Chief of Staff

CHIEF OF STAFF

Raise Financial - Nashville, TN (In-Person)

Reports to CEO · Operations · Full-Time

Why Should You Care?

Most people will never catch up financially. Not because they're lazy or making bad decisions, but because the system isn't built for them to win.

The best financial tools in the world already exist. The problem is capital. They only work if you already have access to a substantial stake.

That's the gap we're closing.

We're building a way for people to own meaningful exposure to the market from day one, not 20 years from now. Same structural exposure the wealthy use, just restructured so it actually works for everyone else.

This isn't about marginally better savings rates or slightly improved returns. It's about changing the starting point entirely.

If you get that, you'll understand why this matters.

If you don't, this probably isn't the right place for you.

The Company

Raise Financial is an early-stage fintech company restructuring how long-term wealth actually gets created. We're not layering on top of the existing system.

The model is simple. The execution is not. We front capital, give members full participation in market returns, and charge a fixed monthly fee. Members get the upside, we get a predictable fee - that incentive alignment is the entire point.

The reason this works now, and didn't five years ago, is that the underlying financial products have matured, the regulatory path is navigable, and the capital is aligned. That window is narrow, and we don't intend to waste it.

What we're building has the potential to become the default way a generation builds wealth. Not a niche product. A category-defining company. That only happens if we move fast and get the details right. That's where you come in.

The Traction

This isn’t a slide deck. It’s real.

• Ran a year-long pilot with paying customers through real market volatility validating the core product mechanics/protections, market performance, and member experience.
• 1,600+ people on the waitlist - organic demand before any paid acquisition.
• $2M seed raised from a strategic partner who shares our long-term vision (TBA Q2 2026).
• Next 18 months: 5,000 paying customers, building the internal systems and regulatory infrastructure that allow this model to scale defensibly, and setting up the Series A.

The Role - What You’ll Actually Do

You are fully focused on operational execution. The simplest test for this role: if you disappear for two weeks, things start slipping. Not because you’re doing everyone’s job, but because you’re the person who makes sure leadership’s strategy becomes operational reality; i.e. you make sure nothing falls through the cracks across various functions of the business.

At a sub-10 person startup, that means you won’t just coordinate work. You’ll do the work. You’ll context-switch between regulatory compliance, investor communications, and process-building - often in the same day.

What You’ll Own

These are outcomes, not tasks:

• The CEO operates faster. You own the operating rhythm - weekly priorities, decision tracking, meeting prep, follow-through. Not email and calendar management. Operational leverage.
• Regulatory workstreams stay on track. Form ADV, state licenses, TILA disclosures, Terms of Service - you project-manage the full compliance program between external counsel and internal teams.
• Investors stay informed and the Series A pipeline builds. Monthly updates, Data Room maintenance, relationship tracking, CEO prep docs - so we’re never starting from zero when the next fundraise begins.
• The company’s knowledge and processes actually exist. You help maintain and scale our organizational operating system alongside the Head of Product & Ops, codify decisions, stand up lightweight processes, and champion our AI-augmented workflows so a small team continues to punch above its weight.
• Cross-functional gaps get filled - temporarily. No HR function? You stand it up, define what the future hire should own, and hand it off. Then you move to the next gap. You build bridges.

Why This Is a Career Bet Worth Making

Most Chief of Staff roles at later-stage companies are coordination jobs with a fancy title. This isn’t that.

• What you’ll learn: How a regulated fintech actually goes from zero to one - a ton about finance, product mechanics, SEC/state compliance, fundraising, go-to-market, and more. You’ll get exposure to every function at a depth that doesn’t exist at a bigger company.
• What you’ll be able to say you built: The operating infrastructure of a company that’s creating a new category in consumer fintech. The regulatory program that got us to launch. The investor relations engine that powered the Series A.
• The autonomy: You’ll have real ownership and the mandate to drive outcomes. This is not a low-authority project management role or a glorified EA position.
• Why early matters: You’ll be among the first ~10 hires. That means meaningful equity, a seat at every important table, and the chance to shape the company’s DNA - not just execute someone else’s playbook.

