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Hiring Sales People like Wolf from Wall Street: Guide by Evgeniia Megrianby@janemeg
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Hiring Sales People like Wolf from Wall Street: Guide by Evgeniia Megrian

by Evgeniia MegrianDecember 31st, 2024
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Hiring top salespeople is essential for driving growth. To catch the salesperson, you have to think like a salesperson. The first step in hiring top salesperson is gaining a deep understanding of the product you're hiring for.
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Okay, gals and boys, we have to admit that the more startups and products we have on the market, the more talent it takes to actually SELL those products. That’s why hiring a great salesperson is a tier-1 mission if you want your product to “fly high.” In this article, I’m breaking down how I hire salespeople in weeks who actually close deals in months and what I would highly recommend implementing in your approach to finding THE salesperson that would boost your growth. Let’s gooo!


Hiring top salespeople is essential for driving growth. As someone who has hired salespeople for over 30 products across industries—from CyberTech to FoodTech—I’ve developed an approach that combines domain expertise, targeted outreach, and a systematic recruitment process. In this guide, I’ll share my approach to help you identify and hire top sales talent for your business.


1. To catch the salesperson, you have to think like a salesperson

The first step in hiring top salespeople is gaining a deep understanding of the product you're hiring for. It’s not just about finding someone who can sell—it’s about finding someone who can sell your product effectively.


In my approach, I start by doing deep research into the product itself—its features, benefits, and the unique selling points (USPs). Then, I analyze the market: who are the target customers? What are the challenges these customers face? What are the competitors doing?


By understanding the product inside and out and knowing how it stands in the marketplace, you’ll be able to identify the skills and experiences your ideal candidate needs. I mean, we have to wear salespeople’s shoes sometimes to understand who can do this job, okay?


2. Highlight key experience points

Once you have a solid understanding of the product and the market, it’s time to define what the perfect candidate looks like. The ideal candidate portrait is a detailed profile that outlines the experience, skills, and characteristics necessary to succeed in the sales role.


For example, if you're hiring for a CyberTech sales position, your ideal candidate might need experience in B2B sales, familiarity with CyberTech products or at least customers, and a proven track record of selling to large enterprises. On the other hand, if you're hiring for a FoodTech sales role, the profile will focus more on an understanding of food industry trends, relationships with suppliers, or experience with smaller, fast-growing companies.


3. Hunt them!

With the Ideal Candidate Portrait in hand, you can begin sourcing candidates from the right places. One of the most effective tools for sourcing high-quality salespeople is LinkedIn. Use LinkedIn Recruiter or Sales Navigator to search for profiles that match your candidate portrait and focus on those with a proven track record in the industry you're hiring for.

While sourcing, focus on:

  • Industries of companies the candidate has worked for (it’s super easy, you can filter it with one click) Company size (also one click)
  • Product they sold (e.g., is it one product or a platform-based solution? The more products, the harder it is to sell)
  • Years of experience at a company (don’t be biased here, but keep in mind that enterprise deals usually take at least 6 months to close, plus a couple of months of training. So, if you see a salesperson who worked in the enterprise segment and left a company in less than a year, that might not be the best signal about their sales results)
  • NUMBERS (good news: salespeople usually have a great culture of sharing numbers. Be careful and see if they have any info in their profile about average deal sizes, deal cycles, quotas, verticals—more stats that match with your product means more chances that it’s a match)

Look for individuals who are excelling in similar roles, and don’t be afraid to expand your search to include candidates with transferable skills from other industries.


4. Melt their heart with your pitch

Once you have identified potential candidates, the next step is reaching out to them. Crafting personalized and relevant messages is crucial for a high conversion rate.

Instead of sending generic outreach emails, take the time to craft tailored messages that show you understand the candidate’s background and how it aligns with your needs. For example:

  • Start by introducing yourself: who you are, what your company is doing, and what your current results are (don’t be shy here).
  • Be direct in saying why you reached out to that person and what your intentions are. Highlight why they are a great fit for the role, what role you offer, and what the role is about.
  • Mention all the perks a salesperson can get from working with you: higher commissions, more ownership, benefits, remote options, etc. (also, don’t be shy).
  • Mention next steps. Be very clear about what the person should do next to proceed.

So, this part is extremely important. We can’t mess up. It’s like that one and only call that the Wolf from Wall Street made in the beginning, and it literally boosted his career! So, my tips are:

  • Be specific. Buzzwords like “you will sell a mind-blowing wow product” are a no-go. Mention the product itself, your current numbers on customers, revenue, deals, and plans for the future. Of course, be specific about what you offer: mention the type of work (full-time, part-time, contract), salary range, and the next step for the candidate.
  • Sell this opportunity: You don’t mess with salespeople when it comes to selling the opportunity, so do your best to highlight your company’s biggest wins and opportunities. Explain why now is the best time to join, with whom they will have a chance to work, and what makes your offer better than their current job (you might be offering more ownership or higher commissions than the market).

ALSO, don’t forget that one email is not enough to get the attention of the best-in-class salesperson. Be ready to create a sequence of 2-3 emails if they don’t reply and send a follow-up in ±3 days after the first message. If emails don’t get replies, use other channels like LinkedIn. More touchpoints = higher response chances.


5. A nice and thorough chit-chat is a must

When it comes to your first call, you have to be ready to make it smooth and as informative for both of you as possible. First and foremost, stick to your company’s culture: if it’s rather informal, keep it easy; if you’re looking for a gentleman, make sure to keep up with it. You’ll start with obvious introductions and agendas, then move to questions from both sides. Here is where it comes to identifying the real talent.



What I would usually ask on the calls:

  • Share their story—how did they end up working in such an aggressive sales industry?
  • Share what type of sales they are covering: full cycle, international, B2B, enterprise?
  • Ask for specific numbers: what’s the average deal size, how many deals do they close, what’s their sales cycle? Those numbers should match when you calculate.
  • Ask about their favorite/biggest/latest deal: ask them to walk me through the process step by step.
  • Ask about their goals in general and where their passion lies.


6. Be nice and keep in touch

Even if a candidate isn’t the right fit for your current role, that doesn’t mean they won’t be a fit for future positions. Keep the door open for future opportunities by maintaining a relationship. Connect with candidates you admire but don’t hire, and keep them updated about future openings. Building a talent pool for future roles is a great way to minimize hiring time when a position opens up, and it keeps you connected with top talent.


Conclusion

To find a salesperson, you have to implement a salesperson's approach. Period. Do your research on the product and on the candidate. It’s better to have a very narrow candidate pipeline that highly matches with your product than a pipeline of 100 salespeople that only match with “sales” in their skills.


To catch those high-maintenance people, you have to invest more in your communication: write a personalized pitch with a very clear intro to the product, clear offer and perks, and next steps. On the call, don’t lose focus and make sure to double-check all points of experience: what products they sold, what numbers they had, and what they want right now.


And last but not least, it’s also about their and your vibe. The Wolf from Wall Street is memorable because of his true passion and hunter mentality, not because of beautiful numbers in reports.


That’s it!

May the force be with you!




Would you like to take a stab at answering some of these questions? The link for the template is HERE. Interested in reading the content from all of our writing prompts? Click HERE.