Dan Parsons’ Post

As a startup founder, hiring a VP of Sales is a critical decision that impacts your company's growth. When assessing potential candidates, here are some things to keep in mind: 1) Sales Expertise: Can they develop a sales playbook and establish an efficient sales process, actively participating in sales calls? 2) Attention to Detail: Are they open to implementing reporting, dashboards, and other crucial aspects of the CRM? 3) Hands-on Approach: Will they close deals themselves and leverage existing client relationships? 4) Resourcefulness: Can they work effectively with a limited tech stack and budget? 5) Marketing Collaboration: Are they comfortable working with a marketing team that may not be fully mature? 6) Hiring Commitment: Will they dedicate (roughly 25%) of their time to hiring activities, such as writing job descriptions, developing comp plans, and actively participating in the interview process? 7) Customer Success Mindset: Are they willing to assist with onboarding as clients transition to the CS team? These are some of the common themes I've encountered. I'd love to hear from fellow founders and hiring managers – what other qualities and skills do you look for when hiring a VP of Sales for your startup? 🤔 #hiring #vpofsales #techstartup #founder

Hiring for this role can make or break your start-up... but it might not be the role you are thinking of. The first sales hire can feel like a huge step—it’s a milestone that marks a transition from founder-led selling to scaling your growth engine. But finding the right person for this role can make or break your early momentum. Here’s what to keep in mind when bringing on your first sales hire: Entrepreneurial Spirit 🌱 Your first sales hire isn’t just “selling” a product—they’re building a sales process from scratch. Look for someone who thrives in ambiguity, who can experiment, pivot, and iterate based on what works. Industry Knowledge 📚 They don’t need decades of experience, but a solid understanding of your market and customer base is invaluable. A great first sales hire will understand the industry well enough to speak the customer’s language and recognize unique challenges. Problem-Solver Mindset 🧩 Early sales are less about traditional pitching and more about identifying customer pain points and adapting your solution to meet their needs. Look for someone who’s naturally curious, asks the right questions, and is relentless in finding answers. Relentless Resilience 💪 Building the first pipeline isn’t easy—there will be rejections, setbacks, and slow days. Your ideal hire won’t get discouraged easily; they’ll see challenges as just another step in the process. Team Fit 🤝 Your first sales hire will be setting the tone for the rest of the sales team as you grow. Cultural fit and alignment with your company’s values are key here. This person will shape your sales culture, so hire someone who embodies the qualities you want in future team members. Bringing on your first sales hire is a big decision. Done right, this role will lay the groundwork for your future growth and help you transition from founder-led sales to a scalable sales machine. #SalesHiring #EarlyStageStartups #StartupSales #Hiring

In early-stage startups, finding the perfect AE, or "unicorn candidate," is daunting. It is complex and it is rare to find someone who meets all your criteria, so it is important to prioritize what is most important to you as talent pools vary in sizing depending on your startup's niche. The below is how I view assessing an early stage AEs fit outside of the typical top performer, culture fit, etc. Stage fit: Has this person been successful as a sales rep at the current stage or not too distant stage of commercial maturation of your startup? Can they thrive with limited resources and playbooks, be adaptable to the change and a lack of product maturity? Industry fit: Do they have experience selling into your specific industry (healthcare, manufacturing, broader enterprise, etc.)? Persona fit: Do they have experience selling into your buyers (CMO, CFO, etc.)? Deal size/complexity of sale fit: Selling a $100k solution often times looks very different than a $10k solution. Does this person have experience selling a product that matches the complexity, deal size and sales cycle timing that you anticipate? Product fit: Do they have experience selling against the problem you solve for? If you have a technical product, do they have experience selling a technical product and can handle a lot of the conversations on their own with limited support? Once you assess what you're looking for, how many do you hire? Early-stage selling is challenging, and hires may fail due to misaligned PMF, industry challenges, or rep performance. Hiring two reps instead of one can mitigate this risk, providing a control to better evaluate performance and external factors. Let's connect and discuss how to navigate early-stage sales hiring together! #startuphiring #saleshiring #AEs #earlystagestartups #recruiting

Founders, when you are ready to build your first sales team, your initial hires are crucial to the team’s success. It's a common thought that hiring a top-performing rep from a well-known established company is the best hire. I mean, that would make sense right? They would check all the boxes: ✔ Multiple years of experience ✔ Proven track record of exceeding quota, President’s Club preferred ✔ Demonstrated ability to close deals ✔ Outstanding customer support and account management skills ✔ Data-driven decision-maker ✔ Experience with CRM ✔ Knowledge of multiple sales methodologies Probably not. These reps would struggle in an ambiguous environment with limited tools, resources, and support. Instead, hire a sales rep with experience as a founding member of a sales team at a startup. These individuals possess the agility, resilience, and innovative mindset required to succeed without many tools, solid frameworks, or extensive support. Their hands-on experience navigating a startup environment makes them a pivotal hire for your founding sales team. Who has been a founding member of a sales team? I would love to hear -your insights or war stories! #Sales #Startups #Hiring #SalesTeam #Leadership #BusinessGrowth

