Senior Vice President of Sales

Prophetic Software is not able to sponsor employment visas now or in the future. Candidates must be authorized to work in the United States without current or future sponsorship to be considered for this role.

About Prophetic:

Real estate development is a multi-billion-dollar industry that has run on fragmented data, manual processes, and gut instinct for decades. Prophetic is changing that. We're building the AI-native platform that enables homebuilders, developers, and investors to find, analyze, and act on land opportunities from a single system — powered by proprietary technologies that process billions of data points across all 50 states. We are the market leader in our space, and our customers don't just use the product — they love it. We're not making teams more efficient. We're changing how they operate.

Prophetic is scaling fast — demand is outpacing our ability to hire, and we're just getting started. This is a once-in-a-lifetime team: sharp, low ego, deeply collaborative, and obsessed with building the best product in the industry. Come disrupt an industry with us.

Opportunity Overview

Prophetic is seeking a Vice President of Sales to lead the next phase of commercial growth for its AI-native land intelligence platform.

This is a player-coach revenue leadership role responsible for leading Prophetic through its next major stage of growth: turning a proven product and strong market pull into a scaled, repeatable revenue engine. The VP of Sales will they'll lead the team, create/monitor/enforce protocols, ensure best practices are maintained, and personally assist with major enterprise deals to ensure max close rate— including enterprise opportunities with the nation's largest homebuilders — while building the segmented sales organization, hiring plan, and operating cadence required to scale.

The ideal candidate is a stage specialist: an elite leader who has taken companies from 5M ARR to 30-50M ARR before. This role calls for a hands-on executive who leads by example and elevates everyone around them.

This VP reports directly to the CEO and will play a critical role in shaping the company's revenue strategy, market presence, and growth trajectory.

What the Vice President of Sales Will Be Doing

Revenue Leadership

• Lead Prophetic's revenue strategy and own new-business growth across enterprise, mid-market, and entry level market segments.

• Drive the company's most strategic opportunities from first conversation to close, partnering closely with Strategic Account Executives throughout.

• Build a balanced revenue plan that pairs high-impact enterprise pursuits with a durable, predictable base of volume business.

• Establish Prophetic as the trusted technology partner for the industry's leading homebuilders, real estate developers, brokerages, and real estate organizations.

Enterprise Deal Leadership

• Lead strategy on Prophetic's largest opportunities with national homebuilders and major real estate brands.

• Map and navigate complex buying committees spanning land acquisition, finance, operations, and executive leadership, typically spanning a 6 - 18 month enterprise sales cycle.

• Lead executive-level negotiations and structure commercial terms for high-value, multi-stakeholder transactions.

• Partner with Client Services on seamless handoffs so new enterprise customers are positioned for long-term success.

Sales Organization Design & Segmentation

• Design and lead the segmentation strategy that moves Prophetic's sales team from a generalist model to a specialized organization built for scale.

• Determine how best to align sellers to the markets we serve — including home building, multifamily, and brokerage — and to customers of every size across these verticals.

• Ensure the structure supports both strategic enterprise pursuits and a growing base of smaller customers.

Team Leadership & Talent

• Lead, coach, and inspire a sharp, low-ego team of Account Executives — leading by example on live deals.

• Own the sales hiring plan, including Account Executive & Inside Sales expansion to drive outbound pipeline and manage inbound demand.

• Recruit and develop sellers who raise the bar, and build a culture of accountability, candor, and competitive drive. Underpromise, over-deliver, and win the business.

Go-To-Market Partnership & Operating Discipline

• Partner with Product and Marketing to refine positioning, messaging, and segment-specific go-to-market strategy.

• Bring the voice of the customer into the product roadmap.

• Establish scalable sales processes, forecasting discipline, and CRM pipeline management.

Market Presence

• Represent Prophetic at industry conferences, executive briefings, and customer events across the homebuilding and real estate ecosystem.

• Build Prophetic's reputation as the trusted platform for land intelligence among the industry's leading brands.

Qualifications

• 8+ years of sales leadership experience, including senior sales leadership roles at high-growth B2B technology companies.

• Proven repeat operator: has led sales through the growth-stage scale-up — taking a company with proven product-market fit to a 5x+ increase in revenue — ideally more than once.

• Experience personally selling to, and closing, large enterprises with multi-stakeholder buying committees and extended sales cycles, with $250k+ ACVs.

• Experience running enterprise and high-velocity sales motions at the same time.

• Demonstrated success designing segmented sales organizations and building the hiring plans to support them.

• A leader Account Executives respect, follow, and want to emulate.

• Disciplined approach to pipeline management, forecasting, and realistic target-setting.

• Exceptional energy and the stamina to thrive at a demanding pace.

• Willingness to travel extensively for major enterprise accounts, particularly during industry conference season.

Differentiators

Candidates who meet the core requirements and also bring the following experience will stand out:

• Experience selling into homebuilding, multifamily, real estate brokerage, land development, or construction technology.

• Established relationships with national and regional homebuilders or major real estate organizations.

• Familiarity with land acquisition workflows and how homebuilders evaluate and buy technology.

• Experience selling AI, data, B2B SaaS, or analytics platforms to enterprise buyers.

• Experience working alongside hands-on founders in a high-visibility executive role.

• Strong references who worked for you, and who you worked for.

Why Prophetic:

• The team. Wide expertise, sharp, low ego, and genuinely fun to work with. We have each other's backs and we celebrate wins together.

• Real ownership and impact from day one. Our customers make million-dollar decisions on our platform. Your work matters immediately.

• AI-native product and AI-native workflows. Every team — engineering, sales, operations — runs on AI tooling daily.

• Founder-led transparency. Leadership shares the financials, the strategy, and the hard calls with the whole team.

• High growth, high demand. The product works, customers love it, and we are hiring to keep up. No shortage of opportunity here.

• Flexibility. Remote, hybrid, or in-office with a great Portland, OR headquarters.

• Self-starters who thrive in ambiguity. We're a startup. If you need someone to tell you what to do every morning, this isn't the place; if you come alive solving hard problems with smart people, it is.

Benefits (US-based Full-time):

• 100% medical, dental & vision insurance coverage for you; 30% coverage for dependents

• Competitive salary and meaningful early-stage equity

• Unlimited PTO

• Hybrid/Remote stipend

• In-office perks: snacks, drinks, coffee, ping-pong table, and more — plus cuddles from Olive, our in-office Doberman!

• Budget for intra-office travel

• 2–3 annual team meetups in person

How We Work:

These four themes are how we think, build, and lead:

• Truth — Say the hard thing. We speak plainly, flag problems early, and share what's actually going on.

• Precision — Sign your name to it. Our customers make million-dollar decisions on our data. We get the details right.

• Velocity — Speed compounds. Waiting doesn't. We ship daily and launch features every two to three weeks.

• Ownership — Own it, then solve it. We own outcomes, not tasks. If something's broken, we fix it.

EEO:

Prophetic Software is an equal opportunity employer. We are committed to creating an inclusive environment for all employees and applicants, and we make employment decisions without regard to race, color, religion, sex (including pregnancy, childbirth, or related medical conditions), gender identity or expression, sexual orientation, national origin, age, disability, genetic information, veteran or military status, marital status, or any other characteristic protected under applicable federal, state, or local law. We actively seek to build a diverse team and encourage candidates from underrepresented backgrounds to apply. Reasonable accommodations are available upon request for qualified individuals with disabilities throughout the application and employment process.