The Team

People join people. Here’s who’s in the room:

• Wesley Belden: Co-founder, CEO - MBA, former portfolio manager and investment analyst, managed $1B in CLO assets, mitigated risk during 2008 crisis for American Financial
• Patrick Cason: Co-founder, CTO - Software developer and UI designer with 15+ years of experience, managed engineering teams of 80+, ex-Meta, ex-OpenAI
• Jack McCann: Head of Product & Ops - 10+ years experience in ops, 10+ years in product, strategy, and data science, ex-Soundstripe
• Brian Delaney: Head of Capital Markets - Capital markets and business development leader with 15+ years of experience, ex-Citi
• Michelle Pieterse: Head of Marketing - MBA & MFA, 18+ years of brand and marketing experience, ex-Coca-Cola
• Analys Falchuk: Head of Community - 6+ years business development experience
• Jaro Vorobey: Senior Engineer - Full stack engineer with 8+ years experience, ex-JPMorgan, ex-Deutsche Bank, ex-OpenAI
• Mike Silver: Lead Counsel - Founding member of the CFPB Office of Regulations with 12+ years there focused on regulatory compliance and strategy

How we work: Nashville-based, in-person. Small team, high trust, fast decisions. Day-to-day use Slack, Google Workspace, Cowork (Claude desktop) and an internal knowledge base extensively - we’re serious about human-AI collaboration as an operational multiplier, not a buzzword.

The Package

Salary

$120k - $140k

Equity

Meaningful early-stage equity grant (details discussed during process)

Benefits

Health insurance, flexible PTO

Upside

Ground-floor role building a new category in consumer fintech

Who Is NOT the Right Fit

We’d rather be honest upfront than waste your time:

• This role is probably not a fit if you need clearly defined swim lanes. The whole point is that you operate across every function, and the priorities shift as the company evolves.
• You’re not a fit if you prefer working remotely. We believe teams, and this role in particular, function optimally when in the same room as leadership. We have an excellent office in Wedgewood-Houston. If you’re not local to HQ we’ll help move the right hire.
• Our environment is hard for people who want to manage process without doing the underlying work. At this stage, you’re both the architect and the builder.
• We move fast and sometimes chaotically. If you need every decision to go through a formal process before anything ships, you’ll be frustrated. We bias toward action and course-correct.

What We’re Looking For

We care far more about how you think than where you’ve worked. That said:

• 3–6 years in operations, consulting, or a Chief of Staff role - ideally at a startup, high-growth company, or venture firm in an operational capacity.
• Nashville-based or willing to relocate.
• You’re organized, type A, and a good communicator.
• You can manage complex, cross-functional projects with multiple stakeholders and competing timelines without someone holding your hand.
• Exceptional writing. You can draft an investor memo, a regulatory summary, and an internal process doc with equal facility.
• Analytical chops. You’re comfortable diving into data, tracking KPIs, and surfacing insights that inform leadership decisions.
• High comfort with ambiguity. You don’t need a job description to tell you what to do on Monday morning.
• Discretion with confidential investor, regulatory, and financial information.

Bonus points:

• Fintech, financial services, or regulated-industry experience (SEC, CFPB, state lending, investment adviser frameworks).
• Prior exposure to fundraising — investor pipeline management, decks, data rooms.
• Excitement about AI-augmented workflows. Depending on the objective we leverage multiple models, agents, and a growing knowledge base that’s coalescing into an organizational operating system. You should want to build processes around human-AI collaboration, not be intimidated by it.
• You don’t put out slop. You actively stay up to date on model use cases, prompting, harnesses, context engineering, and the nuances of AI intent.
• Experience building operational infrastructure from scratch - you’ve helped create playbooks, not just followed them.

How to Apply

You can submit a resume or LinkedIn - but frankly, they don’t tell us much about a person. Far more weight will be placed on your Loom video.

Record a 60–90 second Loom. Turn your camera on. Tell us why you want this role at this company at this moment. Not why you’re qualified. Why you want in. Surprise us.

Send it to wesley@raisefinancial.com and CC jack@raisefinancial.com. We’re excited to hear from you!