Strategic Software Sales Executive


About Frontline Education

Frontline Education is a leading provider of SaaS EdTech solutions for educators and administrators across the United States. Frontline Education serves more than 12,000 educational organizations nationwide.  Our solutions are used in all 50 states and have the largest data set in K12 Human Capital Management.  We partner with school districts whose professionals and staff use our premier software solutions daily. In 2015, we were recognized by INC. Magazine as one of the fastest growing private companies in North America. Our unprecedented growth has created new opportunities in our sales teams nationwide. 


We are currently seeking a Strategic Software Sales Executive for the Mid-West Region based in Chicago, IL.


Reporting to the Regional Sales Manager, the Strategic Software Sales Executive is responsible for promoting and selling Frontline products and services in a professional, well-informed and well-planned manner to prospective school district prospects. The Strategic Software Sales Executive will be tasked with creating long-term, growing and profitable Frontline customer relationships.


They will also be responsible for developing a deep understanding of significant client concerns to be able to propose, describe and defend appropriate solutions in the form of value propositions. Consistent application of this process enables a diligent salesperson to meet or exceed all sales goals, performance quotas and process expectations in his or her assigned territory. Doing so will effectively promote Frontline Technologies and will require significant industry, company and account knowledge. It will also require Frontline product knowledge and successful sales techniques and professional sales skills.


Key Responsibilities

  • Establish regionally focused sales strategy focused on large school districts and state-wide account in the region.
  • Achieve or exceed assigned quota
  • Develop and drive Solution selling strategy to increase bundle adoption rate.
  • Develop deep understanding of the challenges facing Frontline customers and recommend appropriate solutions
  • Demonstrate a tenacious commitment to win.



Key Competencies

  • Demonstrable experience. You will maintain a clear record of quota achievement, excellent account planning skills and a willingness to work hard and persevere to make things happen. You are comfortable with long sales cycles and complex organizational structures.
  • You will possess exemplary communications skills with a variety of influence styles to solve complex customer business challenges and drive results.
  • Metrics driven. You have proficiency in Solution selling (apps per transaction), building pipeline and increasing customer retention rates.
  • Relationships! You easily build and maintain trusted relationships with key stakeholders and influencers at major accounts to ensure that customer needs are met and to be aware of new opportunities.
  • You’re so good at collaboration, it might be your middle name. This role requires a great deal of collaboration both internally and externally. Internally, collaboration with other departments such as Marketing, Finance and Accounting, Customer Success, Sales operations.
  • Continuous improvement mindset. Maintaining the status quo is a “no go” for you. You strive to consistently improve.



  • Bachelor’s Degree or higher
  • Minimum of 7-10 years’ experience with a track record of achieving or exceeding quota of $800k or higher-preferably in education community related field or software sales.
  • Pre-existing K12 relationships and platform sales preferred
  • Maintain a robust pipeline and an effective relationship based account plan in Frontline’s CRM tool leading to successfully retirement of quota.
  • Demonstrate excellent follow-up skills with prospects, customers, internal staff and management.
  • Continually learn new products and services and methods of presentation for these products, demonstrating ability, skills and knowledge of all existing and new products and services.
  • Prepare for and attend assigned state territory conventions; sales & marketing meetings; training meetings and national state shows.
  • Ability to listen for real and perceived customer needs.
  • Ability to travel overnight as required for given sales territory including some weekends.
  • Ability to be flexible in a rapidly growing and evolving business environment.
  • High degree of personal integrity and commitment to the organization’s core values including ethics, honesty, and transparency
  • Demonstrate ability to be a team player.
  • Ability to establish work environment at home.

We offer a competitive compensation package including a base salary, commission plan and stellar benefits.  Our company growth has created a promising environment for career advancement and rewarding challenges.

Are you ready to make a true impact by joining a world class sales team that directly influences the education industry?  Then let’s talk!

Visit or contact our recruiting team at 484-473-3691. 

Frontline Education Vision:

Partnering with the education community to prepare students with the skills for tomorrow and a lifetime of learning

Frontline Education Mission:

Serving members of the education community with integrated solutions, insights and caring people to support them in their pursuit of excellence

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200 W Monroe St. #2100, Chicago, IL 60606
200 W Monroe St. #2100, Chicago, IL 60606

Perks of working here

401(K) Matching
Health Benefits
Onsite Gym
Tuition Reimbursement
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