Demo

Sales Director - Mid Market

Redhill Search, LLC
Chicago, IL Full Time
POSTED ON 3/19/2026
AVAILABLE BEFORE 5/18/2026

The Sales Executive is responsible for sales and revenue growth in their assigned, targeted accounts. This individual is responsible for building a sales pipeline, managing a sales process and developing Conceptual Sales Call Plans for their Regional Mid-Market clients.

About this position:
 
  • Build a pipeline of prospects and manage the sales stages from lead to close
  • Lead efforts to expand and grow market share and presence in the mid market clients through establishment and cultivation of ongoing relationships at the C-Suite level through research, cold-calling and professional networking which lead to a qualified pipeline of prospects
  • Create demand by clearly articulating and educating prospects on the Client value proposition thorough the presentation of products and services through demonstrations and presentations verbally communicating a compelling purchase rationale
  • Develop Sales Call Plans as a best practice for customer meetings for accounts in the sales funnel
  • Cultivate relationships with business partner counterparts and account managers who sell and support complementary applications and services to point of sale systems serving the restaurant industry
  • Plan, direct and coordinate sales support activities, including management of the sales pipeline through client sales tools (Salesforce)
  • Ensure all targeted prospect/client contacts and engagement opportunities are recorded in the client sales tools (Salesforce)
  • Understand the competitive landscape (strengths, weaknesses, benefits) and determine how to position client to win
  • Must collaborate with Account Service and Implementation Teams to ensure that expectations set during the sales process are met in delivery


     
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Qualifications:
 
  • Combination of SaaS and Digital Marketing experience is preferred
  • 2 years of relevant successful technology or professional services sales experience
  • Previous success in selling/leading sales efforts in environments with 3 to 6-month sales cycles
    • Proven sales skills in complex deal development, financial structuring, negotiations and closing with both new and existing clients
  • Comfortable with process driven sales, reporting and tracking
  • Strong written and presentation-based communication skills are required
  • Travel 30% or more


     
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Salary.com Estimation for Sales Director - Mid Market in Chicago, IL
$148,247 to $190,804
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