Jobs at OffDeal (Now Hiring) — 5 open

About OffDeal

OffDeal is the world’s first AI-native investment bank for founder- and family-owned businesses looking to sell their life’s work. We combine experienced investment bankers with purpose-built technology to bring institutional-quality M&A advice and execution to an underserved market.

We’ve closed transactions across trades, healthcare, and business services, built a fast-growing team, raised $17M from top VCs (Radical Ventures, Y Combinator), and we’re just getting started. We have no shortage of stories worth telling, and this is the role that tells them.

See the momentum: The Wall Street Journal · CNBC · Financial Times · Watch our Series A launch

The role

OffDeal has already earned meaningful organic attention and press, but the work has behind it has been founder-led, opportunistic, and built one asset at a time. Meanwhile, our growing volume of closed deals, client outcomes, and company milestones is creating more great raw material than we currently capture.

You will turn that momentum into a scalable trust and proof engine. Your first mandate is to make OffDeal’s success real to business owners considering a sale. The same body of work will also support buyers, partners, and future teammates.

We believe AI radically expands what one exceptional content operator can produce. You’ll use it to research, organize, draft, adapt, and systematize content across formats. You will own what AI cannot: the story, the interview, the voice, the judgment, and the taste that make the finished work worth a business owner’s attention.

This is a hands-on role for an experienced, scrappy builder. You will set the creative bar by making the work yourself and directing the partners who help bring it to life. You’ll own stories from initial concept through final delivery, working directly with the Head of GTM, senior leadership, our investment bankers, and our engineering team.

Once the credibility foundation is in place, you will also have the opportunity to identify and build new organic formats and channels for reaching business owners.

What you’ll own

• Deal and client stories: Turn closed deals and client outcomes into memorable case studies, testimonials, and stories across written, visual, and video formats. Own each story from concept and interview preparation through final delivery.

• Production: Source and direct videographers, photographers, and other creative partners. Own the brief, production plan, handoffs, captions, on-screen text, graphics, and final cut.

• Blog and website credibility: Own OffDeal’s blog and core website content, including case-study pages, tombstones, team content, company updates, and other proof surfaces that help business owners understand and trust OffDeal.

• AI-native content engine: Build repeatable workflows for finding stories, organizing source material, and turning one strong asset into many distinct, channel-native formats. Maintain a content library that teams across OffDeal can easily use.

You might be a fit if you

• Are an outstanding storyteller with taste. You can absorb complex raw material, find the story that matters, and make it clear, human, and memorable.

• Love building with AI. AI is already your default way of working, not a tool you’re evaluating. You’ve built prompt systems, Skills, or AI workflows that materially multiply your output, and you can demonstrate the leverage they create. If you believe AI inherently compromises serious creative work, this isn’t your role.

• Are a builder and owner. You’re energized by taking an idea from initial concept through production and finished output.

• Understand owner-operators. You know that playbooks designed for corporate software buyers do not automatically translate to practical, time-constrained business owners who are skeptical of jargon. You can make complex subjects simple without talking down to the audience.

• Can run the machine. You are highly organized and resourceful, comfortable directing outside partners and managing several productions at once.

Qualifications

• 3–6 years creating content in a marketing, editorial, agency, or startup setting, with meaningful ownership of both the process and finished work.

• A portfolio that demonstrates strong writing and range, including at least one video, customer story, or case study you drove from concept to finished asset.

• Experience creating content for SMB owners and owner-operators, ideally in trades, healthcare practices, industrials, or other Main Street sectors.

Nice to have

• Familiarity with financial services or M&A, or a track record of quickly mastering unfamiliar, technical subjects.

• Experience testing, launching, or growing an organic content format or channel.

A specific degree is not required. We weigh what you’ve built far more heavily than your credentials.

Our hiring process

Our process includes a live work sample: raw material in, finished asset out, using the tools you actually work with. We care about the quality of the work, the speed of execution, and the leverage you create with the tools at your disposal.