Company Overview
Milestone Technologies is a global IT managed services firm that partners with organizations to scale their technology, infrastructure and services to drive specific business outcomes such as digital transformation, innovation, and operational agility. Milestone is focused on building an employee-first, performance-based culture and for over 25 years, we have a demonstrated history of supporting category-defining enterprise clients that are growing ahead of the market. The company specializes in providing solutions across Application Services and Consulting, Digital Product Engineering, Digital Workplace Services, Private Cloud Services, AI/Automation, and ServiceNow. Milestone culture is built to provide a collaborative, inclusive environment that supports employees and empowers them to reach their full potential.
Our seasoned professionals deliver services based on Milestone's best practices and service delivery framework. By leveraging our vast knowledge base to execute initiatives, we deliver both short-term and long-term value to our clients and apply continuous service improvement to deliver transformational benefits to IT. With Intelligent Automation, Milestone helps businesses further accelerate their IT transformation. The result is a sharper focus on business objectives and a dramatic improvement in employee productivity. Through our key technology partnerships and our people-first approach, Milestone continues to deliver industry-leading innovation to our clients. With more than 3,000 employees serving over 200 companies worldwide, we are following our mission of revolutionizing the way IT is deployed.
Job Overview
Milestone Technologies, Inc. is seeking a dynamic and results-driven Vice President of Sales to lead our sales organization across the Pacific Northwest and drive growth in our technology verticals. This strategic leadership role is ideal for a seasoned sales executive with a proven track record of closing high-value deals, building and scaling high-performing teams, and shaping sales strategy and execution. The ideal candidate brings deep experience in defining and optimizing sales operating rhythms, collaborating cross-functionally to accelerate pipeline velocity, and executing growth strategies grounded in experimentation and data. You are passionate about unlocking revenue through innovative go-to-market approaches, leveraging sales automation, AI, and a blend of inbound and outbound sales development tactics. This role is based in Seattle, WA, and reports to the Chief Revenue Officer. Key Responsibilities:
- Drive Market Expansion: Lead market development initiatives by crafting compelling inbound and outbound customer acquisition strategies to generate sustainable and scalable revenue growth.
- Operational Accountability: Maintain performance against regional targets through disciplined operations, pipeline tracking, and strategic incentive programs that motivate teams and drive results.
- GTM Alignment: Collaborate closely with sales leaders and executives to ensure alignment on go-to-market strategy, shared goals, and operational best practices.
- Sales Funnel Optimization: Partner with adjacent teams to define pipeline and quota metrics, establish sales funnel management processes, and set operating principles and standards.
- Team Leadership & Development: Hire, coach, and scale high-performing distributed sales teams in a remote work environment, ensuring professional growth and accountability.
- Financial Stewardship: Oversee sales budgets in coordination with sales operations, finance, and compensation teams, balancing growth goals with team engagement and motivation.
- Culture & Values: Foster a collaborative, inclusive, and success-oriented team culture that celebrates wins, values diversity, and reflects our core company principles.
Qualifications:
- Bachelor's degree in a business or technical discipline; MBA preferred.
- Minimum of 20 years of experience in a global IT services company, with deep expertise in SaaS business models and recurring revenue strategies.
- Proven track record in closing high-profile enterprise deals, meeting and exceeding quota targets, driven by a pipeline growth mindset and a strong bias for execution.
- Meaningful and productive relationships with large enterprise companies in the region.
- Experience hiring, coaching, and developing geographically dispersed sales and market development teams in hybrid and remote work environments.
- High emotional intelligence and the ability to inspire and lead with empathy and accountability.
- Deep knowledge of advanced sales methodologies, team incentive programs, and performance motivation strategies.
- Strong data-driven and analytical rigor and intelligent decision-making skills, with the ability to translate data into actionable insights and support strategic planning.
- Impressive executive presence with the ability to influence and collaborate effectively with senior leaders, customers, and strategic partners.
- Adept at building trusted relationships with clients, identifying key deal influencers, navigating buying processes, and uncovering critical business drivers and decision criteria.
- Exceptional storytelling and presentation skills, with the ability to convey complex ideas with clarity and impact.
- Demonstrated adaptability, resilience, and a passion for taking on new challenges in dynamic, fast-paced environments.
- Ability to travel to client sites and company offices as business needs require.
Join us to shape the future of technology sales and build lasting value for our customers and teams. #LI-NL1
Compensation
Estimated Pay Range: $270K to $300K + Bonus
Exact compensation and offers of employment are dependent on circumstances of each case and will be determined based on job-related knowledge, skills, experience, licenses or certifications, and location.
Our Commitment to Diversity & Inclusion
At Milestone we strive to create a workplace that reflects the communities we serve and work with, where we all feel empowered to bring our full, authentic selves to work. We know creating a diverse and inclusive culture that champions equity and belonging is not only the right thing to do for ouremployees butis also critical to our continued success.
Milestone Technologies provides equal employment opportunity for all applicants and employees. All qualified applicants will receive consideration for employment and will not be discriminated against on the basis of race, color, religion, gender, gender identity, marital status, age, disability, veteran status, sexual orientation, national origin, or any other category protected by applicable federal and state law, or local ordinance. Milestone also makes reasonable accommodations for disabled applicants and employees.
We welcome the unique background, culture, experiences, knowledge, innovation, self-expression and perspectives you can bring to our global community. Our recruitment team is looking forward to meeting you.
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