Blake J. Harber’s Post

𝗦𝗮𝗹𝗲𝘀 𝗶𝘀 𝗮 𝘀𝘁𝗿𝘂𝗴𝗴𝗹𝗲 𝗳𝗼𝗿 𝗺𝗼𝘀𝘁 𝗳𝗼𝘂𝗻𝗱𝗲𝗿𝘀. No secret there. As a multiple-time founder myself, I’ve always felt like sales was a lonely game. Sure, you’ve got co-founders, but when it comes to sales, finding good peers to share the grind with? That’s rare. As founders, we’re responsible for so much, but staying consistent with sales always felt like the toughest part. But here’s the thing: it’s not that founders don’t know how to sell—we’re often the best salespeople because we 𝗹𝗶𝘃𝗲 the product. The real issue? We don’t give sales the consistency it demands. 𝗔 𝗳𝗲𝘄 𝗺𝗼𝗻𝘁𝗵𝘀 𝗮𝗴𝗼, 𝗲𝘃𝗲𝗿𝘆𝘁𝗵𝗶𝗻𝗴 𝗰𝗵𝗮𝗻𝗴𝗲𝗱 𝗳𝗼𝗿 𝗺𝗲. I got an invite to join a group of fellow founders who met every week—in person—to tackle their individual sales challenges. We dedicated the entire morning just to outreach. It felt like an epiphany. 𝗦𝘂𝗱𝗱𝗲𝗻𝗹𝘆, 𝗜 𝘄𝗮𝘀𝗻’𝘁 𝗮𝗹𝗼𝗻𝗲 𝗮𝗻𝘆𝗺𝗼𝗿𝗲. The focus and accountability were game-changers, yes. But what truly hit me was the energy. Working alongside peers who were facing the same challenges, made sales not only less isolating—it actually became fun! Week after week, we showed up, pushed each other forward, and took on the grind together. I walked away with more clarity, more energy, and—most importantly—a consistent habit of working on my outreach. If you’re struggling with sales as a founder, this might just be the breakthrough you’ve been searching for. Find your squad. Share the grind. And watch how a simple shift in focus transforms not just your sales—but your entire mindset. ------------------ • My name is Joost Prins 🤴 • Catalyzing Founders' Sales Success with PeerSessions 👊🏻 • Join one of our founder sessions and let's grow together 🍀🚀😃 • PeerSessions Events: https://lnkd.in/ezEaPiza

Now that I’m a pre-seed founder with no income, I’ve downgraded my commute from Uber to the MTA Bus. It’s humbling but also taught me a lot so I decided to share the biggest lessons I’ve learned from eating this humble pie. 🌟**What Taking the Bus in NYC Taught Me About Enterprise Sales**🌟 Ah, the New York City bus. A beacon of efficiency and comfort. No delays, always on time, and the perfect place to learn about enterprise sales! 🚌💼 1. **Patience is a Virtue:** Just like waiting for that elusive client decision, waiting for the bus teaches you that time is just a construct. Why rush when you can enjoy the scenic view of the same block for 20 minutes? ⏳ 2. **Building Relationships:** Every bus ride is a networking opportunity. Whether it’s the person sharing their life story with you or the one falling asleep on your shoulder, these encounters are invaluable for honing your people skills. 🤝 3. **Handling Rejection:** When the bus doors close right in your face, it’s just like losing a deal you were certain you’d win. Brush it off, wait for the next one, and hope for a better outcome. 🚪❌ 4. **Strategic Planning:** Navigating the bus system requires a level of strategic thinking akin to planning a multi-million dollar sales pitch. One wrong move and you end up in Staten Island. 🗺️ 5. **Optimism:** The sheer optimism of believing the bus will come on time, despite all evidence to the contrary, mirrors the unwavering belief in closing that impossible deal. 🌈 So next time you're frustrated with your sales pipeline, just hop on a bus. It's basically a masterclass in enterprise sales. 🚍📈 #SalesLessons #EnterpriseSales #NYCBus #LinkedInInfluencer #TotallySeriousPost

Don’t take a startup sales job if the founders weren’t the first salespeople. Founder-led sales is a necessary first step. I don’t mean selling a few accounts to their buddies. I mean founders crafting, perfecting, and proving a repeatable sales process. After they’ve proven it can be done, they need to prove it can be replicated. This is where “Founding AE’s” enter the chat. After the founders prove a repeatable sales process, they need to prove they can teach it and replicate it with a couple AE’s. Founding AE’s are a different breed. They don’t just follow a playbook. They take the founder-led playbook and make it work for non-founders. Yes, founder clout makes it easier and founding AE’s need to overcome that. It’s through this process that an achievable quota becomes established. It’s not easy. But it’s a lot easier when your founders somewhat comprehend the challenge. If the founders were too scared to sell it. You should be too. Ignoring this detail almost always results in a disconnect between founder expectations and the sales team’s reality. You’ve been warned.

Ok so you’re the hot sales exec who finally gets to run the whole thing. You know you aren’t ready but who is ever ready for their first top job? All about how you approach it. But now you’re El Jefe! Yay. You’re a rocket ship all about hiring and growing, hot product, market pull, yada yada. Top of the mountain baby. The superstar you always knew you were. Then one day, you miss a quarter badly, don’t really know why, Founder says hey, we have no process or instrumentation and half the team sucks. You built too fast and I’m topping you. What do you do? Most people pout and bail. The right answer is not obvious. Very recently with some of the better startups around, I’ve seen the person stay and study and learn from the person who topped them, at least for a year. Sometimes longer. Luke Skywalker needed more time with Yoda. So do you. You’re never as good as you think you are and I personally study my competitors to learn from them every day and consult with industry “elders” regularly in both VC and search. The opportunity to learn is a GIFT. Don’t squander it because your ego couldn’t handle it.

