The Ultimate Sales Guide for Startup Founders (From $0 to Repeatable Revenue)

INTRO

Most startup founders struggle with sales—among many other reasons, we often find if they've never done sales, they don't even know where to start. This post is your crash course.

No more reading tons of books, watching countless videos, and following influencers that have nothing to do with the product you sell.

Whether you're pre-revenue or doing $1M+ ARR and thinking about scaling your GTM motion, this guide walks you through the real sales motion required to go from founder-led selling to a repeatable process.

WHAT YOU’LL LEARN

• Why most founders confuse marketing problems for sales problems
  
• How to run a real sales process (from first call to signed contract)
  
• The risks of scaling too fast and hiring reps too early
  
• How to find your first customers (with or without a platform)
  
• When to stay SMB vs. when to move upmarket
  

CONTEXT: WHY THIS MATTERS

Founders often focus on their product, it's their baby afterall. Aside from everything that goes into making a good product (that actually solves a REAL problem), most founders feel as if once they finally complete that product, the rest will take care of itself.

As you start to try and attract new customers through marketing, sales emails/calls, and other means, you start to realize that sales is a different beast entirely.

You need real talk about founder-led sales: what works, what breaks, and what to do differently at every stage. In this podcast, Eric Finch and Kris Hari break down the exact sales advice they wish they had before starting Higher Levels—and the playbook they now teach to VC-backed and bootstrapped founders alike.

If you haven't done the sales motion yourself and think you can just hire a sales person to figure it out, you're just setting them, and your company, up to fail.

SALES VS. MARKETING: STOP CONFUSING THE TWO

Most early stage founders think they have a sales problem. In reality, they have a marketing problem. You don't even have a system in place to consistenly attract new customers.

If your cold calls don’t land, if nobody replies to your emails, if your funnel feels empty—it’s probably not your pitch. It’s that nobody knows who you are or trusts you enough to take a meeting.

Founders often try to skip steps. No website (or horrible looking website), no credibility, no audience—yet they expect reps to book meetings and close deals on their behalf when they don't even know how.

It doesn’t work that way. Your job early on is to build trust, visibility, and proof. That’s marketing.

Pending where you are at as a founder, this could be starting to post consistently on one platform. This could be building a reputable site that's not a simple squarespace template. You could actually have a reputable and useful blog and/or case study section on your website that highlights how you're actually solving meaningful issues for people.

Get a solid website in place, and start building something that makes your offer credible.

Pick 1 or 2 things max that you are naturally good at. Spend all day on YouTube? Start making content there. Do you interact with a ton of founders on X or LinkedIn? Start building a presence there.

LinkedIn posts, YouTube tutorials, a basic website, a warm intro. It’s not about looking polished. It’s about proving you know what you’re doing. If you have absolutely no collateral or social proof, it is increasingly more difficult to get noticed.

What almost all founders have to face is that building a repeatable and scalable marketing engine takes time. In many cases you know what you have to do, but aren't willing to put time and energy into it for 6-12 months to get consistent groundswell.

But that's marketing. Let's say you're consistently now getting 3-5 new leads per week taking a phone call with you and struggle to convert them.... now you have sales problems.

#1 MOST COMMON SALES MISTAKE: PITCHING TOO EARLY

Founders get excited. You’re passionate. You want to show your thing. But most of you are pitching way too soon.

The first rule of selling is don’t pitch before you understand everything about your prospect and the problems they are experiencing.

• Do they even know the problem exists?
• Are they ACTUALLY experiencing that problem today?
  
• How are they solving it today? Have they tried to solve it before? Why Not?
  
• How painful is it, really?
• Who does it impact?
• What happens if they don't fix that a year from now?
• etc....
  

Instead of solving their problem on the call, you spend at least 2/3rds of your time asking them questions about what they do and why. It shows you're actually trying to understand them and solve their problem.

Now once you've actually taken the time to understand them, your presentation, even if it's only 5 minutes at the end of a call, will hit home and lead to exponentially more prospects being interested in starting a trial and/or buying your product.

