ABC’s Applied to Recruiting

“Closing the Deal” with your Top Sales Candidates

Jim Wilson
Oct 13, 2016 · 5 min read

One of the hardest parts at an early stage startup is building out the initial sales and marketing team. A lot has been written about when to hire and how to qualify your initial Sales VPs and Reps, such as Greg Sands’ Sales Learning Curve and Jason Lemkin’s How to Hire Your First VP of Sales. But once you’ve found that ideal candidate, how do you close them?

Ironically, closing someone whose job is to close deals is more complex than most realize. Getting your ideal candidate to say yes quickly is critical because sales leaders operating at peak performance are inundated with inquires the moment they spring loose. This was evident during my last transition at Sumo Logic based on the sheer number of enquiries for VP Sales roles.

If you’re a Founder or CEO, here’s how to attract the best talent and close the killer sales candidates you want:

1. Sell First. Earlier in my career, I was brought into a prospective company to meet the CEO. I looked at the website and wanted to learn more, but the moment my meeting started with the CEO, he began grilling me with questions about pipeline management and sales strategy. He assumed I wanted the job and was already sold just because I took the meeting!

The more senior the sales position, the more deeply a candidate needs to understand the risks, the team, vision and market. They need to hear what the founder thinks so they can envision a path to success and see if the founder has realistic expectations. There will be plenty of time to dig into their qualifications after both sides have assessed if it is a match. In fact, the best founders and CEOs make it explicit that they will sell first then will “turn the tables” and expect to be sold.

Here are the types of questions to expect from candidates to make that initial meeting productive:

  • How well do we fit the Candidate’s ideal job and company criteria?
  • Why would they want to work here and what is the career path?
  • Why are we expanding or reorganizing the sales team?
  • Why have customers bought from us and why do we win?
  • Why do we lose, how do we differentiate from the competition?
  • What are the revenue and headcount growth plans? What are the assumptions being made and associated risks?
  • What is our company culture and what is it like to work here?

Great sales people want to understand the opportunity, the risks, and if the founder has a methodical plan and realistic expectations. One bonus to this approach: their engagement level and interactions will give you the first clue if they’re a fit. Do they ask thoughtful questions? Do they want to learn more? (Hint: don’t hire anyone who isn’t genuinely curious and passionate.)

2. Document Your Ideal Profile. I highly recommend both discussing and documenting your ideal candidate profile. If it’s your first Sales Rep hire make sure you are looking for the “sales apprentice”. If it’s your first VP Sales hire, it’s critical that their background and experience are a fit.

Do you value domain expertise or do you want a utility player? Do you need someone who has sold complex Enterprise deals or do you need High Velocity Sales sales experience? Are you selling to an IT Buyer or a Business Buyer? A simple format I have used is KSQ, which stands for Knowledge, Skills, and Qualities. Here’s a sample scorecard (customize for your needs):

The most important part of this exercise is to discuss the criteria’s relative importance with other team members (including your Board) and agree on the ideal candidate. Then use this as your scorecard and stick to the criteria. And always put more weight on qualities over experience and skills. Experience and skills can be learned, qualities cannot.

3. Be Inspirational and Factual. When I met Mark Selcow and Matt Glickman (the Founders of Merced Systems), it was their detailed analysis of the underserved Call Center Performance Management market that closed me. Likewise, I distinctly remember Mike Speiser (Board Member at Sumo Logic) explaining the massive TAM of the Log Management and Data Analytics market, that convinced me to join.

Great sales people dream big – big job, big deals, big pay, big title. Use this to your advantage: whether you’re going to disrupt a huge market, go after an industry leader, or change the world, make sure those huge aspirational goals are clear. But make sure you back it up with facts. Disrupting a huge market? Have the TAM numbers and penetration estimates ready. Chasing an industry leader? Show how will you differentiate and win. Changing the world? Explain the tactical plan and contingencies you’ve considered.

The more you can provide factual, data driven, and realistic analysis, coupled with your “Dream Big” message, the better your chances of closing your candidate.

4. People Work for People They Like. In sales the saying goes “people buy from people they like.” This also applies to recruiting. Make sure a dinner or a good meal is part of your interview and closing process. Not coffee, not a quick bite at the sandwich shop, but a nice meal that involves deep discussion. The founder/CEO relationship with sales is one of the most critical parts of a successful team, and it’s always top of mind for any strong candidate. Encourage as many people as possible to meet the candidate out of the office and make sure to discuss it later. Everyone, including your candidate, should feel like there’s a good cultural fit.

Again, there’s the added bonus that founders get to know their candidate’s personality and how they interact with others outside of the office. One of the best closes I ever experienced was with Vance Loiselle, former Sumo Logic CEO, who took me and my wife to lunch, focused the discussion on our family, then pulled out the written offer at the end of the lunch. I signed the next day, and I am pretty sure my wife would have signed if I hadn’t!

Hiring great sales talent is a challenge for any founder or CEO as the company grows, and closing the right candidates can have a huge impact on future sales growth. Incorporating best practices like these will make it easier and reduce the risk.

Good luck selling and closing your dream sales team!

Costanoa Ventures

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