RealBooks is hiring a Chief Revenue Officer to own our revenue engine end-to-end — capture, generation, and the go-to-market motion that gets us there. This is a C-level executive role reporting directly to the CEO and working alongside the COO and CIO.

You'll define who we sell to, how we sell, what we charge, and how we capture every dollar of opportunity in the market. You'll build the sales and marketing functions, design the pricing and packaging strategy, and forge the partnerships that put RealBooks in front of every serious real estate investor.

This role is equal parts strategic and hands-on. We're pre-Series A, which means you'll be building the revenue playbook from scratch, not inheriting one.

What you'll do:

Revenue capture

Own the closing motion — build, hire, and lead the sales function from first AE through a full team
Build the pipeline-to-close playbook: discovery, demo, qualification, negotiation, and close
Set and run the forecast — quotas, pacing, win rates, and pipeline coverage
Drive expansion revenue — upsell, cross-sell, and net revenue retention across the existing customer base

Revenue generation

Build and lead the marketing function — content, SEO, demand gen, paid acquisition, brand, and lifecycle
Design and iterate on the pricing and packaging model (Bird Dog, DIY'er, Mogul) to maximize conversion, ARPU, and lifetime value
Develop the partnership and channel strategy: property managers, title companies, lenders, brokerages, CPA firms, and investor communities (BiggerPockets, local REIAs, podcasts, conferences)
Stand up the lead-gen engine — events, webinars, content, and community-led growth

Go-to-market strategy

Define the GTM strategy across all customer segments — individual investors through portfolio operators
Identify and prioritize target market segments — determine where RealBooks wins first and how we expand
Own positioning, messaging, and competitive differentiation in the market
Represent RealBooks at industry conferences, podcasts, webinars, and investor communities
Report to the CEO and collaborate with the board on revenue strategy, fundraising narrative, and market opportunity sizing
Define and track revenue KPIs: MRR, ARR, CAC, LTV, churn, win rate, conversion, and pipeline velocity

What we're looking for:

7+ years in revenue leadership — CRO, VP Sales, VP Growth, or similar — ideally at a B2B SaaS, fintech, or proptech company
Proven track record of building revenue from early stage (pre-$1M ARR) through growth phase
Demonstrated success across the full revenue motion: outbound, inbound, partnerships, and expansion
Deep understanding of real estate investing, property management, or adjacent industries — you need to speak the investor's language
Experience designing and iterating on SaaS pricing and packaging
Strong network in the real estate investment community, proptech ecosystem, or CPA/accounting profession
Experience hiring, leading, and operating a sales and marketing team — even a lean one
Comfortable in a startup environment — you'll build the systems and processes, not just manage them
Experience working with founders and boards on revenue strategy and fundraising
Bonus: experience with partnership-led growth or channel sales models
Bonus: experience marketing and selling AI-powered products

Compensation: Competitive base salary + significant equity stake + performance incentives. This is a co-building role — your equity reflects that.

Location: Remote, with preference for candidates east of Denver (Central or Eastern time). Willingness to travel for industry events, partnership meetings, and periodic team gatherings in Sarasota, FL.

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Chief Revenue Officer