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Over the past 10 years, I have probably interviewed more than 100 sales reps.  As the head of marketing I often get asked to weigh in on the success potential for prospective account executives.  My initial approach to these interviews was to attempt to assess the selling skills of these candidates.  However, over the years I have realized that the sales managers are better equipped to evaluate a candidate’s ability to manage deal cycles, reach decision makers and overcome customer objections. As a result, I have changed my approach. Instead, I now focus on asking questions that will help me understand how marketing can better support the sales organization’s needs.

I am always eager to learn about what marketing strategies work (and do not work) for other companies. Asking questions about marketing strategies, sales technologies and sales enablement during the interview process is one of the best sources of new ideas I have found.  Below are some of the questions that I typically ask:

Marketing Strategies

  • What is the best marketing organization you worked with in your career?  What tools did they provide to make you successful?  What campaigns did they run to help generate leads?
  • What is the least helpful thing that your current marketing organization does?  Why was it counterproductive to your selling process?
  • What is the most creative approach you used to get an appointment with a hard-to-reach decision maker?

Sales Technologies

  • What do you like the least about your current CRM application?  What do you like the best?
  • What technologies or mobile apps do you like the best at your current employer.  Are there any that we should be considering?

Sales Enablement

  • Which sales methodology (book, motivational speaker) do you like the best?
  • One of the key success factors in hiring any new sales representative is shortening the time to productivity.  What are some things that marketing or sales enablement organizations at other companies you have worked at done to accelerate the process?
  • How do you learn best?  Classroom training, e-learning, coaching, simulation, on-the-job (shadowing another sales rep)?


Steve Keifer

Steve Keifer has led marketing and product management teams at seven different SaaS and cloud providers ranging from venture-backed, early-stage startups to multi-billion, publicly traded companies - including several that experienced hypergrowth, filed IPOs, and reached unicorn status. In Bantrr, Steve shares many of the best practices and lessons learned from building and scaling marketing organizations. Topics include new category creation, brand development, and demand generation.

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