Regional Sales Director

Accountabilities

• • Own and exceed annual revenue targets, sales quotas, and new-business objectives across the assigned territory.
  • Make new-logo acquisition the primary focus by proactively prospecting, developing qualified opportunities, and converting prospects into customers.
  • Build and maintain a consistent pipeline of prospective and existing business through outbound prospecting, conferences, webinars, calls, and in-person meetings.
  • Develop trusted relationships with regional, enterprise, and executive-level customers through consultative selling and strong interpersonal engagement.
  • Assess customer needs, qualify opportunities, and develop customized solutions that address specific operational and financial challenges.
  • Deliver compelling product demonstrations, sales presentations, webinars, quotations, proposals, and supporting sales documentation.
  • Present complex technology solutions clearly, translating technical capabilities into tangible customer and business value.
  • Manage the complete sales cycle, including opportunity development, negotiation, contracting, and close, involving senior management when required.
  • Provide accurate sales forecasts and maintain strong CRM and pipeline discipline to support revenue planning and management visibility.
  • Manage territory activity and travel expenses effectively while prioritizing the highest-value opportunities.
  • Serve as a senior escalation point for customer service and customer success teams when complex customer issues require sales leadership involvement.
  • Communicate customer requirements, market insights, and solution opportunities to product marketing and engineering teams.
  • Monitor customer insights, competitive developments, and market trends and adapt territory and sales strategies accordingly.
  • Maintain and grow existing customer relationships while identifying opportunities for expansion and repeat business.
  • Represent the organization professionally at customer meetings, industry events, webinars, and other business development activities.

  Requirements

  • 5+ years of consultative sales experience, preferably within transportation, logistics, IoT, M2M, or a related technology-driven industry.
  • Demonstrated success selling cloud-based SaaS or technology solutions, with the ability to sell against customer challenges rather than relying primarily on hardware.
  • Proven track record of consistently meeting or exceeding sales quotas and revenue targets.
  • Experience developing new business while simultaneously managing and expanding existing customer accounts.
  • Experience selling complex solutions to small, mid-market, and/or enterprise organizations.
  • Strong understanding of consultative selling, solution selling, sales processes, and territory development strategies.
  • Ability to articulate complex technical concepts in clear, compelling language for both technical and business audiences.
  • Strong customer-facing presentation and demonstration skills, including experience conducting webinars and executive-level sales presentations.
  • Excellent communication, negotiation, relationship-building, and interpersonal skills.
  • Strong analytical and problem-solving abilities, with the capacity to understand complex customer situations and develop effective solutions.
  • Exceptional organizational and time-management skills, with the ability to manage multiple opportunities and priorities effectively.
  • Strong work ethic, competitive mindset, self-motivation, and a consistent focus on achieving measurable results.
  • Ability to build productive relationships with customers, sales teams, partners, vendors, and internal stakeholders.
  • Proficiency with Microsoft Office and sales technology such as Salesforce, ZoomInfo, and SalesLoft.
  • Bachelor’s degree or equivalent professional experience.
  • Valid driver’s license with a good driving record.
  • Willingness and ability to travel regularly to support customers and sales opportunities.

  Benefits

  • Competitive compensation aligned with experience and sales performance.
  • Opportunity to earn performance-based compensation through achievement of revenue and sales targets.
  • Preferred location in Chicago, Illinois.
  • Opportunity to work in a customer-facing, growth-oriented sales environment.
  • Exposure to SaaS, IoT, transportation, and technology-driven solutions.
  • Opportunity to build relationships with regional and enterprise customers and senior decision-makers.
  • Cross-functional collaboration with sales, customer success, product marketing, and engineering teams.
  • Opportunity to contribute directly to new-business growth, territory expansion, and customer loyalty.
  • Professional environment focused on customer value, innovation, and measurable sales performance.