Mastering Founder-Led Sales: Advice We Give to Our Founders

Founders are uniquely equipped to sell their products, but that doesn't mean it's easy. We gathered tips to master founder-led selling.

Article by
Tatum Lynch
Picture of the High Alpha logo on top of a blue forest background.|Picture of the High Alpha logo on top of a blue forest background.|

Founders have many priorities when starting a company: fundraising, building the minimal viable product (MVP), attracting top talent, and the list goes on. Your time is spread thin, but founder-led selling must be a priority. Why? No one else can sell your product better than you can.

Founders are uniquely equipped to sell their products. You understand the market, customers’ pain points, and what the product needs to do to generate traction and achieve product-market fit. But we know not every founder has sales experience, and even if you do, you’re most likely selling something that may not exist yet. We gathered some concrete tips from our own experience to master founder-led selling and help you manage the transition to hiring full-time sales talent. Let’s get into it.

Tip 1: Talk to As Many Customers As Possible to Validate or Invalidate your Point of View

To succeed at founder-led sales, you must have a clear vision of your problem, who you're solving it for, and why. The best way to do this? Talk to as many potential customers as you can. We recommend our CEOs have 100 conversations in 100 days. 

It is critical to have a point of view which can be tested. Talking to customers without a plan or experiment in mind will not reveal answers. It will make things more confusing. 

As you talk to potential customers, you must be intentional about the questions you ask. At the end of the day, you must determine (1) if the problem exists and (2) if your customer finds that problem meaningful. If your potential customers easily recognize the problem, have a budget set aside to solve it, or are measuring it in any way, you’re on the right track.

Tip 2: Don’t Sell Your Product or Yourself Too Short

As I said before, founders uniquely have all the resources they need to master founder-led sales. You understand your customers better than anyone, which equips you with the tools to be your company's best sales rep. All that to say, be confident in yourself when you go to sell. You are the best person for the job.

Your job as a founder is to create a new and better future for your customers. If you aren’t confident in your ability to deliver this, your prospects will know, and they will not buy from you. Lack of founder confidence is the number one thing inhibiting founder sales success.

And when you do go to sell, don’t sell your product too short. It is much more common for a founder to share in hindsight that they priced their product too low, not too high. Price is a proxy for value, and many customers will assume a cheap product is not a very good product. Of course, don’t overcharge a customer. But don’t sell yourself short, or else someone else just might. 

Tip 3: Personalize Each Product Demo

Similar to how you write tailored resumes for each job you apply to, you must present a different demo to each potential customer. Why? For the same reason: you want to prove that you (and your product) have the best capabilities to do the job.

Each customer will have a different set of circumstances when tackling your problem. Personalizing your pitch to demonstrate how your product will better their organization will go a long way. 

Tip 4: Look to ARR to Determine If Your Founder-Led Sales Strategy Is Working

Okay, so how do you know if your founder-led sales strategy is working? The ultimate metric you must measure against is annual recurring revenue (ARR). A high-quality product will command a high price and customers will commit to multi-year agreements. Investors consider this to be “high quality” ARR and will help you when it comes time to raise funds.

When I asked our Director of Go-to-Market Egan Montgomery which benchmarks founders should measure against, he said, “Founders with an SMB focus should plan to sell between $250-500K ARR, mid-market between $500-750K ARR, and enterprise between 750K-1M ARR.”

Other leading indicators are qualified pipeline and the number of first-time conversations, but ARR should be your prioritized metric. If you’re not hitting these numbers, you’re not solving the right problem. Go back to the drawing board and dive into more customer discovery work.

Tip 5: The Transition from Found-Led Sales to Hiring Sales Talent Should Not Be a Flip of the Switch

Let’s set the record straight. Founders should never fully be out of the sales process. When you’re starting to hit the appropriate ARR targets, you can begin hiring sales talent, but the transition to req selling is a gradient transition rather than a flip of the switch. 

Once our founders hit their ARR targets repeatedly, we recommend they hire two sales reps that they can manage. The founders continue to do the selling as the sales reps observe and organize the back-end work. After a while, the reps can start leading more deals while the founder observes. Once the reps hit quota repeatedly, founders can hire a sales leader to manage the cycle and scale the team.

Final Thoughts

Founder-led selling is crucial to the success of your business. If you can’t sell your product, no one can. You have the right tools and resources to sell your product and adapt it if needed, so be confident in yourself and get after it.

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