Application Support Specialist, (Consultant, Business & Product Delivery)

Application Support Specialist (Consultant, Business & Product Delivery)

Fearless is seeking Application Support Specialists to support a large-scale federal workforce training and learning management program. These individuals will serve as the primary point of contact for system users, providing timely, accurate, and user-focused support for a cloud-hosted Learning Management System (LMS) and associated training platforms.

This role is critical to ensuring a seamless user experience for thousands of federal and state users. Application Support Specialists are responsible for resolving technical issues, guiding users through system functionality, and maintaining high levels of customer satisfaction in a structured, service-level-driven environment.

We are looking for individuals who are responsive, detail-oriented, and technically aware-professionals who can troubleshoot issues, understand system behavior, and clearly communicate with both users and technical teams.

At Fearless, this Consultant role requires versatility and collaboration across teams and stakeholders to maximize value delivery and adoption. The role ensures alignment of product strategy with client goals, facilitates agile ceremonies and continuous improvement, and provides critical business and functional analysis to deliver high-quality, user-centered solutions.This role will possess and/or develop the skills to be able to span the domains of product management, scrum leadership, and business analyst at a practical application level of proficiency . This Consultant role will work on projects that allow them to support agile software development teams and client organizations.

Place of Performance & Travel Requirements

• While this role is primarily remote, the individual must be available to attend in-person customer meetings at the client's headquarters in Baltimore, Maryland, as needed.
• The individual in this role will support approximately three in-person events annually within the greater Baltimore metropolitan area. These events range from one to five

days in length and require full on-site participation

Your Responsibilities in this Role:

• Provide Tier 1 and Tier 2 help desk support for LMS users, including troubleshooting access issues, navigation challenges, and system errors.
• Respond to user inquiries through ticketing systems, email, or other support channels in accordance with established Service Level Agreements (SLAs).
• Log, track, and manage support tickets, ensuring timely resolution and proper escalation of complex issues.
• Diagnose and troubleshoot application and user issues, identifying root causes and determining appropriate resolution or escalation paths.
• Assist users with account management, course access, training completion tracking, and system navigation.
• Escalate technical issues to appropriate teams (engineering, DevOps, or system administrators) with clear documentation, reproduction steps, and impact descriptions.
• Maintain accurate and up-to-date records of support activities, issues, and resolutions.
• Contribute to the development and maintenance of knowledge base articles, FAQs, and user support documentation.
• Monitor recurring issues and trends, providing feedback to improve system functionality and user experience.
• Support system testing and validation efforts by identifying and documenting defects or user experience issues.
• Collaborate with training and instructional design teams to support users during training events and course rollouts.
• Ensure all support activities are conducted in compliance with federal security and privacy requirements.
• Operate Help Desk Monday through Friday, 7AM - 7PM Eastern Time, exclusive of federal holidays, via toll-free phone number and email address
• Support common Help Desk issues types including but not limited to: password resets, user ID issues, account lockouts, errors in training, and training plan questions (Q&A)
• Provide and maintain an automated system for logging and tracking all Help Desk encounters and resolutions and summit monthly summary reports.
• Identify recurring patterns and trends in Help Desk tickets and provide input for system improvement recommendations

The Impact You Will Create in this Role:

Fearless Impact:

• Collaborates with cross functional teams
• Earn the trust of your customer and teammates by delivering world class services.
• Be reliable completing assigned objectives on time.
• Alert your teammates and supervisor immediately when you think a deliverable is at risk.
• Gather intelligence and listen to what your client, other people within the customer's organization and other contractors say about your project, and report back to your Fearless teammates and supervisor (whether it's good, bad or just informational).

Fearless Customer Impact:

• Deliver high-value products that align client goals, user needs, and business outcomes through effective product strategy, backlog management, and agile delivery.
• Enable teams to achieve predictable, high-quality results by facilitating collaboration, removing obstacles, and fostering continuous improvement and offering innovative solutions..
• Provide actionable insights and innovative solutions by translating stakeholder requirements into clear priorities, leveraging data, and applying best practices in product management and agile execution.
• Serve as a trusted advisor in your area of expertise

PROJECT SKILL AND EXPERIENCE REQUIREMENTS

• Minimum of 7 years of experience providing help desk or technical support in enterprise or federal environments.
• Experience supporting Learning Management Systems (LMS) or similar enterprise applications is highly desirable.
• Familiarity with ticketing systems (e.g., ServiceNow, Jira Service Desk, or similar) for issue tracking and resolution.
• Demonstrated ability to troubleshoot application issues, identify root causes, and document findings clearly for technical teams.
• Basic understanding of web-based applications, user account management, and system access controls.
• Ability to interpret system behavior, error messages, and user-reported issues to support effective resolution or escalation.
• Experience working in environments with defined SLAs and performance metrics is preferred.
• Experience providing support to non-technical users, with the ability to explain technical concepts clearly and professionally.
• Familiarity with federal security and privacy requirements is preferred.
• Experience supporting federal government programs and working with federal and state government user populations preferred
• Strong communication and customer service skills, with a focus on responsiveness and user satisfaction.
• Ability to manage multiple requests and prioritize tasks in a fast-paced environment.
• Bachelor's degree in Information Technology, Information Systems, or related field is required.
• Ability to obtain and maintain Public Trust clearance

