Winnipeg, MB

Permission Click is a B2B, Enterprise SaaS company with a growing global footprint. We help K–12 school districts manage risk by automating forms, approvals, and workflows district-wide. The COVID-19 pandemic has underscored the importance for districts to have world-class tools to digitize their operations to better serve staff and families. The ability to increase safety by reducing process contact/touch points builds on the incredible efficiency gains and audit trail capabilities Permission Click delivers above and beyond paper-based manual systems.

At Permission Click, we would be nothing without our successful sales team. We’re seeking a qualified district sales executive to help sell our District Edition products and services to K–12 school districts across North America. The sales executive will have a strong understanding of the sales process, excelling at generating leads, building relationships, and closing deals. The ideal candidate will be a quick learner with strong negotiating skills, and the ability to showcase our offerings in a compelling way. Often tasked with giving presentations, attending networking events, and attending trade shows, it’s essential that our sales executives be both personable and professional.

Objectives of this Role

  • Full stack sales to K–12 school districts
  • Continually developing deep product expertise, user experience understanding, and requirements of districts
  • Generate opportunities via shows, industry events, outreach, and leveraging relationships, associations and partners
  • Deal management and pipeline reporting in HubSpot
  • Working primarily with district leadership, along with school administrators and educators, you will facilitate discovery sessions to understand the district’s current state, pain points, and goals to assess how Permission Click fits with their district
  • Product demonstrations that are tailored to fit district needs and generate excitement and confidence in joining the Permission Click user community
  • Work with our Customer Success and Support team to drive onboarding and adoption during rollout to ensure delighted users
  • Digging into risk management, K–12 district policies, district operations, and more to understand the best practices and frameworks our clients strive to exceed

Daily and Monthly Responsibilities

  • Consistent daily, outbound lead generation and pipeline building activities
  • identify appropriate prospects, set appointments, make effective qualifying sales calls, product demonstrations, and manage sales cycle to close new business
  • Maintain working relationships with existing contacts/clients to support exceptional service and identification of potential new sales opportunities
  • Build and maintain in-depth product knowledge to effectively conduct demos and handle objections
  • Prepare professional, complete, concise and accurate reports, proposals, booking packages, and other documentation required for executive-level sales presentations
  • Coordinate with other sales team members to ensure company quotas and standards are being met, performing market research and regular competitor monitoring

Required Skills and Qualifications

  • Three (3) years, proven experience as an account executive, or in a similar sales role
  • Live and breathe SaaS tools like Intercom,, Slack, HubSpot (or similar)
  • A humble, ‘lead by example’ mindset and drive to inspire everyone on the team
  • Proven experience working with cross-functional teams, preferably with Product, Software, and Sales. You will bring ideas to the table for product features, ways to work better together, and more
  • Excellent time management skills and organizational skills
  • Knowledge of market research, sales, and negotiating principles
  • Strong business writing skills used to compose proposals, presentations, marketing asset copy, and adapting contract boilerplates to suit unique deals
  • Passionate about the details. When we commit to a customer, we do everything possible to deliver, and you’re part of making sure we hit/deliver on these commitments.

Preferred Qualifications

  • Bachelor’s degree or equivalent
  • Proven success rate at levels above quotas
  • Ability to balance persuasion with professionalism
  • Existing relationships with district executives (CTO/CIO/CEO/Superintendents/Associate Superintendents/Business Officers) from a previous sales leaning role
  • Experience in Education Technology sales
  • Experience in the insurance, risk management, or school operations space a major plus
  • Have worked in a growing technology company and understand the entrepreneurial spirit, hustle, and ‘find a way to win’ attitude it takes to thrive
  • Remote working experience, or strong evidence you’re built to thrive in a remote working environment.

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