WHAT A REAL SALES PROCESS LOOKS LIKE

If you're selling B2B, here’s what the actual sales process looks like:

1. Initial Call — Discovery, not pitching. Qualify hard.
   
2. Technical Deep Dive or Demo — Match to their use case.
   
3. Proof of Concept or Trial — Define what success means before starting.
   
4. Follow-Up Calls — Validate progress. Set clear next steps.
   
5. Procurement & Legal — Plan for this early. Don’t wait until it blocks the deal.
   
6. Signed Contract — Only happens if the above was tight.
   

Big mistake? Giving trials with no end date or success criteria. If you don't define what “a win” looks like and when it needs to happen, you’ll end up with silent trials that never close.

Just because a customer wants a trial doesn't mean they'll actually be successful using it. You need to hold firm that you're happy to give a trial once you scope out a 2 week trial run.

What will they test? Why? What outcomes would determine that it is successful? Who would ultimately purchase when the trial is successful and you want to move it to production?

SMALL BUSINESS VS. ENTERPRISE: KNOW YOUR LANE

Everyone wants to sell to Enterprise. Few are ready.

• SMB deals are faster, scrappier, and founder-access is immediate. If you're selling something like AI, smaller companies are way more willing to take chances on exploratory technology.
  
• Enterprise deals are slower, more political, and require security reviews, compliance (like SOC 2), and multiple stakeholder approvals.
• Enterprise deals take on average 12-24 months, whereas a small company may be willing to buy after a month or two long deal cycle.
  

If you're crushing it in SMB, don’t sprint upmarket just to impress your investors. Exhaust the segment first. Use those wins to build case studies. Then make the jump with real leverage.

You think you're moving upmarket by targeting 'big' and 'sexy' logos, but more often than not you're actually slowing down your momentum.

HOW TO FIND YOUR FIRST CUSTOMERS

No cold call script will save you if your offer lacks clarity. Early customers usually come from one of three paths:

1. Warm intros from your network or investors (but be specific—do the work for them)
   
2. Posting valuable content online (LinkedIn, YouTube, niche communities)
   
3. Partnering with creators who already have your audience (with affiliate or rev-share deals)
   

Don’t just ask “who should I reach out to?” Start by asking: “Who already trusts me—or would trust me if I showed up consistently?”

VC-BACKED VS. BOOTSTRAPPED SALES STRATEGY

VC-backed founders feel pressure to scale fast. But fast doesn’t mean smart.

• You’ll be asked to spend on reps, ads, and infrastructure before you’re ready.
  
• You'll waste money on 'experiments' that you could have tested for free by posting on your own beforee trying paid ads.
  
• If you’ve never hired or trained reps, you’re about to burn a lot of cash.
  

Bootstrapped founders? You’ve got less money, but more control. You can run tighter tests, move faster on insights, and actually build a process before hiring reps.

“VC gives you money. Bootstrapping gives you clarity.”

DON’T SCALE UNTIL YOU’VE EARNED IT

If you’ve never sold the product, don’t hire five people to try.

Founder-led selling is a prerequisite to repeatable sales. You need to build the first version of the process, close early customers, and understand what objections are real.

When should you hire?

• When your calendar is full of sales calls and you’re dropping the ball elsewhere.
  
• When you’ve built a repeatable playbook that consistently works, and another person can follow.
  
• When you know how to train someone on your product and pitch because you've done it yourself.
  

Otherwise, you're just hiring people to fail.

FAQ
Q: Should I hire a sales rep if I’m still figuring out product-market fit?
A: No. Do the selling yourself until you’ve closed at least 10–30 deals and identified repeatable patterns.

Q: What’s the biggest sales mistake new founders make?
A: Talking too much. They pitch too early and don’t ask enough questions to qualify the buyer.

Q: How do I sell if I have no personal brand?
A: Partner with creators who do, or start posting value-driven content in niche communities to build credibility.

Q: What’s the difference between sales and marketing?
A: Marketing is everything before the prospect engages. Sales is everything after.

Q: When should I go upmarket from SMB to Enterprise?
A: When Enterprise buyers start coming to you—or when you’ve fully saturated the SMB segment with clear case studies.
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→ If you're a founder building out your GTM motion, join our Founder-Led Sales Accelerator. We work directly with founders at all stages whether you are acquiring your first 10 customers or systematizing your GTM and scaling out.

TL;DR

• Most “sales problems” are actually marketing problems
  
• Don’t pitch until you’ve asked real questions
  
• Run a real sales process from first call to closed deal
  
• Know your segment—don’t rush into Enterprise
  
• Start small, earn your process, then scale with reps