Remote - US Open Location

VP, Sales

North America

Reports to: CEO

Position summary

The VP, Sales has responsibility for defining the Americas go-to-market strategy and for developing strategic Sales Plans to drive the region’s revenue growth. This key role provides sales direction while fostering a culture of accountability and high-performance with the primary goal of growing revenue and guiding Winshuttle to reach its next phase of significant growth. As the most senior salesperson in the region, the VP, Sales has overall accountable for the region’s sales performance.

About Winshuttle

Are you interested in working in a fun, collaborative environment, for an award winning workplace? Winshuttle is dedicated to fostering a culture of respect and innovation to support and empower employees' ambitions. We're constantly looking for entrepreneurs who aren't afraid to think outside the box, and don't take themselves too seriously. We embrace and support our employees who seek opportunities for continued learning, inspire others, and live and breathe our core PACT values. We have a work hard, play hard mentality; we're constantly evolving lean solutions for ERP business processes by day, and dominating on the frisbee golf course by night. Our strength and competitive advantage stems from our awesome employees, and we strive to create a balanced work life that is as inspiring and rewarding as life at home. Think you might be a great fit?

Essential functions and responsibilities

  • Analyses the region, draws conclusions from the analysis and builds a strategic Sales Plans in-line with the global sales strategy
  • Defines, leads and executes the regional Sales Plan to achieve sales targets and grow the business
  • Builds and grows a high-performing sales organization, consisting of inbound, outbound, partner and direct sales methods
  • Provides clear and motivational leadership and creates a culture of success and accountability
  • Implements strategies for expanding the Company’s reach within our current customer base
  • Develops strategic executive level relationships with key customers and participates in closing strategic opportunities
  • Travels for in-person meetings with customers to develop key relationships
  • Serves as the internal and external evangelist for all solutions, working with the sales team, support team, and key customers as necessary
  • Carries out segmentation of the region and defines optimal sales force structure for maximum return
  • Selects, develops and leads Sales Directors for high performance and coaches them to develop their leadership capability
  • Drives operational excellence that supports the delivery of a solid pipeline and revenue goal attainment
  • Directs implementation and execution of sales policies and practices
  • Provides management with regular performance readouts, dashboards, and associated business intelligence
  • Executes against a strong daily/weekly/monthly sales management and pipeline review process while monitoring key performance indicators
  • Defines sales processes that drive desired sales outcomes and identifies improvements where and when required
  • Constantly monitors the competitive landscape and market conditions to identifies opportunities, issues, and risks in order to recommend tactical strategies
  • Creates engagement with go-to-market strategy and lead change initiatives in response to changing competitive/economic landscape


  • Clearly defined go-to-market strategy for the region
  • Forecast accuracy and pipeline management
  • Achievement of revenue targets
  • Top talent development and retention

Desired behaviors

  • Thinks strategically – understands the market, anticipates future trends, and uses this knowledge to create a competitive advantage and set the strategic direction.
  • Translates strategy – converts the strategic agenda into bi-annual corporate goals and key performance indicators.
  • Leads change – recognizes strategic opportunities for change, acts as a change champion and inspire others, sets change direction and pace.
  • Makes sound and timely decisions – integrates stakeholder views and expertise into clearly articulated decisions that achieve targeted outcomes.
  • Uses the full capabilities of Winshuttle – develops level below to be effective leaders, creates a culture of continuous learning and innovation where all employees can reach their highest potential.
  • Builds a shared future – creates an environment where opinions and inputs from employees are regularly sought and acted on. Establishes communication systems and flows.
  • Over communicates – provides a strong vision that inspires confidence in the future and makes employees want to achieve the company vision and goals.
  • Displays ethical character and competence – gains trust by acting with integrity and intent. Creates a culture that fosters high ethical standards.
  • Is a role model – displays high levels of commitment and energy, role models our PACT(People, Action, Continuous Learning, and Trust) values and sets high standards of behavior.


  • BA or BS degree in Business or related areas; MBA preferred
  • Minimum 8 years’ experience in a Senior Leadership Enterprise sales role
  • Leadership in an Enterprise software environment with a strong command of sales funnel management and structuring sales quota and revenue expectations


  • Minimum 10 years relevant and demonstrated Sales leadership experience in Enterprise Software;
  • Experience in lead generation, sourcing, positioning, managing, relationship building, and selling to C-Level executives/customers;
  • Demonstrate a consultative sales approach with experience in constructing and delivering complex account-specific business development and sales plans;
  • Strong track record in maintaining significant customer relationships and identifying new business opportunities;
  • Ability to work collaboratively across multiple departments and geographic regions effectively;
  • Excellent presentation and communication skills, including verbal, written, and listening;
  • Strong business acumen and analytical skills with the ability to interpret client pain into actionable recommendations;
  • Ability to work and deliver under pressure in a fast-paced environment with evolving conditions.

At Winshuttle, we celebrate and support our differences. We know employing a team rich in diverse thoughts, experiences, and opinions allows our employees, our products, and our community to flourish. Winshuttle is honored to be an equal opportunity workplace. We are dedicated to equal employment opportunities regardless of race, color, ancestry, religion, sex, national orientation, age, citizenship, marital status, disability, gender identity, sexual orientation, or Veteran status.

This job posting does not imply that these are the only duties to be performed. Employees occupying this position will be required to follow any other-related instructions and to perform any other job related duties requested by their supervisor. To perform this job successfully, an individual must be able to perform each essential duty and meet the physical requirements satisfactorily. Reasonable accommodations may be made to enable qualified individuals with disabilities to perform the essential functions.

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