• Charles Edge

Founder-led Sales

Many a founder will have no experience in sales - and yet selling is one of the most important aspects of our jobs. It’s often the difference between making money and not making money. While we’re building a product, we might ask for feedback from people we consider potential customers. But at some point, we release a product into the world and need people to give us cold, hard cash (or the digital equivalent) to buy or use the product.

This is a make or break time for any organization. Most founders will start off by emailing the people we worked with during the development that the product is finally ready for them to use. And we expect perhaps that not only will those early users give us gobs of money but that they’ll tell their friends all about how amazing things are and we’ll get more money and they’ll tell their colleagues and so on. This usually isn’t how things work.


Instead, we each have to find our own way and many will have different styles. It is ok to play to our strengths provided we keep trying to sell. It’s about tenacity and sincerity more than charm. So here are a few things to plan on, and put into action:


  • Allocate time every day to do sales. For some this will be emailing prospects to setup demos, for others, this will be picking up the phone and calling people. Each industry - and how different people that sit in various roles at each potential customer, can be different. The important thing is to plan time and experiment with different approaches.

  • Get a CRM early. We don’t want to reach out to potential customers too often but we do want to reach out routinely. A good CRM will help us see who we’ve communicated with and set follow-ups. Many a founder can focus too much on the mechanics of a tool. The most important thing here is to pick a tool and start capturing information about potential customers and every interaction with them. As we get more experience and learn what’s working, we can customize the CRM to better accommodate whatever selling motion is working for us.

  • Find a mentor. This is important. We don’t know what we don’t know. Other people have done whatever it is we are doing. They can share some of what worked for them and some of what didn’t and provide guidance, fresh perspectives, new ideas, and keep us honest with ourselves.

  • Sit in on demos for other companies. When we sit on webinars or demos from other companies we pick up ways of speaking confidently, things we can say that are impactful, hear how potential customers ask questions, see how experienced sellers show different parts of products, or even just a simple turn of phrase that pushes prospects to communicate with us further. We shouldn’t creep on the competition - think about an adjacent market. We can also keep in touch with sellers or presenters we really like.

  • Build a network of sellers who sell into similar customers. Not only can they give us tips on better communicating with potential customers but they can also be valuable potential future employees.

  • Ask around about sites and blogs and methodologies. When we’re talking to other successful people in our industry or sales, make sure to find out where they’re getting their information. Not only can these become valuable sources of understanding for us either about our industry or about sales, but they can also uncover valuable places to try and find influencers to talk about our products and later advertising opportunities.

  • Write an outline of a demo or sales call. Now that we’ve worked with mentors, discussed how to sell with sellers, sat in on demos, and researched sites, let’s write the outline of a demo. We don’t want to seem scripted, so don’t write a full-on script. Instead, just write an outline. According to the complexity of a product or what we want to show, let’s focus on a 45 minute demo where we front-load everything we want to say in 30 minutes and then provide a 15 minute question and answer at the end. We should have enough content to run for another 15 minutes if there are no questions.

  • Dry run the demo with people who can provide critical feedback. Don’t just run through a demo with an employee who will smile and nod the whole time. We want to get better. Record the demo and watch it as well, since we’re all our own worst critics! If possible find someone to do a dry run of a sales call. Role playing these things makes everyone better at it.

  • Provide demos to a small number of small or medium-sized prospects. Now that we’ve practiced, let’s run through a demo with a small, hand-picked cadre of customers. Every single person who has ever done a demo gets better with more repetitions. We are never guaranteed a second chance. If we don’t do well, we may regret front loading the biggest and so potentially riskiest potential customers.

  • Ask a lot of questions. Can you describe how your organization currently handles this? How might this fit into your current workflow? How much time does your team currently spend on this? These are some simple and generic questions. The more tailored to a given industry and function, the better.

  • Document responses, categorizing the responses into themes. Keep it simple at first. Check Airtable or for won-loss call templates and think through what prospects tell us about our product and try to create categories for responses. If every single call is different we might have a problem. But if they all fit into a few buckets then we might be able to either find ways to handle objections with the words we use or find ways to address issues in product or pricing.

  • Be willing to experiment. Try different approaches and double-down on the ones that work. The larger the circle of people we’re working with (be they mentors, peers at potential customers, or sellers in adjacent markets) and the more we research, the more chances we have of uncovering awesome strategies.

  • Be patient, but not too patient. We can’t hit a home run every time. Be patient. It can take a dozen or three dozen attempts before we get the chance to turn a prospect into a customer. Additionally, no matter how good we are, the larger a customer or the newer (and so more innovative) an industry, the longer a sale will take to close. So be patient, provided of course there’s a cash runway to keep in business. At some point, if we aren’t getting traction, we might have to pivot either in approach or product.


Selling is one of the hardest parts of starting a new company. But it’s about just getting in there and doing it every single day. Get prepared for the grind. And as the organization grows, the time we spent selling early will pay off not only in profit, but because we’ll better understand our customers, be able to hire an amazing sales team, and be prepared to manage them.



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