Job Description

UPSTACK i s the leading full-service technology advisory firm, transforming how businesses design, source, implement, support, and optimize IT infrastructure. Clients benefit from decades of expertise, enhanced support, and UPSTACK’s proprietary technology—delivering faster deployments, cost savings, and streamlined access to critical solutions.

Our expertise includes: data center colocation, network connectivity, SD-WAN, unified communications, cloud contact center, CX-AI, private/public cloud, security, mobility, business continuity, and IoT.

Under the leadership of Founder and CEO Christopher Trapp, UPSTACK is committed to exceptional customer experiences, serving 6,500+ clients—from SMBs to enterprises—and managing over $550M in annual technology spend across industries.

About the Role

This is a hunter-first role with a primary focus on generating new business and building a book of business from the ground up While there will be opportunities to expand existing accounts over time, success in this position will be driven by the ability to prospect, penetrate new accounts, and win net-new logos

As an Account Director, Advisory Services, you will take ownership of the full sales cycle—identifying target accounts, creating and executing outreach strategies, and closing new business. You will be expected to self-generate a significant portion of your pipeline, using a combination of outbound prospecting, strategic account targeting, and relationship-building. In addition to new business development, you will grow and expand relationships within accounts by acting as a trusted advisor—understanding customer needs, uncovering opportunities, and delivering solutions that drive measurable business impact.

This role requires strong cross-functional collaboration. You will partner with teams across customer success, marketing, product, sales enablement, solution engineering, and sales development—but are expected to lead the commercial motion and not rely solely on internal teams for pipeline generation The ideal candidate is highly driven, adaptable, and comfortable operating in a fast-paced environment. You are someone who takes initiative, is disciplined in prospecting, and thrives in situations where you are responsible for creating your own opportunities. Strong communication skills, organization, and the ability to navigate complex sales cycles are critical for success.

Location Requirement:

This role is preferred to be based in the Eastern or Central time zones, though flexibility may be offered for the right candidate.

Key Responsibilities

• Generate new business by identifying, targeting, and prospecting into net-new accounts to build a strong, self-sourced pipeline
• Develop and execute strategic account plans for both new and existing accounts, with a focus on land-and-expand opportunities
• Build and maintain relationships with stakeholders across all levels of an organization, from individual contributors to executive leadership
• Lead the full sales cycle, from initial outreach and discovery through negotiation and close
• Drive a coordinated sales approach by effectively leveraging internal teams (e.g., solutions engineering, customer success, marketing, BDRs) and external partners
• Deeply understand customer business objectives and organizational structures to identify opportunities and position solutions effectively
• Proactively research target accounts and document insights to inform outreach and sales strategy
• Maintain accurate pipeline management and forecasting within CRM tools (e.g., Salesforce)
• Partner with Customer Success to support account growth, retention, and expansion opportunities over time
• Conduct regular business reviews and strategic conversations with customers to uncover additional opportunities and drive long-term value

Education

• Bachelor's degree encouraged, but not required

Required Qualifications

• At least 3+ years of proven full-cycle sales experience in the Technology and/or Telecommunications industry
  • While the original scope targeted 7+ years, we are open to high-performing candidates earlier in their careers who demonstrate strong hunting ability and sales fundamentals
• Proven success in new business development and prospecting, with the ability to build pipeline independently
• Experience selling into multiple levels within an organization, including but not limited to the C-suite (e.g., director, VP, and executive stakeholders)
• Strong ability to build and deliver compelling presentations to a range of audiences
• Demonstrated ability to orchestrate cross-functional resources, including solutions engineering, customer success, and product teams
• High degree of adaptability, drive, and coachability, with a willingness to take a hands-on, hunter-oriented approach
• Preferred: Existing network or book of business within the New England region

Additional Requirements

• Hunter Mindset: Demonstrated willingness and ability to proactively prospect, generate pipeline, and win new business—especially in environments with limited inbound support
• Self-Starter: Highly motivated with a strong sense of ownership and accountability; able to operate independently while driving results
• Adaptability: Comfortable working in a fast-paced, evolving environment with changing priorities and growth expectations
• Strong Communication Skills: Ability to engage and influence stakeholders across all levels of an organization, from individual contributors to senior leadership
• Collaborative Approach: Proven ability to work cross-functionally and effectively leverage internal teams (e.g., BDRs, Customer Success, Marketing) as force multipliers—without over-reliance on them for pipeline generation
• Analytical & Organized: Strong pipeline management, forecasting discipline, and attention to detail within CRM tools (e.g., Salesforce)
• Resilience & Grit: Persistence in navigating rejection, long sales cycles, and complex deal environments
• Technology Proficiency: Comfortable using CRM systems, sales engagement platforms, and other digital tools to manage and grow a sales pipeline

Salary Range

Employees new to UPSTACK typically come in at the start of the pay range. UPSTACK focuses on providing a simple and transparent pay structure, which is based on a variety of factors, including location, experience, and job-related skills.

The salary for this role is fixed at $90,000 to $110,000 annually, with no room for negotiation. Please apply with this understanding. The role also includes participation in an uncapped commission and residual structure, with top performers earning an average OTE of $200,000+ in their first year and unlimited earning potential beyond that.

Closing

UPSTACK is an Equal Opportunity Employer and does not discriminate based on race, gender, ethnicity, religion, national origin, age, disability, veteran status, gender identity/expression, sexual orientation, or on any other basis prohibited by law. Consistent with applicable state and local law, UPSTACK will consider employment for all qualified applicants.

UPSTACK is committed to providing reasonable accommodations to individuals with disabilities as required by applicable law. Accommodations may include adjustments to the application, interview, or assessment process, as well as modifications to the work environment or job duties to enable individuals to perform the essential functions of the role. Requests for accommodations will be evaluated on a case-by-case basis and provided unless they impose an undue hardship on the organization.

At this time, UPSTACK will not sponsor a new applicant for employment authorization for this position.

We endeavor to make the application process accessible to all applicants. If you would like to contact us regarding accessibility and/or need assistance completing the application process, please contact us at recruiting@upstack.com