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Harper (YC W25) · 5 hours ago

Field Growth & Engagement Lead

San Francisco, CA

Full-time

Onsite

Senior Level

$100K/yr - $140K/yr

5+ years exp

Harper is building the fastest-growing AI-powered commercial insurance brokerage in the country, and they are seeking a Field Growth & Engagement Lead to own go-to-market execution in the real world. The role involves running field-driven growth initiatives, launching vertical-specific GTM motions, and building relationships in the market to help Harper expand into new segments.

Artificial Intelligence (AI)FinTechInsurance

Responsibilities

Launch and scale field marketing efforts across construction, med spas, manufacturing, and new verticals

Develop deep understanding of buyer behavior, decision cycles, and objections in each segment

Build repeatable vertical-specific GTM playbooks

Meet customers on-site, attend industry events, host roundtables, and build partnerships

Identify conferences, associations, and offline channels worth investing in

Act as a direct extension of Harper’s brand in the field

Translate field insights into better messaging, landing pages, and demand gen strategies

Work closely with sales and engineering to turn insights into automation and tooling

When something works in one vertical, help systematize and scale it across the org

Run fast GTM experiments — events, partnerships, outbound plays, localized campaigns

Measure results, double down on what converts, kill what doesn’t

Optimize for learning speed and impact, not perfection

Deep understanding of Harper’s customers, funnel, and sales process

Actively in the field talking to customers and partners

First GTM experiments launched in at least one vertical

Clear traction from field-driven initiatives (leads, pipeline, or partnerships)

At least one vertical playbook documented and in use

Field insights actively shaping messaging and demand gen upstream

Multiple verticals running repeatable GTM motions you helped build

Field learnings translated into scalable systems and automation

Harper entering new segments faster because of your work

Qualification

Field marketingDemand generationGTM executionCustomer engagementMarket analysisContent creationCommunicationFast-paced environment

Required

5+ years of experience in field marketing, growth, demand generation, sales, or a closely related GTM role

Proven experience launching or scaling new markets, verticals, or regions, ideally in B2B, SMB, or services-heavy industries

Strong track record of field-driven demand creation (events, partnerships, local campaigns, community-building, or direct customer engagement)

Comfortable working directly with sales teams and owning outcomes tied to pipeline and revenue, not just leads

Ability to translate qualitative customer insight into clear GTM playbooks and scalable processes

Experience working in fast-moving environments where priorities change quickly and execution matters more than polish

Strong written and verbal communication skills — able to synthesize what you're seeing in the field and clearly articulate what to do next

Willingness to be on-site in San Francisco and in the market regularly (events, customer visits, partner meetings)

Preferred

Experience in construction, healthcare, med spas, manufacturing, or other regulated / traditional industries

Prior startup experience or exposure to early-stage GTM teams

Experience creating or collaborating on fast, native content for distribution channels (short-form video, social-first, meme-adjacent, or community-driven content)

Familiarity with Overtime-style content — highly engaging, simple, high-signal storytelling designed to travel organically

Ability to spot moments in the field (events, customer stories, wins, trends) and turn them into content ideas that feed demand gen and brand awareness

Comfort working with creators, internal teams, or lightweight tools to get content shipped quickly rather than perfectly