How to Transition From Founder-Led Sales

Founder friend of mine called last night to pick my brain on transitioning from founder-led sales -> building a sales team. Have had this convo dozens of times, and always top of mind for first-time B2B Founders, so here are my thoughts: DO:  ✅ Close at least $100k-$200k ARR yourself before bringing on AEs to help. It's important to have a repeatable motion before you train someone else to do it.  ✅ Hire 1 AE you have extreme confidence in and do everything you can to make them successful or 2 AEs and have them start at a similar time. 2 AEs is generally safer because if 1 AE isn't working out, it de-risks whether it's the AE or your product-market-fit that's broken.  ✅ Make sure the AEs you bring onboard 1) are experienced hunters who are going to build most of their own pipe 2) have experience with a similar motion (e.g., sales cycle length, ACVs, selling to LoB, etc.) and 3) industry experience optional IMO (vs #1 & #2), but a nice bonus.  ✅ Once you hire AEs, give them all your pipe, try to make them wildly successful, and start to think of yourself as a super-SC 💪 ‎ DON'T:  ❌ Don't bring on a sales rep because you're struggling to figure out sales**. A lot of founders think they're struggling to do sales because they don't have the right sales experience, but 9 times out of 10, it's because you haven't figured out PMF.  ❌ ‎Don't hire a VP Sales right away. Most VPs are going to want to hire & scale and you're not ready for that. You need to prove that you can get a few AEs selling instead of a founder first.  ❌ ‎Don't hang onto all the deals once you bring onboard your first 1-2 AEs. Too many founders cling to all the deals they're working or the most important deals that come in to increase the odds of closing them, optimizing for short-term revenue. That's short-sighted. Once you have AEs, your only priority is to de-risk whether someone else can do sales, bc then you can add more 🚀  ❌ ‎Don't be completely hands-off either. Reverse-shadow in the first 1-2 months, continue to inspect every deal in forecast calls, and have them tap you in for their most important deals (esp. with economic buyers).  ** As a founder, you're going to be the best salesperson for your company because you can share your vision, you deeply understand your product & customer, can promise features on the spot, etc..  -> the two places AEs are going to be better than you are 1) qualifying out deals not worth their time (as founders, we think every company should use our product 😅 ‎) and 2) negotiation. Never be in the room while your AE is negotiating 👎 ‎ Bonus early-stage GTM benchmarks from Gem‎:  - Year 1: $100k -> $1M ARR in 9 months with 2 AEs  - Year 2: $1M -> $4M ARR with 4 AEs  - Year 2 (early): added marketing (dir demand gen) and SDRs.  - Year 3-7+: 🤐 ‎ Wdyt? For founders scaling from 0->$1M does this match what you're seeing? Founders who have found PMF and scaled past $1M, keep me honest. What did I miss?

Want to know the right time to transition from founder led sales to hiring a team? Well I have done it 4xs. Every time, there came a moment when I thought: "Maybe it’s time to hire a salesperson and get out of the way.” And every time I learned the same thing the hard way: 👉 You don’t get to skip founder-led sales. Not at $500K. Not even at $1M. Not until you’ve sold enough yourself to really know what’s working—and what’s not. If you’re trying to get to $1–2M in revenue, I’m going to say this plainly: Don’t let anyone but the founders sell. It’s not about saving money. It’s about learning fast, firsthand, and making sure you actually have something that can be sold repeatably. Here’s what’s worked for me (and what I’ve learned by screwing it up): 1. Do the First 10–20 Deals Yourself This is where the gold is. You learn what objections sting. What pitches land. What words buyers actually use. If you outsource this, you’ll miss the entire roadmap. 2. Build a Sales Process (Even if it’s ugly) It doesn’t need to be polished. Just write it down. If you can’t explain how a deal gets done, don’t expect someone else to figure it out for you. 3. Hire 2 Reps, Not 1 You need contrast. Without it, you don’t know if your process is broken or the rep is. Plus, one rep alone will always feel like a coin toss. 4. Sit in the Deals With Them Don’t throw people into the deep end. Show them how you do it. Let them try. Trade notes. Iterate. Co-selling is how you scale confidence. 5. Hire People You’d Buy From Seriously—would you let this person handle your top lead? If not, don’t hire them. No matter how good their resume looks. 6. Be Generous With Equity for Early Reps They’re betting on you. If they crush it, they deserve a meaningful piece. Some of the best people I’ve worked with weren’t founders—but they acted like it. Reward that. 7. Record Everything. Use the CRM. If it’s not recorded, it doesn’t exist. And without tracking, you can’t improve anything. 8. Promote From Within Whenever You Can Some of my best sales leaders started as reps. It works because they’ve been there, and they earn real trust from the team. 9. You’ll Never Fully Leave Sales Even when you have a full team. Even with a great VP of Sales. You’ll still get pulled in. That’s okay. Just expect it—and plan around it. 💡 Here’s one trick that helped me stay close without being a bottleneck: I gave each rep 4 “founder call tokens” per week. They could cash them in anytime. No questions asked. It made it clear I wanted to be involved—just not in every single call. You don’t need to scale sales perfectly. You just need to scale it deliberately. Most of what I’ve figured out was through trial, error, and picking up the pieces after something broke. But if you’re in the middle of this transition now—happy to swap notes. Let me know what you’re learning 👇

