Chief Revenue Officer / Head of Sales

The Opportunity

We are looking for a proven revenue leader to own and scale our commercial organization. Depending on the candidate’s experience, this role will be scoped as a Chief Revenue Officer (owning sales, marketing, and customer success/renewals) or a VP of Sales (owning the sales organization and quota, partnering closely with marketing and product). Either way, you will be the executive accountable for predictable, profitable revenue growth.

This is a builder’s role. You will inherit strong products, marquee references, and durable customer relationships. You will also professionalize how we sell: sharpening our ICP and positioning, building repeatable pipeline, installing a modern sales process and forecasting discipline, and growing and coaching a high-performing team. You’ll translate deep domain credibility in private lending and financial software into a scalable, data-driven revenue machine.

What You'll Own

Revenue Strategy & Growth

• Own the company revenue number, spanning new business (ARR/bookings), expansion, and net revenue retention, and deliver predictable, profitable growth quarter over quarter.
• Define go-to-market strategy: ideal customer profile, segmentation, pricing and packaging, and the path into new customer categories (asset-based / specialty finance, fund managers, MICs, mREITs, commercial and construction lenders, institutions).
• Build an accurate forecasting and pipeline management discipline the CEO and board can rely on.

Sales Leadership & Execution

• Recruit, develop, and lead a high-performing sales organization spanning new logo, account management, and sales development.
• Install a repeatable sales methodology, deal-qualification framework, and metrics-driven operating cadence (pipeline reviews, forecasting, QBRs).
• Personally engage in strategic and enterprise deals with marquee lenders and institutions; be a credible executive presence in the room.

Cross-Functional & Team Building

• At the CRO level, align marketing (demand generation, brand, and pipeline) and customer success/renewals (retention, expansion, and advocacy) under one revenue strategy.
• Partner with Product and Engineering to feed market signal into the roadmap and to launch and monetize new capabilities.
• Build the revenue operations foundation: CRM hygiene, tooling, territory and comp-plan design, and analytics.

What You Bring

Required

• 10+ years in B2B sales with a strong track record of leading and scaling revenue teams; multiple years in a senior sales leadership role (Director/VP/CRO).
• Demonstrated success scaling recurring revenue in a B2B SaaS or FinTech environment, ideally selling into financial services/Mortgage Lenders.
• Experience carrying and consistently exceeding a team quota, with rigorous forecasting and pipeline discipline.
• Proven ability to recruit, coach, and retain top sales talent and to build the operating rhythm of a modern revenue org.
• Comfort with both strategy and execution: you can set direction and get in the deals.

Preferred

• Domain knowledge of private lending, mortgage, loan servicing, or lending/financial software, or the ability to ramp on it quickly and credibly.
• Experience selling to lenders, fund managers, or financial institutions, and navigating multi-stakeholder, compliance-sensitive buying cycles.
• Experience building or scaling marketing and/or customer success functions (for the CRO scope).
• Track record in a founder-led or growth-stage company transitioning to a more scalable, professionalized go-to-market motion.

Benefits & Perks

• Competitive compensation (Base: $180,000 - $225,000), OTE $300,000 - 375,000 (base + performance-based bonus) plus meaningful equity
• Comprehensive health coverage (medical, dental, vision)
• 401(k) matching
• Wellness programs
• Professional development
• Employee recognition programs
• Team building & on-site amenities

What Success Looks Like

• First 90 days: deeply understand the product, customers, pipeline, and team; assess the funnel and forecast accuracy; refine the ICP and go-to-market thesis.
• 6 months: repeatable sales process and forecasting cadence in place; key hires made or plan committed; early pipeline and conversion improvements visible.
• 12 months: measurable, durable growth in new bookings and net revenue retention; a scalable, well-instrumented revenue engine and a team positioned to keep compounding. Establish industry presence as a TMO evangelist and industry leader.

Why This Role

You’ll lead revenue for the category-defining platform in private lending and affordable housing - a market with strong tailwinds, a loyal and prestigious customer base, and real room to grow. You will also assist in unlocking further segments – International, Specialized lenders and the wider asset-based financing loan management market. You’ll have the mandate to build, executive access to the CEO and board, and the chance to turn a great product into a great growth story.

Life at TMO,

TMO pairs 45+ years of category leadership with a culture that's still hands-on and collaborative. Ideas flow freely, every team member has a voice, and we have fun while we build.

Our Values: DRIVE

• Data-Driven: numbers over opinions.
• Respect: high on empathy, low on ego.
• Initiative & Agency: don't wait to be told.
• Value to Customers: create value for them above all else.
• Evolve: progress over perfection.