Head of Learning Experience

Swooped is a Talent Platform (not a staffing agency). We are not the employer for this role and do not make hiring decisions. Clicking "Apply" takes you to Swooped to review the role and hiring company details.

About the Opportunity

The organization offers compliance training that customizes itself to the user. It combines top-rated training content with intelligent AI that builds and adapts training to reflect a company’s unique brand, roles, policies, and risks, making it feel tailored to the team, whether that involves hard hats or virtual meetings. From auto-assigning courses based on HRIS data to transforming policies into interactive training in minutes, this solution helps People, Legal, and Compliance teams launch in days (not months) and cut learner seat time by up to 60% with adaptive learning paths.

The platform supports over 1 million learners across more than 2,000 organizations, with a 93% learner approval rating and a 96% customer renewal rate. Over the past several years, the company has delivered consistent, durable growth, including 120%+ net dollar retention, 95%+ gross dollar retention, and strong enterprise expansion across industries. This has established it as a go-to compliance partner for modern, global organizations.

Beyond training, the platform unifies core compliance tools, Hotline & Case Management, Policy Bot, and Phishing Simulator, into a single platform, with built-in audit trails and compliance controls that teams can trust.

Trusted by teams at various companies, it’s a great time to join the organization.

How we work

The team values diversity in all its forms and enjoys adding new perspectives. They ask thoughtful questions, challenge assumptions, and build with empathy, for customers and for each other. They care about craft, welcome feedback, and take ownership. Humor is also embraced, as doing serious work doesn’t have to feel so serious.

The workforce is fully remote, and personal working hours can be based on individual timezones. All team-wide meetings are scheduled to be inclusive of all North American time zones.

Who we're looking for

The organization is looking for a Head of Learning Experience to join the Learning Experience (LX) team. This role will report to the Co-Founder and Chief Technology Officer and will be responsible for leading and managing the LX team, optimizing the use of team, budget, and tools. This individual will be a key contributor to how efficiently, creatively, and consistently best-in-class compliance training content is produced.

Reports to

Co-Founder and Chief Technology Officer

What you'll do

• Serve as a people manager for the LX team, setting clear expectations, enabling success and growth, and holding the team accountable.
• Define a vision for how the LX team operates, leveraging industry best practices and personal experience with creative teams to do so.
• Identify and implement improvements that increase team capacity and output, making the most of the team, budget, and tools.
• Continuously evaluate and adopt cutting-edge tools, particularly AI and automation, to increase the team's pace and throughput.
• Partner cross-functionally with the Product Management team to align LX's output with organizational priorities.

What makes a great candidate

• Deep experience working in and managing creative teams, particularly in video production.
• A track record of high-accountability management, with the ability to get the most out of a high-performing team.
• Comfort being scrappy and creative under tight timelines or budgets.
• A sharp understanding of constraints: the ability to calibrate quality to the time and resources available.
• Expert knowledge of and energy about tools and automation, particularly AI tools, and a drive to bring that energy to the team.
• A self-starter who thrives in a hands-off management environment, takes ownership of their work with a "roll up your sleeves mentality," is comfortable with ambiguity, and proactively identifies problems and solutions.
• The ability to help build the playbook, not just run it, as this is an early-stage startup.
• Passion for the mission and strong alignment with the organization's core values (which includes an impeccable sense of humor).

What's going to be the hardest part

• The organization moves fast, and the team is always pushing and needs to stay nimble. This leader will need to match that energy immediately, without the benefit of a slow ramp-up period.
• Stepping in to lead a team that was not previously built by them, balancing the need to understand the team as it currently operates with the need to push for change and improvement.

$175,000 - $215,000 a year

The organization is committed to fair and equitable compensation. Skills and qualifications are carefully evaluated to provide the best possible offer upfront. A no-negotiation policy ensures that the first offer is always the best offer, promoting pay equity throughout the organization.

Physical Demands

This is sedentary work that primarily involves sitting/standing in a home office environment.

Location

The organization is a remote-first organization and is currently hiring candidates based in the United States.

Employer visa sponsorship is not currently offered for this role.

AI Usage in Interviews:

The organization is a strong proponent of AI and uses it heavily in day-to-day work. However, to ensure fairness and accurate skill assessment, the use of AI tools (including note takers, transcription tools, or recordings) is not permitted during interviews. If there are questions or accommodations needed, the organization is happy to discuss them.

Benefits

The benefits offered for this position can be found on the careers page. Unlimited PTO is provided.

The hiring company is an equal opportunity employer committed to building a diverse and inclusive team.