Content Marketing & Creative Lead

Location: Berry Hill

The Role

At Pilot, we believe access to the right financial resources and expertise can change the trajectory of a business. Our combination of AI and human experts gives startups and SMBs a level of insight that used to be reserved for companies with full‑time finance teams—an experience that feels boutique, but is actually affordable and scalable. In doing so, we help founders and operators find their flow by taking the burden of the financial back office off their plate.

We’re looking for a Content Marketing & Creative Lead who can bring this story to life across modern marketing channels—especially social‑first short‑form video , editorial content, and structured formats for live panels, round tables, and thought‑leadership moments .

Core Audiences

• Startup founders and SMB operators who should be using Pilot.
• Bookkeeping firms who should partner with or join Pilot.

What You'll Do Build & Evolve Pilot’s Content Narrative

• Shape the overarching story for founders and SMBs about how Pilot’s AI + human experts deliver elite financial operations at an accessible price.
• Craft positioning and messaging that helps bookkeeping firms understand the value of partnering with—or joining—Pilot.
• Develop narrative frameworks that ecosystem partners (CDFIs, SBDCs, trade associations) can confidently adopt when referring businesses to Pilot.

Drive Full‑Funnel Content Strategy

• Build content that moves founders from “my books are overwhelming” to “Pilot has this handled so I can grow.”
• Design parallel content journeys for bookkeeping firms and ecosystem partners, from “why would I work with Pilot?” to “this makes me more effective at serving my community/clients.”
• Build a roadmap across formats: short video, live event scripts, written explainers, templates, and partner assets.

Hands‑On Content Creation Across Channels

• Concept and script social‑first short‑form video.
• Develop outlines for panels and round tables to highlight subject‑matter experts and generate repurposable content.
• Write long‑form content such as guides, teardowns, and playbooks about margins, cash flow, and modern back‑office operations.
• Produce simple visual storyboards and repeatable content series.

AI‑First Content & Creative Ops (Scrappy by Design)

• Use AI for research synthesis, outlining, summarization, and first drafts.
• Turn signature content moments (live events, deep dives) into multi‑asset content families.
• Build scrappy systems and workflows that enable high output with minimal resourcing.

Deeply Understand SMEs, Customers & Partners

• Extract insights from Pilot’s internal finance experts, customers, and ecosystem partners.
• Translate interviews, calls, and raw data into structured narratives and market‑facing content.

Measure, Learn & Optimize

• Define simple, clear KPIs for your work, such as:
  • Engagement and conversion on founder‑, firm‑, and partner‑focused assets.
  • Content‑influenced leads and opportunities from SMBs and bookkeeping firms.
• Partner with Demand Gen, Marketing Ops, Rev Ops, and Product Marketing to understand what’s working and adjust your roadmap accordingly.
• Experiment with different hooks, lengths, visuals, and formats for each audience and double down on the ones that consistently build trust and drive action.

Why You'll Love Working with Pilot’s Marketing Team

You won’t be doing this alone in a corner. You’ll be joining a small but mighty marketing team that cares about both craft and impact.

• Senior, collaborative teammates – You’ll work with experienced demand gen, social media, product marketing, partner/local programs, and ops folks who know their craft and respect yours. You bring the stories and creative formats; they bring distribution, data, and GTM alignment.
• Tight partnership with leadership – You’ll be close to decisions and able to see your work turn into real programs quickly, not stuck in layers of approvals.
• Room to experiment – The team values testing and learning. You’ll have space to try new formats, angles, and ideas as long as we’re learning and getting sharper each time.
• Access to rich raw material – 3,000+ customers, deep finance expertise in‑house, and a growing partner ecosystem mean you’ll never be short on stories, data…