🚀 10 Lessons on Hiring a Great VP of Sales from Jason M. Lemkin 💡 Hiring the right VP of Sales can make or break your #SaaS business, especially when you’re scaling past $5M ARR. Here are 10 key lessons for SaaS founders looking to hire their first (or next) VP of Sales from Jason Lemkin’s #SaaStrAnnual talk. 1. Don’t Exit Sales Too Early The biggest mistake founders make is stepping away from sales too soon after hiring a VP. Even with a new hire, you must remain involved, helping close deals and mentoring your sales leader. 2. Avoid the 'Jaded, Broken or Done' Candidates Lemkin warned about hiring candidates who are jaded or have mentally “checked out.” You need someone who is still hungry and passionate about the hustle of sales, not someone looking for a cushy job. 3. Sales Leaders Must Know the Product One critical hiring mistake is bringing on a VP of Sales who doesn’t understand the product. If your VP can’t have deep conversations about your product with customers, you’re going to lose deals. 4. Founder-Led Sales Can’t Scale Even if you've been burned by a bad VP of Sales hire, don’t fall back into the trap of founder-led sales for too long. You need to keep pushing forward and find the right leader to scale. 5. Look for VPs Who Love Being in Deals When interviewing candidates, ask what they want to do in their first two weeks. If the answer isn’t “meeting customers and closing deals,” they might not be the right fit. 6. A Great VP is Also a Great Recruiter Your VP of Sales needs to be able to build a strong sales team. If they haven’t successfully hired and managed 2-3 top reps before, they’re probably not ready for the role. 7. Full-Stack Sales Leaders Are Rare Finding a VP who can do everything from outbound to closing is rare. Ensure they have experience in the key areas you need—whether it’s managing partnerships, direct sales, or outbound. 8. Be Careful with Process-Heavy Candidates Some VPs are great at managing processes but don’t want to sell. Don’t hire someone who’s more focused on building systems than getting in front of customers and closing deals. 9. Don’t Settle for Mediocre Hiring the wrong VP of Sales can set you back an entire year. It’s better to keep looking than to settle for someone who doesn’t fully align with your vision. 10. Trust Your Gut If you’re not 100% confident in your VP of Sales hire, keep searching. The right person will be someone you believe in fully—and they’ll have the ambition to drive your company’s growth. Hiring the right VP of Sales is one of the toughest decisions a SaaS founder will make, but it’s also one of the most important. #SaaStr #SalesLeadership #GoToMarket #BusinessGrowth #SaaStrAnnual24
Christelle Blanchet-Aïssaoui’s Post
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From the experience of working with 95 businesses in the last 5 years, we've had the pleasure of mentoring over 60 technical founders. One of their desires is to remove themselves as the sole revenue generator, and/or to get totally out of sales but still have predictable sustainable revenue. Paul Sargeant explore this a little more today. Technical Founders try many things to make this happen but have your considered a Fractional Sales Leader. There are many benefits to this approach. #salesframework #salesleadership #pamice #founders https://lnkd.in/gr42SVYJ
Tech Founders, sales is a science (not art). Get a proven structure for sales | Founder Director x 3 | Golf tragic 🏌️
One of the top 5 questions I get from Tech Founders is “How do I get myself out of sales?”, which comes with negative feelings towards selling, and/or a genuine desire to grow the business without sales being dependent on you. You have probably tried to 1. Hire sales reps 2. Hire a full-time sales leader 3. Hire a sales consultant 4. Do some Sales Training 5. Spend money on marketing - Lead gen, Website, Brochures, Events How did that go for you? Still running sales? Ever thought about a fractional sales leader to bridge the gap between you owning sales and the expense of hiring a full-time sales leader? I explore this last question in this article. DM me if you want to discuss. #salesleadership #techfounders #salesframework #salesstructure #pamice https://lnkd.in/gjgpx_DP
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One of the top 5 questions I get from Tech Founders is “How do I get myself out of sales?”, which comes with negative feelings towards selling, and/or a genuine desire to grow the business without sales being dependent on you. You have probably tried to 1. Hire sales reps 2. Hire a full-time sales leader 3. Hire a sales consultant 4. Do some Sales Training 5. Spend money on marketing - Lead gen, Website, Brochures, Events How did that go for you? Still running sales? Ever thought about a fractional sales leader to bridge the gap between you owning sales and the expense of hiring a full-time sales leader? I explore this last question in this article. DM me if you want to discuss. #salesleadership #techfounders #salesframework #salesstructure #pamice https://lnkd.in/gjgpx_DP
Hiring a Sales Leader vs a Fractional Sales Leader
salesdirectorcentral.com
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The founding sales reps can make or break you. In these hires, what matters more... Industry experience or sales experience? It's hard to find both. I get this question often. A few things to consider as a founder: → Where are you stronger? Industry or GTM? Which can you support better → What's the actual expectations of this function? Are they just setting meetings for you to close? Or would they ideally run full cycle. → What's the budget you're willing to work with. The more 'both' you get the more $$ you'll have to put up. In the early days, you'll need to choose a which side → The motion you've run as a founder thus far won't be the motion this sales rep runs. Or it's at least highly unlikely. What motion are you expecting this person to run? How does this compliment what where you are strong as the founder → What other companies have sold to this buyer and what do those successful reps look like? What was their experience prior to joining that company and can you replicate this? → The GTM environment has changed drastically the last 2-3 years. Experience in the last 24 months matters more than the prior 36 months before that. → Are there other paths to achieving the outcome you're hoping for vs. hiring an AE to smile and dial. Are you even hiring for the right role? Get this hire right, it'll transform your business. Get it wrong, it could set you back 12 months.
