Chief People Officer


Maryland, United States Remote Hybrid

Full time

Chief People Officer / CXO

Sep 16

Fearless is looking for a Chief People Officer to add to our diverse team of 200+ employees (and counting!).

What you’ll be doing:

We’re looking to change the world by building software with a soul, and we want your help. 

This role is responsible for cultivating a people-oriented, high-performance culture that emphasizes empowerment, quality, inclusivity, and productivity… the things that help us live purple! This role aligns strategy, policies, programs, and management of the People Ops team across all verticals — including Talent & Development, Human Resources, Recruiting, and Community — to build intuitiveness and ease in our people process throughout the entire employment lifecycle.

One of our core beliefs is that people work best when they do what they love, and that drives us to win impactful work to which our people can apply their skills, energy, and soul. We can create the greatest impact and exceed the expectations of our customers if we effectively staff our people on our projects.

What you should know:

  • Preferred team member in Maryland with a hybrid work environment. Our office is located in the Spark Building in Baltimore!
  • Fully remote options available for candidates located outside of Maryland.
  • To protect our Fearless community, and in consideration of the Executive Order on Ensuring Adequate COVID Safety Protocols for Federal Contractors, the U.S. Centers for Disease Control and Prevention (CDC), the Department of Labor, Occupational Safety and Health. Administration (OSHA), and a variety of public health authorities, Fearless is implementing a mandatory COVID-19 vaccination policy for our full workforce. This vaccine mandate will help keep our people and our community safe through this ongoing health crisis.
  • All new employees must have received or be willing to receive the COVID-19 vaccine by date of hire to be considered for the position. Reasonable accommodations for qualified exemption requests will be considered

We need your Chief People Officer skills! What other skills will help you succeed at Fearless? Glad you asked! We’re excited about candidates who can accomplish the following:

Responsibilities and Contributions 

Organizational and Leadership Role 

  • Scales and leads strategy for People Operations support of our people, business, and development.
  • Directs and stewards the People Ops team, collaborates with Department Executives and leaders across the organization, and provides support to all team members.
  • Directly supervises the vertical leaders within the People Ops department.
  • Grows our eminence as a company that connects culture, community, customer, and a remarkable team member experience.

Functional Role 

Team Member Experience

  • Sets the direction for team member experience strategy and operations. 
  • Ensures a holistic approach across operational elements like HR services (e.g. compensation, compliance, benefits, payroll), talent acquisition, learning (e.g. coaching, training), culture (e.g. inclusion, internal community building, team member experience metrics, events, environment), and community impact (e.g. pipeline programs, community events). This includes integrating those areas into a cohesive team member experience strategy aligned to overall Fearless growth and goals. 
  • Develops metrics-driven approaches to inform strategic decision making. 
  • Leads internal brand communications and change management activities.
  • Influences and rallies people across the Exec Team, People Ops department, and company toward a holistic vision of Fearless' culture and People Ops principles.

Executive Partnership 

  • Partners with the Executive Team to ensure the team member experience is represented within organizational and strategic decision making.
  • Collaborates with leaders to drive understanding and find opportunities to make Fearless a home that attracts and retains the workforce needed to meet our growth. 
  • Sets the direction of key strategic decisions by providing insight or analysis about people and talent implications of policies, programs, or other decisions across the company.
  • Empowers leaders to develop conditions across their portfolios and departments. 

Systems Building 

  • Sets direction, vision, and outcomes for continuous improvement of systems, processes, and roles. 
  • Influences the growth trajectory of the organization to scale the team member experience and continually nurture the value proposition of employment at Fearless. 

External Engagement 

  • Oversees relationships with HR consultants, attorneys, insurance brokers, and carriers. 
  • Engages with customers, partners, vendors, and industry groups to create opportunities and impact. 

Essential Skills, Experience, or Competencies  

Must-Have Skills

  • Experience growing an organization's workforce in number of team members, career paths, and scaling experience across the US.
  • Demonstrated experience growing a workforce and developing scaled recruiting strategies that will help the company succeed over an extended period of time.
  • Demonstrated expertise in leading People Ops in realms like HR, Culture, Learning and Development, Diversity, and Recruitment/Selection. 
  • Demonstrated change management skills and experience within a growing organization (200+ employees) centered on culture and team member experience.
  • Industry expertise in leading practices in financial and operational planning.
  • Deep skill in evaluating and using data to support operational decision making and strategic objectives.
  • Demonstrated ability to lead teams and coach cross-functional teams. 
  • Advanced strategic thinking and planning skills. 
  • Advanced values-based coaching and leadership skills. 
  • Advanced communication skills, from strategic to tactical topics. 
  • Ability to build decision-making systems and processes at all levels of the organization.
  • Ability to align, operate, and manage work strategically through building relationships and influencing others.

Icing-on-the-Cake Skills 

  • Expertise in various software/platforms used in HR, recruitment and selection, and learning and development realms, especially BambooHR and Greenhouse.
  • Understanding of federal contracting, teams, technical agile teams, and consulting workforces. 
  • Coaching or facilitation expertise or experience or certification.
  • Experiencing leading legal or finance functions. 
  • Experience leading People Operations functions within organizations that have multiple service lines, business units, or entities


We believe in paying people fairly, so we've established a compensation model that ensures everyone at Fearless — regardless of race, ethnicity, gender, sexual orientation, disability, religion, age, nationality, or negotiation skills — is given equal pay for equal work.

Culture Fit Expectations

We hold ourselves to the cultural values that make us Fearless. See here for our Cultural Behavior Map.

So, what’s next?

Over the years, we’ve honed a 3-step interview process that helps ensure that every employee we hire is the right addition for us and that we’re the right fit for them. If we think you’re a good addition to the team, we’ll get in touch and start scheduling your interviews!

  • Culture Add Interview - We’re a people-first company, so we always start off by getting to know more about you, how you work, what your career goals are, and what you’re passionate about. This is your opportunity to ask questions and get a feel for Fearless, so don’t be shy!
  • Technical Interview - This is where we get into the nitty gritty of the project. During the Technical Interview, you’ll be interviewed by our Passion Coaches and/or the team’s Project Lead to make sure your skills align with the project requirements.
  • 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.

Why Fearless?

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:

  • Flexible schedule
  • Family-friendly workplace
  • 3 weeks accrued PTO + 1 week sick leave + 11 federal holidays + your birthday off
  • 100% coverage of the employee-only premium for HSA, HMO, or PPO plan and Employee Wellness Plan
  • Tech, education / training, and snack allowances
  • Free parking in downtown Baltimore / public transit coverage
  • Safe Harbor 401(k) plan with employer contributions

About Fearless:

Fearless is a full-stack digital services firm in Baltimore that delivers sleek, modern, and user-friendly software designed to push the boundaries of possibility. It's our mission to build software with a soul — tools that empower communities and make a difference — so we can create a world where good software powers the things that matter.

That’s not our only goal, though. We also strive to create a purple culture that makes our employees excited to come to work every day. That’s why we encourage our employees to pursue their passions, both in and out of the office. With built-in company mentoring, continuing education support, flexible schedules, 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.

Location: Maryland, United States (hybrid)

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