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 perks 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 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.

Milestone Technologies is seeking an experienced, successful Strategic Portfolio Executive - Financial Services to join our growing enterprise solutions team. In this role, you will be responsible for executing account strategy and sales pursuits to realize growth for Milestone’s IT Managed Services, which include:

- End User IT Services (Service Desk, Desktop Support, IT Site Support Service Asset Lifecycle Management
- Audio Visual/Video Conferencing & Event Support Services
- Artificial Intelligence & Automation Services
- Application Services
- ServiceNow Services
- Data Center Infrastructure & Operations Services
- Cloud and Infrastructure Services:
- Project Based IT Services
- Staffing Solutions

How You Make An Impact:

In partnership with the Milestone extended team, including Service Delivery, Finance, Talent Acquisition, and Executive Management, you will work collaboratively to drive Milestone’s solutions in the marketplace. You will serve as a trusted adviser and partner to our prospective and existing clients versus “just another vendor”.

You will have a strong focus on penetrating greenfield/new logo accounts and will be responsible for building your own pipeline and driving opportunities to close in on to meet/exceed sales expectations. Thus, you must have a proven track record of successfully closing high-revenue technology solutions.

You will be on the front line as the face of Milestone, manifesting the excellence and innovative spirit we are building. You will need to understand Milestone services and abilities, and be able to represent these clearly, accurately, and confidently to business leaders at a variety of levels, including C-Suite, and across multiple functional groups. Your aim will be to develop strategies with these key stakeholders to address their ongoing business, financial and technical/IT support needs.

What You Need To Succeed:

10+ years successful sales performance, with a minimum of half of that experience being in managed services with a focus on selling into the fintech, payments and/or financial services sector

Demonstrated track record selling managed services to mid-market/large accounts with cumulative Total Contract Value (TCV) 5 million

To be successful in this position, you must have the skills and drive to govern all aspects of the sales process. This means that in addition to being skilled in Sales, the Strategic Sales Executive must have acumen in cross functional areas such as IT Operations, Finance and Contract Law, as described below.

Experience selling IT Managed and Professional Services

Ability to broker and conduct insightful conversations with client executives that elevates talk from low-level tactical to a higher problem/solution/outcomes’ centric consultation

Skilled at developing strong relationships with clients, identifying key influencers for a deal,



building client sponsorship for your solution, and acquiring key information pertaining to, but not limited to, client budget, client buying process, competitors, clients motivating factors and decision criteria

Ability to sell complex services that span service lines, geographies, and delivery methodologies

Experience managing all aspects of the sales process and demonstrable experience of closing/winning enterprise deals

Well organized and able to keep multiple opportunities moving forward simultaneously

Commitment to following internal Sales process and keeping Customer Relationship Management (CRM) system updated

Skilled at use of common Sales tools including Customer Relationship Management systems, research, and prospecting tools

Ability to formulate comprehensive plans that include account mapping, addressable market analyses

Must understand the following aspects of IT services: Service Delivery structures, staffing (both domestic and international), Key Performance Indicators/Service Level Agreements, Information Technology Infrastructure Library, reporting and analytics

Strong professional network

Effective communication skills, both verbal and written, and excellent interpersonal skills

Demonstrated capability to work effectively with cross-functional teams

Recognized success as a top producing salesperson

Benefits:

We offer comprehensive benefit options which vary depending on role, location, and employment type. Benefit options may include Medical, Dental, Vision, 401(k), Life Insurance, Short-Term Disability, Long-Term Disability, Flexible Spending Accounts, Parental Leave, Paid Time Off, and Holidays. The Talent Acquisition Partner can share more details about compensation or benefits for the specific role during the hiring process.

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Compensation

Estimated Pay Range: $200,000 - $220,0000 USD/yr. base salary + commission

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 our employees but is 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.

📌 Portfolio Executive - Strategic Accounts: Financial Services (Canada)
🏢 Milestone Technologies, Inc. (Corporate)
📍 Canada