Key Lessons for Early Sales Success

In 27 months, we grew Retention.com from $1M-$13M ARR with only 1 salesperson (me) doing 1,000's of sales calls. Here are my 10 biggest pieces of advice for any startup who wants to book and close more sales calls: 1. Ask for 15 mins, but book 30 When booking a meeting outbound, you have a better shot at getting a meeting by asking for 15 mins than 30. You may have piqued their interest but with a busy schedule, they are going to weigh learning about your business vs their time. Ask for 15 but send a meeting invite for 30.  If they can’t do the full 30, they will let you know, but from my experience, this rarely happens. 2. Tell your story People remember a story more than a product  Figure out your short story that you can tell prior to getting into the product pitch. How does your story connect to your business / product? 3. 5X5 Pitch Keep your product deck for your initial call to 5 slides / 5 minutes and make sure you answer any of the common questions you get from prospects. You can always book a follow up call to share more detail once you hook their interest. 4. Always Be Pitching Take control of the call and the sales cycle. You will only learn what does and doesn’t work by actually pitching.  5. Tell a customer story Again, people remember stories more than they do stats. Tell a story of a customer before implementing your product and the business outcome after implementing it. Don’t just talk numbers. Talk about how people felt, what they said, etc. 6. Create Urgency Attach an incentive if the deal is done by the end of the week or month.  (Example: 20% more credits or a 15% discount)  This also sets you up well for follow up as it now makes them feel like you are on their team to try and help them get the deal in for their benefit. 7. Land and expand We all want to close the big ACV deals, but the truth is most buyers don’t want to make a big commitment without seeing how your product works. Find a way to get them on for a small $ amount, with the plan to expand if the product meets their expectations. 8. Opt-Out Period Reduce buyer friction by offering a 90 day opt out period if you are trying to close 12 month agreements. It shows confidence that your product will drive the results you say it will. 9. Deck Recap Create a 1-2 pager highlighting the most important parts of your sales deck that you can send via email after every call (even if they don’t ask for it). The prospect won’t remember all details from the call, so this gives them something to look back on and will help sell internally if other stakeholders are involved. 10. Video for FAQs Create short form talking head video answering all FAQs. This will add value in your follow up, show you listened to the questions they had and that you care about making sure they understand the answers. It also helps internally as others will likely have the same questions as the person on the phone. Have questions about how to book/close more calls? AMA anything 👇

Conor's Startup Sales and Marketing Playbook™ I’ve been asked what our early playbook was and I thought it would be helpful to share. **When we were acquired for $70M, we had ~ $10M in ARR growing ~60% with 86% gross retention, 116% net retention, really good sales and marketing efficiency, and had done so with very limited investment ($4M). We are now north of $50M in ARR.** ----- STEP 1 - GET PEOPLE TO COME TO YOU 1️⃣ We turned our data into research that people subscribed to. Customers that come to you have more trust. This leads to higher retention, better profitability, and greater likelihood of signing up. 2️⃣ Be the first plumber to respond. ~70% of customers choose the first vendor that responds to them. Be first. Anybody who downloaded our research was sent directly to my inbox. I tried to email them within 5 minutes with a personalized message. 3️⃣ Get on the plane. I was on a plane constantly and filled my calendar as much as possible while on the road - 5-10 meetings a day. Nothing replaces face time. Getting on the plane also creates a sense of urgency for meeting while you are in town. 4️⃣ Meet with everyone. Helping someone that can’t help you creates a deep meaningful connection and creates a powerful reputation for you in the market. It's also just a nice thing to do. I would meet with students, teachers, consultants between jobs, influencer marketing enthusiasts. If you subscribed to our newsletter, I tried to be helpful. They told their friends, etc. STEP 2 - DON’T SELL. DELIVER VALUE. 5️⃣ Extreme preparation. Even if I was meeting for coffee, I would come into the conversation having researched the person, their brand, and their competitors. I would even print and bind the research. This made a very strong impression particularly when they didn't expect to receive the research. 6️⃣ Value first. I would never talk about what we do unless asked. I would center all of my attention on delivering value in the conversation. Helping people learn and get better. Inevitably they will ask, “How does this work? What are the next steps?”. This is much much better. STEP 3 - LONG TERM VIEW 7️⃣ 95% of customers aren’t buying today. Don't force a sales conversation. Let them come to you when it is the right time, but stay top of mind with regular touch points. Deliver value in every interaction (here is some new research, we’re holding a really cool event, etc.) 8️⃣ Focus. Sign up the right customers for the things you are best at. 70% of our new customers are either a referral or a user that brought us with them to a new company. Ensure that everyone you bring in is very likely to have a good experience. This compounds over time and creates trust. I turned a customer down for not being an ideal fit and they invited me on their board. I hope that was helpful! I'm happy to help anyone that is early in building their company. Just shoot me a message or comment. Onwards and upwards 🚀

