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9 Sales Insights for first time Founders

An interesting question I bumped into today — How to learn to sell? Asked by an engineer turned first time founder.

The question received interesting answers from from Senior Executive in a Fortune 500, engineer turned founders, sales-related-book authors.

Here are 9 answers:

1. Separate Sales from Marketing

For B2B sales resembles project management: the goal is not to convince everyone to buy your product or service but to diagnose their needs and only engage with firms that will benefit.

For larger deals you “sell with your ears” as much as you talk.

— answered by skmurphy

2. Direct and Indirect Sales

Sales can best be distinguished by indirect sales and direct sales. Direct sales is where you go out and find clients. Indirect sales is where you go out and find partners to bring you clients.

You don’t buy Coca Cola from Coca Cola. You rarely by HP from HP. Companies tend to be more successful when they find ways to grow using “channels”.

— answered by gogopuppygogo

3. Sales is also graded by level of “touch”

For example, selling IT services contracts is very high touch. Signing a deal could involve weeks of written correspondence (RFI, RFP), in-person pitching, contract negotiation, etc. Low touch could be fully automated with simple, non-negotiable pricing. There are lots of levels in between.

— answered by tootie

4. Marketing, Advertsing and Sales

Marketing is the brand, the image, points of differentiation, etc. It’s the message. Advertising is the broadcast. It’s how the message is communicated. It’s the medium.

Marketing + advertising = prospects and leads.

Sales is the last mile. It takes the results of marketing + advertising (i.e., leads and prospects) and guides those to closing.

Contrary to myth, successful sales is about listening, not talking.

— answered by chiefalchemist

5. Listen, but sometimes, articulate


Photo by Headway

Yes, you need to listen. But you’ll never sell anything if you can’t articulate a destination, lay out the path and showcase to the customer how what you’re representing will benefit them more-so than the products you’re trying to displace or something new that will bring with it a myriad of gains for said customer. If a customer is always telling me what they need from me then I’m not providing any value. And, honestly, it’s very rare to find a customer who’s ahead of a good sales team. We have full access to PMs, internal business units and access to far more insight to our bits and pieces than any reseller or customer. Don’t get me wrong, I’m not saying customers can’t be experts. But I’m here to know and bring things to the plate that they just can’t.

Understanding your customer is often times more valuable than listening to them outright. I’ve found paths for the customer that has helped them avoid making mistakes, saved them money or improved their operations through paths they hadn’t considered or didn’t know existed. Good sales teams work hard across the board through strong technical positioning as well as strategic deal creations.

There are sales teams that rinse and repeat for every interaction and then there are sales teams that are looking to help their customers, trying to find where the wins are for the prospect. I’ve walked away from deals by telling a customer we weren’t a fit for them. Sales gets a bad rap, but there are some of us out there that walk into every conversation not with the only intent of closing quota, but trying to make a positive impact.

— answered by windexh8er

6. Don’t Sales, but Consult.

Don’t “learn” sales. A lot of reading material and courses could actually negatively effect you by causing you to overthink things. At best, you will come across as calculating and at worst you’ll lose deals due to getting lost in the weeds.

Here’s two things:

1. Whenever you deal with someone, try to conceptualize yourself as a consultant and not a salesperson. Great sales people are more like matchmakers, people have some kind of problem and you have some kind of solution. People are pretty sensitive to in situations where they could be persuaded. Conversations should have the feelIng like you are trying to convince a friend to watch a really cool movie rather than high pressure, ultra confident wolf of Wall Street closing.

2. I you really want to learn the actual craft of it then put yourself in more situations where you can talk to a salesperson and put them through their paces. Start taking calls from telemarketers and instead of hanging up tell them you would rather they send you an email. Go to a car dealership and tell them the car you want is too expensive. This is a decent way to get experience.

— answered by kinghtown, started B2B since 16, works in sales for years

7. Sales in Startups can be Different


Photo by Austin Distel

First-time founder here who came from sales at a big consulting firm, and then and then had to develop the whole marketing and sales stack for our startup.

Most of the books recommended in this thread assume that you’re working for an established firm, with product/market fit, etc.

Clearly, that’s not the case for a start-up. As Pete Kanzanjy mentioned in his book “Founder Sales”, called it the “founder-led sales” phase.

How I did it:

  • Interview as many prospects and customers as possible
  • Understand what keeps them up at night, what specific pain points they have, the language they use to describe their situation
  • Shape your message to solve those specific pain points, using their own language
  • Wrap your message into a story

The worst you can do is “problem/solution”. People don’t buy that way. People buy change, and you use the story to communicate that change.

— answered by scapecast

8. Hire a Coach to Advanced Your Sales


Photo by Xuan Nguyen

As an engineer turned founder, your instinct to jump in and start doing it is correct. It’s hard to learn from books. I never did, neither did the successful engineers turned sales people that I know. The key is learning to read each situation so you can apply the right approach. You also seem self aware which will help you learn faster.

My biggest advice is get a coach/mentor/consultant who you talk with once per week to get feedback. This is how professional sales people learn in practice (eg from a sales manager). This will accelerate you learning by a factor of 10 versus doing it yourself. They will help you read each situation and push you to focus on the right places. Otherwise it’s easy to flounder on the wrong ones.

RE metrics- closed business is the only one that matters! Do whatever gets you that as fast as possible.

I wasted a year when I first founded Amplitude trying to brute force it myself and closed a grand total of two contracts for $36k. After that I ended up working with a guy named Mitch Morando and got from $36k to $1M in ARR in less than a year. He cost me $5k a month and increased our market cap by $20M, it was well worth the investment

— answered by Spenser Skates, founder of Amplitude

9. Bootstrap then hire a “head of sales”


Photo by Olena Sergienko

You are correct that after the product is ready the rest is ALL sales (closing deals) and marketing (getting the word out).

Sales people are a unique breed of human. You can tell them to F off and they will show up the next day with coffee, just the way you like it. :)

My recommendation is do the job yourself to bootstrap the company, get some revenue coming in but then transition to find an experienced person who can be your “head of sales”. Then you can focus on product and general management. (Unless you want to become a sales professional). A good bonus structure for bringing in new deals is essential. Sales people are motivated by the hunt and payout for success.

There are some good inexpensive cloud CRM tools so that you can stay on top of your sales people, who they are visiting and what they are saying. Weekly meeting with checkups against their sales commitments and their “pipeline” of sales reviewed and pruned by you, is also essential but then let them run.

Small business is like a three legged stool made of Product, Sales (which is external relationship management) and Finance. Almost no founder has all three strengths. Make a team that compliments you and make lots of money.

— answered by lebuffon, Senior Executive in a Fortune 500


From the answers above, there is no a one-size-fit-all sales technique. Though, a common theme is, you need to learn about your target audience. Then try and learn techniques that works best with them.

In case you want to focus on the techincal side, first bootstrap your business with some initial sales. Then hire or work with sales professional, and let them take care of sales.

Originally posted on Learning Sales for Founders

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