Regional Sales Executive, North Central

Regional Sales Executive, North Central

Milestone Systems, a global leader in open-platform Video Management Software (VMS), is seeking a highly skilled and strategic Regional Sales Executive (RSE), North Central to drive growth across mid-market enterprise organizations (under $1B in annual revenue). This role is designed for a true end-user–centric seller who can influence enterprise-wide surveillance strategies, lead complex discovery, and guide risk and compliance-driven modernization efforts in diverse customer environments.

Covering CO, WY, ND, SD, MN, WI, NE, IA, IL, IN, OH, and MI, the RSE engages directly with end users, systems integrators, consultants, and key channel partners to build pipeline, standardize technology architectures, and shape long-term platform adoption. This position requires consultative, business-focused selling well beyond traditional feature-and-function conversations.

The ideal candidate resides within the territory (preference: Minnesota, Nebraska, or Iowa). Relocation assistance is not offered at this time. This role reports to the National Sales Manager, Central.

Key Responsibilities

End-User Leadership & Enterprise Discovery

• Engage directly with mid-market enterprise end users to uncover surveillance program requirements, risk exposure, compliance mandates, and distributed operational workflows.

• Lead conversations that drive standardization of VMS platforms, analytics capabilities, device management, and future-ready architectures across the enterprise.

• Present business outcomes and modernization strategies, framing tradeoffs between legacy infrastructure, sunk-cost investments, and as-a-Service models.

• Influence communities of interest by connecting vertical peers, regional advocates, and industry influencers to accelerate adoption and build market momentum.

Pipeline Development & Sales Execution

• Identify, research, and engage prospective end users through proactive outreach, networking, territory segmentation, and industry event participation.

• Build and maintain a healthy, visible pipeline with disciplined Salesforce utilization, ensuring accurate forecasting and full opportunity transparency.

• Navigate complex sales cycles from discovery through validation, negotiation, and close, ensuring a predictable path to revenue.

• Collaborate with integrators and distributors while maintaining direct ownership of customer discovery, opportunity creation, and solution positioning.

Cross-Functional Collaboration & Channel Alignment

• Partner closely with Milestone channel business managers (CBMs) to ensure all end-user opportunities are ultimately executed through Milestone’s authorized channel ecosystem. The RSE owns end-user engagement and opportunity progression; CBMs align the appropriate integrators and distributors for quoting, procurement, and project delivery.

• Operate with strict adherence to Milestone’s channel-first sales model: Milestone does not sell directly to end users, and all transactions must flow through approved partners.

• Partner with Solutions Engineers, Marketing, Customer Success, and Product teams to enable seamless execution, drive technical validation, and support long-term retention.

• Provide customer insights to internal teams to influence product roadmap decisions and content development.

Thought Leadership & Market Positioning

• Represent Milestone at industry events, regional seminars, partner engagements, and vertical working groups.

• Promote open-platform VMS strategy and Milestone’s role in risk mitigation, analytics readiness, and enterprise modernization.

• Contribute territory-level insights to shape marketing campaigns, enablement programs, and future GTM strategy.

Qualifications

• Minimum 5 years of B2B sales experience with consistent success in net-new pipeline generation and complex sales cycles.

• Demonstrated ability to lead discovery and engage enterprise end users across IT/security, operations, and finance.

• Strong business acumen with the ability to sell outcomes, not just technology: risk reduction, compliance, operational efficiency, modernization, and cost-model transformation.

• Familiarity with VMS, physical security, analytics, or related technologies strongly preferred.

• Proven ability to influence executive and technical stakeholders across distributed customer organizations.

• Proficiency in Salesforce with a disciplined approach to activity tracking, opportunity management, and forecasting.

• Exceptional communication, presentation, and negotiation skills.

• Self-driven, organized, and comfortable operating autonomously in a large geographic territory.

• Willingness to travel 25–30% across the region, including overnight stays.

Why Milestone?

Ranked among the 100 Best Companies to Work for in Oregon, Milestone offers excellent benefits, a flexible work environment, and a distinctive People-First culture. Employees enjoy professional development opportunities and the ability to directly influence organizational growth and customer success.

The annual on-target earnings for this position range from $155,000 to $170,000. Pay is based on level, location, complexity, and responsibility, and is one component of Milestone’s total compensation package. Milestone also offers medical/dental benefits, FSA or HSA, 401(k) with 6% Safe Harbor employer match, paid parental leave, generous PTO, 12 company holidays, and fully paid short- and long-term disability coverage.

Milestone is committed to creating a diverse and inclusive workplace and is proud to be an equal opportunity employer.

Contact & Application

Are you excited about this opportunity? We encourage you to apply as soon as possible. We will continuously take candidates into the recruitment process, and the position will remain open until a suitable candidate is found.

Please apply on our website: www.milestonesys.com 

We look forward to receiving your application.