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Pineapple Contracts

Vice President of Sales

Full-TimeUpdated on 10/17/2026
No salary listed
Expert
Sterling Heights, MI, USA
In PersonOffice-based; 12 work-from-home days per year.
Sales & Account ManagementAccount Executive

About the job

Requirements
  • Proven experience in a senior sales leadership role, ideally within a growing sales organisation.
  • Strong leadership presence, gravitas, confidence and credibility with both sales teams and senior stakeholders.
  • Experience managing sales managers or area-level sales leaders, with the ability to lead through others.
  • Strong people management capability, including coaching, performance management, appraisals and team development.
  • Ability to build culture, set pace and create accountability while maintaining a positive and supportive work environment.
  • Strong commercial awareness and the ability to make rational, business-focused decisions.
  • Confident communicator with the ability to influence internally and externally.
  • Experience using CRM systems, sales data and performance insight to drive improvement.
  • Highly organised, diligent and able to work at pace in a rapidly expanding business.
  • Excellent written and verbal communication skills.
  • Flexible, positive, resilient and comfortable operating through change.
  • Full, clean driver's licence.
Responsibilities
  • Take overall responsibility for the day-to-day leadership of the Sterling Heights site, helping bring the office together and maintain a consistent leadership presence.
  • Build a positive, collaborative and accountable culture that supports continued growth.
  • Provide strong, visible and confident leadership to the US sales team.
  • Set the tone, pace and expectations for the team, creating a high-performing, accountable and positive sales culture.
  • Lead regular sales meetings to review performance, priorities, pipeline and support needs.
  • Manage, mentor, coach and motivate the team, ensuring clear direction and consistent follow-through.
  • Conduct regular one-to-ones and formal appraisals, providing constructive feedback and clear development plans.
  • Address performance, conduct or morale issues promptly, with support from HR where required.
  • Provide greater day-to-day involvement with the sales team and act as the senior leadership presence in the office.
  • Act as a visible role model for Pineapple's people values and expected standards of behaviour.
  • Maintain open and transparent communication across the team, ensuring expectations are clearly understood.
  • Be accountable for overall team performance, activity, behaviours and delivery against agreed sales targets.
  • Coach the team through call listening, live feedback, deal reviews and sales technique development.
  • Identify areas for improvement and implement practical strategies to enhance individual and team effectiveness.
  • Identify and manage recruitment or resource needs.
  • Recruit, onboard and train new sales team members, ensuring they are integrated into the team successfully.
  • Provide ongoing training and development to strengthen capability, confidence, product knowledge and sales consistency.
  • Design, optimise and embed sales processes and workflows to maximise efficiency, consistency and productivity.
  • Ensure expectations and goals are clearly defined, communicated and regularly reviewed.
  • Track and monitor progress against individual and team goals, ensuring accountability is maintained.
  • Ensure CRM and in-house systems are used consistently and accurately by the team.
  • Maintain visibility of team activity, pipeline, customer follow-up and performance trends.
  • Provide regular reports for senior management as required.
  • Use performance data and sales activity insight to drive accountability and improvement across the team.
  • Work within existing pricing and discount approval limits, with escalations remaining with the President of Sales.
  • Influence across the wider business, bringing insight from the sales team and helping to shape practical improvements.
  • Act as a point of escalation for challenging customer situations where sales leadership support is required.
  • Perform other ad hoc duties as reasonably required.

About the company

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