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How to hire your first VP Sales.

Having been a sales person most of my life and now CEO of a SaaS company. Few things I look for in a sales person that I hire (relevant for VP Sales too, you just need to go a lot deeper).

Every person is different and every sales person has a different style of selling, some are Relationship based sales professionals, some are Challenger based. Identify your customer base, would your product be sold to CXO level or Director level. Would it be sold to SMB’s or Enterprises. A sales professional who can sell to a Product Manager in an SMB might not be a good fit to sell to CXO in an enterprise. You also need to understand the price point of your product before you hire the VP Sales. Has the person sold smaller SaaS deals $10/ license or $1000/ license.  Both require different skill sets.

Does your start-up/ company at this stage need a VP Sales from SalesForce, Dropbox, LinkedIn or another growth stage Start-up would do the trick? 

  1. VP Sales at early stage startup is a Sales/ marketer/ growth hacker – is a sales Hustler. This person will get you more deals closed.  Look for this person if you around $500,000 revenue.
  2. VP Sales at a more stable growth stage is one who is looking to grow revenue from existing customers and also getting new business. Look for this person if you are around $2,000,000 revenue
  3. VP Sales at a SMB company would go for few big leaps. S/He can open few enterprise deals for you.  Look for this person when you are around $10,000,000 revenue
  4. VP Sales at a enterprise. This is the person who analyses your growth daily. Lives by reports and dashboards. This is the person you need when you are around 50,000,000+ revenue 

So before you go out to hire a VP Sales, see which stage of the company you are at currently and what does your company sell to understand who can help you at which stage.  There are few things to do before you hire your VP Sales. 

  1. Sell yourself. 
  2. See what the customers are saying. 
  3. Get a feel of the market. 
  4. What questions are your customers asking. 
  5. What are your customers saying post they have tried your product.
  6. Hire 1 /2 Sales Reps. 

Once you have sold the product yourself,  hire a 1/2 Sales Managers/ Reps before you hire your VP Sales. With their help, without spending a lot you will get an idea of how others (other than the Founder/ CEO) sells and the challenges they face. VP Sales would be an expensive hire and you want to make sure that you have tried something, built a pipeline before you take and hire your VP Sales. Few things that you should ask your to-be-hired VP Sales:

  1. The questions that your customer asked you while you sold, ask the ‘to-be-hired” VP Sales the same questions and see how he responds. One of the reasons you need to sell first. They won’t have answers to all the questions about the product but this will give you a good idea about how this person thinks and his analytical thinking. Thinking on the feet is one asset all VP Sales should have.
  2. Who does the “to-be-hired VP Sales” thinks are your competitors – This would give you an idea about how much s/he knows about your product and the market.
  3. How would they sell the product? – Based on how you have sold and the feedback you have received would give you an idea if that will be successful or not.
  4. Sales Strategy 

    1. Ask them what should be the annual target for the coming year. – This will give you an idea if the person is aggressive or conservative. Before you ask them, you have to give them an idea of what you current pipeline looks like
    2. Give them a situation, give them your expected growth number and how will they achieve the same
    3. Give them example of a company and the revenue you are generating from them. How will s/he increase the revenue from this company? How can s/he take 10k to 100k/ year revenue from that company?  
    4. How did you handle a situation where your competitor was already selling their product to the company? 

  5. Have they sold something themselves recently. Most VP Sales that you will hire, would have had a decent team to support him/ her. Make sure that they have closed deals themselves. Ask pointed questions to figure out what they did and how they did it. Challenges they faced. Is s/he  confident of owning part of the quota. 
  6. How has this person handled the growth in the previous organization. What was his contribution. Map it to your current state and see if this person will be a good fit. 
  7. Team Player – 

    1. Make sure that he gives credit to his team. A VP Sales who hogs the limelight is not one you would want to hire. Rest assured that his/ her team members would never be happy. 
    2. How does he hire sales professionals? What does s/he looks for when hiring team members – His/ her answers should give you an indication of how balanced s/he is. Does s/he have the same qualities s/he is looking for? 
    3. Who was the most successful team player he has in his/her current organization – what was his/ her role in making that player successful
    4. Who is the worst sales person in his current organization. What has s/he done to make sure that person becomes successful. 

  8. What was the worst quarter s/he faced? By how much did s/he missed their number? What did s/he do about it?

A great VP Sales can take your company with limited traction to great sales, and a good VP Sales can stop your company’s growth. Make sure you hire the right person at the right time.


Twitter: @relatasHQ


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  1. Very helpful. Thank you, Sudip!

  2. Great insights Sudip… can relate to many things in there…

  3. Thats a great insight Sudip. Something that only an experienced Sales person like you can tell. I was planning to Hire a sales manager for my new venture but guess I have some insights now and that I shouldn’t at this very moment 🙂

    Thanks for sharing.

  4. Thanks for the kind words Sushrut.

  5. Excellent

    Can you share your thoughts on sales incentives and structures?

  6. Thanks Bipul.

  7. Thanks Alok. Possibly my next post 🙂

  8. Thanks Vipul.

  9. It very insightful. Thank you Sudip 🙂

  10. Thanks Tanmay

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