Director Of Sales
Fully Remote Chicago, IL
Description

We are Destify! We focus on our people, our culture, and our technology. We have completely changed the way couples book their destination weddings by combining exceptional technology and service.Our team and platform streamlines every step of the destination wedding journey, from discovery to guest booking to travel.

You are a process-obsessed, performance-driven sales leader with SaaS-style rigor and hospitality-grade empathy. You’ll run a remote team that turns complex, emotionally charged decisions into confident bookings and bring the operational mindset of a RevOps pro to everything you touch.

What You’ll Do

Sales Leadership & Strategy

  • Build, lead, and scale a distributed sales team focused on measurable revenue growth
  • Design and execute a structured, data-backed sales process optimized for long-funnel conversions
  • Forecast accurately, manage pipeline health, and drive quota attainment through metrics and accountability

Coaching & Performance

  • Implement a behavioral coaching framework that blends data, CRM discipline, and consultative storytelling
  • Hold weekly 1:1s and use dashboards to diagnose performance and reinforce winning habits
  • Elevate team standards clear expectations, consistent follow-through, and visible results

Sales Operations & Enablement

  • Own HubSpot CRM sales setup, reporting, and optimization to ensure data integrity and visibility
  • Apply Revenue Ops principles to streamline processes, lead flow, and funnel reporting
  • Collaborate with Marketing and Leadership to improve workflow performance, lead quality, and experience alignment
  • Build and refine dashboards, workflows, and automations that enhance sales productivity and conversion efficiency
  • Evaluate and deploy sales-enablement tools that improve efficiency and clarity

Cross-Functional Collaboration

  • Partner with Marketing, Leadership, and internal stakeholders to align the full revenue funnel
  • Provide performance insights that inform strategy, messaging, and overall user experience resulting in sales
Requirements

What Skills You Must Have

  • 5+ years leading high-performing virtual sales teams
  • Deep expertise in HubSpot or SalesForce (required) and familiarity with sales systems frameworks
  • Proven record in SaaS, tech-enabled services, or high-consideration B2C environments
  • Strong analytical mindset: you forecast, model, and measure everything
    Comfortable selling emotionally driven products through structured, consultative processes
    Exceptional communicator, clear, direct, and data-literate
  • Bachelor’s degree or equivalent experience

Why Destify

  • $135,000-185,000 base + bonus structure
  • Flexible Paid Time Off and Paid Parental Leave
  • Caribbean travel perks to reward high performers
  • Fully remote work environment
  • Comprehensive benefits – Medical, Dental, and Vision
  • 401(k) with company match

You’ll Succeed Here If You …

  • Think like a SaaS operator but sell like a concierge
  • Love turning ambiguity into process
  • Treat CRM data and attribution as the language of leadership
  • Excel at leading and growing a successful sales team
     
Salary Description
135,000-185,000