If you hire your first two sales reps in your startup, do not tie their commission to individual targets You have absolutely 0 idea what those targets should be And it will be massively discouraging What I did instead: In the first 9-12 months, we set a quarterly target for the whole team (incl. CRO, CEO, partners) We sit together end of quarter to discuss the target for next quarter It is usually a mix of pipeline and ambition So that we definitely believe we can achieve it based on pipeline And the target is ambitious at the same time Whatever percentage we reach of that target, everybody gets as commission At the same time, we do calculations of how many opportunities everybody needs to open and how much weighted funnel we need for next quarter Those numbers we set as soft individual goals We need to have those top of mind And still track individual success So that we know what to work on if we don't make it

I win 100% of sales. How? Because I focus less on what we will do for our clients and more on how to make their business successful. Getting a good sense of our company's differentiation has been challenging. I know what's in my brain, but it's been difficult to articulate what sets us apart. I don't want to be 1 OUT of a million engineering agencies; I want to be 1 IN a million. And recently I've discovered exactly what makes us different from our competitors. I start my sales calls asking completely different questions. I was on a call with a team doctor who had an idea for an app. And instead of jumping to solutions and explaining how we plan to get it done, I asked him a few critical questions: ➝ How big is this market? ➝ How will you raise capital? ➝ When you raise capital, how much do you want to spend? ➝ How do you want to extract wealth back from the company? So how does this win us 100% of sales? Because every other company is talking to them about how to build their app. But I'm talking to them about making their business successful. And it doesn't hurt when I share my story of a successful exit. It immediately grabs attention and people realize we've been through the process ourselves—they trust us. As I continue down this path, I'm learning that what makes us unique is our ability to offer startups much more than just tech services.

What does it mean to have a strong founding sales team? The list isn’t as long as you think. I’ve built quite a few first teams for startups, And believe me - there is a right way to do it and a wrong way to do it: 👉The wrong way to do it is to hire strictly based on historical sales metrics and revenue achievement 👉 The right way to do it is to deep screen for, then enable, three key qualities: → Adaptability Early stage startup sales are more often than not, unstandardized. An adaptable salesperson will have the in-field know-how to adapt their approach with agility and direction - bringing you closer to your ICP and playing an integral role in developing your sales playbook. → Creativity What your prospects need to feel confident in the sale will not be obvious at the start - especially for innovative or complex products. A creative salesperson will use every tool in his belt to craft a value-driven buyer journey and map their values to the product using any support resources they can think of. → Test-savviness Your first sales motion likely won’t be your last, so directionality will be your best hedge against time and resource waste. A good founding salesperson will know how to help you test and make data-driven decisions around acquisition - reducing your overall time to goal. The last thing you want to build with, And this should come as a no-brainer, Is a collaborative team culture. Founders, technical staff and salespeople should WANT to be involved in the deal, To give the best odds of closing pipeline and optimizing alignment around revenue growth. 💡 P.S, at what point in your journey did you know it was the right time to hire salespeople? — #StartupSales #SalesTeam #SalesGrowth

Many startups I meet think: "Let’s hire a sales manager, and the million-dollar deals will start rolling in!" For many founders, this isn’t just about growth—it’s also about relief. Sales can feel like a chore they’d rather avoid, and handing it off to someone else seems like the perfect solution. But here’s the truth: Hiring a sales manager without proper groundwork is like trying to fly an airplane without wings. It won’t take off, and you’ll be left guessing in the dark. To set your sales manager (and your business) please have at least the following elements in place: ✅ Know who could benefit from your solution ✅ Pitch Deck & One Pager ✅ A decent digital presence With these in place, your sales manager will have the tools they need to succeed, and you’ll avoid the frustration of unrealistic expectations. Sales isn’t magic—it’s structure, strategy, and consistency. Do the groundwork first. It’ll make life easier for you, your business, and your sales manager. Happy Tuesday ☀️ #salesstrategy #startupgrowth #businessdevelopment

Founder raised $2M seed and wanted to hire a VP of Sales to build out the team The new investors recommended it - Company has been around for 7 months - No product market fit - Initial product has been touched by less than 10 companies - Technical founding team - 1st time founders - No customers yet Its wonderful these founders were able to raise $2M But they are getting bad advice Investors who have never sold or operated an early startup are advising these founders These recommendations are likely to cause wasted energy, unnecessary frustration and burn a ton of money VP of sales don’t come to seed stage companies - too much risk - comp is not there - nothing built out yet - product and market not proven Founders think VP of sales will compromise for “the opportunity’ and upside with a little equity The risk is still too great The job doesn’t align with the VPs skills What are the founders really doing? They are trying to hire someone to do the job they should be doing There is no product market fit yet - that’s a founders job There are no customers yet - that’s a founder job There is a lot to figure out yet - that’s a founder job Ive had a number of these conversations with founders in the past 90 days Technical or not, founders need to be the initial sellers A lot changes at this stage in the company Outsourcing it and hoping someone else finds you product market fit does not work As a technical founder, bring in a sales co-founder if you’re unwilling to do the work It is rare to see a company succeed without the founder selling, talking to customers/prospects, and being on the front lines finding product market fit Takeaways: 1. Be mindful whose advice you listen to about what topics 2. Early stage founders should not hire a VP of sales to find customers and product market fit 3. Don’t build a team before you have something 4. Founders need to be on the front lines selling to listen to customers and the market in order to adapt

What Founders Must Do Before Their First Sales Hire with Mia Murphy