VP, North America Sales
About The Position
Milestone is seeking an experienced Vice President of Sales to lead its North American business and accelerate its next phase of growth. This executive will lead the commercial organization across the United States and Canada, being accountable for overall performance including revenue growth, sales execution, leadership development, customer success, and organizational capability. The role requires an authentic and highly visible leader who combines commercial strategy with operational excellence, building executive-level relationships and developing a high-performing sales organization. The Vice President will also elevate sales excellence by strengthening leadership capability, improving forecast accuracy and pipeline discipline, increasing adoption of value-based and multi-product selling, and building a culture of accountability, coaching, and execution. This role reports to the Chief Revenue Officer and is a key member of the Senior and Global Sales Leadership Teams.
Requirements
- 15+ years of progressive sales leadership experience within enterprise software, SaaS, IT or security, networking, infrastructure, or related technology markets.
- Successfully led large, geographically dispersed sales organizations with consistent revenue growth.
- Extensive experience leading complex two-tier distribution and channel sales models.
- Exceptional executive presence and the ability to influence customers, partners, employees, and senior leadership.
- Successfully transformed sales organizations through coaching, operational discipline, and sales process excellence.
- Strong commercial, financial, and strategic business acumen.
- Experience developing regional go-to-market strategies and leading cross-functional execution.
- Passionate about developing people and building a high-performance culture rooted in accountability and collaboration.
- Bachelor's degree in Business or a related field is required.
- All employees must complete a background check.
- Employees in fiscal roles are also required to undergo a credit check.
Nice To Haves
- MBA or other advanced business degree is preferred.
- Experience with Salesforce CRM and modern sales methodologies is strongly preferred.
Responsibilities
- Develop and execute the North America commercial strategy aligned with Milestone's global growth objectives.
- Translate corporate strategy into clear regional priorities, execution plans, and measurable business outcomes.
- Identify market opportunities, competitive threats, and strategic growth initiatives.
- Own and exceed annual sales targets across the United States and Canada.
- Build, lead, coach, and develop a high-performing regional sales organization.
- Foster a culture of accountability, collaboration, customer focus, and execution excellence.
- Develop sales leaders through coaching, performance management, succession planning and talent development.
- Build organizational capability by attracting, developing, and retaining top commercial talent.
- Drive organizational alignment and consistency across the region.
- Build executive relationships with Milestone’s largest customers, distributors, strategic partners, consultants and system integrators.
- Serve as the executive sponsor for the region's most strategic customer relationships.
- Represent Milestone at executive customer meetings, industry events, and key commercial engagements.
- Partner with Global Channel leadership to support strategic distributor and partner relationships within the region.
- Champion a modern, value-based sales methodology across the organization.
- Improve pipeline quality, forecast accuracy, CRM adoption, and sales operating discipline.
- Increase adoption of multi-product and solution selling across Milestone's portfolio.
- Deliver regional financial performance through effective planning, forecasting, and resource management.
- Serve as a member of the Senior and Global Sales Leadership Team, contributing to worldwide commercial strategy and organizational priorities.
- Partner closely with Product Management, Marketing, Customer Success, Finance, Sales Operations, and Global Channel leadership to align execution.
- Represent the voice of the North American market by providing customer and market insights that influence business strategy.
Benefits
- Individual development plan
- Trainings and certifications
- Flexibility
- Management support and regular pulse check survey
- Opportunities for cross- functional and cross- regional collaboration
- Social events and space to connect
- medical/dental benefits
- FSA or HSA
- 401k with 6% Safe Harbor employer match
- paid parental leave
- generous PTO (20 days' vacation, 10 days paid sick time, and 12 company holidays)
- fully paid Short Term disability policy
- fully paid Long Term disability policy
- Life Insurance
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What This Job Offers
Job Type
Full-time
Career Level
Executive
