Director of Sales - Property Management

About Proof:

Proof is a high-growth startup in the legal tech industry, offering a best-in-class legal services platform used by thousands of law firms. Our platform enables law firms and pro se parties to access efficient, transparent, and accessible legal services, traditionally out of reach. We are on a path to double our business this year and are building a team to help us scale rapidly.

We welcome individuals from all backgrounds who are eager to help build a future where legal services are readily accessible, affordable, and efficient. If you have curiosity, passion, and a collaborative spirit to drive change in an outdated industry, we want you on our team.

About the Opportunity:

We are looking for a senior sales leader who combines strategic thinking, vertical expertise, and hands-on execution. This person will own the full revenue lifecycle for the Property Management vertical including new business, account management, expansion, and retention.
You will play a pivotal role in shaping where the vertical goes next, partnering with Delivery/Operations, Product, and Finance to ensure we deliver exceptional outcomes to the largest Property Management firms and agencies in the country.
This is equal parts strategy, leadership, and roll-up-your-sleeves selling.

Vertical Strategy & Leadership

• Act as the GM of the Property Management vertical, owning strategy, revenue, and go-to-market direction

• Build and refine the vertical GTM plan, including ICP, segmentation, positioning, pricing, and differentiation

• Identify new opportunities, sub-verticals, and whitespace for Proof to expand into

• Influence product and delivery roadmap based on customer trends and operational needs

Sales Leadership & Execution

• Own new business revenue for Property Management firms

• Develop and execute outbound and inbound motions tailored to Property Management workflows

• Lead deal strategy, forecasting, and pipeline health

• Build messaging, talk tracks, and competitive positioning for the vertical

Account Management & Customer Expansion

• Oversee the AM function for Property Management customers, ensuring strong retention and driving expansion

• Build executive relationships with top clients and ensure Proof is seen as a strategic partner

• Conduct QBRs, performance reviews, and strategic planning sessions with the largest accounts

• Map organizational structures at major firms to unlock multi-state or multi-business-unit growth

Cross-Functional Collaboration

• Partner closely with Delivery/Operations to ensure exceptional service execution

• Work with Product on prioritizing features, gaps, and enhancements specific to Collections

• Partner with Marketing to create vertical-specific campaigns, case studies, and events

• Collaborate with Finance and RevOps on forecasting, reporting, and performance analytics

Leadership & Scale

• Help define what the Collections sales team becomes (AEs, AMs, SDR support, etc.)

• Hire and develop future members of the vertical as it scales

• Set the standard for excellence, accountability, and customer-centric execution

Required Skills:

• 5-10+ years in B2B sales or account management leadership (preferably in tech enabled or services businesses

• Proven experience owning a business unit

• Strong experience and comfort operating with both strategy and hands-on execution

• Exceptional cross-functional collaboration skills

Preferred Skills:

• Startup or scale-up experience

• Experience building a vertical from early stages

• Understanding of legal-tech, service-of-process, or compliance-driven workflows

• Strong analytical and forecasting abilities

Benefits:

• Full time, remote, salary position

• Medical, dental, vision, disability insurance, and 401k available

• Phone and Internet monthly stipend

• Flexible time off (paid planned and sick time, and paid holidays)

• Equipment provided

E-Verify

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