Startup Sales — 5 Common Sales Mistakes by Founders
August 12, 2025
Founders are responsible for the first sales a startup will make. For many founders, this is one of their very first experiences of sales and mistakes are often made.
Your startup’s “Sales Playbook” records how you close a sale from start to finish. You can use the Sales Playbook to onboard new salespeople and improve efficiency — by ensuring the current best practices are being executed at each step along the way. In general, the founders should write the first version of the Sales Playbook, as they should conduct the first sales. Here are the elements of a strong Sales Playbook:
What: Begin with an overview of your company including the “1 Liner” and an introductory paragraph from a customer perspective. You should also list the table of contents here.
Why: New employees need to start with the basics of what they are selling, while existing employees can often benefit from the reminder. A linked table of contents makes searching the Playbook easy.
What: Usually 5–10 characteristics that define who you are selling your product to, for example: customer size, location, industry, budget, customer title.
Why: A clearly defined customer profile makes the creation of your target list easier, as the set of potential customers is much smaller. Plus, if you test your customer profiles consecutively not concurrently, it’s easier to ascertain if a particular profile does or doesn’t really need your service.
What: Approximately 3 paragraphs, quickly introducing your service to a potential customer. You should cover what you do, the benefits, and recent successes. It shouldn’t take more than 30 seconds to deliver verbally.
Why: The goal is to incite enough interest from a potential customer that they want to learn more. This will be the most used template for your sales team and will form the foundation of most other templates and call scripts. The Elevator Sales Pitch needs to be defined early, so you can start iterating on it, to optimize success.
What: List your current sources for new sales leads, their current success rates, and best practices per source (e.g. how many contact attempts per lead). You should also list any lead generation experiments you’re currently testing, such as starting your own podcast.
Why: Lead generation is difficult and nuanced. Sources rarely scale or last, so don’t expect more than 10% of your outreach to result in a new lead. Given this reality, it’s important to both track performance, focus on what is working and experiment enough so you’re prepared when current sources deplete.
What: As your lead list grows and potential customers move through the sales process, you’ll need software to track changes from a “qualified new lead” (customer expressed some interest) to “closed sale” (customer has deployed and paid). Most Sterling Road portfolio companies use: Pipedrive, Hubspot or Salesforce.
Why: Viewing your sales process as a funnel makes it easier to see its strengths and weaknesses so you can focus engineering and training efforts accordingly. Sales teams are notorious for not regularly updating their CRM, so expect to spend a lot of time holding them accountable on this (e.g. the CRM should be up to date by 7pm PT each weekday).
What: Provide call scripts and email templates for every stage of the sales process, from initial outreach to thank yous. Most of this content should be based on the details from your first sales. This is often the largest and most used section of the Sales Playbook.
Why: Creates consistency and minimizes repeat work for your sales team; improving success rates, as everyone should be using the most effective content currently available.
What: Make sure shareable assets are accessible and editable for the sales team. This section usually includes: 1 pager, sales decks, logo and branding, customer references, press clips, and demos.
Why: Your internal champion at a potential customer will often need these additional materials to convince others in their company to buy your service. Having these readily available can help avoid lost deals and decision delays, due to a lack of information.
What: List your current pricing with the approved discount each salesperson may offer a potential customer, along with the other scenarios you may offer in exchange for a price decrease. Don’t allow employees to give discounts without something in return, e.g. a price discount should require a longer contract.
Why: Most startups drastically undercharge for their service and your sales team will try to discount further, in an effort to close a sale. Ultimately, discounting changes your customer profile, so you’ll need to stand firm on price to maintain your previously researched strategy.
What: For promising customer prospects that aren’t an immediate yes, provide guidance to your salespeople on when to add the lead to your general mailing list, along with best practices for more personalized follow up.
Why: If a customer prospect expresses interest in your service, there’s a chance they will want to buy at some future point. An active mailing list helps keep your company name on their mind when it is time to buy.
Here’s a simple example, based on this approach. This should be enough to get you started but remember this is a living document and you should expect to iterate on it often. The Sales Playbook usually stabilizes around $1M annual revenue.
Sales is daunting for most founders but, as you close the first sales yourself, recording that process will help form the basis of your first Sales Playbook while you scale your sales team successfully.
