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The challenge when looking to hire a great sales leader is not simply with identifying viable candidates, but how to uncover their "hot buttons" and convince the strong ones to consider leaving a company they are already successful in. Sales headhunters are experts with how to uncover hot buttons and identify potential trigger events in the market.


Whether or not you use a recruiter, the same interview process applies.

  1. Reach out to potential candidates and let your network know you’re hiring

  2. Exhaust internal and external resources for identifying top candidates in the market

  3. Review applications

  4. Schedule short phone calls with promising candidates to screen them for interest

  5. Determine whether the candidate's sales success and product or service sold, verticals, average deal size, quotas and target buyers are inline with your organization

  6. Meet in-person with candidates who passed phone screen

  7. Meet again with candidates who did well in previous interview; have them speak with several members of the team

  8. Follow up with the remaining candidates to determine interest

  9. Have final candidates conduct a mock presentation if they will be conducting sales presentations for clients

  10. Speak with a shortlist of references

  11. Extend job offer to the top candidate


Experienced headhunters generally have large networks they have built over years and know how to gain the interest of candidates at this level.

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Recruiting for Sales hunters is in a league of its own within the recruiting industry since they are evaluated more on their “Soft Skills” or repeatable traits than any other category of candidates.  Sales hunters are the face of the organization and are typically the first touch point for potential customers. A talented Sales hunter will be able to quickly increase brand awareness, create a strong network, build a pipeline and close deals.


Sales hunters are able to operate with an understanding of their sales cycle, pipeline expectations and closing ratios. They are motivated by landing new logos and increasing their organization's brand awareness.


How do we define a Sales Hunter?


A Sales hunter interacts heavily with customers to promote a product or service. They are expected to make a convincing case to their clients and help drive their company’s growth. As the first point of contact for customers, the manner in which Sales Executives carry themselves becomes critical. Their connections, credibility, and like ability influences perceptions about their company.


Besides evangelizing their company’s products or services, a Sales hunter is also responsible for relaying important information about the the client’s pain points, competitor landscape, and industry trends. A great Sales hunter should have strategic targets that allow them the opportunity to influence the design and development of their company’s offerings.


How is recruiting for a Sales Hunter different?


We look for a track record and pattern of sales growth, industry connections, and interpersonal skills in addition to strong stability throughout their career. Finding the right culture fit within a sales organization is paramount to driving growth and cohesiveness within a national sales team.


A strong Sales hunter should have the ability to engage with and persuade potential customers. Since sales professionals depend on networking to build a robust pipeline, the potential candidate’s reputation and relationships do make a difference. A great candidate will have the right mix of strategic and tactical selling skills.


While other executives might go straight to the interview once shortlisted, Sales hunters may undergo additional personality tests, stress tests, and communications tests, among others, to be considered for the role. To put it simply, recruiting Sales hunters is different, and often more challenging, than the search for other executives.


What to look for in a great Sales Hunter?


Sales Executives spend a good of time making presentations to prospects, so it’s important they are presentable, energetic, and comfortable in front of an engaged audience. They should be an experienced public speaker and think quickly on their feet.


A Sales professional carries the company’s brand on their shoulders, so they must have a strong moral compass to uphold the company’s beliefs and values. Although every employee is a brand ambassador, the Sales hunter has a high potential to impact the company image.





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VP of Sales Interview Questions


These questions span from technical and operational to cultural. Modify them to best fit your company, product, and the candidate.

  • If you could build a sales stack from scratch, which tools would you choose?

  • What metrics do you check every day, week, month, and quarter? Why?

  • How do those numbers guide your decisions?

  • Has a strategic shift ever changed which metrics you pay attention to because? Explain.

  • How do you work with other departments in your current job? Which relationship is the most valuable to you?

  • What size ARR growth have you achieved with each company? How did you achieve it?

  • Have you experienced any challenges working with Marketing? If so, how did you overcome them?

  • Have you experienced any challenges working with Support and/or Services? If so, how did you tackle them?

  • What have been your ASPs (Average Selling Price) in each of your previous roles?

  • What motivates our buyers to purchase?

  • How would you approach recruiting and hiring for your initial team?

  • Roughly how many salespeople do you think we need right now? At what level and locations?

  • Approximately how much of your time would you devote to recruiting in this role?

  • How have you successfully managed to retain your best salespeople?

  • How did you create a high-performance cultures?

  • How have you encouraged healthy competition?

  • What are the best non-monetary ways to recognize performance?

  • Have you experimented with sales compensation? Were any of those experiments successful? Failures? What did you learn?

  • What you would accomplish in your first three months? First year? 3 years?

  • I’ll level with you: This job will be tough. [Insert description here, e.g. We’re a small, lean team, operating with few resources and working long hours.) Are you up for that?


Try to be as patient and methodical as possible to avoid hiring someone just because they look good on paper or you need a warm body. The wrong VP of Sales can cripple your startup’s trajectory and burn valuable cash.


The right VP of Sales can double your ARR in their first year.


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