RemoteLeaf Logo
Log in Sign up

Senior Director, Sales

2 months 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 11

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

Similar Roles

Model N

VP, Strategic Accounts - 340b & Gross-to-Net Solutions

Model N 251-1K Professional Services

Model N is hiring a Vice President of Strategic Account Management to lead commercial strategy and revenue growth for Truzo, its platform for 340B and MFP capabilities serving pharmaceutical and life sciences organizations.

United States Full-time Executive Account Executive Head of Sales
$225k-$250k
2 hours ago
Zeta Global

Vice President, Client Partnerships (Publisher Cloud)

Zeta Global 1K-5K Media

Zeta is hiring a VP, Enterprise Sales, Publisher Cloud to lead field execution and drive net new revenue for its integrated publisher-focused platform.

United States Full-time Lead Head of Sales
$250k-$400k
3 hours ago
Garner Health

VP, Employer Sales - East

Garner Health Specialized Consumer Services

Garner Health is seeking a VP, Mid-Market Sales to lead its East Region team focused on growing employer healthcare sales within the 50 to 9,999 life segment.

United States Full-time Lead Head of Sales
$375k-$410k
1 day, 1 hour ago
Parachute Health

Chief Growth Officer

Parachute Health 51-250 Health Care Providers & Services

Parachute Health is hiring a Chief Growth Officer to lead enterprise growth, partnerships, and revenue expansion for its digital ordering platform serving post-acute care.

United States Full-time Executive Head of Marketing Head of Sales
$300k-$400k
1 day, 2 hours ago

You're on a roll! Sign up now to keep applying.

Sign Up

Already have an account? Log in

Used by 14,729+ remote workers