Share of this job’s tasks that AI is already used for at work, from real usage. It is not a forecast of job loss, and a low number means no use seen yet. Source: Anthropic Economic Index.

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About the job

Insurance plays an important role in people’s lives, providing protection and peace of mind through life’s adventures and unexpected turns. In the moments that matter, people want to know their insurer is there for them. At Hi Marley, we help insurers deliver on that promise through communication that brings greater clarity and connection to the policyholder experience.

About the Role

You'll help insurance customers see how technology can solve their toughest workflow challenges—and build the evidence behind that promise. Working alongside Account Executives and Account Managers, you'll connect discovery, demonstrations, and hands-on pilots to the business outcomes that drive purchase and expansion decisions. You'll engage senior business and technology stakeholders, turning complex requirements into clear recommendations. If you enjoy asking thoughtful questions, testing assumptions, and showing customers what's possible, you'll love this role.

We’re in our Boston office Mondays, Tuesdays, and Thursdays to connect, collaborate, and learn together. Recurring meetings typically run between 9:30am and 4:30pm for commuter flexibility.

What you'll do

Lead discovery and tailored demonstrations that connect customer workflows, requirements, and success criteria to our capabilities.

Own pilots from scoping through evaluation, coordinating teams and presenting results that inform buying and expansion decisions.

Build business cases and ROI models from customer data and explicit assumptions; support proposals and explain AI capabilities and limitations.

Create reusable demo and discovery resources, and partner with Product, Implementation, and Customer Success to surface gaps and transfer agreed requirements.

Your first year

First 90 days: You've learned our platform, customer workflows, and discovery approach, and built relationships with your sales and delivery partners.

By 6 months: You've led discovery and tailored demonstrations, built customer business cases, and scoped pilots with clear success criteria.

By 12 months: You've independently led pilots through evaluation, presented outcomes to customer stakeholders, and created reusable resources that strengthen the team's approach.

What you'll bring

5–7+ years in customer-facing consulting, solutions consulting, or sales engineering, including at least three years working in or advising insurance.

Strong discovery, demonstration, and analytical skills: you translate customer data into business cases and explain value clearly to executive, business, and technical audiences.

Working knowledge of SaaS, integrations, APIs, and data flows; experience with AI-enabled software and judgment to explain its uses and limitations responsibly.

Clear writing, organization, and cross-team coordination as priorities change; ability to work in Boston three days weekly and travel up to 50%.

Nice to have

Property & Casualty insurance experience.

Familiarity with claims, service, or digital operations.

Don't check every box? If this role excites you, we'd still love to hear from you.

Compensation, Benefits & Perks: At Hi Marley, we are committed to fair and transparent pay practices. The annual base salary for this role is expected to fall within the range of [$117,000–$154,000], depending on experience, skills, qualifications, and location. Offers are determined based on these factors as well as internal peer equity. It’s most common for new hires to start near the midpoint of the range, allowing room for growth as employees develop in their role. In addition to base pay, this role includes a variable compensation component. Total earnings will vary based on individual and/or team performance.

In addition to base pay, we support your wellbeing and growth with:

Equity grants for all employees

401(k) with a 4% employer match

Medical, dental, vision, disability, and life insurance for employees working 30+ hours per week

Monthly wellness and annual professional development stipends

Paid parental leave

Flexible Time Off to recharge, plus enjoy Wind-down Week, our annual year-end company shutdown

Who We Are:

Three core values guide how we work:

Max Courage: Dream big, try new ideas, and take measured risks to maximize impact.

Be Humble: Lead with appreciation, compassion, and openness to learn from anyone, anywhere.

Ubuntu: Align behind a shared purpose to achieve our fullest potential together.

Life at Hi Marley combines meaningful work with clear expectations. We communicate openly and with care, stay curious, take ownership, and value every perspective. Our flexible, hybrid environment is built on trust, accountability, and mutual support—both at work and when life needs our attention.

Hi Marley is proud to be an equal employment opportunity employer. We celebrate diversity and do not discriminate based on gender, sexual orientation, gender identity, religion, race, veteran status, disability status, or any other characteristic protected by applicable law. We are committed to building an inclusive work environment representing a variety of backgrounds, perspectives, and skills, where all employees are encouraged to be their authentic selves.