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In 6 years, I went from an AE to the CRO of a $200M startup. Here are the 7 biggest mistakes I made as a sales leader (and what they taught me about building high-growth SaaS sales teams): 1. Over-investing in process, too early I'm a process guy and love building. I get energized from seeing a 100+ page playbook. However, build it too early and you lose sight of what matters. Sales leaders need to be comfortable selling during the first few million. They should be running the largest deals even if they have 10 people reporting to them. 2. Developing an over-rigid sales process I used to think that enforcing deep processes was a cure-all. If everyone just followed MEDDIC, deals would flow. The reality is that sales leaders have to develop a process that fits the context of their unique business. 3. Having a system for everything but coaching Your first 1-2 reps can learn from osmosis, but after that, there has to be structured training and coaching. Growth happens when you move from freestyle feedback to quarterly alignment, personalized coaching, and progress tracking. That's when you will see your biggest lift in win rates and ACV. 4. Trying to run RevOps Being a process guy, running operations came naturally. However, I was leaving such a mess in the CRM that eventually it had to be re-built from scratch. Knowing how to let go and work with a strong ops leader is key. A VP Sales should not be building diagrams all day. 5. Overlooking what made sales candidates successful Yes, hiring based on a track record of success is standard practice. However, not all previous success is transferable. Think: A) Big brand pull which made selling easy, B) Support system of a large org that won't be available, C) Low quotas, D) Different sales motions. Past success should never be THE deciding factor in hiring. 6. Hiring leaders in order to solve today's problems When I was hiring I was always looking to solve today's problems, not future ones. Sure, not everyone makes it through all phases of growth. But if you can't see how that person scales through a few stages, they never will. When this happens you risk hitting a wall with a team that has to be replaced. 7. Managing down, but not sideways and up I missed potential expansions. I missed pipeline creation opportunities. I missed getting management approvals. When you are too focused on your team's day-to-day challenges, you miss supporting other leaders’ challenges and getting their support in yours. TAKEAWAY: Running sales for a startup is hard. You need to build the plane while you're flying it. If I’m being honest, I can’t tell you it gets much easier. You’re going to make a TON of mistakes (I know I still do). There will even be days when you want to quit. When this happens, the best thing to do is just keep building. Success is right around the corner.
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How different is working for an enterprise vs a start-up in sales? Seems to be a failing strategy more often than not to look for enterprise sales in hiring for a start/ scale-up. Selling a known product for a company with a good reputation vs selling something where product market fit hasn't been solved fully aren't even close. And that's just the selling part. Working in a start-up isn't the same as working for one of the big four. Just to say, don't look for an ent sales rep in your start-up. Thoughts? PS. That doesn't mean it never works. The odds just aren't great.
