Director, Strategic Sales

About the role

This is a high-impact senior individual contributor role focused on driving new business across a strategic North American market. You'll own the full sales cycle, from territory planning and prospecting through executive engagement, negotiation, and close. You'll sell innovative SaaS and AI-powered solutions to sophisticated brokerage organizations and senior decision-makers. The role combines significant autonomy with close collaboration across Sales, Marketing, Product, and Customer Success. You'll help shape go-to-market strategy by bringing customer, competitive, and market insights back to leadership. Success will come from creating sustainable pipeline, closing complex agreements, and delivering measurable revenue growth.

Accountabilities

• Own the full sales cycle, from identifying and creating opportunities through negotiation, contract execution, and close, while delivering against an individual revenue target.
• Build and execute strategic territory and account plans focused on high-value mid-market and enterprise opportunities across North America.
• Generate pipeline through outbound prospecting, executive networking, referrals, industry relationships, events, and targeted account strategies rather than relying primarily on inbound demand.
• Develop trusted relationships with C-suite and senior leaders across brokerage, operations, marketing, technology, recruiting, and revenue functions.
• Lead sophisticated discovery conversations to uncover business challenges, organizational priorities, buying criteria, and measurable business outcomes.
• Deliver compelling product demonstrations and business cases that connect SaaS, automation, and AI capabilities to customer priorities and commercial objectives.
• Navigate complex, multi-stakeholder sales processes involving executive sponsors, procurement, legal, finance, and technical stakeholders.
• Lead commercial negotiations involving pricing, contract terms, and multi-year SaaS agreements.
• Maintain accurate pipeline management and forecasting, proactively identifying risks, blockers, next steps, and opportunities to improve deal velocity.
• Partner closely with Sales leadership, Marketing, Product, Customer Success, and other teams to advance strategic opportunities and improve the overall go-to-market motion.
• Bring customer feedback, competitive intelligence, and market insights to leadership to influence positioning, product strategy, and sales execution.
• Act as a senior sales voice within the organization by sharing best practices and helping elevate sales performance without formal people-management responsibilities.
• In the first 90–120 days, establish a strong understanding of the platform, customers, and PropTech landscape; develop territory and target-account strategies; build executive relationships; establish 3–4x pipeline coverage; and begin converting priority opportunities into new revenue.

Requirements

• 7+ years of progressive B2B SaaS or technology sales experience with a consistent record of achieving or exceeding quota.
• Demonstrated success closing complex, high-value SaaS agreements with mid-market and/or enterprise customers.
• Proven ability to independently create pipeline through strategic prospecting, relationship building, and account development.
• Experience selling directly to C-suite and senior executive buyers and operating credibly as a trusted advisor.
• Strong command of complex, multi-stakeholder sales cycles from initial outreach and discovery through negotiation and close.
• Ability to develop account strategies, build compelling business cases, identify organizational pain points, and connect technology solutions to measurable business outcomes.
• Strong commercial judgment with experience negotiating pricing, contract terms, and multi-year agreements.
• Executive presence, exceptional communication skills, and the ability to build meaningful relationships with sophisticated customers.
• Comfortable working with significant autonomy, ambiguity, and accountability in a high-growth environment.
• Experience in PropTech, vertical SaaS, or another complex industry-focused technology environment.
• Experience selling CRM, marketing automation, AI-powered, or workflow technology is an advantage.
• Knowledge of the residential real estate brokerage ecosystem is a plus.
• Experience introducing new products or categories into an established market is desirable.
• Ability to collaborate closely with Product and Marketing teams to influence positioning and go-to-market strategy.
• Familiarity with Salesforce, HubSpot, Gong, or comparable sales technologies is beneficial.
• A proactive, resilient, accountable, and execution-focused mindset, with a genuine passion for selling and building customer relationships.

Benefits

• Base salary of $100,000–$110,000, depending on experience, qualifications, and other job-related factors.
• Variable compensation with meaningful earning potential for high performance.
• No commission ceiling, providing top performers with the opportunity to significantly increase total compensation by exceeding targets.
• Medical, dental, and vision coverage.
• Paid time off and 11 paid holidays.
• 5 days of bereavement leave.
• Paid birthday benefit.
• Company-paid short-term and long-term disability coverage.
• Supplemental life, critical illness, and accident insurance.
• Employee Assistance Program and wellbeing programs.
• PerkSpot employee discounts and discounted pet insurance.
• Employee referral program and employee engagement initiatives.
• Office lunch benefits.
• 401(k) matching planned for January 1, 2027.
• Benefits may vary based on country, region, and eligibility.