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Sales Secrets for Technical Startup Founders

· 9 min read
Roy Firestein

Here's something I wish I knew three years ago: Sales is the most difficult function to build in your startup. I would have taken a different approach to building my sales team if I had known this. The best products don't always win; the best sales teams do. At least in the short term.

I've observed subpar products rapidly gaining market share due to excellent sales teams. Conversely, startups with superior products have failed due to the absence of a competent sales team, falling into the trap of merely "order takers".

This guide will show you how to build a sales team adept at closing deals.

How Sales Works

Does this scenario sound familiar? Your sales team struggles to close deals. The initial calls are promising, the demo receives positive feedback, and the rapport seems strong. But then, communication halts. Silence ensues.

You're not alone. Many startups face this challenge. Let me share solutions that work.

Early Engagement is Key

In the early stages of a sales cycle, potential clients are more receptive and curious about what you offer. Use this opportunity to understand their needs, putting less emphasis initially on your product. You will not get a second chance. Focus first on comprehending the client's issues.

During early meetings, keep your team smaller than the client's to foster a less intimidating, more open dialogue.

Center on the Client's Needs and Challenges

It's important to ask probing questions about the client's problems, why they haven't solved these problems yet, and the visibility of these issues within their organization. Understanding the depth and impact of these problems helps in tailoring your sales approach effectively.

Sales as an Ongoing Negotiation

From the very first interaction, the sales process is a negotiation. Holding back information about your product initially can be a strategic move to keep the client engaged and willing to share more about their needs.

Latent vs. Active Need

Understanding the difference between latent needs and active needs is crucial in the field of sales. Latent needs refer to a state where a person is aware of a problem, but not actively seeking a solution. On the other hand, active needs refer to a state where a person is actively seeking a solution to a problem.

It's important to note that only a small percentage of potential clients are in an active need state at any given time. For instance, if you have a leaky roof, you are in an active need state and require the services of a roofer. However, if you know your roof is old and needs to be replaced, you are in a latent need state. You are aware of the problem, but not actively seeking a solution.

If you are selling to prospects in an active need state, you are not a salesperson, but more of an order taker. The real task of a salesperson is to shift the client from a latent to an active need state. This involves creating a sense of urgency and emphasizing the benefits of resolving the issue promptly. By doing so, a salesperson can guide the prospect towards a purchasing decision and help them move from a latent to an active need state.

Highlight the Problem, Not the Solution

Sales communications should focus on the problem rather than the solution, as this resonates with a wider audience. Remember, only a small percentage might be in active need of your solution at any given time.

Don't "show up and throw up", as Mike Weinstein says in his book "Sales Management. Simplified.". This means don't just show up and start talking about your product. Doing that makes you a commodity and you'll be competing on price.

When you deeply focus on discovering the client's problems during the initial sales calls, you'll be able to gather important clues about how to close the deal.

Always Refocus on the Problem

In discussions, consistently steer the conversation back to the client's problem. This keeps the emphasis on their needs and how you can solve them, rather than merely presenting a product.

Compelling Events as Catalysts

A compelling event can shift a potential client from a latent to an active need state. Understanding or even anticipating these events can be crucial in timing your sales approach.

You should expect your sales team to monitor LinkedIn, Google Alerts, and other sources for news that are interesting and relevant to your potential clients. Send them to your prospects, our of authenticate interest in their business. You can't fake this, so learn to be genuinely interested in your prospects.

Doing so achieves two things: it positions you as a trusted advisor, and it can trigger a compelling event.

The Art of Information Withholding

Providing too much information too early can lead to potential clients disengaging. It's important to reveal information gradually to keep their interest and encourage further dialogue.

Deflect and redirect questions about your product by asking questions about their needs. Once a prospects gets all the product information from you, they have no reason to continue the conversation. "I got everything I need, don't call me, I'll call you!". You don't want that.

The longer you keep them engaged, the more likely you are to run a complete discovery and increase your chances of closing the deal.

Have a Strategic Plan

Businesses primarily make purchases to solve a problem or seize an opportunity, with the former being more common. Identifying who is experiencing the pain and how severe it is can guide the sales strategy.

Before you or your salesperson gets on a meeting with a new prospect, you should have a plan. Having a plan allows you to be more confident and in control of the meeting. When you are not controlling the meeting, you're not in control of the sale.

The plan should look something like this:

  • Socializing with the prospect to understand the style of communication
  • Setting an "upfront contract" to establish the purpose of the meeting
  • Quick pitch
  • Discovery questions
  • Sell
  • Next steps


The first step is to socialize with the prospect to understand their style of communication. Ask where they're from, about the last game they watched, or anything else that's not related to business. Allow the prospect to set the length of this phase, keep it as short or as long as they want. We are also hoping this will lower their guard and feel more comfortable with you.

Upfront Contract

The next step is how we start establishing trust with the prospect. We do this by setting an upfront contract. We tell them what we want to accomplish in the meeting and ask if they agree. We then deliver on that promise. So follow the plan.

It goes something like this:

Hi Anton, thanks for taking the time to meet with me today. I believe you and I have 30 minutes scheduled, so we'll stop five minutes before the end to discuss next steps.

Here's what I'd like to accomplish today: I'll spend two minutes or three minutes telling you about our company, the issues we solve for real estate companies, and what makes us different. Then, I'd like to ask you a few questions about your business and your goals. Depending on what I learn, I'll be able to share a few relevant case studies or show you options for how we provide user screening for clients. After that, we can discuss if we might be a fit to help you achieve your goals.

That's my plan for today. Tell me what you were hoping for and what you'd like to accomplish today.

Quick Pitch

The next step is to give a quick pitch. This should be no more than three minutes. You should have some guesses by now about what the prospect's problems are after researching them before the meeting.

I recommend reading the following books to learn how to do this:

You should also read this blog post to help you craft a Sales Story to use in your pitch: Creating a Sales Story With ChatGPT Agents.

Discovery Questions

Spend the majority of the meeting on discovery, using prepared questions to delve deep into the client's problems.

Here are some examples:

  • Who else in your company also cares about this problem?
  • Where are you in the process of evaluating solutions?
  • Where will the money come from to fund this project?
  • This could be a big project. How committed are you to solving this problem?
  • How will you measure success? What are the criteria for evaluating solutions?
  • If you had a magic wand, what would you fix right now?

Listen intently to the answers, and probe further any time you hear something interesting. "Oh, your ID verification process takes 10 minutes? How is that impacting your business?" "What do you mean by 'it's a mess'? Can you tell me more about that?" "So your team is doing a lot of that work manually? How much time does that take?" And on and on. Keep going until you almost run out of time, if there's more to be discovered.

You only leave the discovery phase after you have the complete "shape" of the problem. This will be all the ammunition you need to close the deal and avoid the "crickets" problem.


With a comprehensive grasp of the problem, tailor your sales pitch to leverage the insights gained during discovery. This approach significantly increases your chances of success.