Senior Account Executive

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 37 of the top 40 global asset managers across $101 trillion in AUM and 1,550+ regulated firms, including Fidelity, BNY, Blackstone, and JP Morgan. 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