I’ve always been hesitant to explicitly call out the mindset part of early sales work.
Founders like you need tactics that will work. You need clarity, and you need it fast.
Of course you do. That’s table stakes.
So, you learn the tactics. You’re bought into selling as the way to find product-market fit. You know it won’t be easy, but you sit down at your desk, and make your sales plan.
And that's when things get interesting.
Acting on a sales plan is hard no matter what. It’s especially hard when you don’t love selling. And guess what? Most founders don’t!
I’ve talked to so many founders who think they're the strange ones for not loving sales. They blame themselves for not hitting their goals, or not diving in headfirst.
To me, it makes perfect sense to not love sales. It’s one of the most vulnerable things you can do.
At the beginning of the founder journey, we all understand logically that selling comes with yesses and nos. But putting yourself out there at the mercy of your prospects, to be told no potentially over and over again, every day?!?
And even if you and sales are on reasonable terms – frenemies, perhaps? – the process couldn’t be more overwhelming. Looking to improve one tiny part of the sales pipeline can set off quite the internal tailspin:
“I need to increase my cold outbound open rate. This means that I need to analyze my messaging, the tone of voice, and the subject line, in relation to my target buyer profile to figure out what might not be working. Then I need to send out a new iteration to real prospects and see if things improve. If they don’t, we’ll have to go back and test something else. God that’s a lot of work with no immediate resolution… ooh look, a product bug! I’ll come back to the campaign another day…”
These feelings affect your day-to-day sales execution in ways that shouldn't surprise anyone. But alas, avoiding sales, or avoiding improvements to your sales process, is wasting time that you don’t have and that you won't get back.
This is why I’m passionate about building what I call a “sales-positive mindset.” When you shift your perspective to welcome selling, rather than judge or dread it, it changes how you show up for your sales process every single day. This has a direct and significant impact on your recurring revenue and time-to-product-market fit.
Building a sales-positive mindset takes time and practice. It will likely be an ongoing practice throughout your founder experience. Here's what the mindset starts to feel like:
- Resilience. You accept that not every prospect will say yes, and that’s it’s a necessary part of the process.
- Earnest curiosity. You take pleasure in understanding the prospect’s point of view and experiences, even if what you learn doesn’t match with what you hoped to hear. You see every conversation as a way to improve your understanding of the market.
- Authentic relationships. You approach sales as a genuine conversation where you explore a prospect’s needs and if your startup might be able to support the fulfillment of those needs.
When you build this mindset, here's what becomes possible:
- Your conversations with prospects feel generative, not stressful.
- Your outreach becomes more consistent and less daunting.
- You feel free to be yourself while selling.
- You can confidently drive toward a sale – or disqualify prospects you can't help.
- And most importantly? Your day-to-day experience as a founder leading sales, armed with the right tactics and a supportive mindset, becomes less hellacious. We love to see it.
Thank you for reading. Plenty more to say and offer on this topic – it’s a biggie. On Tuesday I'll wrap up this welcome sequence with the last pillar of my philosophy on founder-led sales.
P.S. How are you liking the newsletter so far? What would you like to see more or less of? Do tell.
This is Extra Extra, a newsletter about the tactics and mindsets that drive early sales. I’m Caroline Fay, and I’m an exited social impact founder that’s spent my career launching and selling new products. I help non-traditional tech founders build sustainable, recurring revenue.
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Caroline Fay