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Scaling your SDR team means scaling your costs, but doesn’t always mean scaling profits. Why? Say you’ve managed to find a solid outbound rep that’s booking meetings consistently. (Although hard to find, good SDRs do exist!) You may want to scale outbound by hiring a gazillion more SDRs. If one rep books 20 meetings a month, two reps should book 40 meetings a month, right? Wrong. Scaling outbound sales teams isn’t linear. You can’t replicate the performance of your best rep: what makes one rep a high performer is different from the next rep. It’s almost impossible to hire solid sales reps consistently. That’s why ⅔ of SDRs fail within their first three months. (Shoutout to Nimarta Dugh for this stat. Super helpful for SDR leadership advice.) The Pareto principle is at play: 80% of your pipeline comes from 20% of your reps. The other 80% aren’t doing much for your bottom line. Even if you do find another solid sales rep, you’ll spend insane time and effort in reviewing resumes, interviewing, hiring, training, etc…especially considering you’ll likely need to make several hires before you find a good fit. Most companies have to hire SDR managers to make up for the fact that most reps aren’t self-sufficient—costing you another full-time salary because your entire team of salaried reps isn’t self-sufficient. Instead, add an outbound ops person to lead the charge on your outbound motion. If you find someone good, they can scale their performance with automation instead of headcount. More pipeline with less time, money, and operational headaches. Let them handle account research, prospecting, and even sending personalized outbound emails. SDRs field warm leads, cold call, book meetings, and qualify prospects. Welcome to 2024 :D
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There's a fantasy that I've seen some new CEOs hold on to about hiring sales reps or outsourced lead gen teams. Fact is, the sooner they let go of this belief, the sooner they'll start making more sales. The fantasy is that a top sales rep who is happy with a 100% commission-only compensation structure actually exists. You might even see lead generation companies offering this. Reality check: no such person exists. Because it puts the risk entirely on the rep. This belief leads to underperforming reps, a revolving door of new staff, and constant frustration by management. It wastes a lot of time. So what works? The sales reps who are worth their weight in gold always have a salary + commission + bonus (in startups, maybe also equity). This distributes the risk to both the company and the rep, which is the fair way to do it. And the really good reps may make more money annually than the CEO - unless the CEO's ego enforces a cap on earnings, in which case the best reps will leave. Bottom line: pay your people well. Even if it means taking a lower salary yourself (remember, you've got more equity). #salary #saas #sales *** If you liked this post, please share with your network and follow me Raj Khera for daily executive coaching to grow your business.
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Need expert sales leadership but don’t require a full-time hire? 💼 Fractional sales management could be the right move for your business as it offers flexibility and cost-effective solutions tailored to your specific needs. 🌟 Learn more now on the BDU Blog: https://lnkd.in/dEK2_Dss #Sales #SalesLeadership #FractionalSalesManagement #SqueezetheLemon #SqueezingtheLemon
Understanding Fractional Sales Management: The Benefits of Flexible Sales Leadership - BUSINESS DEVELOPMENT UNIVERSITY
https://businessdevelopmentuniversity.com
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Lenny and Jason M. Lemkin's discussion on building a world-class sales organization was super insightful for me. I wanted to share my learnings to the wider audience. Here are the key takeaways: 1. Recruit your FIRST 20 customers yourself before hiring a sales rep. 2. Ensure the sales rep hits quota before hiring senior sales talent. 3. Your initial sales hire should be someone you would buy from. Ask yourself, "Would I buy from this person?" 4. Avoid hiring sales reps who don't prioritize earning money. 5. In B2B, focus on problem-solving rather than just selling. 6. Aim for a sales rep who can close at least 3x to 5x more than their take-home pay. 7. A high number of reps not closing deals can lead to significant issues. 8. Quality is better than quantity when it comes to sales reps. 9. When hiring your first 10 reps (including the VP of Sales), look for someone who has successfully sold a product that was harder to sell than yours. 10. Jason's favorite interview question is, "What do you plan to accomplish in the first 14 days?" 11. Discussing lost deals can provide valuable insights. 12. "Switching to annual contracts" may not always be good advice. 13. Avoid creating conflict between departments. 14. Tension between product and sales teams can indicate a healthy deal pipeline. 15. Be patient in hiring to avoid making costly mistakes. Lenny Jason - A question for you - we can differentiate the top performers and the underperforming ones. How do you find the ones who are just doing enough to keep their jobs (muddled middle)? #startups
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Hiring for Success: What to Look for in New Sales Reps Building a successful sales team starts with hiring the right people. Here are my top tips for finding the best sales reps: Two Years of Experience: Focus on hiring reps with a minimum of two years of B2B experience. New hires without experience require too much training and can slow down your growth. Demonstrated Success: Look for candidates who have tangible results like shorter deal cycles, new business acquisition, and significant deal flow management. Relevant Questions: A good sales rep will ask about your pipeline, lead generation, and expected earnings. This shows they’re serious about their potential income and understanding your business model. Always ensure your company has a stable flow of new appointments and a closing rate of at least 30% before bringing on new hires. This preparation sets the stage for their success.
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