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Senior Director, Sales

1 month ago
United States
Full-time
Executive
Head of Sales
Sales and Business Development
ERP
Apply Now
HappyCo

HappyCo

HappyCo provides an AI-powered platform designed to centralize and optimize maintenance operations for multifamily properties, enabling real-time inspection, monitoring, and management of business assets to enhance resident satisfaction and operational...

Professional Services
51-250
Founded 2012
$12M raised
View All Jobs 12

Description

  • Own the sales team’s bookings number, forecast accuracy, and pipeline hygiene.
  • Lead and grow the SMB and mid-market new logo sales engine.
  • Coach and improve the sales playbook, methodology, and rep ramp process.
  • Build and operationalize AI-first workflows for research, deal scoring, business-case creation, and outreach.
  • Manage, coach, and performance-develop the existing sales team and front-line leaders.
  • Recruit high-performing sales talent and expand the team significantly over the next 18 months.
  • Represent sales in leadership, executive, and cross-functional discussions.
  • Partner closely with Key Accounts, Marketing, Customer Success, RevOps, and Product.
  • Improve conversion rates, sales velocity, and repeatability across the funnel.

Requirements

  • 10+ years of B2B SaaS sales experience.
  • 5+ years of experience leading sellers with a history of hitting bookings goals most of the time.
  • Experience coaching and developing front-line managers, not just individual reps.
  • Fluency in modern sales methodologies such as Winning by Design, MEDDPICC, Challenger Sale, or equivalent.
  • Experience building quantified business cases and coaching reps on business-case and cost-of-inaction selling.
  • Experience operating from pipeline math and synthesizing data quickly.
  • Strong recruiting ability and high emotional intelligence.
  • Experience building or championing real AI-supported workflows within a sales team.
  • Preferred experience in PropTech, multifamily, real estate, or vertical SaaS.
  • Preferred background selling business solutions alongside or against incumbents in property operations, ERP, procurement, or workflow categories.
  • Preferred pricing experience with tiered consumption, usage-based, or platform models.
  • Preferred experience shipping an in-production AI agent or workflow inside a sales team.

Benefits

  • Remote work in the U.S., with a strong preference for Chicago or Dallas.
  • Base-heavy compensation structure: 60% base / 40% variable.
  • Meaningful equity commensurate with role impact and ownership.
  • Flexible company culture with work-from-anywhere support.
  • Unlimited vacation time.
  • Generous paid parental leave.
  • Competitive and equitable pay, including stock options.
  • Monthly stipends for wellness and home office expenses.

Interested in this position?

Apply directly on the company website

Apply Now

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