About Red Oak

Red Oak is the singular compliance platform for the financial services industry: content, review, distribution, and supervision working as one system.

Our vision: we become the compliance layer every Financial Services firm runs on. Today, we serve 19 of the top 20 global asset managers across $62 trillion in AUM and 1,550+ regulated firms, including BlackRock, Vanguard, PIMCO, and Morgan Stanley. We're one of the fastest-growing companies in compliance tech, with no direct holistic competitor covering our ground.

Why This Role Matters

A recent merger expanded our product portfolio 4–5x, and a large volume of mid-market and enterprise accounts sit unallocated and underworked. This is a full-cycle seat on a territory that's been waiting for attention.

You'll own a defined book from day one and sell across an expanded product line most reps have never had access to. The team is driven, people help each other win, and winning matters.

High autonomy. High ownership. High impact.

What Success Looks Like

• 30 Days: Fully ramped on Red Oak's product suite, systems, and territory; actively working your book.

• 90 Days: Pipeline built and measured on activity — consistent outbound coverage across the full territory.

• Quarter 1–2: Running your own deals end-to-end — discovery, demo, negotiation, close.

• End of Ramp: Hitting quarterly net new bookings quota.

The Role

You'll own a territory of mid-market to enterprise accounts, running full-cycle sales from outbound prospecting through close. Deal cycles run two to three months and are multi-threaded and competitive. Every deal has a competitor in the room, because compliance is required for regulated firms and you're working prospects who already have the problem. You'll sell across Red Oak's full, newly expanded product line, a broader portfolio than most reps in this market take to the same buyer.

We have a BDR team feeding leads, and the biggest deals on this team are AE-sourced. The reps who win here build their own pipeline.

• Own a defined territory and build pipeline across the full account list, using outbound sequencing tools, LinkedIn Sales Navigator, and call intelligence platforms

• Run the full sales cycle — outreach, discovery, demo, negotiation, close — with minimal leadership involvement

• Multi-thread complex, competitive deals across buying committees

• Sell across Red Oak's expanded product portfolio, tailoring approach to account size and need

• Use AI tools for account research, call prep, outreach personalization, and deal analysis

• Maintain accurate pipeline and forecast discipline in Salesforce

• Partner with team members on deal strategy and account coverage

What You'll Bring

• Full-cycle (outbound-to-close) Account Executive experience in SaaS, with a track record of self-sourcing and closing complex deals

• Experience managing multi-threaded, competitive sales cycles, with a history of winning new business in SaaS

• Real competitive-displacement experience — you know how to win a deal when someone else is already in the room

• Proven territory and opportunity management, with a consistent and disciplined approach to forecasting and pipeline generation

• Fluent with Salesforce, call intelligence tools (e.g., Gong), and outbound sequencing platforms

• Comfortable working to a structured qualification methodology such as MEDDPICC

• AI fluency in your sales workflow: using tools like Claude for prospecting, messaging, and call analysis. This is table stakes here

• Sharp communicator who builds trust fast and navigates buying committees with confidence

• Comfortable traveling roughly once a month for prospect and client meetings

Desirable

• Background selling into financial services or investment management

• Compliance or RegTech SaaS experience

Benefits

• Equity Appreciation Rights: share in what we're building

• Comprehensive health coverage: medical, dental, and vision

• 401(k) with a 3% company contribution

• 20 days PTO annually, plus your birthday off and paid sick leave

• Enhanced family leave

• Life insurance

How We Work

Team-first and urgency-driven. We help each other win and hold each other to a high bar. Once you're ramped, you own your book and your number.

Work Structure

• Location: Remote, East Coast timezone preferred

• Reports to: Vice President, New Business Sales

• Travel: ~1x a month