Technical Team Lead and Advisor (Cyber)

San Antonio, TX, United States

About Fearless Digital

Fearless Digital builds software with a soul. As a division inside Fearless, we're part of its digital services integrator model to unlock the power of organizations, people and tech. Our division designs, engineers, and delivers digital solutions to solve problems and drive impact. Using iterative development cycles, we minimize risk for our customers and efficiently deliver intuitive and responsive technology. In this way, we help set the stage for tech to work better for people. That's not our only goal, though. We also strive to create a purple culture that makes our team members excited to come to work every day. We take a holistic approach to our people's well-being, and our culture and benefits are designed to support our people in working the way they like best. We encourage our people to pursue their passions, both in and out of the office. With flexible schedules, continuing education support, and a family-friendly work environment, we've created a culture that allows our team to thrive professionally and personally.

Fearless believes in equal opportunity employment. We won't discriminate against any employee or applicant on the basis of race, gender, nationality, age, religion, disability, military status, or sexual orientation. As a company and as individuals, we're committed to providing an inclusive and welcoming environment for our team, our family members, our clients, our subcontractors, and our vendors.

Fearless Digital Benefits

Our people make us who we are. We believe that every member of the Fearless team has something to share, and we value the unique viewpoint you'll bring to our community. But we value your community, too, so we offer fulfilling work that stays in balance with the rest of life. Because everyone has different needs, desires, and goals, our benefits offer the choices and flexibility that our team members need to live well and succeed. Here are a few highlights of our benefits package:

Life-friendly schedules

Family-friendly workplace

PTO allowance (not accrued so you get it up front!) We believe in taking time off to be well and thrive. That's why we offer 14 days of PTO, 8.75 days of sick leave, 11 federal holidays, your birthday (floating day), jury duty, and bereavement.

Up 12 weeks of FMLA paid at 100%

We cover 100% of your premium for our medical HSA plan + the deductible portion of HSA contributions, 80% of your premium for our HMO or PPO plans, and offer competitive dependent coverage. We cover 100% of dental and vision premiums for you and your dependents and offer medical and dependent care FSA options. We also offer life insurance, short- and long-term disability coverage, and legal planning and support insurance.

Tech, education / training, and wellness allowances

Safe Harbor 401(k) plan with employer contributions (current match = 4%) and immediate vesting

Referral bonus: Bring your friends! If someone you refer is hired, you'll get a bonus of $6-12k!

Total Pet Plan

Employee Assistance Program

Compensation

Our Compensation System is designed to reward remarkable work, grow your impact and support the whole "you" over the course of your career.

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 negotiation skills - is given equal pay for equal work. Our approach to compensation is intended to ensure our total package serves all of your needs and includes base pay, medical and other benefits, performance rewards, 401k matching, plus a few perks (tech and wellness reimbursement programs)! Our salary ranges are determined based on role, level and location and provide team members salary growth within a salary grade over time. Team members automatically progress within a salary range through annual increases (given to reward service at Fearless) or merit increases (given to reward and individual's demonstrated performance and growth within the position). Fearless team members are also eligible for discretionary bonuses based on company performance.

The salary ranges for this position based on location are listed below. The base pay range is subject to change and may be modified as a part of our annual salary range review.

Salary Range

AL, FL, GA, TN Residents: $126,294 (min) - $167,340 (mid) - $208,385 (max)

NC Residents: $130,200 (min) - $172,515 (mid) - $214,830 (max)

DE, MD, PA, TX, VA Residents: $136,710 (min) - $181,141 (mid) - $225,572 (max)

DC Residents: $153,636 (min) - $203,568 (mid) - $253,500 (max)

CA & NY Residents: $158,844 (min) - $210,468 (mid) - $262,093 (max)

In addition to base pay, the role is eligible for incentive pay on top of base pay. Estimated total incentive pay is targeted at an additional 25% of base pay. Incentive pay targets include: customer satisfaction, account growth and project profitability.

Work Environment/Location

The selected candidate will be expected to report 5 days per week to the customer's site located in San Antonio, Texas. Candidates will ONLY be considered if they live within a commutable distance radius not to exceed 90 miles from San Antonio. Fearless is exploring hybrid options, however, the selected candidate must also be open to an onsite model (potentially, 5 days, weekly).

Responsibilities and Contributions

Fearless is looking for a Technical Team Lead and Advisor to add to our diverse team of 250+

employees (and counting!). We're looking to change the world by building software with a soul, and we want your help.

The Technical Team Lead and Advisor will play a crucial role in supporting the United States Air Force's defensive cyber warfare operations by providing expert coaching, guidance and strategic insights on the implementation, optimization, and maintenance of cyber warfare platforms. In this role, you will not only provide technical support to the customer but also play a major role in redefining team structures and leading organizational change.

The Technical Team Lead and Advisor will work on the strategic level to reevaluate organizational and technology team structure, implement DORA metrics, define impactful mission outcomes, influence stakeholder decisions, provide actionable recommendations, help improve flow of valuable end-to-end mission capability and deliver data-driven technical prototypes.

