Head of User Engagement & Outreach

Our client is an Applied AI company transforming how families organize, protect, and transfer their estates. By integrating with financial and legal systems, they provide a real-time, intelligent estate view and automate complex workflows. Backed by Accel and YC, they operate in a massive, underserved market poised for AI disruption.

LOCATION

Fully remote | 9 AM - 5 PM EST

ROLE OVERVIEW

The Head of User Engagement & Outreach will serve as the frontline voice of the brand, executing and managing cold outbound communications to prospective users, partners, and stakeholders. The role focuses on crafting compelling messages, handling all inbound and outbound replies with professionalism, and continuously refining outreach strategies based on user insights. This position is critical to scaling the company’s growth engine and requires resilience, speed, and exceptional communication skills.

KEY RESPONSIBILITIES

Outbound Communications

- Execute cold outreach (starting with email; expanding to additional channels).

- Craft, personalize, and iterate messaging that captures attention and aligns with the brand.

- Manage outbound batching, including list segmentation, scheduling, throttling, and QA.

Engagement & Follow-Through

- Respond to all inbound and outbound messages with speed, professionalism, and empathy.

- Qualify leads and route opportunities to the appropriate internal teams.

- Maintain detailed communication records within the CRM.

Optimization & Collaboration

- Track performance, analyze reply patterns, and refine outreach templates and strategies.

- Collaborate with leadership on outbound strategy and data-driven improvements.

- Support occasional user-facing initiatives such as surveys, research, and feedback collection.

QUALIFICATIONS

Experience

- Background in outbound communications, customer support, business development, or a similar fast-paced, user-facing role.

Skills

- Excellent written English: clear, concise, and persuasive.

- Fast typing speed and rapid response capability.

- Resilient and composed when handling difficult or high-volume communications.

- Highly organized, able to juggle multiple threads simultaneously.

- Self-directed, fast learner, and comfortable working independently.

- Bonus:

- Familiarity with HubSpot or amplemarket.

- Experience with email automation tools such as Bison.

- Experience in startup or SaaS environments.

WHAT SUCCESS LOOKS LIKE

- High-quality outbound communications that drive strong reply and engagement rates.

- Efficient lead qualification and seamless handoff to internal teams.

- Accurate, consistent CRM documentation and process execution.

- Continuous improvements to messaging based on real user insights.

- A reliable, polished, and empathetic user-facing presence for the brand.

OPPORTUNITY

This role offers the chance to make an immediate impact by shaping a core component of the company’s growth engine. You will work directly with founders and cross-functional leaders, refine outbound strategy, and help scale a category-defining Applied AI platform supporting families through complex life transitions.

APPLICATION PROCESS:

TO BE CONSIDERED FOR THIS ROLE THESE STEPS NEED TO BE FOLLOWED:

- Fill in the application form

- Record a video showcasing your skill sets