Wilson Bowers’ Post

VP Sales. Job descriptions for this position often don't match what is REALLY expected. Many founders and CEOs want a miracle worker. "I've built a fantastic company with an amazing product. Now, I realize that selling it is the tough part. So, I'll just hire a Sales VP or Chief Revenue Officer and expect them to work magic." They believe hiring a top-tier Sales VP is the silver bullet to transform their growth. Here's the truth: It doesn’t work like that. I greatly respect sales professionals and understand their crucial role in taking any business to the next level. However, it’s not as simple as it looks. Salespeople don’t generate demand; they turn it into revenue. Creating demand falls on the product and marketing teams, with a major emphasis on the product itself. Here’s the process: 1. Start with an outstanding product. 2. Add exceptional marketing. 3. Then, bring in excellent sales. You can’t skip any of these "world-class" steps and still expect next-level success. Yet, too often, the first two steps are neglected, and the sales team gets blamed. Did you fire your Head of Product/Chief Technology Officer when you lost deals due to missing features? No, but your VP of Sales was let go for missing revenue targets. #sales

CEO: I'm thinking about hiring our first VP of Sales. Me: Congrats! What does the current sales team look like? Do you have any managers? CEO: No, we haven't hired any. Me: Alright. Have you hired a marketing manager? CEO: No, but we're planning to fill those roles soon. Me: How about Sales Operations? Is there someone responsible for that? CEO: No, we don't have anyone in that role. Me: I understand. A VP of Sales can cost A LOT, typically between $300K to $600k+ per year. How fast do you expect to make a return on this investment? CEO: In less than 6 months, ideally sooner. Me: So, you want to hire a VP of Sales before you have the other key roles in place, and expect them to deliver results in under 6 months? CEO: Yes, of course, that’s their job, right? Me: 🧐 VPs of Sales aren't miracle workers 🪄 They need the right support & team to succeed 🙏

Thinking of hiring a VP of Sales? Many get this hire wrong and pay the price. Here’s how to get it right from day 1: A great VP of Sales can transform your business - but here’s the harsh truth: Too many Founders hire the role before they’re ready—and waste months (or years) figuring that out. The problem? When Founders think a VP of Sales is the cure-all for their sales struggles. In reality, their success depends on what’s already in place—or missing—in your business. If you’re at $200K–$2M Annual Recurring Revenue and struggling to grow, ask yourself: 1️⃣ Do you need a builder or a scaler? → Builders design the entire sales engine—your ICP, outreach playbook, and pipeline structure. → Scalers optimize existing sales processes and grow a team around what already works. If you don’t know which you need, you’re risking $200k+ hiring the wrong person for the wrong job. 2️⃣ Are you stuck in the wrong sales cycle? Founders often rely too heavily on manual deals or "hustle-driven" sales. A VP of Sales thrives with scalable systems, predictable prospecting, and reliable conversion metrics—do you have at least some of these in place? 3️⃣ What happens if it doesn’t work out? Misalignment wastes months (even years), erodes trust with your team, and burns budgets. That’s why it’s crucial to… 👉 Build the systems for revenue growth before handing off the keys to sales leadership. 🟢 The Solution: Hiring a VP of Sales is a game-changer—but only if your revenue engine is ready to scale. P.S. I help Founders and Sales Leaders build predictable revenue systems. Feel free to drop me a message— happy to help you figure it out (you can start with us for free). #Founders #SalesLeadership #RevenueGrowth #BusinessScaling Video Credit: Ryan Walsh

Direct industry experience isn’t the ‘ Be-All and End-All’ in sales. As someone who has spent decades in sales- including years as a hiring manager, I’ve seen a recurring mistake all too often made by hiring managers: over-prioritizing direct industry experience at the expense of overall professional sales expertise, business acumen and….savvy! Sales success isn’t about intimate familiarity with every detail of an industry—it’s about the ability to build relationships, solve problems, and drive results. Sales professionals with a track record of success have honed these skills across various sectors, and the principles of great selling—listening to customer needs, negotiating value, and fostering long-term partnerships—are universal. Sure, industry knowledge helps, but it can be learned. What takes years to master is how to navigate complex buying decisions, lead a team, or close deals that transform businesses. When hiring managers discount, and disregard, seasoned sales professionals because they don’t have specific industry experience, they may be overlooking a wealth of adaptable talent and doing their company and team a disservice. Let’s focus on what truly matters: the skills and experience that deliver results, regardless of the industry. What’s your take? #SalesLeadership #HiringTrends #SalesSuccess #ProblemSolving #SalesGrowth #Recruiting #UnicornsDontExist

Leadership without resources is temporary.

This is a huge challenge for many of the cybersecurity start-ups I'm exposed to. Lots of GTM team churn due to unrealistic expectations. How can this be improved?

"VPs of Sales are not magicians 🪄 Please set them up for success 🙏" Collin Cadmus Setting them up for success means strong onboarding, ongoing coaching, and alignment across marketing, pre-sales, and partners. Winning in the market is a team sport, not a solo act. 🙌 #sales #salesleadership #skillwill #talent #oneteam

Setting up a VP of Sales for success means ensuring the right resources are in place before they join. Investing in sales operations, marketing, and demand generation will not only make their job easier but also ensure they can deliver results within the expected timeframe. It’s not about questioning their abilities but creating an environment where they can thrive.

🚨 Sales leaders – don’t make this hiring mistake! 🚨 Ever hear CEOs and sales leaders say they need a sales pro with industry experience because their industry is “unique”? Sure, sometimes it's true, but more often than not…it’s not! The real deal? You need someone with rock-solid sales skills. If they can generate interest and guide prospects through each stage of the sales process, they'll hit those sales targets. Industry experience? Nice to have. Sales skills? Essential. Hire the skills, teach the industry! #SalesTips #SalesLeadership #SalesSuccess

This hits especially hard if you have experience working at a small startup. I remember when I started doing Revenue Consulting for small startups. I had so many surprises, after being in corporate for so long. “Lucy, who is our CRM guy? I can’t get Hubspot to work.” “Jason, who is our IT guy? I can’t login to our Google Business Profile.” Even simpler, “Alice, when does the Janitor get our trash cans?” These are all stupid questions when you work at a small startup - what you see is what you have. YOU are the resource - and that is why they hired you. That is why early startup revenue leaders are hired - not because they are the best salespeople, but because they can make s**t happen. They are rainmakers. That being said, rainmakers aren’t magicians. I’ve been under the gun with 0 resources more times than I can recall. And you know what I do? Make it happen. I can make it rain on command - but there is still a baseline of resources that you need to be successful. When you don’t have that baseline, and are expected to make cookies from charcoal - the results are never good. #salesleader #startupculture #saturday