Learning & Development Lead – Employee Activation (Hybrid; Travel Required)

Wellist: Learning & Development Lead – Employee Activation

Boston, MA (Hybrid; Travel Required)

At Wellist, we’ve spent the last decade helping people navigate life’s most challenging moments. After building a track record of impact with leading health systems, we have successfully pivoted into the employer market and we are now scaling with large, global employers.

Our platform acts as an activation layer within the HR ecosystem—embedding precision matching capabilities so employees can find the right support at the right time, and employers can maximize the value of their benefit and resource investments.

This is a pivotal moment for Wellist. We are ramping to serve one million employees and frontline activation will be critical to our success.

As our Learning & Development Lead – Employee Activation, you will play a central role in bringing Wellist to life inside organizations—training leaders, directly activating employees, and ensuring that every person experiences Wellist as a white-glove, human, and truly helpful service.

This role has three core mandates:

• Enable leaders to support their teams through Wellist.

• Directly activate employees so they connect to the full breadth of support their company provides.

• Make frontline insights a lever for better product, operations, and client value.

You will be a visible ambassador for Wellist with clients and employees, and a trusted voice inside the company—shaping how we scale frontline engagement.

What You’ll Do

Train HR and Front-Line Managers (Build Internal Advocates)

Your goal is to turn leaders into confident Wellist advocates. You will equip leaders to champion Wellist inside their organizations:

• Delivering onsite and remote training for HR and people managers

• Presenting the Wellist vision, capabilities, and use cases

• Conducting live demos of the Wellist platform and staff tools

• Teaching leaders how to identify employee needs, talk about Wellist effectively and refer employees for support

• Providing managers with materials, talking points, and best practices

• Owning all planning, communications, and logistics with client contacts

• Coordinating closely with internal Wellist teams to align on goals and messaging

Directly Activate Employees (Hands-On Engagement)

You will meet employees where they are and help them get connected to support. Your standard is a white-glove experience—every interaction should feel personal, supportive, and useful. This includes:

• Leading presentations or enrollment drives at benefit fairs, town halls, and company events

• Running group sessions and demos

• Hosting office hours (onsite and virtual)

• Making outbound calls to introduce the Wellist program to key employee segments

• Providing 1:1 onboarding support for employees

• Helping employees surface unmet needs and navigate to the right resources

Capture Insights & Improve the Experience (Close the Feedback Loop)

You will be the voice of employees and frontline reality inside Wellist to help shape how the Wellist Experience works at scale. You will:

• Systematically gather employee and manager feedback

• Identify patterns in unmet needs, barriers to engagement and opportunities to improve activation

• Share insights regularly with the Wellist Operating Committee and Product team

• Recommend improvements to messaging, training materials, activation playbooks, employee onboarding process and product experience

Performance Expectations

You will be accountable for:

• Hitting monthly and quarterly employee enrollment targets

• Improving awareness and engagement with Wellist

• Elevating the frontline experience so employees feel fully supported

• Strengthening relationships with client HR teams and leaders

What Success Looks Like

First 3 Months

• Become fully certified to deliver the Wellist pitch, demo, and employee support

• Execute the existing activation playbook independently

• Run trainings, office hours, and employee sessions with confidence

• Begin building trusted relationships with key client contacts

First 6 Months

• Demonstrate full knowledge of the Wellist platform and business model

• Test new activation tactics and identify opportunities to improve the playbook

• Implement quick wins to increase engagement and efficiency

• Consistently hit or exceed enrollment targets

• Regularly share structured employee feedback with the Operating Committee and Product team

First 12 Months

• Build strong employee and client promoters of Wellist

• Help create a fully validated, scalable activation playbook

• Update all communications, materials, and tactics to reflect best practices

• Fully document frontline operations to support team scaling

• Identify opportunities to unlock additional value for employees, clients and Wellist

What You Bring

You are likely a strong fit if you:

• Love working directly with people

• Are comfortable presenting to leaders and supporting employees 1:1

• Can operate independently while staying aligned with a fast-moving team

• Are highly organized and reliable

• Care deeply about impact, not just outputs

Relevant Experience (any of these are a plus)

• Employee engagement, HR, or People Operations

• Learning & Development or corporate training

• Benefits, wellbeing, or healthcare navigation

• Customer success, implementation, or frontline support

• Community outreach, coaching, or counseling

Core Skills

• Excellent communicator (written + verbal)

• Strong presenter

• Relationship builder

• Detail-oriented project manager

• Comfortable with data, dashboards, and targets

• Empathetic listener

• Comfortable with ambiguity and iteration

Why Work Here

• Play a mission-critical role in helping Wellist build the support network we want for our loved ones.

• Partner closely with clients, employees, and Wellist leadership

• Shape how frontline activation scales globally

• Work at a high-growth, mission-driven company

• Competitive compensation, strong benefits, and meaningful impact