Why Do IT Founders struggle to establish outbound strategies and leadership who can build it? Hiring the right sales leader feels like hunting for a unicorn—magical, rare, and, let’s face it, nearly impossible when you’re looking in the wrong places. Here’s the reality: Many IT founders, especially those who launched their businesses in the last decade, are underestimating what it takes to build a killer outbound engine for lead and demand generation. It’s not magic—it’s a system. Building this sales engine requires time, effort, processes, and yes, investment. But too often, founders fall into the trap of: 1️. Paying peanuts and expecting miracles. 2️. Hiring “star” candidates who don’t deliver the 10x return they promised. Here’s the kicker: The right talent isn’t just about closing deals—it’s about designing, running, and sustaining the whole engine that fuels your growth. This person knows how to: ✔️ Build scalable outbound strategies. ✔️ Set up processes that generate consistent demand. ✔️ Deliver results that multiply your investment. And guess what? They don’t come cheap. You need someone with the experience, grit, and mindset to truly own it—and that’s not a bargain-bin hire. So, IT founders, here’s the question: Are you ready to invest in a "growth architect" who knows how to generate that elusive 10x return? Or will you keep running in circles, wondering why your engine sputters when you’re putting in 2x fuel? Remember, in sales, you get what you pay for. #SalesLeadership #ITBusiness #OutboundSales #LeadGeneration #HiringRight

How to Scale Your Sales Team: Hiring Strategies for Startups Learn valuable advice on hiring for your sales team, including the ideal level and seniority of your first two hires. Discover the importance of having two sales reps hitting quota before hiring a manager, and how to find the right candidates to drive your startup's growth. #SalesTeamScaling #StartupHiring #SalesRepHiring #SalesManager #SalesGrowth #StartupAdvice #HiringStrategies #SalesRepQuota #SalesTeamManagement #StartupGrowth

Hiring fractional sales talent isn't for every startup But for those founders who have sold their product themselves and have an understanding of their sales process Fractional sales talent can be highly impactful Here are just 4 reasons to hire fractional sales talent: ✔️Hiring for expertise: They bring years of sales experience that can be unlocked immediately  ✔️Faster time to market: Hire sales talent with past experience selling to your buyer persona which reduces ramp and helps you move faster ✔️Build your team: If the plan is to hire a sales team, you can hire fractionally and test for skills and cultural fit before building your sales team ✔️Reduce risk: hiring full-time employees can be risky depending on your stage You don't always have to go the traditional way of hiring full-time employees Hiring fractionally could be the answer #startup #entrepreneurship

‘I'll just hire a salesperson to handle sales.’ 🚨🚨🚨 This is where most founders go wrong. Every time a founder shares this with me, I know they're about to make the SAME COMMON MISTAKE. Here's the truth: Hiring your first salesperson is NOT your first sales problem. Before you even think about hiring, you need: ☑️ A repeatable sales process ☑️ 5-10 customers you've closed yourself ☑️ A clear understanding of your customer's lifetime value ☑️ Documented sales playbook ☑️ CAC Idea. Why? Because hiring a salesperson before these fundamentals = setting them up for failure. Your first sales hire isn't just another hire. They're the foundation of your future revenue engine. Key warning signs you're hiring too early: ✅ Your product is still in heavy development ✅ No clear ideal customer profile ✅ Inconsistent pricing strategy ✅ No documented sales process Want to know exactly when you're ready to make that crucial first sales hire? I’m building a comprehensive framework to help founders pinpoint the right moment to make their first sales hire—based on 12 years of experience building and scaling B2B sales teams. I’ll share it once it's ready. P.S. Working with B2B tech founders on their sales strategy is my passion. If you're wrestling with sales hiring decisions or want to build a bulletproof sales process, let's chat. DM me to explore how we can work together. #SalesStrategy #Startups #Leadership #BusinessGrowth #SalesHiring

Superb article about #hiring great startup sales leaders just published by Madrona. Highlights: BUILDERS: "There is a critical distinction between hiring someone who can build and someone who can manage. Often, founders mistakenly hire individuals from larger companies who are adept at managing existing systems but lack the grit to build from scratch." COLLABORATORS: "Successful sales leaders...engage deeply with the business, and partner effectively across different departments. Collaborating directly with product, marketing, and finance teams will drive growth..." SCALERS: "[Successful sales leaders can provide] examples of how they’ve scaled teams" Other interesting tidbits about hiring and getting references. A great read! https://lnkd.in/e2VbacPz

Here are the 3 biggest mistakes startup CEOs make when hiring their first sales leader: 1. Hiring too early: With just a few customers, it’s unlikely that the GTM model is dialed in. Great sales reps (including hands-on sales leaders) are like machine guns. They rapid-fire bullets to hit exactly what they are aimed at. But at this early stage, you likely haven’t figured out what to aim at yet (proven ideal customer) OR what “bullets” to use (a simple and repeatable message and process). Until you figure those out, you should be doing founder-led sales, where your priority is rapid iteration and customer intimacy, so you learn what is needed. 2. Overhiring for your stage Beware hiring experienced leaders! On paper, they are great. They’ve done it before. They've scaled a company just like yours! They can sell and hire in the reps you’ll need! But beware the first law of bureaucracy: give an ambitious person a job, and they'll make it bigger. As soon as you have a leader, they’ll want a team. Very, very quickly, you’ll be onboarding reps you aren’t ready for. See point #1! 3. Hiring for the wrong business model Do you want a rep who can go enterprise and close million dollar deals? Or one who can build consistent machinery and process to have a large team closing $10k deals? One who can sell to technologists or business people? One who can sell product or services? These are very different skillsets and very different sales leaders. The truth is, with just a few customers, you don’t know your model yet. The odds of making this mistake are super high. TAKEAWAY All three of these errors result in the same thing: Overspending on a sales team. With very few results to show for it. Be careful out there!