I secured our first customer by seeing their LinkedIn post complaining about the exact problem we were solving.
I added the author and sent a message straight away, but didn’t get a response by the afternoon, so I called the office.
Receptionist: Hello, XYZ company, how can I help you?
Me: Hi my name is Terry from ABC company, I saw NAME post on LinkedIn about PROBLEM just now. I can solve it for her - is she available?
Receptionist: Sure, one sec.
They became our first customer. It was specific and timely and if I’d waited any longer it would have been less likely to close. Delaying would mean other priorities, distractions and competitors could get in my way.
This customer would go on to refer new customers in, which turned to inbound that was relatively easy to close through a video call and product demo.
It felt like we'd cracked it, so we hired a salesperson to “scale it”. This was my mistake and way too early.
What we'd actually done was quickly (and somewhat randomly) found the small handful of people who needed what we'd built. I mistook this as signal things were working and would continue to.
The sales hire didn’t work out because there wasn’t a big enough market for that product, and we let them go eventually. A bad, easily avoidable experience for everyone involved.
We pivoted to a different idea at this point after realizing this was a false positive.
Here's what I'd do differently, plus how I think about founder led sales and the first sales hire.
1. Sell it yourself long enough to separate luck from signal
Easy wins are great and you should enjoy them, but it’s important to know which parts were skill, timing, luck, intros and everything else.
A few questions I ask myself now, which I didn’t first time round are:
Are customers finding us, or are we finding them? If it's mostly inbound, what's driving it, and will it continue?
Can we attract and close a stranger who's never heard of us? That's the job a salesperson will be doing, so I should understand this before hiring.
Have we lost enough deals to know why people say no? This info helps with product development and building the go-to-market playbook.
If I can't answer these clearly, I know we don't need a salesperson yet and we need more conversations with users / prospects.
2. Learn how your customers talk
This is the part you can't outsource. In founder-led sales, you hear the exact language customers use to describe their problems in their own words, which other prospects in the same market will relate to.
Hiring a salesperson too early adds a layer between the feedback and you, which obscures the real insight.
The challenge here is to build in enough volume and speed to your initial outreach, so the conversations fall in a tight time period. It used to take weeks to run cold outreach through manual emailing / LinkedIn, but it’s much faster with the tools available today.
Tip - One Christmas, I viewed 4,000 LinkedIn profiles manually and wrote one interesting observation for each into a spreadsheet. By 1,000 profiles, I noticed patterns, by 2,000 I was fed up, but by 4,000 I knew these people and the industry connections cold. This made my outreach (cold calls) way more effective. It took 2-3 weeks in total.
3. Respect the craft before managing it
It's easy to believe the product will be so good it sells itself (this would be ideal in most cases).
But however good your product is, it’s true that you could always grow more by doing sales and /or marketing well.
You could have the best product with bad sales and marketing, and lose to a competitor with an average product and great sales and marketing.
You earn that respect for the craft by doing it yourself, not forever, but long enough to understand what you're asking someone else to take on.
By giving it a go yourself, you’ll build a muscle to understand what a good salesperson looks like. That knowledge creates a confidence you can’t fake, which new hires will notice during recruitment. This will help you attract better sales people to work for you.
4. Before you hire, write the playbook
When you can describe the sales motion clearly, write it down:
Who the buyers are: the types of companies, the job titles (together, called ICPs “ideal customer profiles), and the triggers that make them look for a solution
What works: the pitch that works best, how you demo the product, the objections you hear most often and how you handled them successfully
What doesn't: where people drop off and ghost you (includes hard no’s and nice no’s where people are too polite to say no!)
Timeline: deal cycle, how many steps are involved, what moves it forward
How you'll measure it: what does success look like at 30, 60, 90 days for a new hire
How you'll pay them: base, commission structure, what's realistic for your deal size and cycle
Build up this document as you go , and review it with your co-founders at the end of each week. Once you feel like someone fresh could start working from it on day one, you probably have the foundation to hire someone in sales.
5. Hire to amplify, rather than replace
Your first sales hire is unlikely to be a senior closer from the best company in your market.
Those people are already well paid and their transition cost of moving from an established commission structure into a new, cold position probably puts them out of reach early on.
Finding someone who can run the playbook you've built, who will give you honest feedback on what's working and what isn't, and will help you refine the motion rather than reinventing it is probably a good start.
Stay close, listen to, or join their calls where you need to, and review pipeline regularly.
I wrote this after a few people read my undercover pest control post and reached out asking about early stage customer conversations. Let me know what you’re interested in reading next.