The hardest transition B2B startups go through is moving from founder-led sales to a hired sales person. Unfortunately, almost everyone gets this wrong. A founder has several advantages when selling. Beyond knowing the product inside and out, they control the product roadmap. This gives founders the power to adjust the pitch and even promise features on the fly. While helpful in the early days as a way of building for the customer, this approach clearly does not scale beyond the founder. The first sales hire you bring on, no matter the seniority or experience, cannot be driving your roadmap. They likely also aren't intimately aware of exactly how the product was built. As a result, they can't mimic the founders product-led and adaptable approach to sales. And even if they could, playing quasi-product manager isn't really how most salespeople thrive. The way to ensure that your first professional salesperson succeeds is to make sure you have a defined value prop, a structured sales pitch, and a clear product to sell. When they have this they can leverage all of their sales experience and knowhow to dramatically accelerate revenue. And this brings me to why the transition from founder-led sales to the first sales hire fails so often. It is not just a change from one person selling to another. It is a total transformation of the sales process. So how do you avoid the mistakes so many of us have made during this transition? I have seen two things work. But both of them require an explicit understanding that everything sales needs to change for the transition to work. Option a: Start by changing how you as the founder sells. Define the sales pitch, put structure around the product, show that you can sell without leaning into the founder advantages. When you can bring on new customers in this way you are ready to hire your first professional salesperson. Option b: My preferred option is to hire someone as a bridge to go through this transition. I have found that a generalist with a product bent and lots of hustle, can start selling in a way that is a hybrid of what a founder does and what a sales person does. The focus should be on adjusting the sales motion and focusing on how to turn the founders unconstrained pitch into a more structured one.

I recently spoke with an early-stage AI app founder who was desperate to hire sales reps because he dreaded founder-led sales. This is one of the most common failure modes I see with technical founders—and it significantly impedes the path to product-market fit. Here's how to think about the right order of operations in early sales motions: Phase 1: Prototype & Validation In the earliest stage, the feedback loop between customer conversations and product roadmap must be extraordinarily tight—making founder-led sales absolutely non-negotiable. This phase is critical because you're identifying your true ideal customer profile (ICP) and learning how to effectively communicate your product story and address common objections. As you accumulate hundreds of demo repetitions (while refining your product based on feedback), you gradually assemble a winning process. Phase 2: Founder-led Sales Scale-Up Your mission here is to create the sales playbook that will guide future reps. You need sufficient pattern recognition to understand which messages resonate with which personas. I recall meeting Desmond Lim, CEO of Workstream, several years ago (not an Emergence portfolio company, but I deeply admire what they've built). He showed me the remarkable 60-page playbook he crafted documenting their entire sales process—before hiring a single AE. Every nuance. Every objection. Everything a new rep would need to succeed. While perhaps extreme, this perfectly illustrates the principle: scaling go-to-market requires mastering your ideal sales motion before delegating it. Phase 3: Hiring Initial Sales Reps Most founders default to sequential hiring—start with one rep, evaluate results, then proceed. However, we recommend hiring 2-3 sales reps with diverse backgrounds simultaneously, enabling you to effectively A/B test different profiles. Regardless of approach, ensure these early hires are "renaissance reps" with rapid iteration capabilities rather than purely "coin-operated" sellers. Mark Leslie has a great foundational article on the Sales Learning Curve provides excellent guidance. I'll link it below. So embrace the early sales work, even when it feels uncomfortable. It's fundamental to building a foundation for lasting success.

Most founder-led sales efforts fail. Let me be direct - most founder-led sales strategies fail miserably. Not because founders aren't smart or capable, but because they're making the same critical mistakes I've seen destroy hundreds of early-stage companies. And I can tell you that in 2025, founder-led sales is harder than ever. I've helped 150+ SaaS companies scale from $0 to $25M+ in ARR, and just had my 12th exit. Here are the exact reasons why most founder-led sales efforts fail, and more importantly, the proven framework to fix it. This isn't theory - these are battle-tested strategies that have generated billions in enterprise value. 1. The Product-First Trap Most founders think great product = great sales. After working with companies like Salesloft and Gong, I can tell you that's dead wrong. Here's why: - Your product expertise is actually hurting your sales - You're attracting tire-kickers instead of qualified buyers - You're leading with features instead of business outcomes Without a clear value-based sales motion, you'll burn through runway chasing bad-fit customers. Document your ideal customer profile and their top 3 business pain points. Stop talking about features until you validate these pains. 2. The "Wing It" Approach Most founders have no structured sales process. They: - Handle each deal differently - Have no clear qualification criteria - Can't accurately forecast revenue even a month out Without a repeatable process, you can't scale beyond founder-led sales. Map your current sales process and identify where deals get stuck. Create a basic sales playbook with qualification questions. 3. The Time Management Crisis Founders try to do everything: - Jumping on every call - Responding to every note - Never delegating sales tasks You're creating a bottleneck that will kill growth. Track your sales activities for one week. Identify low-value tasks you can automate or delegate. 4. The Wrong Metrics Most founders track vanity metrics like: - Email activity - LinkedIn dms - Number of calls Instead of focusing on: - Average deal size - Sales cycle length - Conversion rates by stage You can't improve what you don't measure correctly. Set up basic pipeline tracking in your CRM with clear stage definitions. 5. The Scaling Too Soon Syndrome Founders rush to hire sales teams before: - Creating proper onboarding - Having a proven sales process - Building sales enablement materials Premature scaling burns cash and kills momentum. Document your successful sales plays and create a basic onboarding checklist. Look, founder-led sales doesn't have to fail. But you need to act now. In 2025's market, you have 12 months or less to prove your sales model works. If you're ready to build a predictable revenue engine for your SaaS company, click the link below to join thousands of other startup founders and executives and sign up for my newsletter full of battle tested tips to grow your business.