In less than 4 years, I went from an AE to VP of Sales at a $960M tech startup. Here are the 8 hardest lessons I learned about startup sales: 1. Hire AEs with different backgrounds EARLY This is the best way to determine the ideal rep profile before scaling. Stop hiring from just your network or the Old Boys Club. I was an ex sales engineer. Our best SDR was a failed startup founder. Can't test what’s working without hiring people from different backgrounds. 2. Set realistic quotas Nothing ruins morale like losing. A winning culture starts with realistic quotas, where top reps make a TON of money and friendly competition is infectious. Shoot to have 80% of reps at 80% attainment. 3. Deep Product Knowledge is Overrated Understanding the problems and goals of your persona + competitive landscape is FAR MORE important than deep product knowledge. Spending weeks going deep in the product is counterproductive. The best reps will discover what they need to learn to win. 4. Invest in RevOps and enablement ASAP Don’t just pay lip service, actually DO IT. I remember setting up Salesforce myself by watching Youtube videos. But better yet, pay a pro to get things right and let the team spend their time with prospects/customers. As for enablement, your reps are more confused than you think! 5. Win/Loss Analysis is Worth Paying For We were nerds with our data and tried to do this in-house. It didn't work. What your AE's put in your CRM is helpful, but only an external party will get the full truth. The first project allowed us to change our pitch deck and increase our outbound meeting to opp conversion 20%. 6. You Are Not Actually Enterprise-Ready We got pressure to hire the classic $350k OTE reps and drop them in major markets. Was a total bust. In the early stages, your company just doesn’t have the resources to make them successful (industry experts, overlays, PS resources, deep solutions bench, etc). 7. Money and Equity is Not the ONLY Solution for Retaining Top Talent I’ll never forget when our new COO asked me, "Do you know what each of your reps is motivated by *besides* money?” Have a cadence to ensure you understand what makes your top performers tick. Find out what they want to learn, who they want to get mentored by, what flexibility in schedules, or side projects motivate them. Then help them get it. 8. Don’t Be Afraid of Senior Leadership Your job is to make the C-suite successful. When we moved on from our first VP-Sales and our new CRO started, I went to him and said - Here is what the team is ACTUALLY feeling and thinking, here are the people that have weight in the organization, here is what I see are the biggest risks. Making your boss successful will help you AND your company. TAKEAWAY: Look, even if you do everything right… Startup sales is hard! You’re going to make a ton of mistakes. I know I did. The key is not making the same mistake twice.

I’ve gone $0-1M ARR three times as CEO. Here’s how you find your first 10 customers: 1. Start with warm intros from your network Forget cold email, ads, or other “scalable” tactics. You haven’t earned the right to scale yet. You haven’t proven that what you do even works—let alone that it scales. And you’re not ready to hire a Head of Sales or even a rep. In the zero-to-10 phase, you are the best (and only) seller that works. Your early traction will come from warm intros. No network? Then borrow one. Lean on your investors. Tap advisors. Ask for 10 intros, not advice. Your first 50–100 customers can all come from warm referrals. Save “scalable” for later—when the model’s proven, you’ve got budget, and your personal + investor networks are fully tapped. 2. Find your “1 in 100” buyer Most founders waste time chasing decision-makers. But your first 10 customers won’t come from job titles—they’ll come from personalities. You need believers. People who want to be first. The ones who light up when they see something new. The ones who forward it to 5 teammates, unprompted. These buyers are rare. But they exist in every market. They’re not just early adopters. They’re internal disruptors—with just enough political capital to get your weird, half-baked product through the finish line. They’ll move fast. They’ll tell you the truth. And they’ll help you scale, not just sell. I call them change agents. They’re startup gold. 3. Be radically transparent If your product is fully baked, you started selling too late. Early customers know they’re buying something unfinished. So don’t pretend you’ve got more than you do. Lead with the problem you’re solving. Show them what’s real—and what isn’t built yet. The right change agents want to co-create the future. 4. Ask your early customers to help. After the sale, stay close and learn from your customers. They’ll understand their problems way better than you do. Listen to how they talk about their problem, your solution, and it’s benefits. Take notes on their product usage and feature requests, listening for the things more customers may want. Your best source to find customers 4-10 is customers 1-3. They’ll know who at the next company will want to solve the same problem. Have any questions about going $0-1M? Or finding your first 10 customers? AMA in the comments 👇

As startups scale, effective sales implementation becomes the difference between stagnation and sustainable growth. After analyzing hundreds of sales organizations across startups, I’ve distilled the key pieces of advice that founders and leaders should keep in mind. 1. Sales Strategy Fundamentals - Start with the right price: Establish pricing that reflects value rather than just covering costs. - Define your ICP: Clearly identify your ideal customer profile before building your sales process. - Understand sales velocity: Recognize that sales success depends on both deal size and deal frequency—optimize for predictability. Your first sales hire should generate predictable and consistent revenue, not just hunt elephants 2. Team Structure - Build a complete sales organization: Structure your team with marketing, SDR/ADRs, and account executives with clear handoffs. - Choose between top-down or bottom-up: Determine whether to pursue enterprise-led or product-led sales motion. - Invest in sales operations: Create systems that maximize selling time and minimize administrative burden. Effective sales organizations separate lead generation, qualification, and closing responsibilities 3. Pipeline Management - Calculate required pipeline coverage: Pipeline is prologue. Maintain a pipeline that’s at least 5x your bookings target. - Master lead qualification: Develop clear criteria for MQLs, SQLs, and PQLs to maintain quality. - Analyze conversion metrics: Track conversion rates at each funnel stage to identify bottlenecks. 4. Sales Process - Implement Challenger selling: Train reps to teach prospects, tailor messaging, and take control of the sale. - Map key stakeholders: Identify champions, opponents, decision-makers, and influential stakeholders. - Create a consistent demo: Develop a compelling product demonstration that clearly shows value and addresses pain points. Great salespeople don’t just ask about problems—they teach customers about problems they didn’t know they had 👉 Read the full post here: https://lnkd.in/gePqUC3g