Get Your Mind Right: The Proper Sales Mentality for Founders

Making the leap from product to sales can be an exceptionally tricky challenge for founders. They are tasked with both being one of the first waves of testing product-market fit and building a foundation for a scalable and repeatable sales process.

In a utopian world, a startup's product hits the market in stride and founding teams are inundated with inbound queries. Still, as you may have already experienced, the reality is usually less glittery. A new product from an unestablished brand in an emerging market rarely soars on an autopilot cruising altitude– it’s up to you to figure out how to sell it.

Ben Horowitz notes in The Hard Thing About Hard Things that the most difficult (and arguably most important) skill for a CEO is to manage their own psychology. Similarly, founders in customer-facing roles such as sales need to become masters of their thought processes, balancing optimistic enthusiasm with realistic, measurable goals.

One of the most significant challenges for founders who are uncomfortable with selling is wrapping their heads around the fact that in the current B2B sales environment, a product can rarely sell itself.

Luckily, there are proper mentalities and attitudes to adopt to help overcome the sales hurdle. Let's jump into the best ways to get your mind right for sales.

Eliminate the disconnect between fact and fiction

When you think of a stereotypical salesperson, your mind likely gravitates to two extremes: the schemey used-car salesperson type or the charismatic alpha capable of moving mountains with words (or a combination of both a la Wolf of Wall Street.)

Trying to fit the mold of how salespeople are portrayed in fiction is a quick way to encourage cognitive dissonance and misalign your expectations.

Start with nixing the idea that “sales” means manipulating or pushing people to buy something they may or may not need. Focus on understanding your prospect’s pain points and how your solution can save them time and money, and ultimately, make the case that the benefit of your product far exceeds the cost of your solution.

Prior to the 2007 economic crisis, sales was generally an amalgam of the following qualities:

  • Smooth-talking & shooting from the hip

  • Always Be Closing (ABC) mentality

  • Leveraging relationships for leads

  • Hard-selling

  • Opinion-heavy pitches

While many of these elements still remain in modern sales for commoditized products, there are a few important distinctions that have evolved in the sales industry after 2017:

  • Thorough discovery process and qualification to determine fit, solving for pain

  • Targeted and thoughtful engagement

  • ROI-based selling

  • Fact-based pitching

The sales industry has also evolved to leverage the advancements in technology for lead qualification, customer relationship management, and organizational sales development.

Sales as a founder is slightly more comfortable if you’re able to effectively utilize supporting technology and services, but you’ll still need the right sales mentality to take full advantage.

Sales Philosophy For Founders

Instead of trying to talk yourself into transforming into Don Draper, you must adhere to a process that ensures a higher success rate when followed correctly.

The ancient Greek poet Archilochus nailed the sentiment when he said, "We don't rise to the level of our expectations; we fall to the level of our training."

You don’t want to hinge your entire sales organization on a single rockstar salesperson. Instead, create a process in which a strong senior sales representative can thrive in and help improve.

As a founder, your job is to “sell” to your salespeople, and your product is why your company is the best at what it does.

As a16z puts it, don’t assume the problem is a lack of sales talent.

Here are some great foundational sales mentality pillars for founders:

  1. Activity over everything: increase the pace of your sales efforts to cast as wide a net as possible around qualified leads.If you’re more enterprise-focused, work on developing a deeper relationship with your most qualified leads.

  2. Be direct: Build sales motions and scripts that ask specific questions, seek specific answers, and offer specific value.

  3. Remember the 5 Ps:

    1. Prepare - do not wing any sales interaction

    2. Practice - until your sales motion becomes natural to you

    3. Positivity - at all times; optimistic mentality

    4. Polite - nice folks do finish first, when used in combo with the rest of these sales pillars

    5. Persistence - every “No” leads your closer to that “Yes”

  4. Build a transparent sales organization from day 1: Plaster your numbers, in real-time, in plain sight for your team to see it.

  5. Do not quit on sales: You will hear no 95%+ of the time, get used to it!

  6. Overcome objections or fail: You should have a detailed contingency plan for every possible objection.

  7. Assume the close: Maintain the attitude that no matter the obstacle, you will overcome

  8. Collaborate: Sales is an important determinant of whether or not your product has a chance of success. Since it plays such a substantial role in product-market fit, your sales efforts must be closely involved with product design and feedback cycles.

Early-Stage Sales Mentality: Find Your Champions

If you can’t sell your own product, it’s a long-shot (or impossible) to find someone that can.

As you go through dozens of conversations with potential early champions, document everything.

What gets measured gets managed, and what gets managed gets improved. Quality documentation is the backbone of any scalable process because it helps sales leaders identify efficiencies and pitfalls of their team’s approach. Current technology allows you to build simple playbooks. For example, Notion is an excellent resource. If you want something free, just drop your process into Google Drive - and keep it intensely organized.

Sales in the earlier sales stages is less about immediate mass adoption and more about finding the few perfect customers who need your solution so badly that they are willing to take the risk of working with a startup.

If your first customers strategically align with your startup's vision, they'll be much more willing to endure any turbulence naturally occurring with an early-stage company and product.

Finding your champions can be a very intricate and narrative-driven process, and founders are often the only people that can have this conversation at a meaningful and effective level. Top-down sales structures are critical for early-stage startups.

Final Thoughts

As the founder, you must set the property mentality for sales, selling, and scaling a sales organization before bringing on others to sell your product.

Even the world’s biggest and best tech companies like Apple, Google, Salesforce, and Microsoft have and had sales teams during their rise to hyper-growth.

Your attitude and passion for getting sales right will influence the rest of your team. Make sure to get it right and believe in sales before installing a formal team.