Strategic Sales Executive

DW SalesFull TimeUnited States

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Strategic Sales Executive

The Strategic Sales Executive is responsible for direct and in-direct selling of Drivewyze subscription-based solutions. The Strategic Sales Executive will build relationships with management-level decision-makers through thoughtful engagement, pre-existing relationships, and connections in the transportation industry. This hunter role will utilize ongoing rapport with potential end customers and create pull through the Drivewyze Channel Partner Program to drive revenue.


Reports to: Director, Strategic Sales

Location: Negotiable, Remote


About the Job: The Strategic Sales Executive is a high-level hunter position, seeking out Private and For-Hire Top 100 fleet prospects and facilitating all sales cycle stages. This role will act as the lead responsible for maintaining strategic relationships primarily with the fleet decision-making team, executives, and through the channel partner contact network.


This role will be accountable to:

  • Identify potential “new logo” sales opportunities, define joint solutions, develop business cases, and drive go-to-market strategies.
  • Drive lead generation activities utilizing partner programs via association participation, outbound calling, email campaigns, conference calls, webinars, and social media such as LinkedIn.
  • Collaborate with Drivewyze Marketing, Product Management, and other cross-functional teams to determine necessary sales strategies and tactics.
  • Identify prospects via existing business relationships and new contact engagement, like cold calls or other relevant means.
  • Set up and deliver sales presentations and product/service demonstrations at the executive level, both online and in person.
  • Facilitate handoff of newly closed business accounts to the Customer Success and Strategic Accounts team where and when appropriate.
  • Work with the Business Development and Channel Partner Sales teams to pull through the partner community.
  • Manage sales forecast and budget plan for the defined sales territory and/or named accounts.
  • Conduct weekly and monthly business and pipeline reviews with Director, Strategic Sales.

Skills and Qualifications:

  • Ten plus years of experience in direct sales in the transportation industry.
  • Demonstrated success converting prospects, closing deals, and meeting sales targets and quotas.
  • Post-secondary degree or diploma in Business, Marketing, or a related field.
  • Strong problem identification and objection resolution skills.
  • Able to build and maintain lasting relationships with customers and the industry in general
  • Exceptional verbal, listening, written communication, and presentation skills.
  • Self-motivated and ambitious, with high energy and an engaging level of enthusiasm.
  • Ability to work individually and as part of a team, in addition to high integrity and work ethic.

Additional Information:

  • Significant travel is required.

Work with us because you believe in what we do.

Want to be part of a team whose mission is to save lives by reducing commercial transportation fatalities? How about being part of a tech company that will disrupt the industry with a radical new idea? Want to experience what it’s like to work in a silicon-valley, start-up-like organization?


Although technically, we have been in business for over 15 years, we are proud to have maintained a start-up feel with each team member acting like owners modeling our values:


  • Create Exceptional Experiences. Think like a customer, colleague, partner, and stakeholder. Strive to go above and beyond and have a positive impact on others.
  • Drive to Succeed. Be purposeful and accountable. Persevere through challenges and seek ways to enable success. Operate with speed, agility, and excellence.
  • Empower and Lead. Take the initiative and be proactive. Identify problems quickly and help tackle them. Have a voice, share ideas and give constructive feedback. Encourage others to do the same.
  • Disrupt Creatively. Be curious, explore ideas without bias, and fearlessly try new things—Foster innovation with diversity of thought. Merit ideas, not titles, and learn from failure.
  • Cultivate Relationships. Build credibility and influence with integrity, honesty, and commitment. Seek win-win outcomes and lead with transparency and high ethical standards.
  • Raise the Bar. Continually improve and grow. Build for the future, develop capability, and help others to learn. Take risks and aim high. Don’t iterate when you can change the game.
  • Play as a Team. Navigate with genuine care, respect, and inclusiveness. Create momentum through time-saving collaborative partnerships. Celebrate successes and have fun.

Let’s talk compensation and perks:

  • Competitive compensation and benefits package
  • Open vacation program with unlimited vacation days
  • Employee stock options
  • Collaborative team and inclusive organization

About Us:


As an organization, our innovative and collaborative culture is woven into the fabric of our DNA and seen through our interactions with one another. Our teams work together to solve problems that have a real-world impact, with all voices being heard at the table, and we believe respectful and inclusive idea-sharing is fundamental to our ability to continue to push into uncharted territories. Our IIS roots are deep with 18 years of cultivating relationships and expertise, and our subsidiary Drivewyze is a testimony of our ability to disrupt industry and change the game. Our incredible journey has been built with teamwork, creativity, and humbly brilliant people ready and willing to explore new possibilities together.

To learn more about the Drivewyze journey, visit: https://www.startupedmonton.com/drivewyze


Intelligent Imaging and its subsidiary, Drivewyze is an equal opportunity employer. All qualified applicants will be given consideration for employment without regard to race, color, religion, sex, national origin, disability, or protected veteran status.