Fearless Skills and Competencies

• Analytical Thinking:The ability to observe and interpret information, break down complex problems into parts, identify patterns/relationships and draw logical conclusions to develop effective solutions.
• Synthetic Thinking: The ability to combine different ideas, information, or concepts to create a new, complex understanding or solution by integrating disparate elements into a new, meaningful whole.
• Adaptability: Comfort with change, flexibility in the face of shifting demands and resilience to setbacks.
• Ownership & Accountability: Committed to taking responsibility for outcomes, ensuring that all commitments are met with a focus on enhancing service delivery.
• Consultative Advising: Identifies and articulates client challenges, scopes projects and aligns recommendations to business goals and client expectations.
• Communicating with Influence: Capable of crafting and delivering clear, persuasive messages that integrate data insights and structured narratives, tailored to the strategic needs of diverse audiences to drive effective decision-making.
• Environmental Awareness: Maintains awareness of external dynamics, power structures within client environments as well asregulatory trends and contract requirements that influence service delivery.

Required Level of Proficiency:

• Practical Application: You can complete tasks in required competency/skill-based areas as requested. Help from an expert may be necessary from time to time, but you can usually perform the skill independently.

Physical Requirements:

• Ability to sit for extended periods while working on a computer or during meetings.
• Must be able to travel occasionally to client sites or company meetings, which may involve driving or flying.
• Ability to communicate effectively via phone, email, and in-person, requiring clear speech, listening, and written communication skills.
• Ability to move within an office environment, including reaching for files, using office equipment, and occasional light lifting (up to 10 pounds).

Life at Fearless

We're a digital integration consultancy on a mission to build a better tomorrow. At Fearless, we combine technology, people, and organizational development to solve meaningful problems. Through iterative development, we deliver smart, user-friendly solutions that make tech work better-for everyone.

But great tech is just part of the story. What really makes us Fearless is our Purple Culture.

What Makes Us Purple?

Being Purple means you:

• Are valued as a whole person-not just a job title
• Get matched with work that plays to your strengths and passions
• Are supported by coaches, not micromanagers
• Have the autonomy and clarity to make decisions and drive impact
• Join a community that celebrates equity, curiosity, and innovation
• Do work that matters-every day

We believe in flexibility, growth, and balance. Our benefits and culture are designed to support you in doing your best work-while making space for what matters to you outside of it.

We're proud to be an equal opportunity employer. At Fearless, we're building a workplace that welcomes and respects everyone-across race, gender, age, religion, identity, background, and ability.All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability status, protected veteran status, or any other characteristic protected by law.

Compensation at Fearless

Fearless is committed to providing a competitive compensation package that will meet your current and future needs. Our philosophy is aimed at rewarding team member contributions, supporting long-term financial growth and security, and overall well-being.

We believe in paying people fairly, so we've established a compensation model aimed to ensure everyone at Fearless - regardless of race, ethnicity, gender, sexual orientation, disability, religion, age, nationality, or willingness/ability to negotiate - is consistently paid fairly based on alignment to the needs and requirements of the role.

The salary range for this position is:

Minimum Salary: $85,832

Salary Midpoint: $111,581

Maximum Salary: $139,477

Hiring Range for Role: $85,832 - $113,500

*This position is eligible for a discretionary bonus based on individual and company performance criteria.

Benefits at Fearless

At Fearless, we take care of our team-because when you're supported, you can do your best work. We offer a flexible, family-friendly environment with benefits designed to support your health, growth, and life outside of work.

For Full-Time Team Members (Starting Day One):

• Flexible, life-friendly schedules
• 100% coverage for our medical HSA plan + HSA contributions
• Dental & vision covered 100% for you and your dependents
• Competitive premiums for HMO/PPO and dependent coverage
• 401(k) with 4% match & immediate vesting
• Paid Parental Leave and 12 weeks paid FMLA
• Generous PTO, 11 Federal Holidays, a Birthday Holiday, and Sick Leave
• Up to 15 days for Jury Duty and Bereavement Leave
• Education, wellness, and tech allowances
• Referral bonus: $6K-$12K for each successful referral
• Pet insurance & discount plans
• Employee Assistance Program (EAP)
• Legal support, life insurance, disability coverage

Reasonable Accommodations

Fearless is committed to providing reasonable accommodations for applicants and candidates with disabilities. If a reasonable accommodation is needed to participate in the job application or interview process, please contact the Human Resources Department at hr@fearless.tech.

So, What's Next?

We've refined our hiring approach to make sure every team member is a great fit for Fearless-and that we're a great fit for you, too. If there's alignment, we'll reach out to kick off the interview process. Depending on the role or project, your experience may vary slightly, but it typically includes:

Introductory Interview

You'll connect with a recruiter to:

• Build rapport and get to know each other
• Review your experience and skills
• Talk through salary expectations and role details
• Set expectations for the rest of the process

Skills + Business Fit Interview

This is where we dig deeper to:

• Review findings from any technical assessments
• Walk through situational and values-based questions
• Explore how your approach aligns with Fearless culture and project needs

Some roles may also include customer interviews based on specific project requirements in addition to background check and security clearance requirements.