here. Here we go. 🧵👇


I was about 6. I was in the car with my mother. We were driving a few hours from home to go to Orlando. My parents were letting me audition for a tv show. It would end up being my first job. I was very excited. But, in the meantime we drove and listened to Rush’s show.

There was some sort of trivia question they posed to the audience. I don’t remember what the riddle was, but I remember I knew the answer right away. It was phrased in this way that was somehow just simpler to see from a kid’s perspective. The answer was CAROUSEL. I was elated.

My mother was THRILLED. She insisted that we call Into the show using her “for emergencies only” giant cell phone. It was this phone:


I called in. The phone rang for a while, but someone answered. It was an impatient-sounding dude. The screener. I said I had the trivia answer. He wasn’t charmed, I could hear him rolling his eyes. He asked me what it was. I told him. “Please hold.”

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