Sales Executive, Senior

Sentinel•Milwaukee, WI

8d•Hybrid

About The Position

Sentinel Technologies is hiring an experienced technology sales professional to develop and execute a territory strategy, grow new business, expand market presence, and build customer relationships. The role involves engaging executive decision-makers, leading complex multi-service sales pursuits, and representing Sentinel as a trusted advisor at customer meetings and industry events. The successful candidate will position and sell Sentinel’s portfolio of infrastructure, cloud, security, collaboration, managed services, and other multi-service solutions, while partnering with engineering and delivery teams to address customer challenges. The position reports to Sentinel’s Milwaukee, Wisconsin office and follows a hybrid work arrangement after onboarding. The first week includes travel to the company’s Downers Grove, Illinois headquarters for onboarding, introductions, and training. Occasional travel to Sentinel offices for meetings, training, and company events is expected, typically two to four times per year. The role also requires travel between locations and client sites using the candidate’s own car. Sentinel describes its culture as entrepreneurial and team-oriented, emphasizing creativity, growth through certification and hands-on training, and rewards based on impact. Candidates must be legally authorized to work in the United States without sponsorship and will be required to complete a background check.

Requirements

At least 8 years of experience selling technology solutions.
Strong business knowledge.
Strong verbal and written communication skills.
Negotiating skills and demonstrated ability to sell solutions.
Must have a car for travel between locations and client sites.
Valid driver’s license and proof of vehicle insurance are required.
Legally authorized to work in the United States without sponsorship.
Must demonstrate a can-do attitude.
Candidates should display the company’s ACE qualities: Attitude, Compassion, and Enthusiasm.

Responsibilities

Develop and execute a strategic territory plan to drive new business, expand market presence, and pursue whitespace opportunities within target accounts.
Use existing industry relationships and proactive prospecting to connect with new customers and key decision-makers.
Represent Sentinel as a trusted advisor and solution expert in executive meetings, customer engagements, industry events, conferences, and trade shows.
Lead complex, multi-stakeholder sales pursuits by engaging executive, business, and technical decision-makers throughout the buying process.
Conduct strategic discovery sessions to understand customer objectives, competitive challenges, long-term initiatives, and technology requirements.
Position and sell Sentinel’s full portfolio, including infrastructure, cloud, security, collaboration, managed services, and multi-service solutions.
Structure, negotiate, and close complex multi-year and multi-service agreements.
Contribute market intelligence and deal-strategy support across the sales organization.
Mentor less experienced sellers and foster long-term customer success and retention.