Organizational and Leadership Role

Represents Fearless at a local level and provides leadership to team members and stakeholders, and builds solid relationships with USAF and other customers.

Strengthens strategic relationships with peers, leaders, customers, users, and stakeholders, interfacing directly with our customers as a technical Subject Matter Expert (SME), including creating revenue growth opportunities for Fearless with incumbent customers.

Maintains accountability for the performance of technical team members, including professional growth and development, ensuring they are equipped with the skills and support needed to thrive in their roles.

Functional Role

Leads the technical direction, working in close collaboration with the National Security Solutions (NSS) Business Group Director and additionally Offerings & Solutions Director to align with the business group and customer's strategy and vision.

Develops and implements strategies for technical solutions and plans, navigating strict regulatory landscapes and addressing key risks and controls.

Grows stakeholders' technical understanding through effective coaching and leadership

Provides technical and management leadership on major tasks or technology assignments.

Oversees the day to day operations of the technical teams.

Facilitates organizational development and growth by promoting effective team structures and enhancing collaboration across the organization.

Advises and develops inputs to strategy, future force design, capability development guidance, and operational capability requirements.

Identifies key areas of innovation and investment where Fearless can actively engage sponsors and provide technical recommendations through rapid and agile development processes.

Essential Skills, Experience, or Competencies

Must-Have Skills

A minimum of 10 years of demonstrated related working experience.

Must be eligible to obtain TS/SCI (but an active clearance is not currently required).

Demonstrated ability to serve as a trusted advisor to senior leadership

Experience working on federal government agency projects as a contractor

Strong interpersonal skills as well as effective verbal and written communication skills

Demonstrated ability to use appropriate breadth and depth of context and data to make sensible and timely decisions, and displays sound judgment when faced with opportunities and challenges

Deep experience in the following domains:

Cloud infrastructure

Software Engineering

Kubernetes

Cybersecurity

DoD Cyber Operations &/or Cyber Acquisition

Experience coaching or leading teams of Software Engineers, Site Reliability Engineers, Test Engineers, and Data Engineers.

Ability to develop product roadmaps, backlogs, and measurable success criteria to ensure effective mission capability delivery.

Experience in supporting organizational or team change initiatives and contributing to adjustments in team structures and processes.

Skilled in translating technical topics, requirements, and processes for non-technical stakeholders to ensure clear understanding and effective collaboration.

Icing-on-the-Cake Skills

BS/MS/M.Eng. in Computer Science, Information Systems, Information Technology, Mathematics, Electrical Engineering, Computer Engineering, or similar technology-related degree.

Holds a current CISSP or other information security certification.

Holds a current AWS Certified Developer Associate, Solutions Architecture Associate, or Solutions Architect Professional, or similar certification in another cloud platform.

Experience with The Party Bus - Platform One, Cloud One, or other DOD-aligned platforms

Proficient in fostering healthy team dynamics and implementing people-focused practices to drive continuous improvement, demonstrating a strong commitment to operational excellence.

Demonstrated experience in driving organizational change, successfully leading initiatives that reshaped organizational structures. E.g. Knowledge and experience applying Team Topologies, FLOW Systems, or the like in order to help organizations business and tech teams achieve fast flow.

Improved technical teams' flow, delivery, and overall performance through strategic organizational development efforts.

Trial Project and Team Interview

In addition to Fearless' Introductory, Technical and Business Fit interviews, candidates will also be evaluated via:

Trial Project (asynchronous) - This is where you get to show us your skills at play. We'll issue a trial project, based on the key functions of the role, designed to highlight your unique approach. It is designed to take 1-2 hrs max, and you'll have 48 hours to complete it (you decide when).

Trial Project Review & Team Interview - During this interview, Fearless team members will ask about your approach to the trial project. Additionally, we'll learn about your ideal team environment, relevant experience, and other things about you that make you a good fit for the role.

(Optional) Reverse Interview - We'd love to give you an opportunity to host an interview of us. Why? We know that committing to work with an organization is a big decision. It's just as important that you get an opportunity to "evaluate" us! We believe the best working relationships are ones where both entities are mutually bought in, so this our attempt to allow for mutual evaluation. Your choice to do this step or not!

So, what's next?

Over the years, we've honed our interview process to help ensure that every employee we hire is the right fit for us and that we're the right fit for them. If we think you're a good fit, we'll get in touch and start scheduling your interviews! Depending on the role's/project's requirements, the interview process may include some differences. At the minimum

Introductory Interview: This is where you and your recruiter will build rapport, explore your career and educational background, discuss salary expectations, role requirements, and set expectations for the interview process, specific to the position of interest.

Technical Interview (Skills Fit) : This is where we get into the nitty gritty of the project. During the Technical Interview, you'll be interviewed by the technical team to dig more into your background and technical capabilities.

Business Interview: At this point, you've made it to the final frontier! The Business Interview is when you'll meet with Fearless leadership to dot the i's, cross the t's, and determine whether or not we'll be moving forward with the hiring process.

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